TW202035387A - Colored composition, compound, color filter, and display device - Google Patents

Abstract

The purpose of the present invention is to provide a colored composition including a compound having a maximum absorption wavelength on the longest wavelength side of the absorption spectrum and/or a compound having a wavelength of a shoulder peak on the longest wavelength side of the absorption spectrum to the longer wavelength side of the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of conventionally known C.I. Pigment Yellow 138. The present invention relates to a colored composition including a compound represented by formula (I) and a solvent.

Description

Coloring composition, compound, color filter and display device

The present invention relates to a coloring composition, compound, color filter and display device.

The coloring composition can be used to manufacture color filters used in display devices such as liquid crystal display devices and electroluminescence display devices. As the coloring agent contained in the coloring composition, C.I. pigment yellow (Pigment Yellow) 138 is known (Patent Document 1).

（C.I.顏料黃138） [現有技術文獻] [專利文獻][化1]

(CI Pigment Yellow 138) [Prior Art Document] [Patent Document]

[Patent Document 1] Japanese Patent Laid-Open No. 2013-82906

[The problem to be solved by the invention] In recent years, the development of display monitors for expanding the color reproduction area that can be displayed is advancing. As one of the steps, color filters are also required to have denser colors. In order to meet this requirement, the following coloring composition is required, which contains a maximum absorption on the longest wavelength side of the absorption spectrum on the longer wavelength side than the longest wavelength side of the absorption spectrum of the previously known CI Pigment Yellow 138 A compound having a wavelength and/or a compound having a wavelength of a shoulder peak on the longest wavelength side of the absorption spectrum. The wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum refers to: Compound · In the case of a longer wavelength side than the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of C.I. Pigment Yellow 138, and no maximum absorption wavelength on the longest wavelength side of the absorption spectrum, And · When there are two or more inflection points of the absorption spectrum on the longer wavelength side than the maximum absorption wavelength on the longest wavelength side of the absorption spectrum, The wavelength of the average value of the wavelength of the inflection point on the longest wavelength side of the absorption spectrum and the wavelength of the inflection point on the second longest wavelength side of the absorption spectrum. [Means to solve the problem]

The present invention provides the following [1] to [6]. [1] A coloring composition comprising: a compound represented by the following formula (I) and a solvent.

[式（I）中， R¹ ～R⁵ 分別獨立地表示氫原子、鹵素原子、氰基、硝基、-SO₃ M、-CO₂ M、MM、碳數1～40的一價烴基或碳數1～40的一價雜環基， 構成該一價烴基及該一價雜環基的-C(-)(-)-亦可取代為-Si(-)(-)-， 構成該一價烴基及該一價雜環基的-CH(-)-亦可取代為-N(-)-， 構成該一價烴基及該一價雜環基的-CH=亦可取代為-N=， 構成該一價烴基及該一價雜環基的-CH₂ -亦可取代為-O-、-S-、-S(O)₂ -或-CO-， 構成該一價烴基及該一價雜環基的氫原子亦可取代為鹵素原子、氰基、硝基、-SO₃ M、-CO₂ M或MM； R¹ 及R² 、R² 及R³ 、以及R³ 及R⁴ 可分別彼此鍵結而形成環； M表示氫原子、鹼金屬原子、可具有配位體的金屬原子或N(Z¹ )(Z² )(Z³ )(Z⁴ )； MM表示鹼金屬原子、可具有配位體的金屬原子或N(Z¹ )(Z² )(Z³ )(Z⁴ )； Z¹ ～Z⁴ 分別獨立地表示氫原子、碳數1～40的一價烴基或碳數1～40的一價雜環基， 構成該一價烴基及該一價雜環基的-C(-)(-)-亦可取代為-Si(-)(-)-， 構成該一價烴基及該一價雜環基的-CH(-)-亦可取代為-N(-)-， 構成該一價烴基及該一價雜環基的-CH=亦可取代為-N=， 構成該一價烴基及該一價雜環基的-CH₂ -亦可取代為-O-、-S-、-S(O)₂ -或-CO-， 構成該一價烴基及該一價雜環基的氫原子亦可取代為鹵素原子、氰基、硝基、-SO₃ M、-CO₂ M或MM； Q¹ 及Q² 分別獨立地表示二價烴基或二價雜環基， 構成該二價烴基及該二價雜環基的-C(-)(-)-亦可取代為-Si(-)(-)-， 構成該二價烴基及該二價雜環基的-CH(-)-亦可取代為-N(-)-， 構成該二價烴基及該二價雜環基的-CH=亦可取代為-N=， 構成該二價烴基及該二價雜環基的-CH₂ -亦可取代為-O-、-S-、-S(O)₂ -或-CO-， 構成該二價烴基及該二價雜環基的氫原子亦可取代為鹵素原子、氰基、硝基、-SO₃ M、-CO₂ M或MM； 於Z¹ ～Z⁴ 、M及MM分別存在多個的情況下，該些可彼此相同或不同] [2] 如[1]所述的著色組成物，其包含樹脂。 [3] 如[1]至[2]中任一項所述的著色組成物，其包含聚合性化合物以及聚合起始劑。 [4] 一種彩色濾光片，其是由如[1]至[3]中任一項所述的著色組成物形成。 [5] 一種顯示裝置，包含如[4]所述的彩色濾光片。 [6] 一種化合物，其由式（I）表示。[化2]

[In formula (I), R ¹ to R ⁵ each independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, MM, a monovalent hydrocarbon group having 1 to 40 carbons, or A monovalent heterocyclic group having 1 to 40 carbon atoms, -C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -Si(-)(-)-, constituting the The -CH(-)- of the monovalent hydrocarbon group and the monovalent heterocyclic group can also be substituted with -N(-)-, and the -CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group can also be substituted with -N =, -CH ₂ -constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -O-, -S-, -S(O) ₂ -or -CO- to form the monovalent hydrocarbon group and the The hydrogen atom of the monovalent heterocyclic group can also be substituted with a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M or MM; R ¹ and R ² , R ² and R ³ , and R ³ and R ⁴ can be bonded to each other to form a ring; M represents a hydrogen atom, an alkali metal atom, a metal atom that may have a ligand, or N(Z ¹ )(Z ² )(Z ³ )(Z ⁴ ); MM represents an alkali metal Atom, a metal atom that may have a ligand, or N(Z ¹ )(Z ² )(Z ³ )(Z ⁴ ); Z ¹ to Z ⁴ each independently represent a hydrogen atom and a monovalent hydrocarbon group with 1 to 40 carbon atoms Or a monovalent heterocyclic group with 1-40 carbon atoms, and -C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -Si(-)(-)- to form The -CH(-)- of the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N(-)-, and the -CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may also be substituted with- N=, -CH ₂ -constituting the monovalent hydrocarbon group and the monovalent heterocyclic group can also be substituted with -O-, -S-, -S(O) ₂ -or -CO- to form the monovalent hydrocarbon group and The hydrogen atom of the monovalent heterocyclic group can also be substituted with a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M or MM; Q ¹ and Q ² each independently represent a divalent hydrocarbon group or a divalent hetero Cyclic group, -C(-)(-)- constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted with -Si(-)(-)-, constituting the divalent hydrocarbon group and the divalent heterocyclic ring -CH(-)- of the group can also be substituted with -N(-)-, -CH= constituting the divalent hydrocarbon group and the divalent heterocyclic group can also be substituted with -N=, constituting the divalent hydrocarbon group and the The -CH ₂ -of the divalent heterocyclic group can also be substituted with -O-, -S-, -S(O) ₂ -or -CO-, and the hydrogen atoms constituting the divalent hydrocarbon group and the divalent heterocyclic group can also be substituted It can be substituted with a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, or MM; when there are multiple Z ¹ to Z ⁴ , M and MM, these may be the same or different from each other] [2] The coloring composition according to [1], which contains a resin. [3] The coloring composition according to any one of [1] to [2], which contains a polymerizable compound and a polymerization initiator. [4] A color filter formed of the coloring composition as described in any one of [1] to [3]. [5] A display device including the color filter as described in [4]. [6] A compound represented by formula (I).

[式（I）中， R¹ ～R⁵ 分別獨立地表示氫原子、鹵素原子、氰基、硝基、-SO₃ M、-CO₂ M、MM、碳數1～40的一價烴基或碳數1～40的一價雜環基， 構成該一價烴基及該一價雜環基的-C(-)(-)-亦可取代為-Si(-)(-)-， 構成該一價烴基及該一價雜環基的-CH(-)-亦可取代為-N(-)-， 構成該一價烴基及該一價雜環基的-CH=亦可取代為-N=， 構成該一價烴基及該一價雜環基的-CH₂ -亦可取代為-O-、-S-、-S(O)₂ -或-CO-， 構成該一價烴基及該一價雜環基的氫原子亦可取代為鹵素原子、氰基、硝基、-SO₃ M、-CO₂ M或MM； R¹ 及R² 、R² 及R³ 、以及R³ 及R⁴ 可分別彼此鍵結而形成環； M表示氫原子、鹼金屬原子、可具有配位體的金屬原子或N(Z¹ )(Z² )(Z³ )(Z⁴ )； MM表示鹼金屬原子、可具有配位體的金屬原子或N(Z¹ )(Z² )(Z³ )(Z⁴ )； Z¹ ～Z⁴ 分別獨立地表示氫原子、碳數1～40的一價烴基或碳數1～40的一價雜環基， 構成該一價烴基及該一價雜環基的-C(-)(-)-亦可取代為-Si(-)(-)-， 構成該一價烴基及該一價雜環基的-CH(-)-亦可取代為-N(-)-， 構成該一價烴基及該一價雜環基的-CH=亦可取代為-N=， 構成該一價烴基及該一價雜環基的-CH₂ -亦可取代為-O-、-S-、-S(O)₂ -或-CO-， 構成該一價烴基及該一價雜環基的氫原子亦可取代為鹵素原子、氰基、硝基、-SO₃ M、-CO₂ M或MM； Q¹ 及Q² 分別獨立地表示二價烴基或二價雜環基， 構成該二價烴基及該二價雜環基的-C(-)(-)-亦可取代為-Si(-)(-)-， 構成該二價烴基及該二價雜環基的-CH(-)-亦可取代為-N(-)-， 構成該二價烴基及該二價雜環基的-CH=亦可取代為-N=， 構成該二價烴基及該二價雜環基的-CH₂ -亦可取代為-O-、-S-、-S(O)₂ -或-CO-， 構成該二價烴基及該二價雜環基的氫原子亦可取代為鹵素原子、氰基、硝基、-SO₃ M、-CO₂ M或MM； 於Z¹ ～Z⁴ 、M及MM分別存在多個的情況下，該些可彼此相同或不同] [發明的效果][化3]

[In formula (I), R ¹ to R ⁵ each independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, MM, a monovalent hydrocarbon group having 1 to 40 carbons, or A monovalent heterocyclic group having 1 to 40 carbon atoms, -C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -Si(-)(-)-, constituting the The -CH(-)- of the monovalent hydrocarbon group and the monovalent heterocyclic group can also be substituted with -N(-)-, and the -CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group can also be substituted with -N =, -CH ₂ -constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -O-, -S-, -S(O) ₂ -or -CO- to form the monovalent hydrocarbon group and the The hydrogen atom of the monovalent heterocyclic group can also be substituted with a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M or MM; R ¹ and R ² , R ² and R ³ , and R ³ and R ⁴ can be bonded to each other to form a ring; M represents a hydrogen atom, an alkali metal atom, a metal atom that may have a ligand, or N(Z ¹ )(Z ² )(Z ³ )(Z ⁴ ); MM represents an alkali metal Atom, a metal atom that may have a ligand, or N(Z ¹ )(Z ² )(Z ³ )(Z ⁴ ); Z ¹ to Z ⁴ each independently represent a hydrogen atom and a monovalent hydrocarbon group with 1 to 40 carbon atoms Or a monovalent heterocyclic group with 1-40 carbon atoms, and -C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -Si(-)(-)- to form The -CH(-)- of the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N(-)-, and the -CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may also be substituted with- N=, -CH ₂ -constituting the monovalent hydrocarbon group and the monovalent heterocyclic group can also be substituted with -O-, -S-, -S(O) ₂ -or -CO- to form the monovalent hydrocarbon group and The hydrogen atom of the monovalent heterocyclic group can also be substituted with a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M or MM; Q ¹ and Q ² each independently represent a divalent hydrocarbon group or a divalent hetero Cyclic group, -C(-)(-)- constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted with -Si(-)(-)-, constituting the divalent hydrocarbon group and the divalent heterocyclic ring -CH(-)- of the group can also be substituted with -N(-)-, -CH= constituting the divalent hydrocarbon group and the divalent heterocyclic group can also be substituted with -N=, constituting the divalent hydrocarbon group and the The -CH ₂ -of the divalent heterocyclic group can also be substituted with -O-, -S-, -S(O) ₂ -or -CO-, and the hydrogen atoms constituting the divalent hydrocarbon group and the divalent heterocyclic group can also be substituted It can be substituted with a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, or MM; when there are multiple Z ¹ to Z ⁴ , M and MM, these may be the same or different from each other] [Effects of the invention]

According to the present invention, there is provided a coloring composition and compound that can be used in the formation of a color filter with a stronger color than a coloring composition containing C.I. Pigment Yellow 138.

[Coloring composition] The coloring composition of the present invention includes a compound represented by formula (I) (hereinafter, sometimes referred to as compound (I)) and a solvent (hereinafter, sometimes referred to as solvent (E)).

[式（I）中， R¹ ～R⁵ 分別獨立地表示氫原子、鹵素原子、氰基、硝基、-SO₃ M、-CO₂ M、MM、碳數1～40的一價烴基或碳數1～40的一價雜環基， 構成該一價烴基及該一價雜環基的-C(-)(-)-亦可取代為-Si(-)(-)-， 構成該一價烴基及該一價雜環基的-CH(-)-亦可取代為-N(-)-， 構成該一價烴基及該一價雜環基的-CH=亦可取代為-N=， 構成該一價烴基及該一價雜環基的-CH₂ -亦可取代為-O-、-S-、-S(O)₂ -或-CO-， 構成該一價烴基及該一價雜環基的氫原子亦可取代為鹵素原子、氰基、硝基、-SO₃ M、-CO₂ M或MM； R¹ 及R² 、R² 及R³ 、以及R³ 及R⁴ 可分別彼此鍵結而形成環； M表示氫原子、鹼金屬原子、可具有配位體的金屬原子或N(Z¹ )(Z² )(Z³ )(Z⁴ )； MM表示鹼金屬原子、可具有配位體的金屬原子或N(Z¹ )(Z² )(Z³ )(Z⁴ )； Z¹ ～Z⁴ 分別獨立地表示氫原子、碳數1～40的一價烴基或碳數1～40的一價雜環基， 構成該一價烴基及該一價雜環基的-C(-)(-)-亦可取代為-Si(-)(-)-， 構成該一價烴基及該一價雜環基的-CH(-)-亦可取代為-N(-)-， 構成該一價烴基及該一價雜環基的-CH=亦可取代為-N=， 構成該一價烴基及該一價雜環基的-CH₂ -亦可取代為-O-、-S-、-S(O)₂ -或-CO-， 構成該一價烴基及該一價雜環基的氫原子亦可取代為鹵素原子、氰基、硝基、-SO₃ M、-CO₂ M或MM； Q¹ 及Q² 分別獨立地表示二價烴基或二價雜環基， 構成該二價烴基及該二價雜環基的-C(-)(-)-亦可取代為-Si(-)(-)-， 構成該二價烴基及該二價雜環基的-CH(-)-亦可取代為-N(-)-， 構成該二價烴基及該二價雜環基的-CH=亦可取代為-N=， 構成該二價烴基及該二價雜環基的-CH₂ -亦可取代為-O-、-S-、-S(O)₂ -或-CO-， 構成該二價烴基及該二價雜環基的氫原子亦可取代為鹵素原子、氰基、硝基、-SO₃ M、-CO₂ M或MM； 於Z¹ ～Z⁴ 、M及MM分別存在多個的情況下，該些可彼此相同或不同][化4]

[In formula (I), R ¹ to R ⁵ each independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, MM, a monovalent hydrocarbon group having 1 to 40 carbons, or A monovalent heterocyclic group having 1 to 40 carbon atoms, -C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -Si(-)(-)-, constituting the The -CH(-)- of the monovalent hydrocarbon group and the monovalent heterocyclic group can also be substituted with -N(-)-, and the -CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group can also be substituted with -N =, -CH ₂ -constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -O-, -S-, -S(O) ₂ -or -CO- to form the monovalent hydrocarbon group and the The hydrogen atom of the monovalent heterocyclic group can also be substituted with a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M or MM; R ¹ and R ² , R ² and R ³ , and R ³ and R ⁴ can be bonded to each other to form a ring; M represents a hydrogen atom, an alkali metal atom, a metal atom that may have a ligand, or N(Z ¹ )(Z ² )(Z ³ )(Z ⁴ ); MM represents an alkali metal Atom, a metal atom that may have a ligand, or N(Z ¹ )(Z ² )(Z ³ )(Z ⁴ ); Z ¹ to Z ⁴ each independently represent a hydrogen atom and a monovalent hydrocarbon group with 1 to 40 carbon atoms Or a monovalent heterocyclic group with 1-40 carbon atoms, and -C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -Si(-)(-)- to form The -CH(-)- of the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N(-)-, and the -CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may also be substituted with- N=, -CH ₂ -constituting the monovalent hydrocarbon group and the monovalent heterocyclic group can also be substituted with -O-, -S-, -S(O) ₂ -or -CO- to form the monovalent hydrocarbon group and The hydrogen atom of the monovalent heterocyclic group can also be substituted with a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M or MM; Q ¹ and Q ² each independently represent a divalent hydrocarbon group or a divalent hetero Cyclic group, -C(-)(-)- constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted with -Si(-)(-)-, constituting the divalent hydrocarbon group and the divalent heterocyclic ring -CH(-)- of the group can also be substituted with -N(-)-, -CH= constituting the divalent hydrocarbon group and the divalent heterocyclic group can also be substituted with -N=, constituting the divalent hydrocarbon group and the The -CH ₂ -of the divalent heterocyclic group can also be substituted with -O-, -S-, -S(O) ₂ -or -CO-, and the hydrogen atoms constituting the divalent hydrocarbon group and the divalent heterocyclic group can also be substituted It can be substituted with a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, or MM; when there are multiple Z ¹ to Z ⁴ , M and MM, these may be the same or different from each other]

Compound (I) also includes its tautomers or these salts. Compound (I) can be used as a coloring agent. The coloring composition of the present invention may contain one or two or more compounds (I). The coloring composition of the present invention may also include a resin (hereinafter, it may be referred to as resin (B)). The colored composition of the present invention may also contain a polymerizable compound (hereinafter, it may be referred to as a polymerizable compound (C)). The colored composition of the present invention may also contain a polymerization initiator (hereinafter, it may be referred to as a polymerization initiator (D)). The colored composition of the present invention may also contain a polymerization initiation aid (hereinafter, it may be referred to as a polymerization initiation aid (D1)). The coloring composition of the present invention may also contain a coloring agent other than the compound (I) (hereinafter, sometimes referred to as coloring agent (A1); and, hereinafter, compound (I) and coloring agent (A1) may be collectively referred to as " Colorant (A)"). The coloring agent (A1) may contain one or two or more coloring agents. The coloring agent (A1) preferably contains one or more selected from a yellow coloring agent, an orange coloring agent, a red coloring agent, and a green coloring agent. The colored composition of the present invention may also include a leveling agent (hereinafter, it may be referred to as a leveling agent (F)). The colored composition of the present invention may also contain an antioxidant (hereinafter, it may be referred to as antioxidant (G)).

[Compound (I)] Hereinafter, the partial structure of compound (I) is listed to more specifically explain the present invention. In each partial structure, even if only the substituent bonded to the ring structure is bonded at any position of the ring structure, the following examples are shown Here, it also includes the aspect in which the substitution is based on all parts of the ring structure separately bonded. One or two or more substituents may be bonded to the ring structure. When two or more substituents are bonded to the ring structure, the substituents may be the same or different.

As a halogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc. are mentioned, A fluorine atom, a chlorine atom, and a bromine atom are preferable.

The carbon number of the hydrocarbon group represented by R ¹ to R ⁵ and Z ¹ to Z ⁴ is 1 to 40, preferably 1 to 30, more preferably 1 to 20, still more preferably 1 to 18, particularly preferably 1 to 12 . The monovalent hydrocarbon group having 1 to 40 carbon atoms represented by R ¹ to R ⁵ and Z ¹ to Z ⁴ may be an aliphatic hydrocarbon group and an aromatic hydrocarbon group, and the aliphatic hydrocarbon group may be saturated or unsaturated, or chain or Cyclic (alicyclic hydrocarbon group).

Examples of the saturated or unsaturated chain hydrocarbon group represented by R ¹ to R ⁵ and Z ¹ to Z ⁴ include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, and nonyl Alkyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, Eicosyl, icosyl, behenyl, tricosyl, tetracosyl, pentadecyl, hexadecyl, heptadecyl, twenty-eight Alkyl, nonadecyl, triacontyl, triadecyl, tridodecyl, triacontanyl, tritetradecyl, tripentadecyl, trihexadecyl, Straight-chain alkyl groups such as thirty-heptadecyl, thirty-octadecyl, thirty-nonadecyl, and forty decyl; isopropyl, isobutyl, second butyl, tertiary butyl, 2-ethyl Butyl, 3,3-dimethylbutyl, 1,1,3,3-tetramethylbutyl, 1-methylbutyl, 1-ethylpropyl, 3-methylbutyl, new Pentyl, 1,1-dimethylpropyl, 2-methylpentyl, 3-ethylpentyl, 1,3-dimethylbutyl, 2-propylpentyl, 1-ethyl-1 , 2-Dimethylpropyl, 1-methylpentyl, 4-methylpentyl, 4-methylhexyl, 5-methylhexyl, 2-ethylhexyl, 1-methylhexyl, 1-ethyl 1-propylpentyl, 1-propylbutyl, 3-ethylheptyl, 2,2-dimethylheptyl, 1-methylheptyl, 1-ethylhexyl, 1-propylpentyl, 1- Methyloctyl, 1-ethylheptyl, 1-propylhexyl, 1-butylpentyl, 1-methylnonyl, 1-ethyloctyl, 1-propylheptyl and 1-butyl Branched chain alkyl groups such as hexyl; vinyl (ethenyl) (vinyl), propenyl (for example, 1-propenyl, 2-propenyl (allyl)), 1-methylvinyl, butylene Alkenyl (for example, 1-butenyl, 2-butenyl, 3-butenyl), 3-methyl-1-butenyl, 1,3-butadienyl, 1-(2-propenyl Base) vinyl, 1-(1-methylvinyl) vinyl, 1,2-dimethyl-1-propenyl, pentenyl (for example, 1-pentenyl, 2-pentenyl, 3 -Pentenyl, 4-pentenyl), 1-(1,1-dimethylethyl) vinyl, 1,3-dimethyl-1-butenyl, hexenyl (for example, 1- Hexenyl, 5-hexenyl), heptenyl (for example, 1-heptenyl, 6-heptenyl), octenyl (for example, 1-octenyl, 7-octenyl), non Alkenyl (for example, 1-nonenyl, 8-nonenyl), decenyl (for example, 1-decenyl, 9-decenyl), undecenyl, dodecenyl, ten Tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, octadecenyl, nonadecenyl, eicosenyl, 1,1 -Dimethyl-2-propenyl, 1-ethyl-2-propenyl and 1-methyl-1-butenyl and other alkenyl groups; ethynyl, propynyl (for example, 1-propynyl, 2 -Propynyl), octynyl (for example, 1-octynyl, 7-octynyl), butynyl, pentynyl, hexynyl, heptynyl, Nonynyl, decynyl, undecynyl, dodecynyl, tridecynyl, tetradecynyl, pentadecynyl, hexadecynyl, heptadecynyl, Alkynyl groups such as octadecynyl, nonadenosynyl and eicosynyl. The carbon number of the saturated or unsaturated chain hydrocarbon group is preferably 1-30, more preferably 1-20, still more preferably 1-18, and particularly preferably 1-12. Among them, particularly preferred is a linear or branched chain alkyl group having 1 to 12 carbon atoms.

Examples of the saturated or unsaturated alicyclic hydrocarbon groups represented by R ¹ to R ⁵ and Z ¹ to Z ⁴ include cyclopropyl, 1-methylcyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, Cycloheptyl, 1-methylcyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 1,2-dimethylcyclohexyl, 1,3-dimethylcyclohexyl Hexyl, 1,4-dimethylcyclohexyl, 2,3-dimethylcyclohexyl, 2,4-dimethylcyclohexyl, 2,5-dimethylcyclohexyl, 2,6-dimethylcyclohexyl Hexyl, 3,4-dimethylcyclohexyl, 3,5-dimethylcyclohexyl, 2,2-dimethylcyclohexyl, 3,3-dimethylcyclohexyl, 4,4-dimethylcyclohexyl Hexyl, cyclooctyl, 2,4,6-trimethylcyclohexyl, 2,2,6,6-tetramethylcyclohexyl, 3,3,5,5-tetramethylcyclohexyl, 4-pentyl Cyclohexyl, 4-octylcyclohexyl and 4-cyclohexylcyclohexyl and other cycloalkyl groups; cyclohexenyl (for example, cyclohex-1-en-1-yl, cyclohex-2-en-1-yl, Cyclohex-3-en-1-yl), cycloheptenyl and cyclooctenyl and other cycloalkenyl groups; norbornyl, norbornenyl, adamantyl and bicyclo[2.2.2]octyl and other saturated or Unsaturated polycyclic hydrocarbon group, etc. The carbon number of the saturated or unsaturated alicyclic hydrocarbon group is preferably 3-30, more preferably 3-20, still more preferably 3-18, and particularly preferably 3-12. Among them, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and adamantyl are particularly preferred.

Examples of the aromatic hydrocarbon groups represented by R ¹ to R ⁵ and Z ¹ to Z ⁴ include phenyl, o-tolyl, m-tolyl, p-tolyl, 2-ethylphenyl, and 3-ethylphenyl , 4-ethylphenyl, 2,3-dimethylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 3, 4-Dimethylphenyl, 3,5-Dimethylphenyl, 4-vinylphenyl, o-isopropylphenyl, m-isopropylphenyl, p-isopropylphenyl, o-tert-butyl Phenyl, m-tertiary butylphenyl, p-tertiary butylphenyl, 3,5-di(tertiary butyl)phenyl, 3,5-di(tertiary butyl)-4-methyl Phenyl, 4-butylphenyl, 4-pentylphenyl, 2,6-bis(1-methylethyl)phenyl, 2,4,6-tris(1-methylethyl)phenyl , 4-cyclohexylphenyl, 2,4,6-trimethylphenyl, 4-octylphenyl, 4-(1,1,3,3-tetramethylbutyl)phenyl, 1-naphthalene Base, 2-naphthyl, 6-methyl-2-naphthyl, 5,6,7,8-tetrahydro-1-naphthyl, 5,6,7,8-tetrahydro-2-naphthyl, fluorene Aromatic hydrocarbon groups such as phenyl group, phenanthryl group, anthryl group, 2-dodecylphenyl group, 3-dodecylphenyl group, 4-dodecylphenyl group, perylene group, phenanthryl group, and pyrenyl group. The carbon number of the aromatic hydrocarbon group is preferably 6-30, more preferably 6-20, still more preferably 6-18, and particularly preferably 6-12.

The hydrocarbon group represented by R ¹ to R ⁵ and Z ¹ to Z ⁴ may be a combination of the aforementioned hydrocarbon groups (for example, an aromatic hydrocarbon group, and at least one of a chain hydrocarbon group and an alicyclic hydrocarbon group). Examples include: benzyl, (2-methylphenyl)methyl, (3-methylphenyl)methyl, (4-methylphenyl)methyl, (2-ethylphenyl)methyl, (3-Ethylphenyl)methyl, (4-ethylphenyl)methyl, (2-(tert-butyl)phenyl)methyl, (3-(tert-butyl)phenyl)methyl Group, (4-(tert-butyl)phenyl)methyl, (3,5-dimethylphenyl)methyl, 1-phenylethyl, 1,1-diphenylethyl, styrene Group, 1-methyl-1-phenylethyl, (1-naphthyl)methyl and (2-naphthyl)methyl and other aralkyl groups; 1-phenylvinyl, 2-phenylvinyl ( 2-phenyl ethenyl) (phenyl vinyl), 2,2-diphenyl vinyl, 2-phenyl-2-(1-naphthyl) vinyl and other aryl alkenyl groups; phenyl acetylene Aryl alkynyl groups such as biphenyl and triphenyl groups; phenyl groups with more than one phenyl group bonded thereto; cyclohexylmethylphenyl, benzylphenyl, (dimethyl(phenyl)methyl) ) Phenyl and so on. The carbon number of these is preferably 4-30, more preferably 4-20, still more preferably 4-18, particularly preferably 4-12. The lower limit of these ranges is preferably 7. Regarding the groups represented by R ¹ to R ⁵ and Z ¹ to Z ⁴ , as a group formed by combining the above-listed hydrocarbon groups (for example, a chain hydrocarbon group and an alicyclic hydrocarbon group), for example, cyclopropylmethyl Cyclopropylethyl, cyclobutylmethyl, cyclobutylethyl, cyclopentylmethyl, cyclopentylethyl, cyclohexylmethyl, (2-methylcyclohexyl)methyl, cyclohexylethyl , Adamantyl methyl and other alkyl groups bonded with more than one alicyclic hydrocarbon group. The carbon number of these is preferably 4-30, more preferably 4-20, still more preferably 4-18, particularly preferably 4-12.

The monovalent heterocyclic group having 1 to 40 carbon atoms represented by R ¹ to R ⁵ and Z ¹ to Z ⁴ means a group containing a hetero atom as a constituent element of the ring. The monovalent heterocyclic group having 1 to 40 carbon atoms may be monocyclic or polycyclic. As a hetero atom, a nitrogen atom, an oxygen atom, a sulfur atom, etc. are mentioned. The number of carbon atoms of the heterocyclic group is preferably 3-30, more preferably 3-20, still more preferably 3-18, and particularly preferably 3-12.

As the heterocyclic ring containing a nitrogen atom, one may cite: Monocyclic saturated heterocycles such as aziridine, azetidine, pyrrolidine, piperidine and piperazine; Pyrrole, 1-methylpyrrole, 2,5-dimethylpyrrole and other pyrrole, pyrazole, 1-methylpyrazole, 2-methylpyrazole, 3-methylpyrazole, 4-methylpyrazole, Five-membered ring system unsaturated heterocycles such as pyrazole, imidazole, 1,2,3-triazole and 1,2,4-triazole such as 5-methylpyrazole; Unsaturated heterocycles of six-membered ring systems such as pyrimidines such as pyridine, pyridazine, pyrimidine and 6-methylpyrimidine, pyrazine and 1,3,5-triazine; Indazole, indoline, isoindoline, indole, indolizine, benzimidazole, quinoline, isoquinoline, 5,6,7,8-tetrahydro(3-methyl)quine Condensed bicyclic heterocycles such as oxaline, 3-methylquinoxaline, quinoxaline, quinazoline, cinnoline, phthalazine, naphthyridine, purine, pteridine, benzopyrazole, benzopiperidine, etc.; Carbazole, acridine and phenazine condensed tricyclic heterocycles, etc.

As a heterocyclic ring containing an oxygen atom, one may cite: Oxetane, oxetane, tetrahydrofuran, tetrahydropyran, 1,3-dioxane and 1,4-dioxane, 1-cyclopentyldioxolane, 2-cyclopentane Monocyclic saturated heterocycles such as dioxolane; 1,4-dioxaspiro[4.5]decane, 1,4-dioxaspiro[4.5]nonane, 1,4-dioxaspiro[4.4]nonane and other bicyclic saturated heterocycles ring; Lactone heterocycles such as α-hydantoin, β-propiolactone, γ-butyrolactone, γ-valerolactone and δ-valerolactone; Five-membered ring system unsaturated heterocycles such as furan, 2,3-dimethylfuran, 2,5-dimethylfuran, etc.; 6-membered ring system unsaturated heterocycles such as 2H-pyran and 4H-pyran; Benzofurans such as 1-benzofuran, benzopyran, 4-methylbenzopyran, benzodioxole, 1,3-benzodioxole, Condensed bicyclic heterocycles such as benzodioxane, chroman and isochroman; Condensed tricyclic heterocycles such as xanthenes and dibenzofurans.

As a heterocyclic ring containing a sulfur atom, one may cite: Dithiolane and other five-membered ring system saturated heterocyclic rings; Six-membered saturated heterocycles such as thiane, 1,3-dithiane and 2-methyl-1,3-dithiane; Thiophene, 3-methylthiophene, 2-carboxythiophene and other thiophenes, 2H-thiopyran, 4H-thiopyran and other thiopyrans, chroman thiopyran and other five-membered ring system unsaturated heterocycles and six Member ring system unsaturated heterocyclic ring; Condensed bicyclic heterocycles such as benzothiopyrans and benzothiophenes, etc.; Thianthracene, dibenzothiophene and other condensed tricyclic heterocycles, etc.

As a heterocyclic ring containing a nitrogen atom and an oxygen atom, one may cite: Morpholine, 2-pyrrolidone, 1-methyl-2-pyrrolidone, 2-methyl-2-pyrrolidone, 2-piperidone, 1-methyl-2-piperidone and 2- Monocyclic saturated heterocycles such as methyl-2-piperidone; Oxazoles such as oxazole, 4-methyloxazole, 2-methylisoxazole, 3-methylisoxazole, 4-methylisoxazole, 5-methylisoxazole and other single Unsaturated heterocyclic ring system; Condensed bicyclic heterocycles such as benzoxazole, benzisoxazole, benzoxazine, benzodioxane, and benzimidazoline; Phenoxazine (phenoxazine) and other condensed tricyclic heterocycles, etc.

As a heterocyclic ring containing a nitrogen atom and a sulfur atom, one may cite: Thiazole, 2-methylthiazole, 3-methylthiazole, 4-methylthiazole, 5-methylthiazole, 2,4-dimethylthiazole and other monocyclic heterocycles; Condensed bicyclic heterocycles such as benzothiazole; Phthiazine and other condensed tricyclic heterocycles, etc.

In addition, the bonding position of the heterocyclic group is a part from which any hydrogen atom contained in each heterocyclic ring is removed.

The heterocyclic group may be a group formed by combining the heterocyclic ring listed above and the hydrocarbon group listed above, and examples thereof include tetrahydrofurylmethyl.

Furthermore, the heterocyclic group may be represented by the following formula. ※Indicating bonding key.

[化5]

-C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -Si(-)(-)-, and-constituting the monovalent hydrocarbon group and the monovalent heterocyclic group CH(-)- can also be substituted with -N(-)-, -CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group can also be substituted with -N=, constituting the monovalent hydrocarbon group and the monovalent hetero The -CH ₂ -of the cyclic group can also be substituted with -O-, -S-, -S(O) ₂ -or -CO-, and the hydrogen atoms constituting the monovalent hydrocarbon group and the monovalent heterocyclic group can also be substituted with Halogen atom, cyano group, nitro group, -SO ₃ M, -CO ₂ M or MM. Examples of such groups include the following groups.

Examples include: trichloromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, 2,2-dibromoethyl, 2,2,3,3-tetrafluoropropyl, 2- Ethoxyethyl, 2-butoxyethyl, 2-nitropropyl, diethylaminoethyl, (4-methoxyphenyl)methyl, (2-methoxyphenyl) Methyl, (3-methoxyphenyl)methyl, (4-nitrophenyl)methyl, (2,4-dichlorophenyl)methyl, (4-fluorophenyl)methyl, ( 3,5-difluorophenyl)methyl, 2,2,2-trifluoro-1-trifluoromethyl-1-phenylethyl, (phenoxy)(phenyl)methyl, (benzyl) Oxy)(phenyl)methyl, pyrrolylmethyl, pyrrolylethyl, (4-aminophenyl)methyl, (4-cyanophenyl)methyl, 2-hydroxy-1-methyl -1-phenylethyl, 2-chloro-1-methyl-1-phenylethyl; -CH ₂ CH ₂ OCH ₂ CH ₃ , -CH ₂ CH ₂ O(CH ₂ ) ₃ CH ₃ , -( CH ₂ CH ₂ O) ₂ CH ₂ CH ₃ , -(CH ₂ CH ₂ O) ₃ CH ₂ CH ₃ , -(CH ₂ CH ₂ O) ₄ CH ₂ CH ₃ , -(CH ₂ CH ₂ O) ₅ CH ₂ CH ₃ , -(CH ₂ CH ₂ O) ₆ CH ₂ CH ₃ , -(CH ₂ CH ₂ O) ₇ CH ₂ CH ₃ , -(CH ₂ CH ₂ O) ₈ CH ₂ CH ₃ , -(CH ₂ CH ₂ O) ₉ CH ₂ CH ₃ , -(CH ₂ CH ₂ O) ₁₀ CH ₂ CH ₃ , -(CH ₂ CH ₂ O) ₁₁ CH ₂ CH ₃ , -(CH ₂ CH ₂ O) ₁₂ CH ₂ CH ₃ , -(CH ₂ CH ₂ O) ₁₃ CH ₃ , -CH ₂ CH ₂ OH, -(CH ₂ CH ₂ O) ₂ H, -(CH ₂ CH ₂ O) ₃ H, -(CH ₂ CH ₂ O ) ₄ H, -(CH ₂ CH ₂ O) ₅ H, -(CH ₂ CH ₂ O) ₆ H, -(CH ₂ CH ₂ O) ₇ H, -(CH ₂ CH ₂ O) ₈ H, -( CH ₂ CH ₂ O) ₉ H, -(CH ₂ CH ₂ O) ₁₀ H, -(CH ₂ CH ₂ O) ₁₁ H, -(CH ₂ CH ₂ O) ₁₂ H, -(CH ₂ CH ₂ O) ₁₃ H, -CH ₂ CH ₂ OCH ₃ , -(CH ₂ CH ₂ O) ₂ CH ₃ , -(CH ₂ CH ₂ O) ₃ CH ₃ , -(CH ₂ CH ₂ O) ₄ CH ₃ ,- (CH ₂ CH ₂ O) ₅ CH ₃ , -(CH ₂ CH ₂ O) ₆ CH ₃ , -(CH ₂ CH ₂ O) ₇ CH ₃ , -(CH ₂ CH ₂ O) ₈ CH ₃ , -(CH ₂ CH ₂ O) ₉ CH ₃ , -(CH ₂ CH ₂ O) ₁₀ CH ₃ , -(CH ₂ CH ₂ O) ₁₁ CH ₃ , -(CH ₂ CH ₂ O) ₁₂ CH ₃ , -(CH ₂ CH ₂ O) ₁₃ CH _3, etc. The monovalent hydrocarbon group or monovalent heterocyclic group -CH ₂ -is substituted with -O- and other substituted alkyl groups (hereinafter referred to as group The case of the base of group A).

Examples include: 4-bromophenyl, 4-nitrophenyl, 4-methoxyphenyl, 2,4-dichlorophenyl, pentafluorophenyl, 2-aminophenyl, 2-methyl 4-chlorophenyl group, 4-hydroxy-1-naphthyl group, 4,5,8-trichloro-2-naphthyl group, anthraquinone group, 2-aminoanthraquinone group and other substituted aryl groups ( Hereinafter, these may be referred to as the basis of group B).

For example, examples include formyl, acetyl, propyl, butyryl, 2,2-dimethyl propyl, pentam, hexyl, 2-ethylhexyl, heptyl, Octyl, nonyl, decyl, undecyl, dodecyl, benzyl, benzyl,

及鍵結有所述群組A～群組B的基或者所述一價烴基或一價雜環基的羰基等，[化6]

And the carbonyl group to which the group A to the group B or the monovalent hydrocarbon group or the monovalent heterocyclic group are bonded,

Preferably, it is a carbonyl group to which a hydrocarbon group having 1 to 30 carbon atoms, the group A to group B or the monovalent hydrocarbon group or the monovalent heterocyclic group are bonded, More preferably, it is a carbonyl group to which a hydrocarbon group having 1 to 20 carbon atoms, a group of the group A to group B or the monovalent hydrocarbon group or a monovalent heterocyclic group are bonded, and More preferably, it is a carbonyl group to which a hydrocarbon group having 1 to 18 carbon atoms, a group of the group A to group B or the monovalent hydrocarbon group or the monovalent heterocyclic group are bonded, Particularly preferred is a carbonyl group to which a hydrocarbon group having 1 to 12 carbon atoms, the group A to group B or the monovalent hydrocarbon group or the monovalent heterocyclic group are bonded. ※Indicating bonding key.

Examples include: methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, tertiary butoxycarbonyl, butoxycarbonyl, pentyloxycarbonyl, hexyloxycarbonyl, (2-ethylhexyl) Oxycarbonyl, heptyloxycarbonyl, octyloxycarbonyl, nonyloxycarbonyl, decyloxycarbonyl, undecyloxycarbonyl, dodecyloxycarbonyl, phenyloxycarbonyl, Eicosyloxycarbonyl,

及鍵結有所述群組A～群組B的基或者所述一價烴基或一價雜環基的氧基羰基等，[化7]

And the oxycarbonyl group to which the group A to the group B or the monovalent hydrocarbon group or the monovalent heterocyclic group are bonded,

Preferably, it is an oxycarbonyl group to which a hydrocarbon group having 1 to 30 carbon atoms, a group of the group A to group B or the monovalent hydrocarbon group or the monovalent heterocyclic group are bonded, More preferably, it is an oxycarbonyl group to which a hydrocarbon group having 1 to 20 carbon atoms, the group A to group B or the monovalent hydrocarbon group or the monovalent heterocyclic group are bonded, and It is further preferably an oxycarbonyl group to which a hydrocarbon group having 1 to 18 carbon atoms, the group A to group B or the monovalent hydrocarbon group or the monovalent heterocyclic group are bonded, Particularly preferred is an oxycarbonyl group to which a hydrocarbon group having 1 to 12 carbon atoms, the group A to group B or the monovalent hydrocarbon group or the monovalent heterocyclic group are bonded. ※Indicating bonding key.

For example, examples include: formyloxy, acetoxy, propanoyloxy, butanoyloxy, (2,2-dimethyl propanoyl)oxy, pentanoyloxy, hexyloxy Oxy, (2-ethylhexyl)oxy, heptanoyloxy, octanoyloxy, nonanoyloxy, decanoyloxy, undecanoyloxy, dodecanoyloxy Oxy, icosanoyloxy, benzyloxy, vinylcarbonyloxy, (2-propenyl)carbonyloxy, (1-methylvinyl)carbonyloxy, And the carbonyloxy group to which the group A to the group B or the monovalent hydrocarbon group or the monovalent heterocyclic group are bonded,

Preferably, it is a carbonyloxy group to which a hydrocarbon group having 1 to 30 carbon atoms, a group of the group A to group B or the monovalent hydrocarbon group or the monovalent heterocyclic group are bonded, More preferably, it is a carbonyloxy group to which a hydrocarbon group having 1 to 20 carbon atoms, a group of the group A to group B or the monovalent hydrocarbon group or the monovalent heterocyclic group are bonded, and More preferably, it is a carbonyloxy group to which a hydrocarbon group having 1 to 18 carbon atoms, a group of the group A to group B or the monovalent hydrocarbon group or the monovalent heterocyclic group are bonded, Particularly preferred is a carbonyloxy group to which a hydrocarbon group having 1 to 12 carbon atoms, the group A to group B or the monovalent hydrocarbon group or the monovalent heterocyclic group are bonded.

For example, examples include: hydroxyl; methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, second butoxy, tertiary butoxy, pentyloxy, Neopentyloxy, 1-ethyl-1,2-dimethylpropoxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy Oxy, dodecyloxy, (2-ethylhexyl)oxy, stearyloxy, eicosyloxy, 1-phenylethoxy, 1-methyl-1-phenyl Ethoxy, phenyloxy, benzyloxy, 2,3-dimethylphenyloxy, 2,4-dimethylphenyloxy, 2,5-dimethylphenyloxy, 2,6-Dimethylphenyloxy, 3,4-dimethylphenyloxy, 3,5-dimethylphenyloxy, 2,3-dicyanophenyloxy, 2, 4-dicyanophenyloxy, 2,5-dicyanophenyloxy, 2,6-dicyanophenyloxy, 3,4-dicyanophenyloxy, 3,5- Dicyanophenyloxy, 4-methoxyphenyloxy, 2-methoxyphenyloxy, 3-methoxyphenyloxy, 4-ethoxyphenyloxy, 2- Ethoxyphenyloxy, 3-ethoxyphenyloxy; Trichloromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, 2,2,3,3- Tetrafluoropropoxy, 3,3,3-trifluoro-2-trifluoromethyl-2-methylpropoxy, 2-butoxyethoxy, 2-nitropropoxy, -OCH ₂ CH ₂ OH, -O(CH ₂ CH ₂ O) ₄ H, -OCH ₂ CF ₂ CF ₂ H, -OCH ₂ CH ₂ O(CH ₂ ) ₃ CH ₃ , -OCH ₂ CH ₂ OCH ₂ CH ₃ ,- O(CH ₂ CH ₂ O) ₂ CH ₂ CH ₃ , -O(CH ₂ CH ₂ O) ₄ CH ₂ CH ₃ , -OCH ₂ CH ₂ O(CH ₂ ) ₃ CH ₃ ,

[化8]

及鍵結有所述群組A～群組B的基或者所述一價烴基或一價雜環基的氧基等，[化9]

And the oxy group to which the group A to the group B or the monovalent hydrocarbon group or the monovalent heterocyclic group are bonded,

Preferably, it is an oxy group or a hydroxyl group to which a hydrocarbon group having 1 to 30 carbon atoms, the group A to group B or the monovalent hydrocarbon group or the monovalent heterocyclic group are bonded, More preferably, a hydrocarbon group having 1 to 20 carbon atoms, a group of the group A to group B, or an oxy group or a hydroxyl group, which is preferably one of the monovalent hydrocarbon group or monovalent heterocyclic group, is bonded, More preferably, it is an oxy group or a hydroxyl group which is bonded to a hydrocarbon group having 1 to 18 carbon atoms, the group A to group B, or the monovalent hydrocarbon group or the monovalent heterocyclic group, and Particularly preferred is an oxy group or a hydroxyl group to which a hydrocarbon group having 1 to 12 carbon atoms, the group A to group B or the monovalent hydrocarbon group or the monovalent heterocyclic group are bonded. ※Indicating bonding key.

Examples include: mercapto; methylthio, ethylthio, propylthio, butylthio, tertiary butylthio, pentylthio, hexylthio, (2-ethylhexyl) Thio, heptylthio, octylthio, nonylthio, decylthio, undecylthio, dodecylthio, eicosylthio, phenylthio, ortho Tolylthio,

及將氫原子取代為所述群組A～群組B的基或所述一價烴基或一價雜環基而成的巰基等，[化10]

And a mercapto group obtained by substituting a hydrogen atom with a group of the group A to group B or the monovalent hydrocarbon group or a monovalent heterocyclic group, etc.,

It is preferably a mercapto group or a mercapto group obtained by substituting a hydrogen atom with a hydrocarbon group having 1 to 30 carbon atoms, a group of the group A to group B, or the monovalent hydrocarbon group or the monovalent heterocyclic group , More preferably, it is a mercapto group or a mercapto group obtained by substituting a hydrogen atom with a hydrocarbon group having 1 to 20 carbon atoms, the group A to group B, or the monovalent hydrocarbon group or the monovalent heterocyclic group. , More preferably, a mercapto group or a mercapto group obtained by substituting a hydrogen atom with a hydrocarbon group having 1 to 18 carbon atoms, the group A to group B, or the monovalent hydrocarbon group or the monovalent heterocyclic group , Particularly preferred is a mercapto group or a mercapto group obtained by substituting a hydrogen atom with a hydrocarbon group having 1 to 12 carbon atoms, the group A to group B, or the monovalent hydrocarbon group or the monovalent heterocyclic group . ※Indicating bonding key.

Examples include: methylsulfonyl, ethylsulfonyl, propylsulfonyl, butylsulfonyl, pentylsulfonyl, hexylsulfonyl, (2-ethylhexyl)sulfonyl , Heptylsulfonyl, octylsulfonyl, nonylsulfonyl, decylsulfonyl, undecylsulfonyl, dodecylsulfonyl, eicosylsulfonyl, benzene Sulfonyl, p-tolylsulfonyl,

及鍵結有所述群組A～群組B的基或者所述一價烴基或一價雜環基的磺醯基等，[化11]

And the sulfonyl group to which the group A to the group B or the monovalent hydrocarbon group or the monovalent heterocyclic group are bonded,

Preferably, it is a sulfonyl group to which a hydrocarbon group having 1 to 30 carbon atoms, the group A to group B or the monovalent hydrocarbon group or the monovalent heterocyclic group are bonded, More preferably, it is a sulfonyl group to which a hydrocarbon group having 1 to 20 carbon atoms, the group A to group B or the monovalent hydrocarbon group or the monovalent heterocyclic group are bonded, More preferably, it is a sulfonyl group to which a hydrocarbon group having 1 to 18 carbon atoms, a group of the group A to group B or the monovalent hydrocarbon group or the monovalent heterocyclic group are bonded, Particularly preferred is a sulfonyl group to which a hydrocarbon group having 1 to 12 carbon atoms, the group A to group B or the monovalent hydrocarbon group or the monovalent heterocyclic group are bonded. ※Indicating bonding key.

For example, examples include: sulfasulfonyl; N-methylsulfasulfonyl, N-ethylsulfasulfonyl, N-propylsulfasulfonyl, N-isopropylsulfasulfonyl, N-butyl Sulfonamide, N-isobutyl sulfasulfonyl, N-(second butyl) sulfasulfonyl, N-(tertiary butyl) sulfasulfonyl, N-pentyl sulfasulfonyl , N-(1-Ethylpropyl)sulfasulfonyl, N-hexylsulfasulfonyl, N-(2-ethylhexyl)sulfasulfonyl, N-heptylsulfasulfonyl, N-octyl Sulfonyl, N-Nonyl Sulfonyl, N-Decyl Sulfonyl, N-Undecyl Sulfonyl, N-Dodecyl Sulfonyl, N-Twenty Alkylsulfasulfonyl, N-phenylsulfasulfonyl, -SO ₂ NH(CH ₂ ) ₂ N(CH ₂ CH ₃ ) ₂ , -SO ₂ NHCH ₂ CH ₂ CH ₂ Si(OCH ₂ CH ₃ ) ₃ , and a sulfasulfonyl group formed by substituting one of the group A to group B or one of the monovalent hydrocarbon group or the monovalent heterocyclic group;

N,N-Dimethylsulfasulfonyl, N-ethyl-N-methylsulfasulfonyl, N,N-Diethylsulfasulfonyl, N-propyl-N-methylsulfasulfonyl Group, N,N-dipropylsulfamate, N-isopropyl-N-methylsulfamate, N,N-diisopropylsulfamate, N,N-diisobutyl Sulfamoyl, N,N-bis(second butyl)sulfamethonyl, N-(tertiary butyl)-N-methylsulfamethonyl, N,N-bis(tertiary butyl) Sulfamate, N-butyl-N-methylsulfasulfonyl, N,N-dibutylsulfasulfonyl, N-butyl-N-octylsulfasulfonyl, N,N-di Pentylsulfasulfonyl, N,N-bis(1-ethylpropyl)sulfasulfonyl, N-butyl-N-hexylsulfasulfonyl, N-hexyl-N-methylsulfasulfonyl , N,N-Dihexylsulfasulfonyl, N-(2-ethylhexyl)-N-methylsulfasulfonyl, N,N-bis(2-ethylhexyl)sulfasulfonyl, N, N-Diheptylsulfasulfonyl, N-octyl-N-Methylsulfasulfonyl, N,N-Dioctylsulfasulfonyl, N,N-Dinonylsulfasulfonyl, N- Decyl-N-methylsulfasulfonyl, N-undecyl-N-methylsulfasulfonyl, N-dodecyl-N-methylsulfasulfonyl, N-eicosyl -N-Methylsulfamate, N-phenyl-N-Methylsulfamate, N,N-diphenylsulfamate, and A group selected from the group A to group B, the sulfasulfonyl group formed by substituting two of the monovalent hydrocarbon group and the monovalent heterocyclic group, etc.,

Preferably, it is one selected from the group consisting of a hydrocarbon group having 1 to 30 carbons, a group of the group A to group B, a preferable one of the monovalent hydrocarbon group, and a preferable one of the monovalent heterocyclic group, or Two substituted sulfamoyl groups, -SO ₂ NH(CH ₂ ) ₂ N(CH ₂ CH ₃ ) ₂ or sulfamoyl groups, more preferably selected from hydrocarbon groups having 1 to 20 carbon atoms, A sulfonamide group formed by substituting one or two of the group A to group B, the preferable one of the monovalent hydrocarbon group, and the preferable one of the monovalent heterocyclic group, -SO ₂ NH(CH ₂ ) ₂ N(CH ₂ CH ₃ ) ₂ or a sulfamsulfonyl group, more preferably selected from a hydrocarbon group having 1 to 18 carbon atoms, groups A to B, and the monovalent hydrocarbon group The preferred one and the preferred one or two of the monovalent heterocyclic group are substituted with sulfasulfonyl, -SO ₂ NH(CH ₂ ) ₂ N(CH ₂ CH ₃ ) ₂ or The sulfamoyl group is particularly preferably selected from the group consisting of a hydrocarbon group having 1 to 12 carbons, the group A to group B, the preferred one of the monovalent hydrocarbon group, and the preferred one of the monovalent heterocyclic group Sulfonamide, -SO ₂ NH(CH ₂ ) ₂ N(CH ₂ CH ₃ ) ₂ or sulfamsulfonyl substituted by one or two of them.

For example, examples include: carboxamide; N-methylaminocarboxyl, N-ethylaminocarboxyl, N-propylaminocarboxyl, N-isopropylaminocarboxyl, N-butyl Carboxylic carboxamide, N-isobutyl carboxylic acid, N-(second butyl) carboxylic acid, N-(tertiary butyl) carboxylic acid, N-pentyl carboxylic acid , N-(1-ethylpropyl)aminomethanyl, N-hexylaminomethanyl, N-(2-ethylhexyl)aminomethanyl, N-heptylaminomethanyl, N-octyl N-Aminomethyl, N-Nonyl Aminomethyl, N-decyl Aminomethyl, N-Undecyl Aminomethyl, N-Dodecyl Aminomethyl, N-Twenty Alkylamine formyl, N-phenylamine formyl, -CONH(CH ₂ ) ₂ N(CH ₂ CH ₃ ) ₂ , -CONHCH ₂ CH ₂ CH ₂ Si(OCH ₂ CH ₃ ) ₃ , and all The group A to group B or the aminomethyl group formed by substituting one of the monovalent hydrocarbon group or the monovalent heterocyclic group, etc.;

N,N-dimethylaminoformyl, N-ethyl-N-methylaminoformyl, N,N-diethylaminoformyl, N-propyl-N-methylaminoformyl Group, N,N-dipropylaminomethanyl, N-isopropyl-N-methylaminomethanyl, N,N-diisopropylaminomethanyl, N,N-diisobutyl Carboxamide, N,N-bis(second butyl)carboxamide, N-(tertiary butyl)-N-methylcarboxamide, N,N-bis(tertiary butyl) Carboxamide, N-butyl-N-methylcarboxamide, N,N-dibutylaminocarboxyl, N-butyl-N-octylcarboxamide, N,N-di Pentylaminoformyl, N,N-bis(1-ethylpropyl)aminoformyl, N-butyl-N-hexylaminoformyl, N-hexyl-N-methylaminoformyl , N,N-dihexylaminomethanyl, N-(2-ethylhexyl)-N-methylaminomethanyl, N,N-bis(2-ethylhexyl)aminomethanyl, N, N-Diheptylaminoformyl, N-octyl-N-methylaminoformyl, N,N-dioctylaminoformyl, N,N-Dinonylaminoformyl, N- Decyl-N-methylaminomethanyl, N-undecyl-N-methylaminomethanyl, N-dodecyl-N-methylaminomethanyl, N-eicosyl -N-methylcarbamate, N-phenyl-N-methylcarbamate, N,N-diphenylcarbamate, and A group selected from the group A to group B, the amine methanoyl group formed by substituting two of the monovalent hydrocarbon group and the monovalent heterocyclic group, etc.,

Preferably, it is one selected from the group consisting of a hydrocarbon group having 1 to 30 carbons, a group of the group A to group B, a preferable one of the monovalent hydrocarbon group, and a preferable one of the monovalent heterocyclic group, or Two carbamate groups or carbamate groups formed by substitution, More preferably, it is one selected from the group consisting of a hydrocarbon group having 1 to 20 carbon atoms, the group A to group B, the preferable one of the monovalent hydrocarbon group, and the preferable one of the monovalent heterocyclic group, or Two carbamate groups or carbamate groups formed by substitution, More preferably, it is one selected from the group consisting of a hydrocarbon group having 1 to 18 carbon atoms, the group A to group B, the preferable one of the monovalent hydrocarbon group, and the preferable one of the monovalent heterocyclic group, or Two carbamate groups or carbamate groups formed by substitution, Particularly preferred is one selected from the group consisting of a hydrocarbon group having 1 to 12 carbons, the group A to group B, the preferred one of the monovalent hydrocarbon group, and the preferred one of the monovalent heterocyclic group, or Two carbamate groups or carbamate groups formed by substitution.

For example: Amino group N-methylamino, N-ethylamino, N-propylamino, N-isopropylamino, N-butylamino, N-isobutylamino, N-(second butyl Group) amino group, N-(tertiary butyl) amino group, N-pentyl amino group, N-(1-ethylpropyl) amino group, N-hexyl amino group, N-(2-ethylhexyl) ) Amino, N-heptylamino, N-octylamino, N-nonylamino, N-decylamino, N-undecylamino, N-dodecylamino, N-eicosylamino group, N-phenylamino group, and the group A to group B or the amino group formed by substituting one of the monovalent hydrocarbon group or the monovalent heterocyclic group, etc. ；

N,N-dimethylamino, N-ethyl-N-methylamino, N,N-diethylamino, N-propyl-N-methylamino, N,N-dipropyl Amino group, N-isopropyl-N-methylamino group, N,N-diisopropylamino group, N,N-diisobutylamino group, N,N-di(second butyl) Amino, N-(tertiary butyl)-N-methylamino, N,N-di(tertiary butyl)amino, N-butyl-N-methylamino, N,N-di Butylamino, N-butyl-N-octylamino, N,N-dipentylamino, N,N-bis(1-ethylpropyl)amino, N-butyl-N- Hexylamino, N-hexyl-N-methylamino, N,N-dihexylamino, N-(2-ethylhexyl)-N-methylamino, N,N-bis(2-ethyl Hexyl) amino, N,N-diheptylamino, N-octyl-N-methylamino, N,N-dioctylamino, N,N-dinonylamino, N- Decyl-N-methylamino, N-undecyl-N-methylamino, N-dodecyl-N-methylamino, N-eicosyl-N-methylamine Group, N-phenyl-N-methylamino group, N,N-diphenylamino group, and A group selected from the group A to group B, an amine group in which two of the monovalent hydrocarbon group and the monovalent heterocyclic group are substituted, etc.,

Preferably, it is one selected from the group consisting of a hydrocarbon group having 1 to 30 carbons, a group of the group A to group B, a preferable one of the monovalent hydrocarbon group, and a preferable one of the monovalent heterocyclic group, or Two substituted amino groups, or amino groups, More preferably, it is one selected from the group consisting of a hydrocarbon group having 1 to 20 carbon atoms, the group A to group B, the preferable one of the monovalent hydrocarbon group, and the preferable one of the monovalent heterocyclic group, or Two substituted amino groups, or amino groups, More preferably, it is one selected from the group consisting of a hydrocarbon group having 1 to 18 carbon atoms, the group A to group B, the preferable one of the monovalent hydrocarbon group, and the preferable one of the monovalent heterocyclic group, or Two substituted amino groups, or amino groups, Particularly preferred is one selected from the group consisting of a hydrocarbon group having 1 to 12 carbons, the group A to group B, the preferred one of the monovalent hydrocarbon group, and the preferred one of the monovalent heterocyclic group, or Two amino groups or amino groups formed by substitution.

For example, examples include: formylamino, acetylamino, propylamino, butyrylamino, (2,2-dimethylpropanyl)amino, pentamylamino, hexylamino Amino, (2-ethylhexyl)amino, heptanoylamino, octanoylamino, nonanoylamino, decanoylamino, undecylamino, dodecylamino Benzylamino, eicosanylamino, benzylamino,

及鍵結有所述群組A～群組B的基或者所述一價烴基或一價雜環基的羰基胺基等，[化12]

And the carbonylamino group to which the group A to the group B or the monovalent hydrocarbon group or the monovalent heterocyclic group are bonded,

Preferably, it is a carbonylamino group to which a hydrocarbon group having 1 to 30 carbon atoms, a group of the group A to group B, or the monovalent hydrocarbon group or the monovalent heterocyclic group are bonded, More preferably, it is a carbonylamino group to which a hydrocarbon group having 1 to 20 carbon atoms, a group of the group A to group B or the monovalent hydrocarbon group or the monovalent heterocyclic group are bonded, and More preferably, it is a carbonylamino group to which a hydrocarbon group having 1 to 18 carbon atoms, a group of the group A to group B or the monovalent hydrocarbon group or the monovalent heterocyclic group are bonded, and Particularly preferred is a carbonylamino group to which a hydrocarbon group having 1 to 12 carbon atoms, the group A to group B or the monovalent hydrocarbon group or the monovalent heterocyclic group are bonded. ※Indicating bonding key.

For example, examples include: -SiH ₃ ; -Si(CH ₃ ) ₃ , -Si(CH ₂ CH ₃ ) ₃ , -Si((CH ₂ ) ₂ CH ₃ ) ₃ , -Si(CH(CH ₃ ) ₂ ) ₃ , -Si((CH ₂ ) ₃ CH ₃ ) ₃ , -Si((CH ₂ ) ₄ CH ₃ ) ₃ , -Si((CH ₂ ) ₅ CH ₃ ) ₃ , -Si((CH ₂ ) ₆ CH ₃ ) ₃ , -Si((CH ₂ ) ₇ CH ₃ ) ₃ , -Si((CH ₂ ) ₈ CH ₃ ) ₃ , -Si((CH ₂ ) ₉ CH ₃ ) ₃ , -Si((CH ₂ ) ₁₀ CH ₃ ) ₃ , -Si((CH ₂ ) ₁₁ CH ₃ ) ₃ , -Si((CH ₂ ) ₁₂ CH ₃ ) ₃ , -Si(C ₆ H ₅ ) ₃ , -Si(C ₁₀ H ₇ ) ₃ , -Si(CH ₃ ) ₂ (CH ₂ CH ₃ ), -Si(CH ₃ ) ₂ ((CH ₂ ) ₂ CH ₃ ), -Si(CH ₃ ) ₂ (CH(CH ₃ ) ₂ ),- Si(CH ₃ ) ₂ ((CH ₂ ) ₃ CH ₃ ), -Si(CH ₃ ) ₂ ((CH ₂ ) ₅ CH ₃ ), -Si(CH ₃ ) ₂ ((CH ₂ ) ₇ CH ₃ ), -Si(CH ₃ ) ₂ ((CH ₂ ) ₉ CH ₃ ), -Si(CH ₃ ) ₂ ((CH ₂ ) ₁₁ CH ₃ ), -Si(CH ₃ ) ₂ ((CH ₂ ) ₁₃ CH ₃ ) , -Si(CH ₃ ) ₂ ((CH ₂ ) ₁₅ CH ₃ ), -Si(CH ₃ ) ₂ ((CH ₂ ) ₁₇ CH ₃ ), -Si(CH ₃ ) ₂ ((CH ₂ ) ₁₉ CH ₃ ), -Si(CH ₃ ) ₂ ((CH ₂ ) ₂₉ CH ₃ ), -Si(CH ₃ ) ₂ (C ₆ H ₅ ), -Si(CH ₃ )(C ₆ H ₅ ) ₂ , -Si( CH ₃ ) ₂ (C ₁₀ H ₇ ), and one, two, or three of the group selected from the group A to group B, the monovalent hydrocarbon group, and the monovalent heterocyclic group are substituted -SiH ₃ etc.;

-Si(OH) ₃ ; -Si(OCH ₃ ) ₃ , -Si(OCH ₂ CH ₃ ) ₃ , -Si(O(CH ₂ ) ₂ CH ₃ ) ₃ , -Si(OCH(CH ₃ ) ₂ ) ₃ , -Si(O(CH ₂ ) ₃ CH ₃ ) ₃ , -Si(O(CH ₂ ) ₄ CH ₃ ) ₃ , -Si(O(CH ₂ ) ₅ CH ₃ ) ₃ , -Si(O(CH ₂ ) ₆ CH ₃ ) ₃ , -Si(O(CH ₂ ) ₇ CH ₃ ) ₃ , -Si(O(CH ₂ ) ₈ CH ₃ ) ₃ , -Si(O(CH ₂ ) ₉ CH ₃ ) ₃ ,- Si(O(CH ₂ ) ₁₀ CH ₃ ) ₃ , -Si(O(CH ₂ ) ₁₁ CH ₃ ) ₃ , -Si(OC ₆ H ₅ ) ₃ , -Si(OC ₁₀ H ₇ ) ₃ , -Si( OCH ₃ ) ₂ (OCH ₂ CH ₃ ), -Si(OCH ₃ ) ₂ (O(CH ₂ ) ₂ CH ₃ ), -Si(OCH ₃ ) ₂ (OCH(CH ₃ ) ₂ ), -Si(OCH ₃ ) ₂ (O(CH ₂ ) ₃ CH ₃ ), -Si(OCH ₃ ) ₂ (O(CH ₂ ) ₅ CH ₃ ), -Si(OCH ₃ ) ₂ (O(CH ₂ ) ₇ CH ₃ ),- Si(OCH ₃ ) ₂ (O(CH ₂ ) ₉ CH ₃ ), -Si(OCH ₃ ) ₂ (O(CH ₂ ) ₁₁ CH ₃ ), -Si(OCH ₃ ) ₂ (O(CH ₂ ) ₁₃ CH ₃ ), -Si(OCH ₃ ) ₂ (O(CH ₂ ) ₁₅ CH ₃ ), -Si(OCH ₃ ) ₂ (O(CH ₂ ) ₁₇ CH ₃ ), -Si(OCH ₃ ) ₂ (O(CH ₂ ) ₁₉ CH ₃ ), -Si(OCH ₃ ) ₂ (O(CH ₂ ) ₂₉ CH ₃ ), -Si(OCH ₃ ) ₂ (OC ₆ H ₅ ), -Si(OCH ₃ )(OC ₆ H ₅ ) ₂ , -Si(OCH ₃ ) ₂ (OC ₁₀ H ₇ ), and one or two of a group selected from the group A to group B, the monovalent hydrocarbon group and the monovalent heterocyclic group One or three substituted -Si(OH) ₃ etc.;

-SiH(OH) ₂ ; -Si(CH ₃ )(OCH ₃ ) ₂ , -Si((CH ₂ ) ₁₁ CH ₃ )(O(CH ₂ ) ₁₁ CH ₃ ) ₂ , -Si(C ₆ H ₅ ) (OC ₆ H ₅ ) ₂ , -Si(CH ₃ )(OH) ₂ , -Si((CH ₂ ) ₃₆ CH ₃ )(OH) ₂ , -Si(C ₆ H ₅ )(OH) ₂ , and optional -SiH(OH) ₂ etc. substituted by one, two or three of the group A to group B, the monovalent hydrocarbon group and the monovalent heterocyclic group;

-SiH ₂ (OH); -Si(CH ₃ ) ₂ (OCH ₃ ), -Si((CH ₂ ) ₁₁ CH ₃ ) ₂ (O(CH ₂ ) ₁₁ CH ₃ ), -Si(C ₆ H ₅ ) ₂ (OC ₆ H ₅ ), -Si(CH ₃ ) ₂ (OH), -Si((CH ₂ ) ₁₇ CH ₃ ) ₂ (OH), -Si(C ₆ H ₅ ) ₂ (OH), and optional -SiH ₂ (OH) substituted by one, two, or three of the group A to group B, the monovalent hydrocarbon group, and the monovalent heterocyclic group, etc.,

Preferably it is one selected from the group consisting of a hydrocarbon group having 1 to 30 carbon atoms, the group A to group B, the preferable one of the monovalent hydrocarbon group, and the preferable one of the monovalent heterocyclic group, -SiH ₃ , -Si(OH) ₃ , -SiH(OH) ₂ and -SiH ₂ (OH), or -Si(OH) ₃ which are substituted by two or three, more preferably selected from carbon number One, two or three of the hydrocarbon group of 1-20, the group of the group A to the group B, the preferable one of the monovalent hydrocarbon group, and the preferable one of the monovalent heterocyclic group are substituted Formed -SiH ₃ , -Si(OH) ₃ , -SiH(OH) ₂ and -SiH ₂ (OH), or -Si(OH) ₃ , more preferably selected from hydrocarbon groups having 1 to 18 carbon atoms, -SiH ₃ , substituted by one, two or three of the groups of the group A to group B, the preferable one of the monovalent hydrocarbon group, and the preferable one of the monovalent heterocyclic group, -Si(OH) ₃ , -SiH(OH) ₂ and -SiH ₂ (OH), or -Si(OH) ₃ , particularly preferably selected from hydrocarbon groups having 1 to 12 carbons, the group A to group -SiH ₃ , -Si(OH) ₃ , -SiH ₃ , -Si(OH) ₃ , substituted by one, two or three of the group of B, the preferable one of the monovalent hydrocarbon group, and the preferable one of the monovalent heterocyclic group -SiH(OH) ₂ and -SiH ₂ (OH), or -Si(OH) ₃ .

For example, the phthaliminomethyl group (C ₆ H ₄ (CO) ₂ N-CH ₂ -) which may have a substituent can be mentioned, and the substituent can be selected from the halogen atom, the At least one of the group consisting of the group A to the group B, the monovalent hydrocarbon group, and the monovalent heterocyclic group.

As other groups, one can cite: -SCOCH ₃ ,

等。 ※表示鍵結鍵。[化13]

Wait. ※Indicating bonding key.

For the monovalent hydrocarbon group or the monovalent heterocyclic group, -SO ₃ ^- N ⁺ (C ₁₂ H ₂₅ )(CH ₃ ) ₃ , -CO ₂ ^- N ⁺ (C ₁₂ H ₂₅ )(CH ₃ ) ₃ ,- SO ₃ ^-, -CO ₂ ^-, etc. can also be substituted.

R ¹ and R ² , R ² and R ³ , and R ³ and R ⁴ may be bonded to each other to form a ring.

Examples of the alkali metal atoms represented by M and MM include alkali metal atoms such as lithium atoms, sodium atoms, and potassium atoms.

Examples of the metal atom that may have a ligand-containing metal atom represented by M and MM include metal atoms belonging to groups 2 to 15 of the periodic table. As the metal atom which may have a ligand, the metal atom is more preferably Mg, Ca, Sr, Ba, Cd, Ni, Zn, Cu, Hg, Fe, Co, Sn, Pb, Mn, Al, Cr, Rh, Ir, Pd, Ti, Zr, Hf, Si, Ge, more preferably Mg, Ca, Sr, Ba, Ni, Zn, Cu, Fe, Co, Sn, Mn, Al, Cr, more preferably Mg, Ca, Sr, Ba, Ni, Zn, Cu, Fe, Co, Mn, Al, Cr.

The ligand of the metal atom that may have a ligand is not particularly limited. For example, it may be a halogen atom, NO, NO ₃ , SO ₄ , CH ₃ CO ₂ , OH, etc., a ligand coordinated to the metal atom , And the carbon atom, nitrogen atom, oxygen atom or sulfur atom contained in the same ligand can be coordinated to the same metal atom. In the metal atom, multiple different ligands can coordinate to the same metal atom, It can also form oligomers or polymers. In this ligand, when the compound (I) contains a metal atom that may have a ligand, it may also contain a compound (I) that removes the metal atom that may have a ligand. The compound (I) of the present invention also contains such oligomers or polymers. Among them, the charge of compound (I) is zero.

As such a compound (I), the metal salt etc. which are represented by following formula (EN1)-a formula (EN5), etc. are mentioned, for example. Among them, in the formulas (EN1) to (EN5), the structure shown in () means that the structure is repeatedly bonded like an oligomer and a polymer. For example, the metal salt represented by formula (EN1) means that the same ligand is coordinated to the same metal atom. For example, the metal salt represented by formula (EN2) to formula (EN3) means that a plurality of different ligands are coordinated to the same metal atom to form an oligomer. For example, the metal salt represented by formula (EN4) to formula (EN5) means that a plurality of different ligands are coordinated to the same metal atom to form an oligomer or polymer.

[化14]

[化15]

[化16]

[化17]

[化18]

Examples of N(Z ¹ )(Z ² )(Z ³ )(Z ⁴ ) represented by M and MM include: NH ₄ ; NH ₃ ((CH ₂ ) ₇ CH ₃ ), NH ₃ ((CH ₂ ) ₁₁ CH ₃ ), NH ₃ ((CH ₂ ) ₁₇ CH ₃ ), etc. An alkyl group substituted with NH ₄ ; N(CH ₃ ) ₃ ((CH ₂ ) ₁₅ CH ₃ ), N(CH ₃ ) ₃ ((CH ₂ ) ₁₁ CH ₃ ), N(CH ₃ ) ₂ ((CH ₂ ) ₁₁ CH ₃ ) ₂ , N(CH ₃ ) ₂ ((CH ₂ ) ₁₇ CH ₃ ) ₂ and other four alkyl groups A group formed by substituting NH ₄ ; and one, two, three, or four selected from the group A to B, the monovalent hydrocarbon group, and the monovalent heterocyclic group Substituted NH ₄ etc.

M is preferably: a hydrogen atom; an alkali metal atom; Mg which may have a ligand, Ca which may have a ligand, Sr which may have a ligand, Ba which may have a ligand, and a ligand which may have a ligand Ni, Zn which may have ligands, Cu which may have ligands, Fe which may have ligands, Co which may have ligands, Sn which may have ligands, Mn which may have ligands, Al with ligand, Cr with ligand; NH ₄ ; NH ₃ ((CH ₂ ) ₇ CH ₃ ), NH ₃ ((CH ₂ ) ₁₁ CH ₃ ), NH ₃ ((CH ₂ ) ₁₇ CH ₃ ) and other alkyl groups substituted by NH ₄ ; N(CH ₃ ) ₃ ((CH ₂ ) ₁₅ CH ₃ ), N(CH ₃ ) ₃ ((CH ₂ ) ₁₁ CH ₃ ), N(CH ₃ ) ₂ ((CH ₂ ) ₁₁ CH ₃ ) ₂ , N(CH ₃ ) ₂ ((CH ₂ ) ₁₇ CH ₃ ) ₂ and other four alkyl groups substituted by NH ₄ ,

More preferably: hydrogen atom; sodium atom, potassium atom; Mg which may have a ligand, Ca which may have a ligand, Sr which may have a ligand, Ba which may have a ligand, and a ligand which may have a ligand Ni, Zn which may have ligands, Cu which may have ligands, Fe which may have ligands, Co which may have ligands, Mn which may have ligands, Al which may have ligands , Cr which may have ligands; NH ₄ ; NH ₃ ((CH ₂ ) ₇ CH ₃ ), NH ₃ ((CH ₂ ) ₁₁ CH ₃ ), NH ₃ ((CH ₂ ) ₁₇ CH ₃ ), etc. The group formed by substituting NH ₄ ; N(CH ₃ ) ₃ ((CH ₂ ) ₁₅ CH ₃ ), N(CH ₃ ) ₃ ((CH ₂ ) ₁₁ CH ₃ ), N(CH ₃ ) ₂ ( (CH ₂ ) ₁₁ CH ₃ ) ₂ , N(CH ₃ ) ₂ ((CH ₂ ) ₁₇ CH ₃ ) ₂ and other four alkyl groups substituted with NH ₄ .

MM is preferably: an alkali metal atom; Mg which may have a ligand, Ca which may have a ligand, Sr which may have a ligand, Ba which may have a ligand, Ni which may have a ligand, Zn with a ligand, Cu with a ligand, Fe with a ligand, Co with a ligand, Sn with a ligand, Mn with a ligand, Mn with a ligand, Al, Cr that may have ligands; NH ₄ ; NH ₃ ((CH ₂ ) ₇ CH ₃ ), NH ₃ ((CH ₂ ) ₁₁ CH ₃ ), NH ₃ ((CH ₂ ) ₁₇ CH ₃ ), etc. An alkyl group substituted by NH ₄ ; N(CH ₃ ) ₃ ((CH ₂ ) ₁₅ CH ₃ ), N(CH ₃ ) ₃ ((CH ₂ ) ₁₁ CH ₃ ), N(CH ₃ ) ₂ ((CH ₂ ) ₁₁ CH ₃ ) ₂ , N(CH ₃ ) ₂ ((CH ₂ ) ₁₇ CH ₃ ) ₂ and other four alkyl groups substituted by NH ₄ ,

More preferably: sodium atom, potassium atom; Mg which may have a ligand, Ca which may have a ligand, Sr which may have a ligand, Ba which may have a ligand, Ni which may have a ligand, Zn which may have ligands, Cu which may have ligands, Fe which may have ligands, Co which may have ligands, Mn which may have ligands, Al which may have ligands, Ligand Cr; NH ₄ ; NH ₃ ((CH ₂ ) ₇ CH ₃ ), NH ₃ ((CH ₂ ) ₁₁ CH ₃ ), NH ₃ ((CH ₂ ) ₁₇ CH ₃ ) and other alkyl groups to NH ₄ substituted groups; N(CH ₃ ) ₃ ((CH ₂ ) ₁₅ CH ₃ ), N(CH ₃ ) ₃ ((CH ₂ ) ₁₁ CH ₃ ), N(CH ₃ ) ₂ ((CH ₂ ) ₁₁ CH ₃ ) ₂ , N(CH ₃ ) ₂ ((CH ₂ ) ₁₇ CH ₃ ) ₂ and other four alkyl groups substituted with NH ₄ .

Q ¹ and Q ² each independently represent a divalent hydrocarbon group or a divalent heterocyclic group, and -C(-)(-)- constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted with -Si(-) (-)-, -CH(-)- constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted with -N(-)-, -CH constituting the divalent hydrocarbon group and the divalent heterocyclic group = Can also be substituted with -N=, -CH ₂ -constituting the divalent hydrocarbon group and the divalent heterocyclic group can also be substituted with -O-, -S-, -S(O) ₂ -or -CO-, The hydrogen atoms constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted with a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, or MM. As the hydrogen atoms constituting the group of divalent hydrocarbon group and the divalent heterocyclic group is substituted is preferably a halogen atom, a cyano group, a nitro group, -SO ₃ H, or -CO ₂ H.

Q ¹ and Q ² may be the same or different, and are preferably the same. Q ¹ and Q ^{2 are} preferably groups represented by formula (QQ1) to formula (QQ19).

[化19]

[化20]

[In formulas (QQ1) to (QQ19), R ^Q1 to R ^Q94 each independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, MM, and a carbon number of 1 to 40 The monovalent hydrocarbon group or the monovalent heterocyclic group with 1 to 40 carbon atoms, -C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -Si(-)(- )-, -CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group can also be substituted with -N(-)-, and -CH= also constituting the monovalent hydrocarbon group and the monovalent heterocyclic group It can be substituted with -N=, and -CH ₂ -constituting the monovalent hydrocarbon group and the monovalent heterocyclic group can also be substituted with -O-, -S-, -S(O) ₂ -or -CO- to form the The hydrogen atom of the monovalent hydrocarbon group and the monovalent heterocyclic group can also be substituted with a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M or MM; R ^Q1 to R ^Q94 can be mutually selected from R More than one of ^Q1 ～R ^Q94 is bonded to form a ring; M and MM have the same meaning as described above; ※means bonding bond]

Regarding the monovalent hydrocarbon group having 1 to 40 carbon atoms or the monovalent heterocyclic group having 1 to 40 carbon atoms represented by R ^Q1 to R ^Q94 , and -C(-) constituting the monovalent hydrocarbon group and the monovalent heterocyclic group )(-)- can also be substituted to -Si(-)(-)-, -CH(-)- which constitutes the monovalent hydrocarbon group and the monovalent heterocyclic group can also be substituted to -N(-)-, constitute -CH= of the monovalent hydrocarbon group and the monovalent heterocyclic group can also be substituted with -N=, and -CH ₂ -constituting the monovalent hydrocarbon group and the monovalent heterocyclic group can also be substituted with -O-, -S -, -S(O) ₂ -or -CO-, the hydrogen atoms constituting the monovalent hydrocarbon group and the monovalent heterocyclic group can also be substituted with halogen atoms, cyano groups, nitro groups, -SO ₃ M, -CO ₂ The group of M or MM includes a monovalent hydrocarbon group with 1 to 40 carbons or a monovalent heterocyclic group with 1 to 40 carbons represented by R ¹ to R ⁵ and Z ¹ to Z ⁴ , and constitutes the one The -C(-)(-)- of the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -Si(-)(-)-, the -CH(-) constituting the monovalent hydrocarbon group and the monovalent heterocyclic group )- can also be substituted with -N(-)-, -CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group can also be substituted with -N=, constituting the monovalent hydrocarbon group and the monovalent heterocyclic group -CH ₂ -can also be substituted with -O-, -S-, -S(O) ₂ -or -CO-, and the hydrogen atoms constituting the monovalent hydrocarbon group and the monovalent heterocyclic group can also be substituted with halogen atoms, Those having the same group of cyano, nitro, -SO ₃ M, -CO ₂ M or MM.

Preferred ones of R ^Q1 to R ^Q94 include the same ones as preferred ones of R ¹ to R ⁵ and Z ¹ to Z ⁴ .

Regarding Q ¹ and Q ² , the group represented by formula (QQ1) to formula (QQ12) is preferable, the group represented by formula (QQ1) to formula (QQ5) is more preferable, and the group represented by formula (QQ1) to formula is more preferable. The base represented by (QQ4) is particularly preferably the base represented by formula (QQ1) and formula (QQ2), and more preferably the base represented by formula (QQ2).

As formulas (QQ1) to (QQ19), for example, the following Formula (Qa1) ~ Formula (Qa50); Formula (Qb1) ~ Formula (Qb27); Formula (Qc1) ~ Formula (Qc56); Formula (Qd1) ~ Formula (Qd41); Formula (Qe1) ~ Formula (Qe16); Formula (Qf1) ~ Formula (Qf15); Formula (Qg1) ~ Formula (Qg40); Formula (Qh1) ~ Formula (Qh40); Formula (Qj1) ~ Formula (Qj29); Formula (Qk1) ~ Formula (Qk22); Formula (Qm1) ~ Formula (Qm20); Formula (Qn1) ~ Formula (Qn16); Formula (Qo1) ~ Formula (Qo15); Formula (Qp1) ~ Formula (Qp83); Formula (Qq1) ~ Formula (Qq72); Formula (Qr1) ~ Formula (Qr17); Formula (Qs1) ~ Formula (Qs26); Formula (Qt1) ~ Formula (Qt26); Formula (Qu1) ~ Formula (Qu17); Formula (Qv1) ~ Formula (Qv26); Formula (Qx1) ~ Formula (Qx2); and Formula (Qy1) ~ Formula (Qy10) and the like represented. Among them, ※ represents the bonding key.

[化21]

[化22]

[化23]

[化24]

[化25]

[化26]

[化27]

[化28]

[化29]

[化30]

[化31]

[化32]

[化33]

[化34]

[化35]

[化36]

[化37]

[化38]

[化39]

[化40]

[化41]

[化42]

[化43]

[化44]

[化45]

[化46]

[化47]

[化48]

[化49]

[化50]

[化51]

[化52]

[化53]

[化54]

[化55]

[化56]

[化57]

[化58]

[化59]

[化60]

As the compound (I), for example, the compound represented by the formula (Ia) shown in the following Tables 1 to 14 or an alkali metal salt thereof can be cited. In addition, the symbols described in the "Q ¹ "column and the "Q ² " column in Tables 1 to 14 respectively correspond to the groups represented by the above formulas. ※Indicating bonding key.

[化61]

[Table 1]

[Table 2]

[table 3]

[Table 4]

[table 5]

[Table 6]

[Table 7]

[Table 8]

[Table 9]

[Table 10]

[Table 11]

[Table 12]

[Table 13]

[Table 14]

As the compound (I), for example, the compound represented by the formula (Ib) shown in the following Table 15 to Table 31 or an alkali metal salt thereof can be cited.

[化62]

In formula (Ib), any one of R ^Ib1 to R ^Ib5 is a substituent other than a hydrogen atom (hereinafter, sometimes referred to as an RR group), and the other four are hydrogen atoms. The symbols described in the "Q ¹ "column and the "Q ² " column in Table 15 to Table 31 correspond to the basis represented by the above formula, respectively. The symbols described in the "RR" column in Tables 15 to 31 represent RR groups, and respectively correspond to the following formulas (a1) to (a69); formulas (b1) to (b4); formulas (c1) to Formula (c4); Formula (d1) ~ Formula (d5); Formula (e1) ~ Formula (e20); Formula (f1) ~ Formula (f5); Formula (g1) ~ Formula (g9); Formula (h1) ~ Formula (h9); Formula (j1) ~ Formula (j9); Formula (k1) ~ Formula (k4); Formula (m1) ~ Formula (m9); Formula (n1) ~ Formula (n3); Formula (o1) ~ Formula (o5); Formula (p1) ~ Formula (p23); Formula (q1) ~ Formula (q26); Formula (r1) ~ Formula (r26); Formula (s1) ~ Formula (s26) represented by the group, table The numerical values in the "No" column of 15 to Table 31 respectively indicate the position where the RR group is substituted, "1" indicates that the RR group is substituted for R ^Ib1 , "2" indicates that the RR group is substituted for R ^Ib2 , and "3 "Indicates that the RR group is substituted for R ^Ib3 , "4" indicates that the RR group is substituted for R ^Ib4 , and "5" indicates that the RR group is substituted for R ^Ib5 . ※Indicating bonding key.

[Table 15]

[Table 16]

[Table 17]

[Table 18]

[Table 19]

[Table 20]

[Table 21]

[Table 22]

[Table 23]

[Table 24]

[Table 25]

[Table 26]

[Table 27]

[Table 28]

[Table 29]

[Table 30]

[Table 31]

[化63]

[化64]

[化65]

[化66]

[化67]

[化68]

[化69]

[化70]

[化71]

As the compound (I), for example, a compound represented by the formula (If) shown in the following Table f1 to Table f44 or an alkali metal salt thereof can be cited. In addition, the symbols described in the "Q ¹ "column and the "Q ² " column in Table f1 to Table f44 respectively correspond to the basis represented by the formula. ※Indicating bonding key.

[化72]

[Table f1]

[Table f2]

[Table f3]

[Table f4]

[Table f5]

[Table f6]

[Table f7]

[Table f8]

[Table f9]

[Table f10]

[Table f11]

[Table f12]

[Table f13]

[Table f14]

[Table f15]

[Table f16]

[Table f17]

[Table f18]

[Table f19]

[Table f20]

[Table f21]

[Table f22]

[Table f23]

[Table f24]

[Table f25]

[Table f26]

[Table f27]

[Table f28]

[Table f29]

[Table f30]

[Table f31]

[Table f32]

[Table f33]

[Table f34]

[Table f35]

[Table f36]

[Table f37]

[Table f38]

[Table f39]

[Form f40]

[Table f41]

[Table f42]

[Table f43]

[Table f44]

As the compound (I), for example, the compound represented by the formula (It) shown in the following tables t1 to t5, the compound represented by the formula (Iu) shown in the following tables u1 to u11, and the Some alkali metal salts. Furthermore, the symbols in the "aq", "Q ¹ ", "Q ² ", and "Q ^u+1 " columns in Table t1 to Table t5 and Table u1 to Table u11 correspond to the The group represented by the above formula and the group represented by the following formula (aq1) to (aq36). The "Q ^u+1 " column in Table u1 to Table u11 shows that the group represented by Q ¹ and the group represented by Q ² in the compound represented by formula (Iu) are the same as those described in the column "Q ^u+1 " The symbol corresponds to the base. In the groups represented by the following formulas (aq1) to (aq36), # represents a bonding bond with Q ¹ and & represents a bonding bond with Q ² .

[化73]

[化74]

[化75]

[化76]

[化77]

[Table t1]

[Table t2]

[Table t3]

[Table t4]

[Table t5]

[Table u1]

[Table u2]

[Table u3]

[Table u4]

[Table u5]

[Table u6]

[Table u7]

[Table u8]

[Table u9]

[Table u10]

[Table u11]

As the compound (I), for example, compounds represented by formula (Ia1) to formula (Ia2216) and formula (Ib1) to formula (Ib1312), and compounds represented by formula (If1) to formula (If13090) , The compounds represented by formula (It1) to formula (It900), and the compounds represented by formula (Iu1) to formula (Iu3238) are substituted with selected from -SO ₃ H, -CO ₂ H, -SO ₃ NH ₄ , -CO ₂ NH ₄ , -SO ₂ NH ₂ , -CONH ₂ , phthaliminomethyl (C ₆ H ₄ (CO) ₂ N-CH ₂ -), -SO ₂ NH(CH ₂ ) ₂ A compound of at least one of N(CH ₂ CH ₃ ) ₂ , -N(CH ₃ )((CH ₂ ) ₁₁ CH ₃ ), fluorine atom, chlorine atom, and bromine atom.

For example, in the compound represented by formula (Ia1) in Table 1, the compound substituted with -SO ₃ H represents the following structure. However, in the formula, -(SO ₃ H) means that -SO ₃ H replaces all or one or more of the hydrogen atoms of the compound represented by the formula (Ia1).

[化78]

As this compound, for example, a compound in which all of the hydrogen atoms of the aromatic ring represented by the formula (Ic1) to the formula (Ic12) are substituted with one or more selected from a fluorine atom, a chlorine atom, and a bromine atom can also be cited.

[化79]

[化80]

As the compound (I), for example, compounds represented by formula (Ia1) to formula (Ia2216) and formula (Ib1) to formula (Ib1312), and compounds represented by formula (If1) to formula (If13090) , The compounds represented by formula (It1) to formula (It900), and the compounds represented by formula (Iu1) to formula (Iu3238) are substituted with 1 to 6 selected from -SO ₃ H, -CO ₂ H,- SO ₃ NH ₄ , -CO ₂ NH ₄ , -SO ₂ NH ₂ , -CONH ₂ , phthaliminomethyl (C ₆ H ₄ (CO) ₂ N-CH ₂ -), -SO ₂ NH (CH ₂ ) ₂ N(CH ₂ CH ₃ ) ₂ , -N(CH ₃ ) ((CH ₂ ) ₁₁ CH ₃ ), a compound of at least one of a fluorine atom, a chlorine atom, and a bromine atom.

For example, in the compound represented by the formula (Ia1) in Table 1, the compound substituted with 1 to 6 -SO ₃ H represents the following structure. However, in the formula, -(SO ₃ H) _{1 to 6} means that -SO ₃ H replaces any one to 6 hydrogen atoms of the compound represented by the formula (Ia1).

[化81]

Examples of the compound (I) include compounds represented by formula (Ia1) to formula (Ia2216) and formula (Ib1) to formula (Ib1312), and compounds represented by formula (If1) to formula (If13090) The compounds represented by formula (It1) to formula (It900) and the compounds represented by formula (Iu1) to formula (Iu3238) are substituted with one or more anions selected from -SO ₃ ^- and -CO ₂ ^- , And selected from Mg ²⁺ , Ca ²⁺ , Sr ²⁺ , Ba ²⁺ , Ni ²⁺ , Zn ²⁺ , Fe ²⁺ , Co ²⁺ , Sn ²⁺ , Mn ²⁺ , Al ³⁺ , Fe ³⁺ , Cr ³⁺ , Sn ⁴⁺ , Mn ⁴⁺ , Cu ²⁺ , Li ⁺ , Na ⁺ and K ⁺ cation metal salt.

The compound (I) includes, for example, an anion represented by the formula (Id) and an anion represented by the formula (Ih) shown in the following Table 32 to Table 33 and Table h1 to Table h6, and an anion selected from Mg ²⁺ , Ca ²⁺ , Sr ²⁺ , Ba ²⁺ , Ni ²⁺ , Zn ²⁺ , Fe ²⁺ , Co ²⁺ , Sn ²⁺ , Mn ²⁺ , Al ³⁺ , Fe ³⁺ , Cr ³⁺ , Sn ⁴⁺ , Mn ⁴⁺ , Cu ²⁺ , Li ⁺ , Na ⁺ and K ⁺ cation metal salt.

The symbols described in the “Q ¹ ”column and the “Q ² ” column in Table 32 to Table 33 and Table h1 to Table h6 correspond to the base represented by the formula and the following formula (Qw1) to formula (Qw11 ).

[化82]

[化83]

[化84]

[化85]

[化86]

[Table 32]

[Table 33]

[Table h1]

[Table h2]

[Table h3]

[Table h4]

[Table h5]

[Table h6]

As this metal salt, the metal salt represented by the formula (Ie) shown in following Table 34-Table 38, and the metal salt represented by the formula (Ik) shown in Table k1-Table k14, for example are mentioned. As the symbols described in the "Met" column in Tables 34 to 38 and Tables k1 to k14, Mg2+ means Mg ²⁺ , Ca2+ means Ca ²⁺ , Sr2+ means Sr ²⁺ , Ba2+ means Ba ²⁺ , and Ni2+ means Ni ²⁺ , Zn2+ means Zn ²⁺ , Fe2+ means Fe ²⁺ , Co2+ means Co ²⁺ , Sn2+ means Sn ²⁺ , Mn2+ means Mn ²⁺ , Al3+ means Al ³⁺ , Fe3+ means Fe ³⁺ , Cr3+ means Cr ^{3 +} , Sn4+ represents Sn ⁴⁺ , Mn4+ represents Mn ⁴⁺ , Cu2+ represents Cu ²⁺ , Li+ represents Li ⁺ , Na+ represents Na ⁺ , and K+ represents K ⁺ .

The symbols described in the "Q ¹ "column and the "Q ² " column in Table 34 to Table 38 and Table k1 to Table k14 respectively correspond to the basis represented by the formula. M in Formula (Ie) and Formula (Ik) is an integer of 1 or more, preferably an integer of 1-20, and more preferably an integer of 1-10. N in Formula (Ie) and Formula (Ik) is an integer of 1 or more, preferably an integer of 1-20, more preferably an integer of 1-10. Wherein, when the compound (I) of the present invention is the oligomer or polymer, m and n represent the number of ligands and the number of metal atoms such that the charge of the compound (I) is zero The smallest integer of the ratio of, thereby, means that compound (I) is the oligomer or polymer.

[化87]

[化88]

[Table 34]

[Table 35]

[Table 36]

[Table 37]

[Table 38]

[Table k1]

[Table k2]

[Table k3]

[Table k4]

[Table k5]

[Table k6]

[Table k7]

[Table k8]

[Table k9]

[Table k10]

[Table k11]

[Table k12]

[Table k13]

[Table k14]

The compound (I) is preferably: a compound represented by formula (Ia1) to formula (Ia2216); a compound represented by formula (If1) to formula (If13090); a compound represented by formula (It1) to formula (It900) Compounds; and compounds represented by formula (Iu1) to formula (Iu3238); compounds represented by formula (Ib8); compounds represented by formula (Ib14); compounds represented by formula (Ia1) to formula (Ia2216), Compounds represented by formulas (If1) to (If13090), compounds represented by formulas (It1) to (It900), compounds represented by formulas (Iu1) to (Iu3238), compounds represented by formula (Ib8) , And the compound represented by formula (Ib14) is substituted with selected from -SO ₃ H, -CO ₂ H, -SO ₃ NH ₄ , -CO ₂ NH ₄ , -SO ₂ NH ₂ , -CONH ₂ , phthalate Formiminomethyl (C ₆ H ₄ (CO) ₂ N-CH ₂ -), -SO ₂ NH(CH ₂ ) ₂ N(CH ₂ CH ₃ ) ₂ , -N(CH ₃ )((CH ₂ ) ₁₁ CH ₃ ), a compound containing at least one of fluorine atom, chlorine atom, and bromine atom; and compounds represented by formula (Ia1) to formula (Ia2216), formula (If1) to formula (If13090) Compounds, compounds represented by formula (It1) to formula (It900), compounds represented by formulas (Iu1) to formula (Iu3238), compounds represented by formula (Ib8), and compounds represented by formula (Ib14) are substituted There are one or more anions selected from -SO ₃ ^- and -CO ₂ ^- , and selected from Mg ²⁺ , Ca ²⁺ , Sr ²⁺ , Ba ²⁺ , Ni ²⁺ , Zn ²⁺ , Fe ²⁺ , One or more cations among Co ²⁺ , Sn ²⁺ , Mn ²⁺ , Al ³⁺ , Fe ³⁺ , Cr ³⁺ , Sn ⁴⁺ , Mn ⁴⁺ , Cu ²⁺ , Li ⁺ , Na ⁺ and K ⁺ Metal salt,

More preferred are: compounds represented by formula (Ia1) to formula (Ia2216); compounds represented by formula (If1) to formula (If13090); compounds represented by formula (It1) to formula (It900); formula (Iu1) ~ The compound represented by the formula (Iu3238); the compound represented by the formula (Ia1) ~ formula (Ia2216), the compound represented by the formula (If1) ~ formula (If13090), the compound represented by the formula (It1) ~ formula (It900) The compound represented by formula (Iu1) to formula (Iu3238), the compound represented by formula (Ib8), and the compound represented by formula (Ib14) are substituted with -SO ₃ H, -CO ₂ H, -SO ₃ NH ₄ , -CO ₂ NH ₄ , a compound containing at least one of fluorine atom, chlorine atom, and bromine atom; and a compound containing an anion represented by formula (Id1) to formula (Id304) and formula (Ih1) to formula ( Ih1666) the anion represented by Mg ²⁺ , Ca ²⁺ , Sr ²⁺ , Ba ²⁺ , Ni ²⁺ , Zn ²⁺ , Fe ²⁺ , Co ²⁺ , Sn ²⁺ , Mn ²⁺ , A metal salt of one or more cations among Al ³⁺ , Fe ³⁺ , Cr ³⁺ , Sn ⁴⁺ , Mn ⁴⁺ , Cu ²⁺ , Li ⁺ , Na ⁺ and K ⁺ ,

More preferred are: compounds represented by formula (Ia1) to formula (Ia2216); compounds represented by formula (If1) to formula (If13090); compounds represented by formula (It1) to formula (It900); formula (Iu1) ~ The compound represented by the formula (Iu3238); the compound represented by the formula (Ia1) ~ formula (Ia2216), the compound represented by the formula (If1) ~ formula (If13090), the compound represented by the formula (It1) ~ formula (It900) The compound represented by formula (Iu1) to formula (Iu3238), the compound represented by formula (Ib8), and the compound represented by formula (Ib14) are substituted with -SO ₃ H, -CO ₂ H, -SO ₃ NH ₄ , -CO ₂ NH ₄ , a compound of at least one of a chlorine atom and a bromine atom; compounds represented by formula (Ie1) to formula (Ie76); and formula (Ik1) to formula (Ik114) Compounds represented by formulas (Ik1615) to (Ik1633); compounds represented by formulas (Ik1822) to (Ik1983); compounds represented by formula (Ie117); compounds represented by formula (Ie123); Compound represented by (Ik172); Compound represented by Formula (Ik171); Compound represented by Formula (Ik1777); Compound represented by Formula (Ik181); Compound represented by Formula (Ik397); Compound represented by Formula (Ie273) The compound; and the compound represented by the formula (Ie116),

Particularly preferred are: compounds represented by formula (Ia1) to formula (Ia2216); Compounds represented by formula (If1) to formula (If13090); Compounds represented by formula (It1) to formula (It900); Compounds represented by formula (Iu1) to formula (Iu3238); The compound represented by formula (Ib8); and The compound represented by formula (Ib14),

More preferably, they are: compounds represented by formula (Ia1) to formula (Ia1241), compounds represented by formula (It1) to formula (It900),

Particularly preferred are: the compound represented by formula (Ia1), the compound represented by formula (Ia2), the compound represented by formula (Ia3), the compound represented by formula (Ia10), the compound represented by formula (Ia22), The compound represented by (Ia23), the compound represented by formula (Ia33), the compound represented by formula (Ia35), the compound represented by formula (Ia315), the compound represented by formula (Ia696), the compound represented by formula (Ia703) The compound represented by the formula (Ia973), the compound represented by the formula (It232), the compound represented by the formula (It242), and the compound represented by the formula (It750),

Very preferred are: the compound represented by formula (Ia1), the compound represented by formula (Ia2), the compound represented by formula (Ia3), the compound represented by formula (Ia22), the compound represented by formula (Ia23), The compound represented by (Ia35), the compound represented by formula (Ia696), the compound represented by formula (Ia703), the compound represented by formula (Ia973), the compound represented by formula (It232), the compound represented by formula (It242) And the compound represented by the formula (It750),

Most preferably: a compound represented by formula (Ia1), a compound represented by formula (Ia2), a compound represented by formula (Ia3), a compound represented by formula (Ia696), a compound represented by formula (Ia703), The compound represented by (Ia973), the compound represented by formula (It232), the compound represented by formula (It242), and the compound represented by formula (It750).

The compound represented by formula (I) can be produced by reacting the compound represented by formula (pt1) with the compound represented by formula (pt2) and the compound represented by formula (pt3).

[化89]

In formulas (pt1) to (pt3), R ¹ to R ⁵ , Q ¹ and Q ^{2 have} the same meanings as described above.

In the reaction of the compound represented by the formula (pt1), the compound represented by the formula (pt2), and the compound represented by the formula (pt3), the usage amount of the compound represented by the formula (pt2) is relative to that of the formula (pt1) 1 mol of the compound shown is usually 0.1 mol to 30 mol, preferably 1 mol to 20 mol, more preferably 1 mol to 16 mol, and still more preferably 1 mol to 10 mol.

In the reaction of the compound represented by the formula (pt1), the compound represented by the formula (pt2) and the compound represented by the formula (pt3), the usage amount of the compound represented by the formula (pt3) is relative to that of the formula (pt1) 1 mol of the compound shown is usually 0.1 mol to 30 mol, preferably 1 mol to 20 mol, more preferably 1 mol to 16 mol, and still more preferably 1 mol to 10 mol.

The reaction temperature is usually -100°C to 300°C, preferably 0°C to 280°C, more preferably 50°C to 250°C, still more preferably 100°C to 230°C, and particularly preferably 150°C to 200°C.

The reaction time is usually 0.5 hours to 500 hours.

The reaction of the compound represented by the formula (pt1), the compound represented by the formula (pt2), and the compound represented by the formula (pt3) is usually carried out in the presence of a solvent.

Examples of solvents include: water; nitrile solvents such as acetonitrile; methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethane Alcohol solvents such as 1-hexanol, 1-octanol and phenol; amine solvents; ether solvents such as diethyl ether, tetrahydrofuran and diphenyl ether; ketone solvents such as acetone and methyl isobutyl ketone; ethyl acetate , Methyl benzoate and other ester solvents; aliphatic hydrocarbon solvents such as hexane; toluene, trimethylbenzene (for example, 1,3,5-trimethylbenzene), decalin, tetralin and other aromatic hydrocarbon solvents ; Dichloromethane, chloroform, 1,2-dichlorobenzene, trichlorobenzene (for example, 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene and other halogenated hydrocarbon solvents; nitrobenzene, etc. Nitrolated hydrocarbon solvents; N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone and other amine solvents; dimethyl sulfide and other sulfide solvents,

Preferable examples include: diphenyl ether, methyl benzoate, trimethylbenzene (for example, 1,3,5-trimethylbenzene), decalin, tetrahydronaphthalene, 1,2-dichlorobenzene , Trichlorobenzene (for example, 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N,N-dimethylformamide, N,N-dimethyl Acetamide, N-methylpyrrolidone, dimethyl sulfide,

More preferably, diphenyl ether, methyl benzoate, trimethylbenzene (for example, 1,3,5-trimethylbenzene), decalin, tetralin, 1,2-dichlorobenzene , Trichlorobenzene (for example, 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N-methylpyrrolidone,

More preferred is methyl benzoate.

The amount of solvent used is relative to 1 part by mass of the compound represented by formula (pt1) in the reaction between the compound represented by formula (pt1), the compound represented by formula (pt2) and the compound represented by formula (pt3) It is usually 1 part by mass to 1000 parts by mass.

In the reaction of the compound represented by the formula (pt1), the compound represented by the formula (pt2), and the compound represented by the formula (pt3), it is preferable to coexist at least one selected from an acid and a metal salt.

Examples of the acid include inorganic acids such as hydrogen chloride, hydrogen bromide, hydrogen iodide, sulfuric acid, nitric acid, fluorosulfonic acid, and phosphoric acid; sulfonic acids such as methanesulfonic acid, trifluoromethanesulfonic acid, and p-toluenesulfonic acid; Carboxylic acids such as fluoroacetic acid, citric acid, formic acid, gluconic acid, lactic acid, oxalic acid, benzoic acid and tartaric acid, etc., preferably include: hydrogen chloride, hydrogen bromide, sulfuric acid, methanesulfonic acid, trifluoromethanesulfonic acid, p-toluene Sulfonic acid and carboxylic acid are more preferably exemplified by carboxylic acid, and still more preferably benzoic acid may be mentioned.

The amount of acid used in the reaction of the compound represented by the formula (pt1), the compound represented by the formula (pt2), and the compound represented by the formula (pt3) is usually relative to 1 mole of the compound represented by the formula (pt1) It is 1 mol to 90 mol, preferably 1 mol to 70 mol, more preferably 1 mol to 50 mol, and still more preferably 1 mol to 30 mol.

Examples of the metal salt include zinc chloride and aluminum chloride.

The amount of the metal salt used in the reaction of the compound represented by the formula (pt1), the compound represented by the formula (pt2), and the compound represented by the formula (pt3) is relative to 1 mole of the compound represented by the formula (pt1) It is usually 0.01 mol to 30 mol, preferably 0.01 mol to 20 mol, more preferably 0.01 mol to 10 mol, and still more preferably 0.01 mol to 3 mol.

The method of taking out the compound (I) from the reaction mixture is not particularly limited, and various known methods can be used for taking out. For example, after the completion of the reaction, the compound (I) in the reaction mixture may be difficult to dissolve. After mixing a solvent such as methanol that easily dissolves compounds other than the compound (I) with the reaction mixture, filtration is performed to extract the compound ( I). Furthermore, amine solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone, sulfenite solvents such as dimethyl sulfoxide, or these After washing the obtained residue with mixed solvents, alkaline aqueous solutions such as sodium hydroxide aqueous solution, and/or acidic aqueous solutions such as hydrochloric acid, washing with low-boiling alcohols such as water, methanol or these mixed solvents, the compound (I ). Furthermore, it may be purified by column chromatography and/or recrystallization. Alternatively, after the reaction, the solvent of the reaction mixture can be distilled off, and the obtained residue can be purified by column chromatography and/or recrystallization. After the reaction, the reaction mixture can also be purified by column chromatography and/or recrystallization. After the reaction is completed, the compound (I) in the reaction mixture may be difficult to dissolve. A solvent such as methanol that easily dissolves compounds other than the compound (I) is thoroughly mixed with the reaction mixture, and then filtered to extract the compound (I). . Furthermore, it may be purified by column chromatography and/or recrystallization.

The compound represented by the formula (I) can be produced by reacting the compound represented by the formula (pt1) with the compound represented by the formula (pt2) to produce the compound represented by the formula (I') (hereinafter , There is a case called compound (I')), and then, the compound represented by formula (I') is hydrolyzed in the presence of a base to produce a compound represented by formula (IM1) (hereinafter, the presence is called compound (IM1) In the case of )), the reaction between the compound represented by formula (IM1) and the compound represented by formula (pt3) proceeds. [化90]

In formula (pt1), formula (pt2), formula (pt3), formula (I'), and formula (IM1), R ¹ to R ⁵ , Q ¹ , and Q ^{2 have} the same meaning as described above.

In the reaction between the compound represented by the formula (pt1) and the compound represented by the formula (pt2), the usage amount of the compound represented by the formula (pt2) is usually 0.1 per mole of the compound represented by the formula (pt1) Mole ~ 60 moles, preferably 1 mole ~ 40 moles, more preferably 1 mole ~ 32 moles, and still more preferably 2 moles ~ 20 moles.

The usage amount of the compound represented by the formula (pt3) in the reaction between the compound represented by the formula (IM1) and the compound represented by the formula (pt3) is usually 0.1 mole with respect to 1 mole of the compound represented by the formula (IM1) Ear ~ 30 moles, preferably 1 mole ~ 20 moles, more preferably 1 mole ~ 16 moles, and still more preferably 1 mole ~ 10 moles.

The reaction temperature in the reaction between the compound represented by formula (pt1) and the compound represented by formula (pt2), or the reaction temperature in the reaction between the compound represented by formula (IM1) and the compound represented by formula (pt3) is usually -100°C to 300°C, preferably 0°C to 280°C, more preferably 50°C to 250°C, still more preferably 100°C to 230°C, particularly preferably 150°C to 200°C.

The reaction time in the reaction between the compound represented by formula (pt1) and the compound represented by formula (pt2) or the reaction time in the reaction between the compound represented by formula (IM1) and the compound represented by formula (pt3) is usually 0.5 hour to 500 hours.

The reaction between the compound represented by formula (pt1) and the compound represented by formula (pt2) or the reaction between the compound represented by formula (IM1) and the compound represented by formula (pt3) is usually carried out in the presence of a solvent.

As a solvent in the reaction between the compound represented by the formula (pt1) and the compound represented by the formula (pt2) or the reaction between the compound represented by the formula (IM1) and the compound represented by the formula (pt3), water; Nitrile solvents such as acetonitrile; methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1 -Alcohol solvents such as octanol and phenol; amine solvents; ether solvents such as diethyl ether, tetrahydrofuran and diphenyl ether; ketone solvents such as acetone and methyl isobutyl ketone; ester solvents such as ethyl acetate and methyl benzoate ; Aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene, trimethylbenzene (for example, 1,3,5-trimethylbenzene), decalin and tetralin; dichloromethane, chloroform, 1 ,2-Dichlorobenzene, trichlorobenzene (for example, 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene and other halogenated hydrocarbon solvents; nitrobenzene and other nitrolated hydrocarbon solvents; N, N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone and other amine solvents; dimethyl sulfide and other sulfide solvents, etc.,

Preferable examples include: diphenyl ether, methyl benzoate, trimethylbenzene (for example, 1,3,5-trimethylbenzene), decalin, tetrahydronaphthalene, 1,2-dichlorobenzene , Trichlorobenzene (for example, 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N,N-dimethylformamide, N,N-dimethyl Acetamide, N-methylpyrrolidone, dimethyl sulfide,

More preferably, diphenyl ether, methyl benzoate, trimethylbenzene (for example, 1,3,5-trimethylbenzene), decalin, tetralin, 1,2-dichlorobenzene , Trichlorobenzene (for example, 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N-methylpyrrolidone,

More preferred is methyl benzoate.

The use amount of the solvent in the reaction of the compound represented by the formula (pt1) and the compound represented by the formula (pt2) is usually 1 part by mass to 1000 parts by mass with respect to 1 part by mass of the compound represented by the formula (pt1).

The use amount of the solvent in the reaction of the compound represented by the formula (IM1) and the compound represented by the formula (pt3) is usually 1 part by mass to 1000 parts by mass relative to 1 part by mass of the compound represented by the formula (IM1).

In the reaction between the compound represented by the formula (pt1) and the compound represented by the formula (pt2), or the reaction between the compound represented by the formula (IM1) and the compound represented by the formula (pt3), it is preferable to select an acid and More than one kind of metal salts coexist.

Examples of the acid in the reaction between the compound represented by the formula (pt1) and the compound represented by the formula (pt2) or the reaction between the compound represented by the formula (IM1) and the compound represented by the formula (pt3) include: hydrogen chloride, Hydrogen bromide, hydrogen iodide, sulfuric acid, nitric acid, fluorosulfonic acid, phosphoric acid and other inorganic acids; methanesulfonic acid, trifluoromethanesulfonic acid and p-toluenesulfonic acid and other sulfonic acids; acetic acid, trifluoroacetic acid, citric acid, formic acid, Carboxylic acids such as gluconic acid, lactic acid, oxalic acid, benzoic acid and tartaric acid, etc., preferably include: hydrogen chloride, hydrogen bromide, sulfuric acid, methanesulfonic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid and carboxylic acid, more preferably A carboxylic acid is mentioned, more preferably, benzoic acid is mentioned.

The amount of acid used in the reaction between the compound represented by formula (pt1) and the compound represented by formula (pt2) is usually 1 mol to 90 mol relative to 1 mol of the compound represented by formula (pt1). It is preferably 1 mol to 70 mol, more preferably 1 mol to 50 mol, and still more preferably 1 mol to 30 mol.

The amount of the acid used in the reaction between the compound represented by the formula (IM1) and the compound represented by the formula (pt3) is usually 1 mol to 90 mol relative to 1 mol of the compound represented by the formula (IM1). It is preferably 1 mol to 70 mol, more preferably 1 mol to 50 mol, and still more preferably 1 mol to 30 mol.

The metal salt in the reaction between the compound represented by the formula (pt1) and the compound represented by the formula (pt2) or the reaction between the compound represented by the formula (IM1) and the compound represented by the formula (pt3) includes chlorination Zinc and aluminum chloride, etc.

The amount of the metal salt used in the reaction between the compound represented by the formula (pt1) and the compound represented by the formula (pt2) is usually 0.01 mol to 30 mol relative to 1 mol of the compound represented by the formula (pt1), It is preferably 0.01 mol to 20 mol, more preferably 0.01 mol to 10 mol, and still more preferably 0.01 mol to 3 mol.

The amount of the metal salt used in the reaction between the compound represented by the formula (IM1) and the compound represented by the formula (pt3) is usually 0.01 mol to 30 mol with respect to 1 mol of the compound represented by the formula (IM1), It is preferably 0.01 mol to 20 mol, more preferably 0.01 mol to 10 mol, and still more preferably 0.01 mol to 3 mol.

The method of taking out the compound represented by formula (I′) from the reaction mixture in the reaction of the compound represented by formula (pt1) and the compound represented by formula (pt2) is not particularly limited, and it can be taken out by various known methods. For example, after the completion of the reaction, the compound (I') in the reaction mixture may be difficult to dissolve. After mixing a solvent such as methanol that easily dissolves compounds other than the compound (I') with the reaction mixture, it can be removed by filtering. Compound (I'). Furthermore, amine solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone, sulfenite solvents such as dimethyl sulfoxide, or these After washing the obtained residue with mixed solvents, alkaline aqueous solutions such as sodium hydroxide aqueous solution, and/or acidic aqueous solutions such as hydrochloric acid, washing with low-boiling alcohols such as water, methanol or these mixed solvents, the compound (I '). Furthermore, it may be purified by column chromatography and/or recrystallization. Alternatively, after the reaction, the solvent of the reaction mixture can be distilled off, and the obtained residue can be purified by column chromatography and/or recrystallization. After the reaction, the reaction mixture can also be purified by column chromatography and/or recrystallization. After the completion of the reaction, the compound (I') in the reaction mixture may be difficult to dissolve. A solvent such as methanol that easily dissolves compounds other than the compound (I') is thoroughly mixed with the reaction mixture, and then filtered to extract the compound ( I'). Furthermore, it may be purified by column chromatography and/or recrystallization.

The method of taking out the compound represented by formula (I) from the reaction mixture in the reaction of the compound represented by formula (IM1) and the compound represented by formula (pt3) is not particularly limited, and it can be taken out by various known methods. For example, after the completion of the reaction, the compound (I) in the reaction mixture may be difficult to dissolve. After mixing a solvent such as methanol that easily dissolves compounds other than the compound (I) with the reaction mixture, filtration is performed to extract the compound ( I). Furthermore, amine solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone, sulfenite solvents such as dimethyl sulfoxide, or these After washing the obtained residue with mixed solvents, alkaline aqueous solutions such as sodium hydroxide aqueous solution, and/or acidic aqueous solutions such as hydrochloric acid, washing with low-boiling alcohols such as water, methanol or these mixed solvents, the compound (I ). Furthermore, it may be purified by column chromatography and/or recrystallization. Alternatively, after the reaction, the solvent of the reaction mixture can be distilled off, and the obtained residue can be purified by column chromatography and/or recrystallization. After the reaction, the reaction mixture can also be purified by column chromatography and/or recrystallization. After the reaction is completed, the compound (I) in the reaction mixture may be difficult to dissolve. A solvent such as methanol that easily dissolves compounds other than the compound (I) is thoroughly mixed with the reaction mixture, and then filtered to extract the compound (I). . Furthermore, it may be purified by column chromatography and/or recrystallization.

Examples of the base in the hydrolysis reaction of the compound represented by formula (I') in the presence of a base include triethylamine, 4-(N,N-dimethylamino)pyridine, pyridine, piperidine, 1 ,8-diazabicyclo[5.4.0]undec-7-ene, 1,5-diazabicyclo[4.3.0]non-5-ene, 1,5-diazabicyclo[4.3. 0] Organic bases such as non-5-ene, metal alkoxides such as sodium methoxide, sodium ethoxide, sodium tertiary butoxide, potassium tertiary butoxide, methyl lithium, butyl lithium, tertiary butyl lithium and phenyl lithium Organic metal compounds such as sodium bicarbonate, potassium bicarbonate, sodium carbonate, potassium carbonate, lithium hydroxide, sodium hydroxide, and potassium hydroxide and other inorganic bases, Preferably it is an inorganic base, More preferably lithium hydroxide, sodium hydroxide, and potassium hydroxide, Further preferred are sodium hydroxide and potassium hydroxide, Potassium hydroxide is particularly preferred.

The amount of the base used in the hydrolysis reaction of the compound represented by formula (I') in the presence of a base is usually 0.1 mol to 100 mol relative to 1 mol of the compound represented by formula (I'), preferably It is 1 mol to 70 mol, more preferably 2 mol to 40 mol.

The amount of water used in the hydrolysis reaction of the compound represented by formula (I') in the presence of a base is usually 1 part by mass to 1000 parts by mass relative to 1 part by mass of the compound represented by formula (I'), preferably It is 1 part by mass to 200 parts by mass, more preferably 1 part by mass to 100 parts by mass, and still more preferably 1 part by mass to 50 parts by mass.

The reaction temperature in the hydrolysis reaction of the compound represented by formula (I') in the presence of a base is usually 0°C to 100°C, preferably 5°C to 100°C, more preferably 20°C to 100°C, and still more preferably 40℃～100℃, particularly preferably 60℃～100℃.

The reaction time in the hydrolysis reaction of the compound represented by formula (I') in the presence of a base is usually 0.5 hour to 120 hours, preferably 1 hour to 72 hours, more preferably 1 hour to 24 hours.

The method of taking out the compound represented by formula (IM1) from the reaction mixture in the hydrolysis reaction of the compound represented by formula (I′) in the presence of a base is not particularly limited, and it can be taken out by various known methods. For example, after the reaction is completed, an acidic aqueous solution such as hydrochloric acid is added to the reaction mixture to neutralize it, and then filtration is performed to extract the compound (IM1). Furthermore, amine solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone, sulfenite solvents such as dimethyl sulfoxide, acetone, etc. can be used Wash the obtained residue with ketone solvent, alcohol solvent such as methanol, nitrile solvent such as acetonitrile, water or mixed solvents of these, alkaline aqueous solution such as sodium hydroxide aqueous solution, and/or acidic aqueous solution such as hydrochloric acid, and take out the compound (IM1) . Furthermore, it may be purified by column chromatography and/or recrystallization. Alternatively, after the reaction, the solvent of the reaction mixture can be distilled off, and the obtained residue can be purified by column chromatography and/or recrystallization. After the reaction, the reaction mixture can also be purified by column chromatography and/or recrystallization.

The compound represented by the formula (I) can be produced by the following method: the compound represented by the formula (IM2) is produced by the reaction of the compound represented by the formula (pt1) and the compound represented by the formula (pt3) (hereinafter, there is Called compound (IM2)), and then, The reaction of the compound represented by formula (IM2) and the compound represented by formula (pt2) is performed.

[化91]

In formula (pt1), formula (pt2), formula (pt3), and formula (IM2), R ¹ to R ⁵ , Q ¹ , and Q ^{2 have} the same meaning as described above.

In the reaction between the compound represented by the formula (pt1) and the compound represented by the formula (pt3), the usage amount of the compound represented by the formula (pt3) is usually 0.1 per mole of the compound represented by the formula (pt1) The molar range is ∼10 mol, preferably 0.1 mol to 5 mol, more preferably 0.5 mol to 2 mol, and still more preferably 0.8 mol to 1.5 mol.

The reaction temperature in the reaction between the compound represented by formula (pt1) and the compound represented by formula (pt3) is usually -100°C to 300°C, preferably 0°C to 280°C, more preferably 50°C to 250°C, It is more preferably 100°C to 230°C, and particularly preferably 120°C to 200°C.

The reaction time in the reaction between the compound represented by the formula (pt1) and the compound represented by the formula (pt3) is usually 0.5 to 500 hours.

The reaction between the compound represented by the formula (pt1) and the compound represented by the formula (pt3) is usually carried out in the presence of a solvent.

Examples of the solvent in the reaction between the compound represented by formula (pt1) and the compound represented by formula (pt3) include: water; nitrile solvents such as acetonitrile; methanol, ethanol, 1-propanol, 2-propanol, 1- Alcohol solvents such as butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-octanol, phenol; amine solvents; diethyl ether, tetrahydrofuran, diphenyl Ether solvents such as base ether; ketone solvents such as acetone and methyl isobutyl ketone; ester solvents such as ethyl acetate and methyl benzoate; aliphatic hydrocarbon solvents such as hexane; toluene, trimethylbenzene (for example, 1,3 ,5-Trimethylbenzene), decalin, tetralin and other aromatic hydrocarbon solvents; dichloromethane, chloroform, 1,2-dichlorobenzene, trichlorobenzene (for example, 1,3,5-trichloro Benzene), 1-chloronaphthalene, 2-chloronaphthalene and other halogenated hydrocarbon solvents; nitrobenzene and other nitrated hydrocarbon solvents; N,N-dimethylformamide, N,N-dimethylacetamide, N -Methylpyrrolidone and other amide solvents; dimethyl sulfide and other sulfide solvents, etc.,

Preferably, examples include phenol, diphenyl ether, methyl benzoate, trimethylbenzene (for example, 1,3,5-trimethylbenzene), decalin, tetrahydronaphthalene, 1,2-di Chlorobenzene, trichlorobenzene (for example, 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N,N-dimethylformamide, N,N-di Methyl acetamide, N-methyl pyrrolidone, dimethyl sulfide,

More preferably, phenol, diphenyl ether, methyl benzoate, trimethylbenzene (for example, 1,3,5-trimethylbenzene), decalin, tetrahydronaphthalene, 1,2-bis Chlorobenzene, trichlorobenzene (for example, 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N-methylpyrrolidone,

More preferred examples include phenol and methyl benzoate,

Particularly preferred is phenol.

The amount of solvent used in the reaction between the compound represented by formula (pt1) and the compound represented by formula (pt3) is usually 1 part by mass to 1000 parts by mass relative to 1 part by mass of the compound represented by formula (pt1). It is preferably 1 part by mass to 200 parts by mass, more preferably 1 part by mass to 100 parts by mass, and still more preferably 1 part by mass to 50 parts by mass.

The method of extracting the compound (IM2) from the reaction mixture in the reaction of the compound represented by the formula (pt1) and the compound represented by the formula (pt3) is not particularly limited, and can be extracted by various known methods. For example, after the completion of the reaction, the compound (IM2) in the reaction mixture may be difficult to dissolve. A solvent such as methanol, which easily dissolves compounds other than the compound (IM2), is thoroughly mixed with the reaction mixture and filtered to extract the compound ( IM2). Furthermore, amine solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone, sulfenite solvents such as dimethyl sulfoxide, and ketones such as acetone are used. Solvents, alcohol solvents such as methanol, nitrile solvents such as acetonitrile, water or mixed solvents of these, alkaline aqueous solutions such as sodium hydroxide aqueous solution, and/or acidic aqueous solutions such as hydrochloric acid are used to clean the obtained residue and the compound (IM2) . Furthermore, it may be purified by column chromatography and/or recrystallization. Alternatively, after the reaction, the solvent of the reaction mixture can be distilled off, and the obtained residue can be purified by column chromatography and/or recrystallization. After the reaction, the reaction mixture can also be purified by column chromatography and/or recrystallization. After the reaction is completed, the compound (IM2) in the reaction mixture is difficult to dissolve. The reaction mixture is added to a solvent such as methanol that easily dissolves compounds other than the compound (IM2), and the mixture is thoroughly mixed and filtered to extract the compound (IM2). Furthermore, it may be purified by column chromatography and/or recrystallization.

In the reaction between the compound represented by the formula (IM2) and the compound represented by the formula (pt2), the usage amount of the compound represented by the formula (pt2) is usually 0.1 per mole of the compound represented by the formula (IM2) It is ～30 mol, preferably 1 mol ～20 mol, more preferably 1 mol～16 mol, and still more preferably 1 mol～10 mol.

The reaction temperature in the reaction of the compound represented by formula (IM2) and the compound represented by formula (pt2) is usually -100°C to 300°C, preferably 0°C to 280°C, more preferably 50°C to 250°C, It is more preferably 100°C to 230°C, and particularly preferably 150°C to 200°C.

The reaction time in the reaction of the compound represented by the formula (IM2) and the compound represented by the formula (pt2) is usually 0.5 hour to 500 hours.

The reaction of the compound represented by formula (IM2) and the compound represented by formula (pt2) is usually carried out in the presence of a solvent.

Examples of the solvent in the reaction between the compound represented by the formula (IM2) and the compound represented by the formula (pt2) include: water; nitrile solvents such as acetonitrile; methanol, ethanol, 1-propanol, 2-propanol, 1- Alcohol solvents such as butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-octanol, phenol; amine solvents; diethyl ether, tetrahydrofuran, diphenyl Ether solvents such as base ether; ketone solvents such as acetone and methyl isobutyl ketone; ester solvents such as ethyl acetate and methyl benzoate; aliphatic hydrocarbon solvents such as hexane; toluene, trimethylbenzene (for example, 1,3 ,5-Trimethylbenzene), decalin, tetralin and other aromatic hydrocarbon solvents; dichloromethane, chloroform, 1,2-dichlorobenzene, trichlorobenzene (for example, 1,3,5-trichloro Benzene), 1-chloronaphthalene, 2-chloronaphthalene and other halogenated hydrocarbon solvents; nitrobenzene and other nitrated hydrocarbon solvents; N,N-dimethylformamide, N,N-dimethylacetamide, N -Methylpyrrolidone and other amine solvents; dimethyl sulfide and other sulfide solvents,

Preferable examples include: diphenyl ether, methyl benzoate, trimethylbenzene (for example, 1,3,5-trimethylbenzene), decalin, tetrahydronaphthalene, 1,2-dichlorobenzene , Trichlorobenzene (for example, 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N,N-dimethylformamide, N,N-dimethyl Acetamide, N-methylpyrrolidone, dimethyl sulfide,

More preferably, diphenyl ether, methyl benzoate, trimethylbenzene (for example, 1,3,5-trimethylbenzene), decalin, tetralin, 1,2-dichlorobenzene , Trichlorobenzene (for example, 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N-methylpyrrolidone,

More preferred is methyl benzoate.

The amount of the solvent used in the reaction of the compound represented by formula (IM2) and the compound represented by formula (pt2) is usually 1 part by mass to 1000 parts by mass with respect to 1 part by mass of the compound represented by formula (IM2).

In the reaction between the compound represented by the formula (IM2) and the compound represented by the formula (pt2), it is preferable that one or more kinds selected from an acid and a metal salt coexist.

Examples of the acid in the reaction between the compound represented by formula (IM2) and the compound represented by formula (pt2) include inorganic acids such as hydrogen chloride, hydrogen bromide, hydrogen iodide, sulfuric acid, nitric acid, fluorosulfonic acid, and phosphoric acid; Sulfonic acids such as methanesulfonic acid, trifluoromethanesulfonic acid, and p-toluenesulfonic acid; carboxylic acids such as acetic acid, trifluoroacetic acid, citric acid, formic acid, gluconic acid, lactic acid, oxalic acid, benzoic acid and tartaric acid, etc., preferably include : Hydrogen chloride, hydrogen bromide, sulfuric acid, methanesulfonic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid, and carboxylic acid, more preferably carboxylic acid, more preferably benzoic acid.

The amount of the acid used in the reaction between the compound represented by the formula (IM2) and the compound represented by the formula (pt2) is usually 1 mol to 90 mol relative to 1 mol of the compound represented by the formula (IM2). It is preferably 1 mol to 70 mol, more preferably 1 mol to 50 mol, and still more preferably 1 mol to 30 mol.

As a metal salt in the reaction of the compound represented by formula (IM2) and the compound represented by formula (pt2), zinc chloride, aluminum chloride, etc. are mentioned.

The amount of the metal salt used in the reaction between the compound represented by the formula (IM2) and the compound represented by the formula (pt2) is usually 0.01 mol to 30 mol with respect to 1 mol of the compound represented by the formula (IM2), It is preferably 0.01 mol to 20 mol, more preferably 0.01 mol to 10 mol, and still more preferably 0.01 mol to 3 mol.

The method of taking out the compound represented by formula (I) from the reaction mixture in the reaction of the compound represented by formula (IM2) and the compound represented by formula (pt2) is not particularly limited, and it can be taken out by various known methods. For example, after the completion of the reaction, the compound (I) in the reaction mixture may be difficult to dissolve. After mixing a solvent such as methanol that easily dissolves compounds other than the compound (I) with the reaction mixture, filtration is performed to extract the compound ( I). Furthermore, amine solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone, sulfenite solvents such as dimethyl sulfoxide, or these After washing the obtained residue with mixed solvents, alkaline aqueous solutions such as sodium hydroxide aqueous solution, and/or acidic aqueous solutions such as hydrochloric acid, washing with low-boiling alcohols such as water, methanol or these mixed solvents, the compound (I ). Furthermore, it may be purified by column chromatography and/or recrystallization. Alternatively, after the reaction, the solvent of the reaction mixture can be distilled off, and the obtained residue can be purified by column chromatography and/or recrystallization. After the reaction, the reaction mixture can also be purified by column chromatography and/or recrystallization. After the reaction is completed, the compound (I) in the reaction mixture may be difficult to dissolve. A solvent such as methanol that easily dissolves compounds other than the compound (I) is thoroughly mixed with the reaction mixture, and then filtered to extract the compound (I). . Furthermore, it may be purified by column chromatography and/or recrystallization.

The compound represented by the formula (I) can be produced by the following method: the compound represented by the formula (IM2) is produced by the reaction of the compound represented by the formula (pt1) and the compound represented by the formula (pt3) (hereinafter, there is This is referred to as a compound (IM2)), and then the reaction of the compound represented by the formula (IM2) and the compound represented by the formula (pt2) proceeds. [化92]

In formula (pt1), formula (pt2), formula (pt3), and formula (IM2), R ¹ to R ⁵ , Q ¹ , and Q ^{2 have} the same meaning as described above.

The usage amount of the compound represented by the formula (pt3) in the reaction between the compound represented by the formula (pt1) and the compound represented by the formula (pt3) is usually 0.1 mol relative to 1 mol of the compound represented by the formula (pt1) Ear ~ 10 mol, preferably 0.1 mol ~ 5 mol, more preferably 0.5 mol ~ 2 mol, and still more preferably 0.8 mol ~ 1.5 mol.

The reaction temperature in the reaction between the compound represented by formula (pt1) and the compound represented by formula (pt3) is usually -100°C to 300°C, preferably 0°C to 280°C, more preferably 50°C to 250°C, It is more preferably 100°C to 230°C, and particularly preferably 120°C to 200°C.

The reaction time in the reaction between the compound represented by the formula (pt1) and the compound represented by the formula (pt3) is usually 0.5 to 500 hours.

The reaction between the compound represented by the formula (pt1) and the compound represented by the formula (pt3) is usually carried out in the presence of a solvent.

Examples of the solvent in the reaction between the compound represented by formula (pt1) and the compound represented by formula (pt3) include: water; nitrile solvents such as acetonitrile; methanol, ethanol, 1-propanol, 2-propanol, 1- Alcohol solvents such as butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-octanol, phenol; amine solvents; diethyl ether, tetrahydrofuran, diphenyl Ether solvents such as base ether; ketone solvents such as acetone and methyl isobutyl ketone; ester solvents such as ethyl acetate and methyl benzoate; aliphatic hydrocarbon solvents such as hexane; toluene, trimethylbenzene (for example, 1,3 ,5-Trimethylbenzene), decalin, tetralin and other aromatic hydrocarbon solvents; dichloromethane, chloroform, 1,2-dichlorobenzene, trichlorobenzene (for example, 1,3,5-trichloro Benzene), 1-chloronaphthalene, 2-chloronaphthalene and other halogenated hydrocarbon solvents; nitrobenzene and other nitrated hydrocarbon solvents; N,N-dimethylformamide, N,N-dimethylacetamide, N -Methylpyrrolidone and other amide solvents; dimethyl sulfide and other sulfide solvents, etc.,

Preferably, examples include phenol, diphenyl ether, methyl benzoate, trimethylbenzene (for example, 1,3,5-trimethylbenzene), decalin, tetrahydronaphthalene, 1,2-di Chlorobenzene, trichlorobenzene (for example, 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N,N-dimethylformamide, N,N-di Methyl acetamide, N-methyl pyrrolidone, dimethyl sulfide,

More preferably, phenol, diphenyl ether, methyl benzoate, trimethylbenzene (for example, 1,3,5-trimethylbenzene), decalin, tetrahydronaphthalene, 1,2-bis Chlorobenzene, trichlorobenzene (for example, 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N-methylpyrrolidone,

More preferred examples include phenol and methyl benzoate,

Particularly preferred is phenol.

The amount of solvent used in the reaction between the compound represented by formula (pt1) and the compound represented by formula (pt3) is usually 1 part by mass to 1000 parts by mass relative to 1 part by mass of the compound represented by formula (pt1). It is preferably 1 part by mass to 200 parts by mass, more preferably 1 part by mass to 100 parts by mass, and still more preferably 1 part by mass to 50 parts by mass.

The method of extracting the compound (IM2) from the reaction mixture in the reaction of the compound represented by the formula (pt1) and the compound represented by the formula (pt3) is not particularly limited, and can be extracted by various known methods. For example, after the completion of the reaction, the compound (IM2) in the reaction mixture may be difficult to dissolve. A solvent such as methanol, which easily dissolves compounds other than the compound (IM2), is thoroughly mixed with the reaction mixture and filtered to extract the compound ( IM2). Furthermore, amine solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone, sulfenite solvents such as dimethyl sulfoxide, and ketones such as acetone are used. Solvents, alcohol solvents such as methanol, nitrile solvents such as acetonitrile, water or mixed solvents of these, alkaline aqueous solutions such as sodium hydroxide aqueous solution, and/or acidic aqueous solutions such as hydrochloric acid are used to clean the obtained residue and the compound (IM2) . Furthermore, it may be purified by column chromatography and/or recrystallization. Alternatively, after the reaction, the solvent of the reaction mixture can be distilled off, and the obtained residue can be purified by column chromatography and/or recrystallization. After the reaction, the reaction mixture can also be purified by column chromatography and/or recrystallization. After the completion of the reaction, the compound (IM2) in the reaction mixture may be difficult to dissolve. After mixing a solvent such as methanol that easily dissolves compounds other than the compound (IM2) with the reaction mixture, it is filtered to extract the compound (IM2) . Furthermore, it may be purified by column chromatography and/or recrystallization.

In the reaction between the compound represented by the formula (IM2) and the compound represented by the formula (pt2), the usage amount of the compound represented by the formula (pt2) is usually 0.1 per mole of the compound represented by the formula (IM2) It is ～30 mol, preferably 1 mol ～20 mol, more preferably 1 mol～16 mol, and still more preferably 1 mol～10 mol.

The reaction temperature in the reaction of the compound represented by formula (IM2) and the compound represented by formula (pt2) is usually -100°C to 300°C, preferably 0°C to 280°C, more preferably 50°C to 250°C, It is more preferably 100°C to 230°C, and particularly preferably 150°C to 200°C.

The reaction time in the reaction of the compound represented by the formula (IM2) and the compound represented by the formula (pt2) is usually 0.5 hour to 500 hours.

The reaction of the compound represented by formula (IM2) and the compound represented by formula (pt2) is usually carried out in the presence of a solvent.

Examples of the solvent in the reaction between the compound represented by the formula (IM2) and the compound represented by the formula (pt2) include: water; nitrile solvents such as acetonitrile; methanol, ethanol, 1-propanol, 2-propanol, 1- Alcohol solvents such as butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-octanol, phenol; amine solvents; diethyl ether, tetrahydrofuran, diphenyl Ether solvents such as base ether; ketone solvents such as acetone and methyl isobutyl ketone; ester solvents such as ethyl acetate and methyl benzoate; aliphatic hydrocarbon solvents such as hexane; toluene, trimethylbenzene (for example, 1,3 ,5-Trimethylbenzene), decalin, tetralin and other aromatic hydrocarbon solvents; dichloromethane, chloroform, 1,2-dichlorobenzene, trichlorobenzene (for example, 1,3,5-trichloro Benzene), 1-chloronaphthalene, 2-chloronaphthalene and other halogenated hydrocarbon solvents; nitrobenzene and other nitrated hydrocarbon solvents; N,N-dimethylformamide, N,N-dimethylacetamide, N -Methylpyrrolidone and other amide solvents; dimethyl sulfide and other sulfide solvents, etc.,

Preferable examples include: diphenyl ether, methyl benzoate, trimethylbenzene (for example, 1,3,5-trimethylbenzene), decalin, tetrahydronaphthalene, 1,2-dichlorobenzene , Trichlorobenzene (for example, 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N,N-dimethylformamide, N,N-dimethyl Acetamide, N-methylpyrrolidone, dimethyl sulfide,

More preferably, diphenyl ether, methyl benzoate, trimethylbenzene (for example, 1,3,5-trimethylbenzene), decalin, tetralin, 1,2-dichlorobenzene , Trichlorobenzene (for example, 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N-methylpyrrolidone,

More preferred is methyl benzoate.

The amount of the solvent used in the reaction of the compound represented by formula (IM2) and the compound represented by formula (pt2) is usually 1 part by mass to 1000 parts by mass with respect to 1 part by mass of the compound represented by formula (IM2).

In the reaction between the compound represented by the formula (IM2) and the compound represented by the formula (pt2), it is preferable that one or more kinds selected from an acid and a metal salt coexist.

Examples of the acid in the reaction between the compound represented by formula (IM2) and the compound represented by formula (pt2) include inorganic acids such as hydrogen chloride, hydrogen bromide, hydrogen iodide, sulfuric acid, nitric acid, fluorosulfonic acid, and phosphoric acid; Sulfonic acids such as methanesulfonic acid, trifluoromethanesulfonic acid, and p-toluenesulfonic acid; carboxylic acids such as acetic acid, trifluoroacetic acid, citric acid, formic acid, gluconic acid, lactic acid, oxalic acid, benzoic acid and tartaric acid, etc., preferably include : Hydrogen chloride, hydrogen bromide, sulfuric acid, methanesulfonic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid, and carboxylic acid, more preferably carboxylic acid, more preferably benzoic acid.

The amount of the acid used in the reaction between the compound represented by the formula (IM2) and the compound represented by the formula (pt2) is usually 1 mol to 90 mol relative to 1 mol of the compound represented by the formula (IM2). It is preferably 1 mol to 70 mol, more preferably 1 mol to 50 mol, and still more preferably 1 mol to 30 mol.

As a metal salt in the reaction of the compound represented by formula (IM2) and the compound represented by formula (pt2), zinc chloride, aluminum chloride, etc. are mentioned.

The amount of the metal salt used in the reaction between the compound represented by the formula (IM2) and the compound represented by the formula (pt2) is usually 0.01 mol to 30 mol with respect to 1 mol of the compound represented by the formula (IM2), It is preferably 0.01 mol to 20 mol, more preferably 0.01 mol to 10 mol, and still more preferably 0.01 mol to 3 mol.

The method of taking out the compound represented by formula (I) from the reaction mixture in the reaction of the compound represented by formula (IM2) and the compound represented by formula (pt2) is not particularly limited, and it can be taken out by various known methods. For example, after the completion of the reaction, the compound (I) in the reaction mixture may be difficult to dissolve. After mixing a solvent such as methanol that easily dissolves compounds other than the compound (I) with the reaction mixture, filtration is performed to extract the compound ( I). Furthermore, amine solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone, sulfenite solvents such as dimethyl sulfoxide, or these After washing the obtained residue with mixed solvents, alkaline aqueous solutions such as sodium hydroxide aqueous solution, and/or acidic aqueous solutions such as hydrochloric acid, washing with low-boiling alcohols such as water, methanol or these mixed solvents, the compound (I ). Furthermore, it may be purified by column chromatography and/or recrystallization. Alternatively, after the reaction, the solvent of the reaction mixture can be distilled off, and the obtained residue can be purified by column chromatography and/or recrystallization. After the reaction is completed, column chromatography and/or Or recrystallize and refine the reaction mixture. After the reaction is completed, the compound (I) in the reaction mixture may be difficult to dissolve. A solvent such as methanol that easily dissolves compounds other than the compound (I) is thoroughly mixed with the reaction mixture, and then filtered to extract the compound (I). . Furthermore, it may be purified by column chromatography and/or recrystallization.

By reacting compound (I) with a sulfonating agent such as fuming sulfuric acid or chlorosulfonic acid, a sulfonic group or -SO ₃ M can be introduced to compound (I). A compound obtained by introducing a sulfo group or -SO ₃ M to the compound (I) (hereinafter, sometimes referred to as "sulfonated compound (I)") is also a compound of the present invention.

The amount of SO ₃ used in fuming sulfuric acid is usually 1 mol to 200 mol, preferably 2 mol to 150 mol, more preferably 3 mol to 100 mol relative to 1 mol of compound (I). Ears, more preferably 5 mol to 80 mol.

The SO ₃ in fuming sulfuric acid is usually 1 part by mass to 90 parts by mass in 100 parts by mass of oleum, preferably 5 parts by mass to 70 parts by mass, more preferably 10 parts by mass to 60 parts by mass, and still more preferably 15 parts by mass to 50 parts by mass.

The amount of chlorosulfonic acid used is usually 1 mol to 500 mol relative to 1 mol of compound (I), preferably 1 mol to 300 mol, more preferably 1 mol to 200 mol, and more preferably It is 1 mol ~ 150 mol.

When chlorosulfonic acid is used to introduce a sulfo group or -SO ₃ M into the compound (I), the reaction can be carried out in the presence of a solvent. Examples of the solvent include halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichlorobenzene, trichlorobenzene (for example, 1,3,5-trichlorobenzene), 1-chloronaphthalene and 2-chloronaphthalene Solvent.

The usage-amount of this solvent is 1 mass part-1000 mass parts normally with respect to 1 mass part of compound (I).

The reaction temperature of sulfonation is usually -20°C to 200°C, preferably -10°C to 150°C, and more preferably 0°C to 100°C. The reaction time is usually 0.5 hour to 300 hours.

The method of taking out the sulfonated compound (I) from the reaction mixture is not particularly limited, and various known methods can be used for taking out. For example, after the reaction is completed, the reaction mixture is added dropwise to ice, and the obtained mixture is filtered, whereby the sulfonated compound (I) can be taken out. Furthermore, it may be purified by column chromatography and/or recrystallization. Alternatively, after the reaction, the reaction mixture is added dropwise to ice, and the obtained mixture is mixed with alcohol solvents such as methanol, acetonitrile, etc., which are difficult to dissolve the sulfonated compound (I) but easily dissolve compounds other than the sulfonated compound (I) The nitrile solvent and hydrophilic organic solvents such as these mixed solvents are mixed and filtered, whereby the sulfonated compound (I) can be taken out. Furthermore, it may be purified by column chromatography and/or recrystallization. Alternatively, after the completion of the reaction, the reaction mixture is added dropwise to ice, and the obtained mixture is neutralized with an aqueous solution such as ammonia, water-soluble amine, or a mixture of these, and then the mixture is mixed with an alcohol solvent such as methanol and a nitrile such as acetonitrile. The solvent is mixed with hydrophilic organic solvents such as these mixed solvents, and filtered, and the solvent of the obtained filtrate is distilled off, whereby the sulfonated compound (I) can be taken out. Furthermore, it may be purified by column chromatography and/or recrystallization.

The compound (I) having -SO ₃ H and/or -CO ₂ H (hereinafter, sometimes referred to as "acid group-containing compound (I)") is reacted with a salt having MM to produce -SO ₃ (MM) and/or -CO ₂ (MM) compound (I) (hereinafter, it may be referred to as "MM-containing compound (I)").

The usage amount of the salt having MM is usually 0.01 mol to 100 mol, preferably 0.02 mol to 50 mol, more preferably 0.1 mol to 30 mol relative to 1 mol of the acid group-containing compound (I). Mol.

The reaction temperature is usually 0°C to 100°C, preferably 0°C to 80°C, more preferably 0°C to 60°C, and still more preferably 0°C to 40°C.

The reaction time is usually 0.5 hours to 500 hours.

The reaction between the acid group-containing compound (I) and the salt having MM is usually carried out in the presence of a solvent. Examples of the solvent include: water; nitrile solvents such as acetonitrile; methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2- Alcohol solvents such as ethyl-1-hexanol, 1-octanol and phenol; amine solvents; ether solvents such as diethyl ether, tetrahydrofuran, and diphenyl ether; ketone solvents such as acetone and methyl isobutyl ketone; ethyl acetate Ester solvents such as esters and methyl benzoate; aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbons such as toluene, trimethylbenzene (for example, 1,3,5-trimethylbenzene), decalin and tetralin Solvent; dichloromethane, chloroform, 1,2-dichlorobenzene, trichlorobenzene (for example, 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene and other halogenated hydrocarbon solvents; nitrobenzene Equal nitrated hydrocarbon solvents; N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone and other amine solvents; dimethyl sulfide and other sulfide solvents , Preferably: water; nitrile solvents such as acetonitrile; alcohol solvents such as methanol, ethanol, 1-propanol, 2-propanol; ether solvents such as tetrahydrofuran; ketone solvents such as acetone; N,N-dimethylformamide, N , N-dimethylacetamide, N-methylpyrrolidone and other amide solvents; dimethyl sulfide and other sulfide solvents; and these mixed solvents, more preferably water.

The amount of the solvent used is usually 1 part by mass to 1000 parts by mass relative to 1 part by mass of the acid group-containing compound (I), preferably 10 parts by mass to 500 parts by mass, more preferably 20 parts by mass to 300 parts by mass .

The reaction between the acid group-containing compound (I) and the salt having MM can be carried out in the presence of a base.

Examples of the base include triethylamine, 4-(N,N-dimethylamino)pyridine, pyridine, piperidine, 1,8-diazabicyclo[5.4.0]undec-7- Ene, 1,5-diazabicyclo[4.3.0]non-5-ene, 1,5-diazabicyclo[4.3.0]non-5-ene and other organic bases, sodium methoxide, sodium ethoxide, Metal alkoxides such as sodium tributoxide and potassium tert-butoxide, organic metal compounds such as methyl lithium, butyl lithium, tertiary butyl lithium and phenyl lithium, sodium bicarbonate, potassium bicarbonate, sodium carbonate, potassium carbonate , Lithium hydroxide, sodium hydroxide, and potassium hydroxide and other inorganic bases, etc., Preferably it is an inorganic base, More preferably lithium hydroxide, sodium hydroxide, and potassium hydroxide, Further preferred are sodium hydroxide and potassium hydroxide, Particularly preferred is sodium hydroxide.

The amount of the base used is usually 1 mol to 100 mol, preferably 1 mol to 50 mol, more preferably 1 mol to 20 mol relative to 1 mol of the acid group-containing compound (I) , And more preferably 1 mol to 10 mol.

The method for extracting the compound (I) containing MM from the reaction mixture is not particularly limited, and various known methods can be used for extracting. For example, after the reaction is completed, the reaction mixture is filtered, whereby the compound (I) having -SO ₃ (MM) and/or -CO ₂ (MM) can be taken out. Furthermore, amine solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone, sulfenite solvents such as dimethyl sulfoxide, acetone, etc. can be used After washing the obtained residue with a ketone solvent, an alcohol solvent such as methanol, a nitrile solvent such as acetonitrile, water or these mixed solvents, it is washed and purified with a low boiling point alcohol such as water and methanol or these mixed solvents.

[Coloring composition] The coloring composition of the present invention includes compound (I) and solvent (E). According to the coloring composition of the present invention, compared with the coloring composition containing C.I. Pigment Yellow 138, a color filter having a stronger color can be formed. The color filter formed from the coloring composition of the present invention can be suitably used in display devices such as liquid crystal display devices. The colored composition of the present invention is preferably a yellow composition, an orange composition, a red composition, and a green composition.

The solid content in the coloring composition is less than 100% by mass relative to the total amount of the coloring composition, preferably 0.01% by mass or more and less than 100% by mass, more preferably 0.1% by mass or more and 99.9% by mass or less, More preferably, it is 0.1 mass% or more and 99 mass% or less, particularly preferably 1 mass% or more and 90 mass% or less, still more preferably 1 mass% or more and 80 mass% or less, and particularly preferably 1 mass% or more and 70 mass%. % Or less, extremely preferably 1 mass% or more and 60 mass% or less, most preferably 1 mass% or more and 50 mass% or less. In this specification, the "total amount of solid content" refers to the total amount of the components after removing the solvent (E) from the colored composition of the present invention. The total amount of solid content and the content of each component relative to it can be measured by known analysis means such as liquid chromatography or gas chromatography.

In the total solid content, the content of the compound (I) in the coloring composition is 100% by mass or less, preferably 0.0001% by mass or more and 99.9999% by mass or less, more preferably 0.0001% by mass or more and 99% by mass Or less, more preferably 0.0001 mass% or more and 90 mass% or less, particularly preferably 0.0001 mass% or more and 80 mass% or less, still more preferably 0.0001 mass% or more and 70 mass% or less, particularly preferably 0.0001 mass% or more and 60% by mass or less, extremely preferably 0.0001% by mass or more and 55% by mass or less, and most preferably 0.1% by mass or more and 55% by mass or less.

[Solvent (E)] The solvent (E) is not particularly limited, and solvents generally used in this field can be used. Examples of the solvent (E) include ester solvents (solvents containing -CO-O- and no -O- in the molecule), ether solvents (solvents containing -O- and no -CO-O- in the molecule) ), ether ester solvents (solvents containing -CO-O- and -O- in the molecule), ketone solvents (solvents containing -CO- and no -CO-O- in the molecule), alcohol solvents (in the molecule It contains OH and does not contain -O-, -CO- and -CO-O- solvents), aromatic hydrocarbon solvents, amide solvents, and dimethyl sulfide.

Examples of ester solvents include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutyrate, ethyl acetate, n-butyl acetate, isobutyl acetate, pentyl formate, and isoamyl acetate , Butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetate, ethyl acetate, cyclic Hexanol acetate and γ-butyrolactone, etc.

Examples of ether solvents 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, and Ethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-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, phenylethyl ether and methyl anisole, etc.

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

Examples of the ketone solvent include: 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2- Pentanone, cyclopentanone, cyclohexanone and isophorone, etc.

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

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

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

Two or more of these solvents may be used in combination.

Among the solvents, in terms of coatability and drying properties, an organic solvent having a boiling point of 120°C or more and 180°C or less at 1 atm is preferred. As the solvent, preferably, propylene glycol monomethyl ether acetate, ethyl lactate, propylene glycol monomethyl ether, 3-ethoxy ethyl propionate, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, Diethylene glycol monoethyl ether, 4-hydroxy-4-methyl-2-pentanone, and N,N-dimethylformamide, more preferably propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether , Ethyl lactate, ethyl 3-ethoxypropionate, and 4-hydroxy-4-methyl-2-pentanone, etc.

The content of the solvent (E) is less than 100% by mass relative to the total amount of the coloring composition, preferably 99.99% by mass or less, more preferably 0.1% by mass or more and 99.9% by mass or less, still more preferably 1% by mass or more, and 99.9% by mass or less, particularly preferably 10% by mass or more and 99% by mass or less, more preferably 20% by mass or more and 99% by mass or less, particularly preferably 30% by mass or more and 99% by mass or less, and extremely preferably 40% by mass % Or more and 99% by mass or less, most preferably 50% or more and 99% by mass or less.

[Resin (B)] The resin (B) is preferably an alkali-soluble resin, and more preferably a polymer having a structural unit derived from the following monomer (hereinafter referred to as "monomer (a)"), the monomer It is at least one selected from the group consisting of unsaturated carboxylic acid and unsaturated carboxylic anhydride. The resin (B) preferably has a structure derived from a monomer containing a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond (hereinafter, there is a case called "monomer (b)") Units, and copolymers of other structural units. As other structural units, examples include monomers derived from monomers (a) copolymerizable with monomers (which are different from monomers (a) and monomers (b); hereafter, there is a monomer called "monomer (C) "In the case of ") structural units, structural units having ethylenically unsaturated bonds, etc.

In this specification, the term "(meth)acrylic acid" means at least one selected from the group consisting of acrylic acid and methacrylic acid. Expressions such as "(meth)acryloyl" and "(meth)acrylate" also have the same meaning.

As the monomer (a), for example, unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, ortho-vinyl benzoic acid, m-vinyl benzoic acid, and p-vinyl benzoic acid can be cited; Maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid Unsaturated dicarboxylic acids such as dicarboxylic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyltetrahydrophthalic 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-2-ene, 5-carboxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-carboxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-carboxy-6-methylbicyclo[ 2.2.1]Hept-2-ene, 5-carboxy-6-ethylbicyclo[2.2.1]hept-2-ene and other bicyclic unsaturated compounds containing carboxyl groups; Maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinyl phthalic anhydride, 4-vinyl phthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1, Unsaturated dicarboxylic acid anhydrides such as 2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride; Succinic acid mono[2-(meth)acryloyloxyethyl] ester and phthalic acid mono[2-(meth)acryloyloxyethyl] ester and other polycarboxylic acids with more than two valence Unsaturated mono[(meth)acryloxyalkyl] ester; α-(Hydroxymeth)acrylic acid is equivalent to unsaturated acrylates containing hydroxyl and carboxyl groups in the same molecule.

Among these, acrylic acid, methacrylic acid, ortho-vinyl benzoic acid, m-vinyl benzoic acid, and para-vinyl benzoic acid are preferred in terms of copolymerization reactivity or solubility of the obtained resin in an alkaline aqueous solution. Vinyl benzoic acid and maleic anhydride, etc.

Monomer (b) means a cyclic ether structure having 2 to 4 carbon atoms (for example, at least one selected from the group consisting of an oxetane ring, an oxetane ring and a tetrahydrofuran ring) and Polymeric compounds with ethylenically unsaturated bonds. The monomer (b) is preferably a monomer having a cyclic ether structure having 2 to 4 carbon atoms and a (meth)acryloxy group.

As the monomer (b), for example, a monomer having an oxirane group and an ethylenically unsaturated bond (hereinafter, sometimes referred to as "monomer (b1)"), an oxa Monomers of cyclobutyl and ethylenically unsaturated bonds (hereinafter referred to as "monomers (b2)") and monomers with tetrahydrofuran groups and ethylenically unsaturated bonds (hereinafter, there are "Single body (b3)") etc.

As the monomer (b1), for example, a monomer having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized (hereinafter, there is a single body (b1) -1)") and a monomer having a structure in which an alicyclic unsaturated hydrocarbon is epoxidized (hereinafter, there is a case referred to as "monomer (b1-2)").

The monomer (b1-1) is preferably a monomer having a glycidyl group and an ethylenically unsaturated bond. As a single body (b1-1), for example: Glycidyl (meth)acrylate, β-methyl glycidyl (meth)acrylate, β-ethyl glycidyl (meth)acrylate, glycidyl vinyl ether, o-vinyl benzyl glycidyl ether , M-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, α-methyl-o-vinylbenzyl glycidyl ether, α-methyl-m-vinylbenzyl glycidyl ether, α-methyl Base-p-vinylbenzyl glycidyl ether, 2,3-bis(glycidyloxymethyl)styrene, 2,4-bis(glycidyloxymethyl)styrene, 2,5-bis (Glycidyloxymethyl)styrene, 2,6-bis(glycidyloxymethyl)styrene, 2,3,4-tris(glycidyloxymethyl)styrene, 2, 3,5-Tris(glycidyloxymethyl)styrene, 2,3,6-tris(glycidyloxymethyl)styrene, 3,4,5-tris(glycidyloxymethyl) Yl)styrene and 2,4,6-tris(glycidyloxymethyl)styrene, etc.

As the monomer (b1-2), for example, vinylcyclohexene monooxide, 1,2-epoxy-4-vinylcyclohexane (for example, Celloxide (registered Trademark) 2000; Daicel (manufactured by Daicel), 3,4-epoxycyclohexylmethyl (meth)acrylate (for example, Cyclomer (registered trademark) A400; Daicel) ( Stock), 3,4-epoxycyclohexyl methyl (meth)acrylate (for example, Cyclomer (registered trademark) M100; Daicel (Stock) manufacturing), formula (BI) The compound represented and the compound represented by formula (BII), etc.

[式（BI）及式（BII）中，R^a 及R^b 彼此獨立地表示氫原子、或碳數1～4的烷基，該烷基中所含的氫原子可經羥基取代； X^a 及X^b 彼此獨立地表示單鍵、*-R^c -、*-R^c -O-、*-R^c -S-或*-R^c -NH-； R^c 表示碳數1～6的烷二基； *表示與O的鍵結鍵][化93]

[In formula (BI) and formula (BII), 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 may be substituted by a hydroxyl group; X ^a and X ^b each independently represents a single ^{bond, * - R c -, *} - R c -O -, * - R c -S- or * -R ^c -NH-; R ^c represents alkyl having 1 to 6 carbon atoms in the Dibasic; * indicates the bond with O]

Examples of the alkyl group having 1 to 4 carbon atoms include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, and tert-butyl.

Examples of the alkyl group in which a hydrogen atom is substituted with a hydroxy group include hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 1-hydroxypropyl, 2-hydroxypropyl, and 3-hydroxypropyl. , 1-hydroxy-1-methylethyl, 2-hydroxy-1-methylethyl, 1-hydroxybutyl, 2-hydroxybutyl, 3-hydroxybutyl, 4-hydroxybutyl, etc.

As R ^a and R ^b, preferably include a hydrogen atom, methyl, hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, more preferably include a hydrogen atom, a methyl group.

Examples of alkanediyl groups include methylene, ethylene, propane-1,2-diyl, propane-1,3-diyl, butane-1,4-diyl, and pentane-1, 5-diyl, hexane-1,6-diyl, etc.

X ^a and X ^b preferably include single bonds, methylene groups, ethylene groups, *-CH ₂ -O- and *-CH ₂ CH ₂ -O-, more preferably single bonds, * -CH ₂ CH ₂ -O- (* indicates the bonding bond with O).

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

[化94]

[化95]

As the compound represented by the formula (BII), a compound represented by any one of the formula (BII-1) to the formula (BII-15) and the like can be mentioned. Among them, the formula (BII-1) and the formula Compounds represented by (BII-3), formula (BII-5), formula (BII-7), formula (BII-9) and formula (BII-11) to formula (BII-15), more preferably, include Compounds represented by formula (BII-1), formula (BII-7), formula (BII-9) and formula (BII-15).

[化97]

[化96]

[化97]

The compound represented by formula (BI) and the compound represented by formula (BII) may be used alone, respectively, or two or more of them may be used in combination. The compound represented by formula (BI) and the compound represented by formula (BII) may also be used in combination. When the compound represented by formula (BI) and the compound represented by formula (BII) are used in combination, the content ratio of these [compound represented by formula (BI): compound represented by formula (BII)] is expressed in moles It is preferably from 5:95 to 95:5, more preferably from 10:90 to 90:10, and still more preferably from 20:80 to 80:20.

As the monomer (b2), a monomer having an oxetanyl group and a (meth)acryloxy group is more preferable. As the monomer (b2), for example, 3-methyl-3-methacryloxymethyloxetane, 3-methyl-3-methacryloxymethyloxy Etidine, 3-ethyl-3-methylpropenyloxymethyloxetane, 3-ethyl-3-propenyloxymethyloxetane, 3-methyl 3-methylpropenyloxyethyloxetane, 3-methyl-3-propenyloxyethyloxetane, 3-ethyl-3-methylpropenyl Oxyethyl oxetane, 3-ethyl-3-propenyloxyethyl oxetane and the like.

The monomer (b3) is more preferably a monomer having a tetrahydrofuran group and a (meth)acryloxy group. As a monomer (b3), for example, tetrahydrofurfuryl acrylate (for example, Viscoat V#150, manufactured by Osaka Organic Chemical Industry Co., Ltd.), tetrahydrofurfuryl methacrylate Wait.

As the single-weight body (b), the single-weight body (b1) is preferable in terms of further improving the reliability of the obtained color filter such as heat resistance and chemical resistance. Furthermore, in terms of the excellent storage stability of the coloring composition, the monomer (b1-2) is more preferable.

As the monomer (c), for example, methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, second butyl (meth)acrylate, (meth)acrylate Base) tertiary butyl acrylate, 2-ethylhexyl (meth)acrylate, lauryl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, Cyclopentyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclo[5.2.1.0 ^2,6 ]decane-8 (meth)acrylate -Yl ester, (meth)acrylate tricyclo[5.2.1.0 ^2,6 ]decane-9-yl ester, (meth)acrylate tricyclo[5.2.1.0 ^2,6 ]decene-8-yl ester, (Meth) tricyclo [5.2.1.0 ^2,6 ] decene-9-yl ester, (meth) acrylate dicyclopentyl oxyethyl, (meth) acrylate isobornyl ester, (meth) Yl)adamantyl acrylate, allyl (meth)acrylate, propargyl (meth)acrylate, phenyl (meth)acrylate, naphthyl (meth)acrylate and (meth)acrylate (Meth)acrylates such as benzyl acrylate; (meth)acrylates containing hydroxyl groups such as 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate; (meth)acrylic acid 2 ,2,3,3,4,4,5,5-octafluoropentyl ester and other (meth)acrylates containing halogen atoms; diethyl maleate, diethyl fumarate and diethyl itaconic acid Dicarboxylic acid diesters such as esters; Bicyclo[2.2.1]hept-2-ene, 5-methylbicyclo[2.2.1]hept-2-ene, 5-ethylbicyclo[2.2.1]hept-2-ene Ene, 5-hydroxybicyclo[2.2.1]hept-2-ene, 5-hydroxymethylbicyclo[2.2.1]hept-2-ene, 5-(2'-hydroxyethyl)bicyclo[2.2.1] Hept-2-ene, 5-methoxybicyclo[2.2.1]hept-2-ene, 5-ethoxybicyclo[2.2.1]hept-2-ene, 5,6-dihydroxybicyclo[2.2. 1]Hept-2-ene, 5,6-bis(hydroxymethyl)bicyclo[2.2.1]hept-2-ene, 5,6-bis(2'-hydroxyethyl)bicyclo[2.2.1]hept -2-ene, 5,6-dimethoxybicyclo[2.2.1]hept-2-ene, 5,6-diethoxybicyclo[2.2.1]hept-2-ene, 5-hydroxy-5 -Methylbicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxymethyl-5-methylbicyclo[2.2.1 ]Hept-2-ene, 5-tertiary butoxycarbonylbicyclo[2.2.1]hept-2-ene, 5-cyclohexyloxycarbonylbicyclo[2.2.1]hept-2-ene, 5-phenoxy Carbonyl bicyclo[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-2-ene and other bicyclic unsaturated compounds物; N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimide benzoic acid Ester, N-succinimidyl-4-maleiminobutyrate, N-succinimidyl-6-maleiminohexanoate, N-succinimidyl-3- Dicarbonyl amide derivatives such as maleimide propionate and N-(9-acridinyl) maleimide; styrene, o-methylstyrene, m-methylstyrene, p-methyl Aromatic compounds containing vinyl groups such as styrene, vinyl toluene, 9-vinylcarbazole and p-methoxystyrene; (meth)acrylonitrile and other vinyl-containing nitriles; vinyl chloride and vinylidene chloride, etc. Halogenated hydrocarbons; (meth)acrylamide and other vinyl-containing amides; vinyl acetate and other esters; 1,3-butadiene, isoprene and 2,3-dimethyl-1,3- Diene such as butadiene etc.

Among these, in terms of copolymerization reactivity and heat resistance, styrene, vinyl toluene, tricyclo[5.2.1.0 ^2,6 ]decane-8-yl (meth)acrylate, (Meth) acrylate tricyclo[5.2.1.0 ^2,6 ]decane-9-yl ester, (meth)acrylate tricyclo[5.2.1.0 ^2,6 ]decene-8-yl ester, (meth) Acrylic tricyclo[5.2.1.0 ^2,6 ]decene-9-yl ester, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo [2.2.1] Hept-2-ene, phenyl (meth)acrylate, 2,2,3,3,4,4,5,5-octafluoropentyl (meth)acrylate, 9-vinyl Carbazole, benzyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, etc.

Specific examples of the resin (B) include: 3,4-epoxycyclohexylmethyl (meth)acrylate/(meth)acrylic acid copolymer, and 3,4-epoxy tricyclic (meth)acrylate [5.2. 1.0 ^2,6 ]decyl ester/(meth)acrylic acid copolymer, (meth)acrylic acid 3,4-epoxy tricyclo[5.2.1.0 ^2,6 ]decyl ester/(meth)acrylic acid benzyl ester/( (Meth)acrylic acid copolymer, (meth)acrylic acid 3,4-epoxy tricyclo[5.2.1.0 ^2,6 ]decyl ester/9-vinylcarbazole/(meth)acrylic acid copolymer, (meth)acrylic acid Acrylic acid 3,4-epoxy tricyclic [5.2.1.0 ^2,6 ]decyl ester/(meth)acrylate/o-vinyl benzoic acid copolymer, (meth)acrylic acid 3,4-epoxy tricyclic [5.2.1.0 ^2,6 ] Decyl ester/(meth)acrylic acid phenyl ester/m-vinyl benzoic acid copolymer, (meth)acrylic acid 3,4-epoxy tricyclo[5.2.1.0 ^2,6 ]deca Ester/phenyl(meth)acrylate/p-vinylbenzoic acid copolymer, 3,4-epoxy tricyclo[5.2.1.0 ^2,6 ]decyl(meth)acrylate/phenyl(meth)acrylate Ester/(meth)acrylic acid copolymer, (meth)acrylic acid 3,4-epoxy tricyclo[5.2.1.0 ^2,6 ]decyl/(meth)acrylic acid 2,2,3,3,4,4 ,5,5-octafluoropentyl ester/(meth)acrylic acid copolymer, glycidyl (meth)acrylate/benzyl (meth)acrylate/(meth)acrylic acid copolymer, (meth)acrylic acid condensation Glycerol ester/styrene/(meth)acrylic acid copolymer, (meth)acrylic acid 3,4-epoxy tricyclo[5.2.1.0 ^2,6 ]decyl ester/(meth)acrylic acid/N-cyclohexyl maleate Amide copolymer, (meth)acrylic acid 3,4-epoxy tricyclo[5.2.1.0 ^2,6 ]decyl ester/(meth)acrylic acid/N-cyclohexylmaleimide/(meth) Acrylic acid 2-hydroxyethyl copolymer, (meth)acrylic acid 3,4-epoxy tricyclo[5.2.1.0 ^2,6 ]decyl/(meth)acrylic acid/vinyl toluene copolymer, (meth)acrylic acid 3,4-epoxy tricyclo[5.2.1.0 ^2,6 ]decyl ester/(meth)acrylic acid/(meth)acrylic acid 2-ethylhexyl ester copolymer, (meth)acrylic acid 3,4-epoxy Tricyclo[5.2.1.0 ^2,6 ]decyl ester/(meth)acrylate tricyclo[5.2.1.0 ^2,6 ]decenyl ester/(meth)acrylic acid/N-cyclohexylmaleimide copolymer , 3-Methyl-3-(meth)acryloxymethyloxetane/(meth)acrylic acid/styrene copolymer, benzyl (meth)acrylate/(meth)acrylic acid Copolymers, styrene/(meth)acrylic copolymers, and resins described in Japanese Patent Laid-Open No. 9-106071, Japanese Patent Laid-Open No. 2004-29518, and Japanese Patent Laid-Open No. 2004-361455, etc. . Among them, the resin (B) is preferably a copolymer containing a structural unit derived from the monomer (a) and a structural unit derived from the monomer (b). The resin (B) can be a combination of two or more types. In this case, the resin (B) preferably contains at least one containing a structural unit derived from the monomer (a) and a structural unit derived from the monomer (b) The copolymer is more preferably a copolymer containing at least one structure unit derived from the monomer (a) and a structure unit derived from the monomer (b1), and more preferably at least one copolymer derived from the monomer ( The copolymer of the structural unit of a) and the structural unit derived from the monomer (b1-2), particularly preferably containing 3,4-epoxy tricyclic ring selected from (meth)acrylic acid [5.2.1.0 ^2,6 ] Decyl ester/(meth)acrylic acid copolymer, (meth)acrylic acid 3,4-epoxy tricyclo[5.2.1.0 ^2,6 ]decyl ester/(meth)acrylate/(meth)acrylic acid copolymer , (Meth)acrylic acid 3,4-epoxy tricyclo[5.2.1.0 ^2,6 ]decyl ester/(meth)acrylic acid/N-cyclohexylmaleimide/(meth)acrylic acid 2-hydroxy Ethyl copolymer, (meth)acrylic acid 3,4-epoxy tricyclo[5.2.1.0 ^2,6 ]decyl ester/(meth)acrylic acid/vinyl toluene copolymer, (meth)acrylic acid 3,4- One or more of epoxy tricyclic [5.2.1.0 ^2,6 ] decyl ester/(meth)acrylic acid/(meth)acrylic acid 2-ethylhexyl ester copolymer.

The weight average molecular weight (Mw) in terms of polystyrene of the resin (B) is preferably 1,000 to 100,000, more preferably 1,000 to 50,000, further preferably 1,000 to 30,000, particularly preferably 3,000 to 30,000, particularly preferably 5,000 to 30,000 .

The degree of dispersion [weight average molecular weight (Mw)/number average molecular weight (Mn)] of the resin (B) is preferably 1 to 6, more preferably 1 to 5, and still more preferably 1 to 4.

The acid value (solid content conversion value) of the resin (B) is preferably 10 mg-KOH/g to 500 mg-KOH/g, more preferably 20 mg-KOH/g to 450 mg-KOH/g, and still more preferably 20 mg-KOH/g～400 mg-KOH/g, more preferably 20 mg-KOH/g～370 mg-KOH/g, still more preferably 30 mg-KOH/g～370 mg-KOH/g, Still more preferably 30 mg-KOH/g～350 mg-KOH/g, particularly preferably 30 mg-KOH/g～340 mg-KOH/g, most preferably 30 mg-KOH/g～335 mg-KOH/ g. Here, the acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of the resin (B), and it can be determined, for example, by titration using an aqueous potassium hydroxide solution.

In the coloring composition, the content of the resin (B) relative to the total solid content is less than 100% by mass, preferably 0.00001% by mass or more and 99.99999% by mass or less, more preferably 1% by mass or more and 99% by mass or less , More preferably 1% by mass or more and 97% by mass or less, more preferably 1% by mass or more and 95% by mass or less, still more preferably 3% by mass or more and 95% by mass or less, particularly preferably 5% by mass or more and 95% by mass Mass% or less, very preferably 10 mass% or more and 95 mass% or less.

[Preparation of liquid containing compound (I)] The coloring composition of the present invention can be used to prepare a coloring composition after preparing a compound (I)-containing liquid containing the compound (I) and a solvent (E) in advance, and then using the compound (I)-containing liquid. In the case where the compound (I) is not dissolved in the solvent (E), the liquid containing the compound (I) can also be prepared by dispersing the compound (I) in the solvent (E) and mixing. The liquid containing the compound (I) may contain a part or all of the solvent (E) contained in the coloring composition. Furthermore, the liquid containing the compound (I) is included in the coloring composition of the present invention.

The solid content of the liquid containing the compound (I) is less than 100% by mass relative to the total amount of the liquid containing the compound (I), preferably 0.01% by mass to 99.99% by mass, more preferably 0.1% by mass Above and 99.9 mass% or less, more preferably 0.1 mass% or more and 99 mass% or less, particularly preferably 1 mass% or more and 90 mass% or less, still more preferably 1 mass% or more and 80 mass% or less, particularly preferably 1% by mass or more and 70% by mass or less, extremely preferably 1% by mass or more and 60% by mass or less, most preferably 1% by mass or more and 50% by mass or less.

The content rate of the compound (I) in the liquid containing the compound (I) in the total amount of solids in the liquid containing the compound (I) is 100% by mass or less, preferably 0.0001% by mass or more and 99.9999% by mass or less , More preferably 0.0001 mass% or more and 99 mass% or less, still more preferably 1 mass% or more and 99 mass% or less, particularly preferably 3 mass% or more and 99 mass% or less, and still more preferably 5 mass% or more and 99 mass% Less than mass%.

Compound (I) may be treated with rosin, surface treatment using derivatives introduced with acidic or basic groups, etc., grafting treatment on the surface of compound (I) with polymer compounds, etc., and micronization with sulfuric acid Micronization treatment such as method, salt milling method, etc., cleaning treatment with organic solvent or water for removing impurities, removal treatment of ionic impurities by ion exchange method, etc. In addition, the compound (I) may also be subjected to the following treatments as needed: crystal structure conversion, particle shaping, and/or substantially uniformizing the particle size; Compound (I) is mixed with water and/or an organic solvent, stirred and/or heated while stirring to obtain a suspension, and then the suspension is filtered to obtain a compound (I) with a changed crystal structure ； Treatment of changing the crystal structure of compound (I) by performing recrystallization; Mix compound (I) with water, sulfuric acid or organic solvent, stir and/or stir while heating to obtain a solution or suspension, then mix the solution or suspension with a poor solvent for compound (I) , After obtaining the suspension, filtering the suspension to obtain the compound (I) whose crystal structure has changed; The compound (I), the derivative, and water and/or organic solvent are mixed, stirred and/or heated while stirring to obtain a suspension, and then the suspension is filtered to obtain a crystal structure containing a change Treatment of a mixture of compound (I) and/or treatment of mixing compound (I) with a derivative; By recrystallizing the mixture of the compound (I) and the derivative to obtain a mixture containing the compound (I) whose crystal structure has changed and/or the treatment of mixing the compound (I) and the derivative; The compound (I) is mixed with the derivative, water, sulfuric acid or an organic solvent, and stirred and/or heated while stirring to obtain a solution or suspension, and then the solution or the suspension is mixed with the compound (I) After mixing with poor solvents and obtaining a suspension, the suspension is filtered to obtain a mixture containing the compound (I) whose crystal structure has changed and/or a treatment to mix the compound (I) with a derivative, etc. In the case of using a plurality of compounds (I) or derivatives, these treatments may be performed individually, or a plurality of types may be mixed to perform these treatments. The particle size of the compound (I) is preferably substantially uniform.

As the organic solvent used in the transformation of the crystal structure, one may cite: Nitrile solvents such as acetonitrile; methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1 -Alcohol solvents such as octanol and phenol; amine solvents; ether solvents such as diethyl ether, tetrahydrofuran and diphenyl ether; ketone solvents such as acetone and methyl isobutyl ketone; ester solvents such as ethyl acetate and methyl benzoate ; Aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene, trimethylbenzene (for example, 1,3,5-trimethylbenzene), decalin and tetralin; dichloromethane, chloroform, 1 ,2-Dichlorobenzene, trichlorobenzene (for example, 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene and other halogenated hydrocarbon solvents; nitrobenzene and other nitrolated hydrocarbon solvents; N, N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone and other amine solvents; dimethyl sulfide and other sulfide solvents.

Examples of the poor solvent include: Nitrile solvents such as acetonitrile; methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1 -Alcohol solvents such as octanol and phenol; amine solvents; ether solvents such as diethyl ether, tetrahydrofuran and diphenyl ether; ketone solvents such as acetone and methyl isobutyl ketone; ester solvents such as ethyl acetate and methyl benzoate ; Aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene, trimethylbenzene (for example, 1,3,5-trimethylbenzene), decalin and tetralin; dichloromethane, chloroform, 1 ,2-Dichlorobenzene, trichlorobenzene (for example, 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene and other halogenated hydrocarbon solvents; nitrobenzene and other nitrolated hydrocarbon solvents.

As a derivative, the compound represented by formula (z), the compound represented by formula (z1), etc. are mentioned.

[化98]

[化99]

When the liquid containing the compound (I) contains a derivative, the content of the derivative relative to 100 parts by mass of the compound (I) is 0.01 part by mass or more and 100 parts by mass or less, preferably 0.01 part by mass or more and 70 parts by mass or less, more preferably 0.1 parts by mass or more and 50 parts by mass or less, still more preferably 0.1 parts by mass or more and 30 parts by mass or less, and particularly preferably 0.1 parts by mass or more and 20 parts by mass or less.

The compound (I) can be in a state where the compound (I) is uniformly dispersed in a liquid containing the compound (I) by containing a dispersant and performing a dispersion treatment. When multiple types of compounds (I) are used, the dispersion treatment may be performed individually, or multiple types may be mixed to perform the dispersion treatment.

As a dispersing agent, surfactant etc. are mentioned, It can be any of a cationic, anionic, nonionic, and amphoteric surfactant. Specific examples include polyester-based, polyamine-based, and acrylic-based surfactants. These dispersants can be used alone or in combination of two or more. As a dispersant, if it is represented by a trade name, it can include: KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Flowlen (manufactured by Kyoeisha Chemical Co., Ltd.), and Solsperse (Registered trademark) (manufactured by Zeneca (shares)), EFKA (registered trademark) (manufactured by BASF), Ajisper (registered trademark) (Ajinomoto Fine technology (manufactured by Ajinomoto Fine-Techno (stock)), DISPERBYK (registered trademark) (manufactured by BYK-Chemie (stock)), and BYK (registered trademark) ) (Manufactured by BYK-Chemie (stock)) etc.

When the liquid containing the compound (I) contains a dispersant, the amount of the dispersant (solid content) used relative to 100 parts by mass of the compound (I) is, for example, 0.01 part by mass or more and 10,000 parts by mass or less, preferably 0.01 parts by mass or more and 5000 parts by mass or less, more preferably 0.01 parts by mass or more and 1000 parts by mass or less, still more preferably 0.1 parts by mass or more and 500 parts by mass or less, particularly preferably 0.1 parts by mass or more and 300 parts by mass or less, and further It is particularly preferably 1 part by mass or more and 300 parts by mass or less, and particularly preferably 5 parts by mass or more and 260 parts by mass or less. If the amount of the dispersant used is within the above range, there is a tendency that a liquid containing the compound (I) in a more uniform dispersion state can be obtained.

The coloring composition of the present invention includes resin (B), and a liquid containing compound (I) containing compound (I) and solvent (E) is prepared in advance, and then the liquid containing compound (I) is used to prepare the coloring of the present invention In the case of a composition, the liquid containing the compound (I) may contain a part or all of the resin (B) contained in the coloring composition, and preferably contains a part in advance. By including the resin (B) in advance, the dispersion stability of the liquid containing the compound (I) can be further improved.

When the liquid containing compound (I) contains resin (B), the content of resin (B) relative to 100 parts by mass of compound (I) is, for example, 0.01 part by mass or more and 10,000 parts by mass or less, preferably 0.01 parts by mass Part or more and 5000 parts by mass or less, more preferably 0.01 part by mass or more and 1000 parts by mass or less, still more preferably 0.1 part by mass or more and 500 parts by mass or less, particularly preferably 0.1 part by mass or more and 300 parts by mass or less.

[Polymerizable compound (C)] The polymerizable compound (C) is a compound that can be polymerized by living radicals and/or acid generated from the polymerization initiator (D), for example, a polymerizable compound having an ethylenically unsaturated bond, etc., preferably (Meth)acrylate compound.

As a polymerizable compound having one ethylenically unsaturated bond, for example, nonylphenyl carbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexyl carbitol acrylate Ester, 2-hydroxyethyl acrylate, N-vinylpyrrolidone, etc., as well as the monomer (a), the monomer (b), and the monomer (c).

As a polymerizable compound having two ethylenically unsaturated bonds, for example, 1,6-hexanediol di(meth)acrylate, ethylene glycol di(meth)acrylate, neopentyl glycol di (Meth)acrylate, triethylene glycol di(meth)acrylate, bis(acryloxyethyl) ether of bisphenol A, 3-methylpentanediol di(meth)acrylate, etc.

Among them, the polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds. Examples of such polymerizable compounds include trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, and dipentaerythritol penta(meth)acrylate. Acrylate, dipentaerythritol hexa(meth)acrylate, tripentaerythritol octa(meth)acrylate, tripentaerythritol hepta(meth)acrylate, pentaerythritol deca(meth)acrylate, pentaerythritol nine(meth)acrylate Acrylate, tris(2-(meth)acryloyloxyethyl) isocyanurate, ethylene glycol modified pentaerythritol tetra(meth)acrylate, ethylene glycol modified dipentaerythritol hexa(methyl) )Acrylate, propylene glycol modified pentaerythritol tetra(meth)acrylate, propylene glycol modified dipentaerythritol hexa(meth)acrylate, caprolactone modified pentaerythritol tetra(meth)acrylate and caprolactone modified dipentaerythritol The hexa(meth)acrylate etc. preferably include dipentaerythritol penta(meth)acrylate and dipentaerythritol hexa(meth)acrylate.

The weight average molecular weight of the polymerizable compound (C) is preferably 50 or more and 4000 or less, more preferably 50 or more and 3500 or less, still more preferably 50 or more and 3000 or less, particularly preferably 150 or more and 2,900 or less, particularly preferably 250 Above and below 1,500.

In the coloring composition, the content of the polymerizable compound (C) relative to the total solid content is less than 100% by mass, preferably 0.00001% by mass or more and 99.99999% by mass, more preferably 1% by mass or more and 99% by mass % Or less, more preferably 1 mass% or more and 97 mass% or less, particularly preferably 1 mass% or more and 95 mass% or less, still more preferably 1 mass% or more and 90 mass% or less, particularly preferably 2 mass% or more And 80% by mass or less, very preferably 3% by mass or more and 70% by mass or less.

[Polymerization initiator (D)] The polymerization initiator (D) is not particularly limited as long as it is a compound that can generate a living radical, acid, etc. by the action of light or heat to initiate polymerization, and a known polymerization initiator can be used. Examples of the polymerization initiator (D) include oxime compounds such as O-acyl oxime compounds, phenalkyl ketone compounds, biimidazole compounds, triazine compounds, and acyl phosphine oxide compounds.

As the O-acetoxime compound, for example, N-benzyloxy-1-(4-phenylthiophenyl)butan-1-one-2-imine, N-benzyloxy-1-(4-phenylthiophenyl)butan-1-one-2-imine Baseoxy-1-(4-phenylthiophenyl)octane-1-one-2-imine, N-benzyloxy-1-(4-phenylthiophenyl)-3- Cyclopentylpropane-1-one-2-imine, N-acetoxy-1-(4-phenylthiophenyl)-3-cyclopentylpropane-1-one-2-imine, N -Acetyloxy-1-(4-phenylthiophenyl)-3-cyclohexylpropane-1-one-2-imine, N-acetoxy-1-[9-ethyl-6- (2-Methylbenzyl)-9H-carbazol-3-yl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6-{2-methyl -4-(3,3-Dimethyl-2,4-dioxolanemethyloxy)benzyl}-9H-carbazol-3-yl)ethane-1-imine , N-acetoxy-1-[9-ethyl-6-(2-methylbenzyl)-9H-carbazol-3-yl]-3-cyclopentylpropane-1-imine And N-benzyloxy-1-[9-ethyl-6-(2-methylbenzyl)-9H-carbazol-3-yl]-3-cyclopentylpropane-1- Keto-2-imine, etc. In addition, as O-acetoxime compounds, commercial products such as Irgacure OXE01, OXE02 (above, manufactured by BASF) and N-1919 (manufactured by ADEKA (stock)) can also be used. Product. Among them, the O-acyl oxime compound is preferably selected from N-benzyloxy-1-(4-phenylthiophenyl)butan-1-one-2-imine, N-benzene Formyloxy-1-(4-phenylthiophenyl)octane-1-one-2-imine and N-benzyloxy-1-(4-phenylthiophenyl)- At least one of the group consisting of 3-cyclopentylpropane-1-one-2-imine, more preferably N-benzyloxy-1-(4-phenylthiophenyl)octane -1-keto-2-imine.

Examples of phenalkyl ketone compounds include 2-methyl-2-morpholinyl-1-(4-methylthiophenyl)propane-1-one, 2-dimethylamino-1-(4 -Morpholinylphenyl)-2-benzylbutane-1-one and 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-( 4-morpholinyl)phenyl]butan-1-one and the like. As the phenalkyl ketone compound, commercial products such as Irgacure 369, 907, and 379 (above, manufactured by BASF) can also be used. Examples of phenalkyl ketone compounds include 2-hydroxy-2-methyl-1-phenylpropane-1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy Yl)phenyl]propan-1-one, 1-hydroxycyclohexylphenyl ketone, 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propan-1-one oligomer, α,α-diethoxyacetophenone and benzyl dimethyl ketal, etc.

As the biimidazole compound, for example, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3 -Dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole (for example, refer to Japanese Patent Laid-Open No. 6-75372, Japanese Patent Laid-Open No. 6-75373, etc.), 2, 2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(alkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4 ',5,5'-tetrakis(dialkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetrakis(trialkoxybenzene) Group) biimidazole (for example, refer to Japanese Patent Publication No. 48-38403, Japanese Patent Application Publication No. 62-174204, etc.) and the 4,4',5,5'-position phenyl group is composed of an alkoxycarbonyl group ( carboalkoxy) substituted biimidazole compounds (for example, refer to Japanese Patent Laid-Open No. 7-10913 etc.).

Examples of triazine compounds include: 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 2,4-bis(trichloromethyl) Yl)-6-(4-methoxynaphthyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxystyryl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-〔2 -(5-Methylfuran-2-yl)vinyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)ethylene Base]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)vinyl]-1 ,3,5-triazine and 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)vinyl]-1,3,5-triazine, etc. .

As an acylphosphine oxide compound, 2,4,6-trimethylbenzyldiphenylphosphine oxide etc. are mentioned. Commercial products such as Irgacure (registered trademark) 819 (made by BASF) can also be used.

Furthermore, as the polymerization initiator (D), benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, and the like; benzophenone, methyl benzoin benzoate , 4-phenylbenzophenone, 4-benzyl-4'-methyldiphenyl sulfide, 3,3',4,4'-tetra(tert-butylperoxycarbonyl)diphenyl Benzophenone compounds such as ketone and 2,4,6-trimethylbenzophenone; Quinone compounds such as 9,10-phenanthrenequinone, 2-ethylanthraquinone and camphorquinone; 10-Butyl-2- Chloracridone, benzil, methyl phenylglyoxylate and titanocene compounds, etc. These are preferably used in combination with the polymerization initiation aid described later (hereinafter, sometimes referred to as polymerization initiation aid (D1)), especially amines.

The polymerization initiator (D) is preferably a polymerization initiator comprising at least one selected from the group consisting of a phenalkyl ketone compound, a triazine compound, an phosphine oxide compound, an oxime compound, and a biimidazole compound, It is more preferably a polymerization initiator containing an oxime compound, and still more preferably a polymerization initiator containing an O-acyl oxime compound.

The content of the polymerization initiator (D) relative to the total amount of the resin (B) and the polymerizable compound (C) is preferably 0.001 mass% or more and 60 mass% or less, more preferably 0.01 mass% or more and 50 mass% %the following.

[Polymerization initiation aid (D1)] The coloring composition of the present invention may also contain a polymerization initiation assistant (D1). The polymerization start auxiliary agent (D1) is a compound or a sensitizer for accelerating the polymerization of the polymerizable compound (C) that starts polymerization by the polymerization initiator (D). When the polymerization initiator (D1) is contained, it is usually used in combination with the polymerization initiator (D). Examples of the polymerization initiation aid (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds, and carboxylic acid compounds.

Examples of amine compounds include: triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, 4-dimethyl Isoamyl aminobenzoate, 2-dimethylaminoethyl benzoate, 2-ethylhexyl 4-dimethylaminobenzoate, N,N-dimethyl-p-toluidine, 4,4 '-Bis(dimethylamino)benzophenone (commonly known as Michler's ketone), 4,4'-bis(diethylamino)benzophenone and 4,4'-bis (Ethylmethylamino)benzophenone and the like, preferably 4,4'-bis(diethylamino)benzophenone. In addition, as the amine compound, commercially available products such as EAB-F (manufactured by Hodogaya Chemical Co., Ltd.) can also be used.

Examples of alkoxyanthracene compounds include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl- 9,10-diethoxyanthracene, 9,10-dibutoxyanthracene and 2-ethyl-9,10-dibutoxyanthracene, etc.

Examples of the thioxanthone compound include: 2-isopropyl thioxanthone, 4-isopropyl thioxanthone, 2,4-diethyl thioxanthone, 2,4-dichlorothioxanthone Anthrone and 1-chloro-4-propoxythioxanthone, etc.

Examples of carboxylic acid compounds include: thiophenylacetic acid, methylthiophenylacetic acid, ethylphenylthioacetic acid, methylethylthiophenylacetic acid, dimethylthiophenylacetic acid, and methoxyphenylthioacetic acid. Acetic acid, dimethoxyphenylthioacetic acid, chlorophenylthioacetic acid, dichlorophenylthioacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine And naphthoxyacetic acid and so on.

In the case of using these polymerization initiation aids (D1), their content relative to the total amount of the resin (B) and the polymerizable compound (C) is preferably 0.00001 mass% or more and 60 mass% or less, and more Preferably, it is 0.0001 mass% or more and 50 mass% or less.

[Colorant (A1)] The coloring composition of the present invention may contain a coloring agent other than the compound (I) (hereinafter, it may be referred to as a coloring agent (A1)). The coloring agent (A1) may contain one or two or more coloring agents. The colorant (A1) preferably contains one or more selected from a yellow colorant, an orange colorant, a red colorant, and a green colorant, and more preferably contains one or more selected from a yellow colorant and a green colorant.

The colorant (A1) may be a dye or a pigment. As the dye, known dyes can be used. For example, the dye index (Color Index) (published by The Society of Dyers and Colourists) and dyeing notes (Shikisensha) can be cited. Of well-known dyes. In addition, according to the chemical structure, azo dyes, cyanine dyes, triphenylmethane dyes, xanthene dyes, anthraquinone dyes, naphthoquinone dyes, quinonimine dyes, methine dyes, azomethine Dyes, squaraine dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline dyes, nitro dyes, phthalocyanine dyes, perylene dyes, quinophthalone dyes, isoindoline dyes, etc. These dyes can be used alone or in combination of two or more.

Specific examples include the following general dye index (C.I.) dyes. CI solvent yellow 4, 14, 15, 23, 24, 25, 38, 62, 63, 68, 79, 81, 82, 83, 89, 94, 98, 99, 117, 162, 163, 167 , 189; CI solvent red (solvent red) 24, 45, 49, 90, 91, 111, 118, 119, 122, 124, 125, 127, 130, 132, 143, 145, 146, 150, 151, 155, 160, 168 , 169, 172, 175, 181, 207, 218, 222, 227, 230, 245, 247; C.I. Solvent orange 2, 7, 11, 15, 26, 41, 54, 56, 77, 86, 99; C.I. Solvent violet (solvent violet) 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60; CI solvent blue 4, 5, 14, 18, 35, 36, 37, 38, 44, 45, 58, 59, 59: 1, 63, 67, 68, 69, 70, 78, 79, 83 , 90, 94, 97, 98, 100, 101, 102, 104, 105, 111, 112, 122, 128, 132, 136, 139; C.I. Solvent green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35, etc. C.I. Solvent dyes, CI acid yellow (acid yellow) 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99 , 111, 112, 113, 114, 116, 119, 123, 128, 134, 135, 138, 139, 140, 144, 150, 155, 157, 160, 161, 163, 168, 169, 172, 177, 178 , 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251 ； CI acid red (acid red) 1, 4, 8, 14, 17, 18, 26, 27, 29, 31, 33, 34, 35, 37, 40, 42, 44, 50, 51, 52, 57, 66 , 73, 76, 80, 87, 88, 91, 92, 94, 95, 97, 98, 103, 106, 111, 114, 129, 133, 134, 138, 143, 145, 150, 151, 155, 158 , 160, 172, 176, 182, 183, 195, 198, 206, 211, 215, 216, 217, 227, 228, 249, 252, 257, 258, 260, 261, 266, 268, 270, 274, 277 , 280, 281, 289, 308, 312, 315, 316, 339, 341, 345, 346, 349, 382, 383, 388, 394, 401, 412, 417, 418, 422, 426; CI acid orange (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. acid violet (acid violet) 6B, 7, 9, 15, 16, 17, 19, 21, 23, 24, 25, 30, 34, 38, 49, 72, 102; CI acid blue (acid blue) 1, 3, 5, 7, 9, 11, 13, 15, 17, 18, 22, 23, 24, 25, 26, 27, 29, 34, 38, 40, 41, 42 , 43, 45, 48, 51, 54, 59, 60, 62, 70, 72, 74, 75, 78, 80, 82, 83, 86, 87, 88, 90, 90: 1, 91, 92, 93 ,93:1,96,99,100,102,103,104,108,109,110,112,113,117,119,120,123,126,127,129,130,131,138,140,142 ,143,147,150,151,154,158,161,166,167,168,170,171,175,182,183,184,187,192,199,203,204,205,210,213,229 , 234, 236, 242, 243, 249, 256, 259, 267, 269, 278, 280, 285, 290, 296, 315, 324:1, 335, 340; CI acid green 1,3,5,6,7,8,9,11,13,14,15,16,22,25,27,28,41,50,50:1,58,63 , 65, 80, 104, 105, 106, 109 and other CI acid dyes, CI direct yellow 2, 4, 28, 33, 34, 35, 38, 39, 43, 44, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95 , 98, 102, 108, 109, 129, 132, 136, 138, 141; CI direct red 79, 82, 83, 84, 91, 92, 96, 97, 98, 99, 105, 106, 107, 172, 173, 176, 177, 179, 181, 182, 184, 204 , 207, 211, 213, 218, 220, 221, 222, 232, 233, 234, 241, 243, 246, 250; C.I. direct orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107; C.I. direct violet 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104; CI direct blue (direct blue) 1, 2, 3, 6, 8, 15, 22, 25, 28, 29, 40, 41, 42, 47, 52, 55, 57, 71, 76, 77, 78, 80 , 81, 84, 85, 86, 87, 90, 93, 94, 95, 97, 98, 99, 100, 101, 106, 107, 108, 109, 113, 114, 115, 117, 119, 120, 137 , 149, 150, 153, 155, 156, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168, 170, 171, 172, 173, 188, 189, 190, 192, 193 , 194, 195, 196, 198, 199, 200, 201, 202, 203, 207, 209, 210, 212, 213, 214, 222, 225, 226, 228, 229, 236, 237, 238, 242, 243 ,244,245,246,247,248,249,250,251,252,256,257,259,260,268,274,275,293; C.I. direct green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 79, 82 and other C.I. direct dyes, C.I. Disperse yellow 51, 54, 76; C.I. disperse violet (disperse violet) 26, 27; C.I. Disperse blue (disperse blue) 1, 14, 56, 60 and other C.I. Disperse dyes, C.I. Basic red (basic red) 1, 10; CI basic blue (basic blue) 1, 3, 5, 7, 9, 19, 21, 22, 24, 25, 26, 28, 29, 40, 41, 45, 47, 54, 58, 59, 60, 64, 65, 66, 67, 68, 81, 83, 88, 89; C.I. Basic violet (basic violet) 2; C.I. Basic Red 9; C.I. basic green (basic green) 1 and other C.I. basic dyes, C.I. Reactive yellow (reactive yellow) 2, 76, 116; C.I. Reactive orange (reactive orange) 16; C.I. reactive red 36 and other C.I. reactive dyes, C.I. Mordant yellow (mordant yellow) 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65; CI mordant red 1, 2, 3, 4, 9, 11, 12, 14, 17, 18, 19, 22, 23, 24, 25, 26, 27, 29, 30, 32, 33, 36 , 37, 38, 39, 41, 42, 43, 45, 46, 48, 52, 53, 56, 62, 63, 71, 74, 76, 78, 85, 86, 88, 90, 94, 95; CI Mordant orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48 ； CI mordant violet (mordant violet) 1, 1: 1, 2, 3, 4, 5, 6, 7, 8, 10, 11, 14, 15, 16, 17, 18, 19, 21, 22, 23, 24 , 27, 28, 30, 31, 32, 33, 36, 37, 39, 40, 41, 44, 45, 47, 48, 49, 53, 58; CI mordant blue (mordant blue) 1, 2, 3, 7, 8, 9, 12, 13, 15, 16, 19, 20, 21, 22, 23, 24, 26, 30, 31, 32, 39, 40 , 41, 43, 44, 48, 49, 53, 61, 74, 77, 83, 84; C.I. Mordant green 1, 3, 4, 5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 41, 43, 53, etc. C.I. Mordant dyes, C.I. vat green 1 etc. C.I. vat dyes etc.

Furthermore, Lumogen (registered trademark) which is a product of BASF can be cited, including: Lumogen (registered trademark) F yellow 083 (made by BASF), Lumogen (Registered trademark) F yellow 170 (made by BASF), Lumogen (registered trademark) F orange 240 (made by BASF) and Lumogen (registered trademark) F red 305 (made by BASF) BASF) manufactured).

In addition, the compound represented by the formula (z), the compound represented by the formula (z1), and the like can be mentioned.

[化100]

[化101]

As the pigment, a well-known pigment can be used, for example, pigments classified as pigments in the Dye Index (published by The Society of Dyers and Colourists). These can be used alone or in combination of two or more kinds. Specific examples include: CI Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 129 , 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 185, 194, 214, 231 and other yellow pigments; C.I. Pigment orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73 and other orange pigments; CI pigment red (pigment red) 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 178, 179, 180, 190, 192, 209, 215, 216, 224, 242, 254 , 255, 264, 265, 266, 268, 269, 273 and other red pigments; C.I. Pigment blue 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 60 and other blue pigments; C.I. purple pigments such as pigment violet 1, 19, 23, 29, 32, 36, 38; C.I. Pigment green 7, 36, 58, 59, 62, 63 and other green pigments; C.I. pigment brown (pigment brown) 23, 25 and other brown pigments; C.I. Pigment black (pigment black) 1, 7, 31, 32 and other black pigments.

As the coloring agent (A1), preferred are yellow dyes and yellow pigments (hereinafter, these are collectively referred to as "yellow colorants"), orange dyes and orange pigments (hereinafter, these are collectively referred to as "orange coloring In the case of "agents"), red dyes and red pigments (hereinafter, these are collectively referred to as "red colorants"), green dyes and green pigments (hereinafter, these may be collectively referred to as "green colorants" ), more preferably a yellow colorant and a green colorant, further preferably a yellow pigment and a green pigment, and particularly preferably a green pigment.

Examples of the yellow dye include dyes whose hue is classified as yellow among the dyes, and examples of yellow pigments include those whose hue is classified as yellow among the pigments. As the yellow colorant, yellow dyes and yellow pigments are preferred, yellow pigments are more preferred, quinophthalone pigments, metal-containing pigments, isoindoline pigments are more preferred, and CI Pigment Yellow 129, 138, 139 are particularly preferred. , 150, 185, 231, and more preferably CI Pigment Yellow 138, 139, 150, 185, 231.

Examples of orange dyes include those whose hue is classified as orange among the dyes, and examples of orange pigments include those whose hue is classified as orange among the pigments. As orange colorants, orange dyes and orange pigments are preferred, orange pigments are more preferred, and CI pigment orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73.

Examples of the red dye include dyes whose hue is classified as red among the dyes, and examples of red pigments include pigments whose hue is classified as red among the pigments. As the red colorant, red dyes and red pigments are preferred, and azo dyes, anthraquinone dyes, triphenylmethane dyes, xanthene dyes, perylene dyes, azo pigments, diketopyrrolopyrrole pigments, Anthraquinone pigments, triphenylmethane dyes, xanthene pigments, and perylene pigments, and more preferably CI Acid Red 52, CI Pigment Red 144, 177, 179, 242, 254, and 269.

Moreover, as a yellow coloring agent, an orange coloring agent, or a red coloring agent, you may use the xanthene compound etc. which are described in Unexamined-Japanese-Patent No. 2013-235257.

Examples of the green dye include dyes whose hue is classified as green among the dyes, and examples of green pigments include those whose hue is classified as green among the pigments. As the green coloring agent, green dyes and green pigments are preferred, green pigments are more preferred, and phthalocyanine pigments are further preferred, and copper phthalocyanine halide pigments, zinc phthalocyanine halide pigments, and aluminum-zinc phthalocyanine halide pigments are particularly preferred. Particularly preferred are CI Pigment Green 7, 36, 58, 59, 62 and 63.

[Preparation of liquid containing colorant (A1)] In the case where the coloring composition of the present invention contains a colorant (A1), a liquid containing the colorant (A1) containing the colorant (A1) and the solvent (E) can be used beforehand. ) Liquid to prepare the coloring composition. In the case where the colorant (A1) is not dissolved in the solvent (E), the liquid containing the colorant (A1) can also be prepared by dispersing and mixing the colorant (A1) in the solvent (E). The liquid containing the coloring agent (A1) may contain a part or all of the solvent (E) contained in the coloring composition.

The solid content of the liquid containing the colorant (A1) is less than 100% by mass relative to the total amount of the liquid containing the colorant (A1), preferably 0.01% by mass or more and 99.99% by mass or less, and more preferably 0.1% by mass or more and 99.9% by mass or less, more preferably 0.1% by mass or more and 99% by mass or less, more preferably 1% by mass or more and 90% by mass or less, and still more preferably 1% by mass or more and 80% by mass or less, It is particularly preferably 1% by mass or more and 70% by mass or less, extremely preferably 1% by mass or more and 60% by mass or less, and most preferably 1% by mass or more and 50% by mass or less.

The content of the coloring agent (A1) in the liquid containing the coloring agent (A1) is 100% by mass or less, preferably 0.0001% by mass or more, among the total amount of solids in the liquid containing the colorant (A1). 99.9999 mass% or less, more preferably 0.0001 mass% or more and 99 mass% or less, furthermore preferably 1 mass% or more and 99 mass% or less, particularly preferably 3 mass% or more and 99 mass% or less, and still more preferably 5 mass% % Or more and 99% by mass or less.

The coloring agent (A1) can be treated with rosin, surface treatment using derivatives introduced with acidic or basic groups, etc., grafting treatment to the surface of the coloring agent (A1) using polymer compounds, and sulfuric acid Micronization treatment such as micronization method, salt milling method, etc., cleaning treatment using organic solvents or water to remove impurities, removal treatment of ionic impurities by ion exchange method, etc., the same crystal as compound (I) Transformation of structure, shaping of particles and/or approximate uniformization of particle size, etc. The particle size of the colorant (A1) is preferably approximately uniform.

The coloring agent (A1) contains a dispersing agent and performing a dispersion treatment, so that the coloring agent (A1) can be uniformly dispersed in a liquid containing the coloring agent (A1). The coloring agent (A1) may be separately subjected to the dispersion treatment, or a plurality of types may be mixed and subjected to the dispersion treatment.

As a dispersing agent, surfactant etc. are mentioned, It can be any of a cationic, anionic, nonionic, and amphoteric surfactant. Specific examples include polyester-based, polyamine-based, and acrylic-based surfactants. These dispersants can be used alone or in combination of two or more. As a dispersant, if it is represented by a trade name, it can include: KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Flowlen (manufactured by Kyoeisha Chemical Co., Ltd.), and Solsperse (Registered trademark) (manufactured by Zeneca (shares)), EFKA (registered trademark) (manufactured by BASF), Ajisper (registered trademark) (Ajinomoto Fine technology (manufactured by Ajinomoto Fine-Techno (stock)), DISPERBYK (registered trademark) (manufactured by BYK-Chemie (stock)), and BYK (registered trademark) ) (Manufactured by BYK-Chemie (stock)) etc.

When the liquid containing the colorant (A1) contains a dispersant, the amount of the dispersant (solid content) used is, for example, 0.01 part by mass or more and 10,000 parts by mass or less with respect to 100 parts by mass of the colorant (A1). It is preferably 0.01 part by mass or more and 5000 parts by mass or less, more preferably 0.01 part by mass or more and 1000 parts by mass or less, further preferably 0.1 part by mass or more and 500 parts by mass or less, particularly preferably 0.1 part by mass or more and 300 parts by mass or less More preferably, it is 1 part by mass or more and 300 parts by mass or less, and particularly preferably 5 parts by mass or more and 260 parts by mass or less. If the amount of the dispersant used is in the above range, there is a tendency that a colorant (A1)-containing liquid in a more uniform dispersion state can be obtained.

When the coloring composition of the present invention contains a resin (B), and a liquid containing a colorant (A1) containing a colorant (A1) and a solvent (E) is prepared in advance, the colorant (A1)-containing liquid is used to prepare the present In the case of the coloring composition of the invention, the liquid containing the coloring agent (A1) may contain a part or all of the resin (B) contained in the coloring composition, and preferably contains a part in advance. By including the resin (B) in advance, the dispersion stability of the liquid containing the colorant (A1) can be further improved.

When the liquid containing the colorant (A1) contains the resin (B), the content of the resin (B) relative to 100 parts by mass of the colorant (A1) is, for example, 0.01 part by mass or more and 10,000 parts by mass or less, preferably 0.01 parts by mass or more and 5000 parts by mass or less, more preferably 0.01 parts by mass or more and 1000 parts by mass or less, still more preferably 0.1 parts by mass or more and 500 parts by mass or less, particularly preferably 0.1 parts by mass or more and 300 parts by mass or less.

When the coloring composition of the present invention contains a coloring agent (A1), in the coloring composition, the content of the coloring agent (A) in which the compound (I) and the coloring agent (A1) are combined is relative to the solid content The total amount is 100% by mass or less, preferably 0.0001% by mass or more and 99.9999% by mass or less, more preferably 0.0001% by mass or more and 99% by mass or less, still more preferably 0.0001% by mass or more and 90% by mass or less, particularly preferred 0.0001 mass% or more and 80 mass% or less, more preferably 0.0001 mass% or more and 70 mass% or less, particularly preferably 0.0001 mass% or more and 60 mass% or less, extremely preferably 0.0001 mass% or more and 55% mass% or less , The best content is 0.1% by mass or more and 55% by mass or less.

When the coloring composition of the present invention contains the colorant (A1), the content of the compound (I) in the total amount of the colorant (A) is usually 0.0001% by mass or more, preferably 0.0003% by mass or more, It is more preferably 0.0005 mass% or more, still more preferably 0.001 mass% or more, and the upper limit is less than 100 mass%, preferably 99.9999 mass% or less, more preferably 99 mass% or less, still more preferably 98 mass% or less, and particularly preferably 97 Less than mass%.

[Leveling Agent (F)] Examples of the leveling agent (F) include silicone-based surfactants, fluorine-based surfactants, and silicone-based surfactants having fluorine atoms. These may have a polymerizable group in the side chain.

As the silicone-based surfactant, a surfactant having a siloxane bond in the molecule, and the like can be cited. Specific examples include: Toray Silicone DC3PA, Toray Silicone SH7PA, Toray Silicone DC11PA, Toray Silicone SH21PA, Toray Silicone Silicone) SH28PA, Toray Silicone (Toray Silicone) SH29PA, Toray Silicone (Toray Silicone) SH30PA, Toray Silicone (Toray Silicone) SH8400 (trade name: Toray Dow Corning (stock) manufacturing) , KP321, KP322, KP323, KP324, KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452 and TSF4460 (Momentive Performance Materials Japan) Co., Ltd.), etc.

Examples of the fluorine-based surfactant include surfactants having a fluorocarbon chain in the molecule, and the like. Specific examples can include: Fluorad (registered trademark) FC430, Fluorad (Fluorad) FC431 (manufactured by Sumitomo 3M (stock)), Megafac (registered trademark) F142D, Megafac F171, Megafac F172, Megafac F173, Megafac F177, Megafac F183, Megafac F554, Megafac R30, Megafac RS-718 -K (manufactured by DIC (shares)), Eftop (registered trademark) EF301, Eftop EF303, Eftop EF351, Eftop EF352 ( Mitsubishi Materials Electronics Co., Ltd.), Surflon (registered trademark) S381, Surflon S382, Surflon SC101, Surflon SC105 (Asahi Glass Co., Ltd.) Manufacturing) and E5844 (manufactured by Daikin Fine Chemical Research Institute (stock)), etc.

Examples of the silicone-based surfactant having a fluorine atom include surfactants having a silicone bond and a fluorocarbon chain in the molecule. Specific examples can include: Megafac (registered trademark) R08, Megafac BL20, Megafac F475, Megafac F477 and Megafac F443 (DIC) (shares ) Manufacturing) etc.

When the leveling agent (F) is contained, its content is usually 0.00001 mass% or more and 5 mass% or less, preferably 0.00001 mass% or more and 3 mass% or less, with respect to the total amount of the coloring composition, more preferably It is 0.0001% by mass or more and 2% by mass or less, and more preferably 0.0001% by mass or more and 1% by mass or less. If the content of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.

[Antioxidant (G)] From the viewpoint 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. The antioxidant is not particularly limited as long as it is an antioxidant generally used in industry, and phenol-based antioxidants, phosphorus-based antioxidants, sulfur-based antioxidants, and the like can be used.

As the phenolic antioxidant, for example, Irganox 1010 (Irganox 1010: pentaerythritol tetra[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], BASF (BASF), Irganox 1076 (Irganox 1076: octadecyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl) propionate, BASF) ), Yi Lu Nuosi 1330 (Irganox 1330: 3,3',3'',5,5',5''-hexa-tertiary butyl-a,a',a''-(Mesitylene- 2,4,6-tolyl) tris-p-cresol, manufactured by BASF (BASF), Irganox 3114 (Irganox 3114: 1,3,5-tris(3,5-di-tertidine) 4-hydroxybenzyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione, manufactured by BASF (BASF), Irganox 3790 (Irganox 3790: 1,3,5-Tris((4-tert-butyl-3-hydroxy-2,6-xylenyl)methyl)-1,3,5-triazine-2,4,6(1H,3H ,5H)-Triketone, manufactured by BASF (BASF), Irganox 1035 (Irganox 1035: thiodiethylenebis[3-(3,5-di-tert-butyl-4-hydroxyphenyl) ) Propionate], made by BASF (BASF), Irganox 1135 (Irganox 1135: phenylpropionic acid, 3,5-bis(1,1-dimethylethyl)-4-hydroxy, C7-C9 Side chain alkyl ester, manufactured by BASF), Irganox 1520L (Irganox 1520L: 4,6-bis(octylsulfanylmethyl)-o-cresol, manufactured by BASF), Yi Lu Nuo 3125 (Irganox 3125, manufactured by BASF), Irganox 565 (Irganox 565: 2,4-bis(n-octylthio)-6-(4-hydroxy-3',5'-di- Tertiary butylanilino)-1,3,5-triazine, manufactured by BASF (BASF), Adekastab AO-80 (Adekastab AO-80: 3,9-bis(2-(3-( 3-tert-butyl-4-hydroxy-5-methylphenyl)propanyloxy)-1,1-dimethylethyl)-2,4,8,10-tetraoxaspiro ( 5,5) Undecane, ADEKA (made by ADEKA), Sumilizer BHT (Sumilizer BHT, manufactured by Sumitomo Chemical (Stock)), Sumilizer GA-80 (Sumilizer GA-80, Sumitomo Chemical Co., Ltd.), Sumilizer GS (Sumilizer GS, Sumitomo Chemical Co., Ltd.), Shannox 1790 (Cyanox 1790, Cytec (Stock) manufacturing), and Vitamin ( Vitamin E (manufactured by Eisai (Stock)) etc.

Examples of the phosphorus-based antioxidant include: Irgafos 168 (Irgafos 168: tris(2,4-di-tert-butylphenyl) phosphite, manufactured by BASF), Yi Lu Irgafos 12 (Irgafos 12: three [2-[[2,4,8,10-tetra-tert-butyldibenzo[d,f][1,3,2] dioxaphosphine-6-yl ]Oxy]ethyl]amine, manufactured by BASF (BASF), Irgafos 38 (Irgafos 38: bis(2,4-bis(1,1-dimethylethyl)-6-methylphenyl) ) Ethyl ester phosphorous acid, BASF (BASF) manufacture), Adekastab (Adekastab) 329K (made by ADEKA (Stock)), Adekastab (Adekastab) PEP36 (Adekastab) ADEKA (share) manufacturing), Adekastab (Adekastab) PEP-8 (ADEKA (share) manufacturing), Sandstab P-EPQ (Clariant) Manufacturing), Weston 618 (Weston 618, manufactured by GE), Weston 619G (Weston 619G, manufactured by GE), Utranox 626 (Ultranox 626, manufactured by GE) and Sumilize GP (Sumilizer GP: 6-[3-(3-tert-butyl-4-hydroxy-5-methylphenyl) propoxy]-2,4,8,10-tetra-tert-butyl dibenzo [d,f][1.3.2] Dioxaphosphapine) (manufactured by Sumitomo Chemical Co., Ltd.), etc.

As the sulfur-based antioxidant, for example, dilauryl thiodipropionate, dimyristyl thiodipropionate, or distearyl thiodipropionate and the like can be mentioned. Β-alkyl mercaptopropionate compounds of polyhydric alcohols such as alkyl ester compounds and tetra[methylene(3-dodecylthio)propionate]methane.

[Other ingredients] The coloring composition of the present invention may contain fillers, other polymer compounds, adhesion promoters, light stabilizers, chain transfer agents, and other additives known in the technical field as necessary. As the adhesion promoter, for example, vinyl trimethoxy silane, vinyl triethoxy silane, vinyl tris (2-methoxyethoxy) silane, 3-glycidyloxy propyl trimethyl Oxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 2-(3,4-epoxycyclohexyl)ethyl Trimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-mercaptopropyltrimethyl Oxysilane, 3-thiopropyltrimethoxysilane, 3-isocyanatopropyltriethoxysilane, N-2-(aminoethyl)-3-aminopropylmethyldimethoxy Silane, N-2-(aminoethyl)-3-aminopropylmethyl diethoxysilane, N-2-(aminoethyl)-3-aminopropyltrimethoxysilane, N -2-(Aminoethyl)-3-aminopropylmethyl diethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, N-benzene 3-aminopropyl trimethoxysilane and N-phenyl-3-aminopropyl triethoxysilane, etc.

[Method of manufacturing coloring composition] The coloring composition of the present invention can be obtained by combining compound (I), solvent (E), and optionally resin (B), polymerizable compound (C), polymerization initiator (D), and polymerization initiator (D1), coloring agent (A1), leveling agent (F), antioxidant (G) and/or other ingredients are mixed to prepare. The mixing can be carried out by known or customary devices or conditions. Compound (I) is preferably used in the form of a liquid containing compound (I). The liquid containing compound (I) is prepared by mixing compound (I) with a part or all of solvent (E) in advance and using a bead mill Organically dispersed until the average particle diameter of the compound (I) is about 0.2 μm or less. At this time, part or all of the dispersant and resin (B) can be adjusted as needed. The coloring agent (A1) is preferably used in the state of a liquid containing the coloring agent (A1), and the coloring agent (A1)-containing liquid is preliminarily mixed with a part or all of the coloring agent (A1) and the solvent (E), It is dispersed using a bead mill or the like until the average particle diameter of the colorant (A1) is about 0.2 μm or less. At this time, part or all of the dispersant and resin (B) can be adjusted as needed. The compound (I) is preferably used in the state of a solution (the solution is contained in a liquid containing the compound (I)) previously dissolved in a part or all of the solvent (E). Furthermore, it is preferable to filter the liquid containing the compound (I) with a filter having a pore diameter of 0.01 μm or more and 1 μm or less. The coloring agent (A1) is preferably used in a state of a solution (the solution is contained in a liquid containing the coloring agent (A1)) previously dissolved in a part or all of the solvent (E). Furthermore, it is preferable to filter the liquid containing the coloring agent (A1) with a filter with a pore diameter of about 0.01 μm or more and 1 μm or less. It is preferable to filter the mixed colored composition with a filter having a pore diameter of 0.01 μm or more and 10 μm or less.

[Color filter] A color filter can be formed from the coloring composition of the present invention. The colored composition is applied on the substrate, and volatile components such as the solvent are removed and dried to form a colored coating film. The colored coating film thus formed is included in the color filter of the present invention. As a method of forming a colored pattern, a photolithography method, an inkjet method, a printing method, etc. may be mentioned. Among them, the photolithography method is preferred. The photolithography method is a method of coating the colored composition on a substrate, drying it to form a colored composition layer, and exposing and developing the colored composition layer through a photomask. In the photolithography method, by not using a photomask during exposure and/or not performing development, a colored coating film can be formed as a cured product of the colored composition layer. The colored pattern or colored coating film thus formed is the color filter of the present invention. The thickness of the color filter produced is not particularly limited, and can be appropriately adjusted according to the purpose or application. For example, it is 0.1 μm to 30 μm, preferably 0.1 μm to 20 μm, and more preferably 0.5 μm to 6 μm.

As the substrate, glass plates such as quartz glass, borosilicate glass, alumina silicate glass, soda lime glass coated with silica on the surface, or polycarbonate, polymethylmethacrylate, Polyethylene terephthalate and other resin plates, silicon, aluminum, silver, silver/copper/palladium alloy thin films, etc. are formed on the substrate. Other color filter layers, resin layers, transistors and circuits can also be formed on these substrates.

The formation of pixels of each color by the photolithography method can be performed by known or customary devices or conditions. For example, it can be produced as follows. First, the colored composition is coated on a substrate, and volatile components such as the solvent are removed by heating and drying (pre-baking) and/or under reduced pressure and dried to obtain a smooth colored composition layer. As the coating method, a spin coating method, a slit coating method, a slit and spin coating method, and the like can be cited. The temperature during heat drying is preferably 30°C to 120°C, more preferably 50°C to 110°C. In addition, the heating time is preferably 10 seconds to 60 minutes, and more preferably 30 seconds to 30 minutes. In the case of drying under reduced pressure, it is preferably performed at a pressure of 50 Pa to 150 Pa and a temperature range of 20°C to 25°C. The film thickness of the colored composition layer is not particularly limited, as long as it is appropriately selected according to the film thickness of the target color filter.

Next, the coloring composition layer is interposed by the mask for forming the target coloring pattern to be exposed. The pattern on the mask is not particularly limited, and a pattern corresponding to the intended use can be used. As the light source used for exposure, a light source that generates light with a wavelength of 250 nm to 450 nm is preferred. For example, for light less than 350 nm, use a filter that cuts off the wavelength range, or for light near 436 nm, 408 nm, and 365 nm, use bandpass filters that take out these wavelength ranges Perform selective removal. Specific examples of the light source include mercury lamps, light-emitting diodes, metal halide lamps, and halogen lamps. In order to uniformly irradiate the entire exposure surface with parallel light, or to enable accurate position alignment of the mask and the substrate on which the colored composition layer is formed, it is preferable to use an exposure device such as a mask aligner and a stepper.

By contacting the exposed coloring composition layer with a developing solution for development, a coloring pattern is formed on the substrate. By developing, the unexposed part of the colored composition layer is dissolved in the developing solution and removed. As the developer, for example, aqueous solutions of alkaline compounds such as potassium hydroxide, sodium hydrogen carbonate, sodium carbonate, and tetramethylammonium hydroxide are preferred. The concentration of the basic compound is preferably 0.01% by mass to 10% by mass, more preferably 0.02% by mass to 5% by mass. The developer may contain a surfactant. The development method may be any of a liquid coating method, a dipping method, and a spray method. Furthermore, during development, the substrate can be inclined at any angle. The developed substrate is preferably washed with water. Furthermore, it is preferable to post-bak the obtained colored pattern. The post-baking temperature is preferably 150°C to 250°C, more preferably 160°C to 235°C. The post-baking time is preferably 1 minute to 120 minutes, more preferably 10 minutes to 60 minutes. The colored pattern or colored coating film obtained in this way, that is, a color filter, may be further used for surface coating treatment in order to impart various characteristics.

The color filter is used as a color filter used in a display device (for example, a liquid crystal display device, an organic electroluminescence (EL) device, electronic paper, etc.) and a solid-state imaging element, especially as a liquid crystal display device The color filter used in it is useful.

This application claims the benefit of priority based on Japanese Patent Application No. 2019-026911 filed on February 18, 2019. The entire contents of the specification of Japanese Patent Application No. 2019-026911 filed on February 18, 2019 are incorporated into this application for reference. [Example]

The following examples are given to explain the present invention more specifically, but the present invention is not limited by the following examples at all. Of course, it can also be implemented with appropriate changes within the scope that can be adapted to the above and the following subject matter. These include Within the technical scope of the present invention. In addition, in the following, unless otherwise specified, "parts" means "parts by mass", and "%" means "% by mass".

In the following synthesis examples, the structure of the compound was confirmed by mass analysis (LC; Agilent (Agilent) Model 1200, MASS; Agilent (Agilent) LC/MSD6130 Model).

The measurement of the weight average molecular weight (Mw) and the number average molecular weight (Mn) in terms of polystyrene of the resin was performed by Gel Permeation Chromatography (GPC) under the following conditions. Device: HLC-8120GPC (manufactured by Tosoh (stock)) Column: TSK-GELG2000HXL Column temperature: 40℃ Solvent: Tetrahydrofuran Flow rate: 1.0 mL/min The solid content concentration of the analysis sample: 0.001% by mass to 0.01% by mass Injection volume: 50 μL Detector: RI Standard materials for calibration: TSK Standard Polystyrene (TSK STANDARD POLYSTYRENE) F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh (Stock)) The ratio (Mw/Mn) of the weight average molecular weight (Mw) and the number average molecular weight (Mn) in terms of the obtained polystyrene is defined as the degree of dispersion.

Example 1 3.02 parts of 4-amino-2-methylquinoline (manufactured by Tokyo Chemical Industry Co., Ltd.), 2,3-naphthalenedicarboxylic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) 8.33 parts, and benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) (Stock) Manufacturing) 11.7 parts and methyl benzoate (Tokyo Chemical Industry Co., Ltd.) 66.7 parts mixed. The mixture was stirred for 9 hours while maintaining the temperature at 170°C. Add 13.6 parts of 2,3-naphthalene dicarboxylic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 22.9 parts of benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.), and methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.) Manufacturing) 66.4 parts. The mixture was stirred for 49 hours while maintaining 170°C. To this mixture were added 8.32 parts of 2,3-naphthalene dicarboxylic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 11.7 parts of benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.), and methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.) Manufacturing) 43.5 copies. The mixture was stirred for 28 hours while maintaining 170°C. The mixture was cooled to room temperature, and 1300 parts of methanol was added to the mixture. After stirring this mixture at room temperature, it filtered, and the obtained residue was wash|cleaned 7 times with 400 parts of methanol. The obtained residue was dried under reduced pressure at 60°C. 875 parts of N,N-dimethylformamide was added to this residue. After the mixture was stirred at room temperature, it was filtered, and the obtained residue was washed three times with the same volume of N,N-dimethylformamide as the obtained residue. This residue was washed three times with 200 parts of methanol. The obtained residue was dried under reduced pressure at 60°C to obtain 7.25 parts of a compound represented by formula (Ia2).

[化102]

<Identification of the compound represented by the formula (Ia2)> (mass analysis) ionization mode=ESI+: m/z=[M+H] ⁺ 519 (mass analysis) ionization mode=ESI-: m/z=[MH ] ^--517 exact mass (exact mass): 518

Example 2 2.05 parts of 4-amino-2-methylquinoline (manufactured by Tokyo Chemical Industry Co., Ltd.), 8.16 parts of tetrachlorophthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), and benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) Co., Ltd.) 8.05 parts and 58.6 parts of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.). The mixture was stirred for 5 hours while maintaining the temperature at 170°C. To this mixture were added 3.72 parts of tetrachlorophthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 8.00 parts of benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.), and methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.) ) 18.0 copies. The mixture was stirred for 6 hours while maintaining the temperature at 170°C. To this mixture were added 1.89 parts of tetrachlorophthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 4.09 parts of benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.), and methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.) ) 54.5 copies. The mixture was stirred for 6 hours while maintaining the temperature at 170°C. To the mixture were added 11.4 parts of tetrachlorophthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 12.6 parts of benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) and methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.) ) 18.4 copies. The mixture was stirred for 16 hours while maintaining the temperature at 170°C. The mixture was cooled to room temperature, and 1200 parts of methanol was added to the mixture. After stirring this mixture at room temperature, it filtered, and the obtained residue was wash|cleaned 8 times with 400 parts of methanol. The obtained residue was dried under reduced pressure at 60°C to obtain 8.88 parts of a compound represented by formula (Ia23).

[化103]

<Identification of the compound represented by formula (Ia23)> (mass analysis) ionization mode=ESI+: m/z=[M+H] ⁺ 691 (mass analysis) ionization mode=ESI-: m/z=[MH ] ^--689 exact mass (exact mass): 690

Example 3 1.01 parts of 4-amino-2-methylquinoline (manufactured by Tokyo Chemical Industry Co., Ltd.), 4-phenylethynyl phthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) 3.49 parts, and benzoic acid ( 3.95 parts of Tokyo Chemical Industry Co., Ltd. and 28.7 parts of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.) were mixed. The mixture was stirred for 20 hours while maintaining the temperature at 170°C. To this mixture were added 0.476 parts of 4-phenylethynyl phthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 1.32 parts of benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.), and methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.). (Share) Manufacturing) 3.3 copies. The mixture was stirred for 10 hours while maintaining the temperature at 170°C. To this mixture were added 0.801 parts of 4-phenylethynyl phthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 2.90 parts of benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.), and methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.). (Share) Manufacturing) 9.13 copies. The mixture was stirred for 29 hours while maintaining 170°C. This mixture was cooled to room temperature, 400 parts of methanol was added to this mixture, and it stirred for 1 hour. This mixture was filtered, and the obtained residue was washed 6 times with 140 parts of methanol. The obtained residue was dried under reduced pressure at 60°C to obtain 3.12 parts of a compound represented by formula (Ia22).

[化104]

<Identification of the compound represented by formula (Ia22)> (mass analysis) ionization mode=ESI+: m/z=[M+H] ⁺ 619 (mass analysis) ionization mode=ESI-: m/z=[MH ] ^--617 exact mass (exact mass): 618

Example 4 4.04 parts of 4-amino-2-methylquinoline (manufactured by Tokyo Chemical Industry Co., Ltd.), 10.8 parts of trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), and benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) ) 15.6 parts and 92.3 parts of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.) are mixed. The mixture was stirred for 5 hours while maintaining the temperature at 167°C. 40.2 parts of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.) was added to the mixture. The mixture was stirred for 9 hours while maintaining the temperature at 167°C. 28.0 parts of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.) was added to this mixture. The mixture was stirred for 11 hours while maintaining the temperature at 170°C. The mixture was cooled to room temperature, and 2000 parts of methanol was added to the mixture. The mixture was stirred at room temperature. 173 parts of methanol was added to the obtained mixture. This mixture was filtered, and the obtained residue was washed once with 124 parts of methanol, once with 160 parts of methanol, and once with 400 parts of methanol. The obtained residue was dried under reduced pressure at 60°C to obtain a compound represented by formula (Ia10), a compound represented by formula (Ia2143), a compound represented by formula (Ia850), and a compound represented by formula (Ia315) The mixture is 9.91 parts.

[化105]

<Identification of the compound represented by the formula (Ia10)> (mass analysis) ionization mode=ESI+: m/z=[M+H] ⁺ 507 (mass analysis) ionization mode=ESI-: m/z=[MH ] ^--505 exact mass (exact mass): 506

[化106]

<Identification of the compound represented by the formula (Ia2143)> (mass analysis) ionization mode=ESI+: m/z=[M+H] ⁺ 521 (mass analysis) ionization mode=ESI-: m/z=[MH ] ^--519 exact mass (exact mass): 520

[化107]

<Identification of the compound represented by formula (Ia850)> (mass analysis) ionization mode=ESI+: m/z=[M+H] ⁺ 521 (mass analysis) ionization mode=ESI-: m/z=[MH ] ^--519 exact mass (exact mass): 520

[化108]

<Identification of the compound represented by formula (Ia315)> (mass analysis) ionization mode=ESI+: m/z=[M+H] ⁺ 535 (mass analysis) ionization mode=ESI-: m/z=[MH ] ^--533 exact mass (exact mass): 534

Example 5 Combining 5-amino-2-methylquinoline (manufactured by Tokyo Chemical Industry Co., Ltd.) 5.23 parts, 3-nitrophthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) 14.2 parts, and benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) 20.2 parts of Industrial Co., Ltd. and 119 parts of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.). The mixture was stirred for 12 hours while maintaining the temperature at 168°C. To this mixture were added 7.12 parts of 3-nitrophthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 10.3 parts of benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.), and methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.). ) Manufacturing) 16.0 parts. The mixture was stirred for 26 hours while maintaining 170°C. The mixture was cooled to room temperature, and 2400 parts of methanol was added to the mixture. After stirring the obtained mixture at room temperature, it filtered. The obtained residue was washed 5 times with 400 parts of methanol. The obtained residue was dried under reduced pressure at 60°C to obtain 13.0 parts of a compound represented by formula (Ia35).

[化109]

<Identification of the compound represented by formula (Ia35)> (mass analysis) ionization mode=ESI+: m/z=[M+H] ⁺ 509 (mass analysis) ionization mode=ESI-: m/z=[MH ] ^--507 exact mass (exact mass): 508

Example 6 4-Amino-2-methylquinoline (manufactured by Tokyo Chemical Industry Co., Ltd.) 3.67 parts, phthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) 7.59 parts, and benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) Manufacturing) 14.4 parts of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.) were mixed with 84.3 parts. The mixture was stirred for 10 hours while maintaining the temperature at 170°C. To this mixture were added 7.92 parts of phthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 15.5 parts of benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.), and methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.) 45 Copies. The mixture was stirred for 9 hours while maintaining the temperature at 170°C. 9 parts of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.) was added to the mixture. The mixture was stirred for 18 hours while maintaining the temperature at 170°C. To this mixture were added 7.77 parts of phthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 14.6 parts of benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) and 11.1 parts of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.) Copies. The mixture was stirred for 27 hours while maintaining 170°C. To this mixture were added 3.88 parts of phthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 7.33 parts of benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.), and 12.3 parts of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.). Copies. The mixture was stirred for 8 hours while maintaining the temperature at 170°C. The mixture was cooled to room temperature, and 2800 parts of methanol was added to the mixture. After stirring the obtained mixture at room temperature, it filtered. The obtained residue was washed twice with 400 parts of methanol and once washed with 800 parts of methanol. The obtained residue was dried under reduced pressure at 60°C to obtain 7.67 parts of a compound represented by formula (Ia1).

[化110]

<Identification of the compound represented by the formula (Ia1)> (mass analysis) ionization mode=ESI+: m/z=[M+H] ⁺ 419 (mass analysis) ionization mode=ESI-: m/z=[MH ] ^--417 accurate mass (exact mass): 418

Example 7 1.05 parts of a mixture of the compound represented by the formula (Ia10), the compound represented by the formula (Ia2143), the compound represented by the formula (Ia850), and the compound represented by the formula (Ia315) obtained in Example 4 and 106 parts of water mixing. At room temperature, 22.1 parts of 1% sodium hydroxide aqueous solution was added to the mixture. At room temperature, 8.19 parts of a mixture of 3.23 parts of iron (III) nitrate nonahydrate (manufactured by Wako Pure Chemical Industries, Ltd.) and 29.1 parts of water was added to the obtained mixture. The obtained mixture is filtered, and the obtained residue is washed twice with the same volume of water as the obtained residue. The obtained residue was dried under reduced pressure at 60° C. to obtain 1.17 parts of a mixture containing the compound represented by formula (Ie12).

[化111]

Example 8 5.03 parts of 4-amino-2-methylquinoline (manufactured by Tokyo Chemical Industry Co., Ltd.), 13.6 parts of 4-nitrophthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), and benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) A mixture of 19.5 parts by Industrial Co., Ltd. and 116 parts of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.). The mixture was stirred for 4 hours while maintaining the temperature at 170°C. To the mixture were added 7.12 parts of 4-nitrophthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 10.5 parts of benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.), and methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.). ) Manufacturing) 30.1 parts. The mixture was stirred for 18 hours while maintaining the temperature at 170°C. To this mixture were added 13.6 parts of 4-nitrophthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 19.9 parts of benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.), and methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.). ) Manufacturing) 29.1 parts. The mixture was stirred for 27 hours while maintaining 170°C. The mixture was cooled to room temperature, and 2800 parts of methanol was added to the mixture. After stirring the obtained mixture at room temperature, it filtered. The obtained residue was washed 4 times with 400 parts of methanol. The obtained residue was dried under reduced pressure at 60°C to obtain 14.8 parts of a compound represented by formula (Ia33).

[化112]

<Identification of the compound represented by formula (Ia33)> (mass analysis) ionization mode=ESI+: m/z=[M+H] ⁺ 509 (mass analysis) ionization mode=ESI-: m/z=[MH ] ^--507 exact mass (exact mass): 508

Example A-1 1 mol of 4-amino-2-methylquinoline (manufactured by Tokyo Chemical Industry Co., Ltd.), 3-methylphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) 8 mol, Benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) 21 moles and 4-amino-2-methylquinoline (manufactured by Tokyo Chemical Industry Co., Ltd.) was mixed with methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.) at a weight 73 times the weight of 1 mol. The mixture was stirred for 120 hours while maintaining 170°C. The mixture was cooled to room temperature, and methanol was added 13 times the weight of the mixture to the mixture. After stirring the obtained mixture at room temperature, it filtered. The obtained residue was washed with methanol. The obtained residue was purified by column chromatography to obtain the compound represented by formula (Ia5).

[化113]

<Identification of the compound represented by formula (Ia5)> (mass analysis) ionization mode=ESI+: m/z=[M+H] ⁺ 447 (mass analysis) ionization mode=ESI-: m/z=[MH ] ^--445 exact mass (exact mass): 446

Example A-2 Except that 3-methylphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) is replaced with 1,2-naphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), the same as Example A-1 except that It is carried out to obtain the compound represented by formula (Ia3).

[化114]

<Identification of the compound represented by the formula (Ia3)> (mass analysis) ionization mode=ESI+: m/z=[M+H] ⁺ 519 (mass analysis) ionization mode=ESI-: m/z=[MH ] ^--517 exact mass (exact mass): 518

Example A-3 The same as Example A-1 except that 3-methylphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with 3-chlorophthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) It is carried out to obtain the compound represented by formula (Ia17).

[化115]

<Identification of the compound represented by formula (Ia17)> (mass analysis) ionization mode=ESI+: m/z=[M+H] ⁺ 487 (mass analysis) ionization mode=ESI-: m/z=[MH ] ^--485 exact mass (exact mass): 486

Example A-4 Except that 3-methylphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with 4-chlorophthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), the same as Example A-1 except that It is carried out to obtain the compound represented by formula (Ia7).

[化116]

<Identification of the compound represented by formula (Ia7)> (mass analysis) ionization mode=ESI+: m/z=[M+H] ⁺ 487 (mass analysis) ionization mode=ESI-: m/z=[MH ] ^--485 exact mass (exact mass): 486

Example A-5 Replace 3-methyl phthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) with 3-acetamide phthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.). Otherwise, the same as Example A- 1 The same procedure was carried out to obtain a compound represented by formula (Ia36).

[化117]

<Identification of the compound represented by formula (Ia36)> (mass analysis) ionization mode=ESI+: m/z=[M+H] ⁺ 533 (mass analysis) ionization mode=ESI-: m/z=[MH ] ^--531 exact mass (exact mass): 532

Example A-6 Replacement of 3-methylphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) with 3-hydroxyphthalic anhydride (manufactured by Sigma-Aldrich Japan Co., Ltd.), except for , It carried out similarly to Example A-1, and obtained the compound represented by Formula (Ia51).

[化118]

<Identification of the compound represented by the formula (Ia51)> (mass analysis) ionization mode=ESI+: m/z=[M+H] ⁺ 451 (mass analysis) ionization mode=ESI-: m/z=[MH ] ^--449 exact mass (exact mass): 450

Example A-7 Except that 3-methylphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) is replaced with 3-fluorophthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), the same as Example A-1 except that It is carried out to obtain the compound represented by formula (Ia19).

[化119]

<Identification of the compound represented by formula (Ia19)> (mass analysis) ionization mode=ESI+: m/z=[M+H] ⁺ 455 (mass analysis) ionization mode=ESI-: m/z=[MH ] ^--453 exact mass (exact mass): 454

Example A-8 Except for replacing 3-methylphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) with the compound represented by formula (sm1), the same procedure as in Example A-1 was carried out to obtain the formula (Ia248) Represents the compound.

[化120]

[化121]

<Identification of the compound represented by formula (Ia248)> (mass analysis) ionization mode=ESI+: m/z=[M+H] ⁺ 507 (mass analysis) ionization mode=ESI-: m/z=[MH ] ^--505 exact mass (exact mass): 506

Example A-9 Replace 3-methylphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) with 4-methylphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.). Otherwise, the same as Example A-1 In the same manner, the compound represented by formula (Ia4) is obtained.

[化122]

<Identification of the compound represented by formula (Ia4)> (mass analysis) ionization mode=ESI+: m/z=[M+H] ⁺ 447 (mass analysis) ionization mode=ESI-: m/z=[MH ] ^--445 exact mass (exact mass): 446

Example A-10 Replaced 4-amino-2-methylquinoline (manufactured by Tokyo Chemical Industry Co., Ltd.) with 4-amino-6-fluoro-2-methylquinoline (Sigma-Aldrich Japan) Co., Ltd.), replacing 3-methylphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) with 2,3-naphthalene dicarboxylic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), and in addition to Example A-1 was implemented in the same manner to obtain a compound represented by formula (It242).

[化123]

<Identification of the compound represented by formula (It242)> (mass analysis) ionization mode=ESI+: m/z=[M+H] ⁺ 537 (mass analysis) ionization mode=ESI-: m/z=[MH ] ^--535 exact mass (exact mass): 536

Example A-11 Replaced 4-amino-2-methylquinoline (manufactured by Tokyo Chemical Industry Co., Ltd.) with 4-amino-6-methoxy-2-methylquinoline (Sigma-Aldrich Japan) Co., Ltd.), replacing 3-methylphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) with 2,3-naphthalene dicarboxylic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), except for that , It carried out similarly to Example A-1, and obtained the compound represented by Formula (It232).

[化124]

<Identification of the compound represented by formula (It232)> (mass analysis) ionization mode=ESI+: m/z=[M+H] ⁺ 549 (mass analysis) ionization mode=ESI-: m/z=[MH ] ^--547 exact mass (exact mass): 548

Example A-12 Replaced 4-amino-2-methylquinoline (manufactured by Tokyo Chemical Industry Co., Ltd.) with 4-amino-6-bromo-2-methylquinoline (Sigma-Aldrich Japan) Co., Ltd.), except that it carried out similarly to Example A-1, and obtained the compound represented by Formula (It750).

[化125]

<Identification of the compound represented by the formula (It750)> (mass analysis) ionization mode=ESI+: m/z=[M+H] ⁺ 525 (mass analysis) ionization mode=ESI-: m/z=[MH ] ^--523 exact mass (exact mass): 524

Synthesis Example B-1 A mixture of 1 mol of compound represented by formula (Ia2), 20 mol of potassium hydroxide, and water of 10 times the weight of compound 1 mol represented by formula (Ia2) are mixed. The mixture was stirred while being maintained at 90°C until the compound represented by the formula (Ia2) disappeared. This mixture was mixed with 36% hydrochloric acid and neutralized. The mixture was filtered. The residue obtained is washed with water. This residue was purified by column chromatography to obtain a compound represented by formula (IM1-1).

[化126]

<Identification of the compound represented by formula (IM1-1)> (mass analysis) ionization mode=ESI+: m/z=[M+H] ⁺ 339 (mass analysis) ionization mode=ESI-: m/z= [MH] ^- 337 exact mass (exact mass): 338

Synthesis Example B-2 Except for replacing the compound represented by formula (Ia2) with the compound represented by formula (Ia23), the same procedure as in Synthesis Example B-1 was carried out to obtain a compound represented by formula (IM1-2).

[化127]

<Identification of the compound represented by the formula (IM1-2)> (mass analysis) ionization mode=ESI+: m/z=[M+H] ⁺ 425 (mass analysis) ionization mode=ESI-: m/z= [MH] ^- 423 exact mass (exact mass): 424

Synthesis Example B-3 Except for replacing the compound represented by formula (Ia2) with the compound represented by formula (Ia5), the same procedure as in Synthesis Example B-1 was carried out to obtain a compound represented by formula (IM1-3).

[化128]

<Identification of the compound represented by formula (IM1-3)> (mass analysis) ionization mode=ESI+: m/z=[M+H] ⁺ 303 (mass analysis) ionization mode=ESI-: m/z= [MH] ^- 301 exact mass (exact mass): 302

Synthesis Example B-4 Except for replacing the compound represented by formula (Ia2) with the compound represented by formula (Ia4), the same procedure as in Synthesis Example B-1 was carried out to obtain the compound represented by formula (IM1-4).

[化129]

<Identification of the compound represented by the formula (IM1-4)> (mass analysis) ionization mode=ESI+: m/z=[M+H] ⁺ 303 (mass analysis) ionization mode=ESI-: m/z= [MH] ^- 301 exact mass (exact mass): 302

Synthesis Example B-5 Except for replacing the compound represented by formula (Ia2) with the compound represented by formula (Ia36), the same procedure as in Synthesis Example B-1 was carried out to obtain the compound represented by formula (IM1-5).

[化130]

<Identification of the compound represented by the formula (IM1-5)> (mass analysis) ionization mode=ESI+: m/z=[M+H] ⁺ 346 (mass analysis) ionization mode=ESI-: m/z= [MH] ^- 344 exact mass (exact mass): 345

Synthesis Example B-6 Except for replacing the compound represented by formula (Ia2) with the compound represented by formula (Ia1), the same procedure as in Synthesis Example B-1 was carried out to obtain the compound represented by formula (IM1-6).

[化131]

<Identification of the compound represented by the formula (IM1-6)> (mass analysis) ionization mode=ESI+: m/z=[M+H] ⁺ 289 (mass analysis) ionization mode=ESI-: m/z= [MH] ^- 287 exact mass (exact mass): 288

Example C-1 Compound 1 mole represented by formula (IM1-1), Trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) 8 mol, Benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) 21 moles and The compound represented by formula (IM1-1) was mixed with methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.) at a weight 73 times the weight of 1 mole. The mixture was stirred for 120 hours while maintaining 170°C. The mixture was cooled to room temperature, and methanol was added 13 times the weight of the mixture to the mixture. After stirring the obtained mixture at room temperature, it filtered. The obtained residue was washed with methanol. The obtained residue was purified by column chromatography to obtain the compound represented by formula (Ia699).

[化132]

<Identification of the compound represented by formula (Ia699)> (mass analysis) ionization mode=ESI+: m/z=[M+H] ⁺ 513 (mass analysis) ionization mode=ESI-: m/z=[MH ] ^--511 exact mass (exact mass): 512

Example C-2 Replace the compound represented by formula (IM1-1) with the compound represented by formula (IM1-2), and replace trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) with 2,3-naphthalenedicarboxylic anhydride (Tokyo Chemical Industry Co., Ltd.), except that it carried out similarly to Example C-1, and obtained the compound represented by Formula (Ia970).

[化133]

<Identification of the compound represented by formula (Ia970)> (mass analysis) ionization mode=ESI+: m/z=[M+H] ⁺ 605 (mass analysis) ionization mode=ESI-: m/z=[MH ] ^--603 exact mass (exact mass): 604

Example C-3 Except that trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with tetrachlorophthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), the same procedure as in Example C-1 was carried out to obtain the formula ( Ia703) the compound represented.

[化134]

<Identification of the compound represented by formula (Ia703)> (mass analysis) ionization mode=ESI+: m/z=[M+H] ⁺ 605 (mass analysis) ionization mode=ESI-: m/z=[MH ] ^--603 exact mass (exact mass): 604

Example C-4 Except that trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with 3-methylphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), the same procedure as in Example C-1 was carried out to obtain The compound represented by the formula (If3796).

[化135]

<Identification of the compound represented by the formula (If3796)> (mass analysis) ionization mode=ESI+: m/z=[M+H] ⁺ 483 (mass analysis) ionization mode=ESI-: m/z=[MH ] ^--481 exact mass (exact mass): 482

Example C-5 Except that trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with phthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), the same procedure as in Example C-1 was carried out, and the formula (Ia696) was obtained. The compound represented.

[化136]

<Identification of the compound represented by formula (Ia696)> (mass analysis) ionization mode=ESI+: m/z=[M+H] ⁺ 469 (mass analysis) ionization mode=ESI-: m/z=[MH ] ^--467 exact mass (exact mass): 468

Example C-6 Replace the compound represented by formula (IM1-1) with the compound represented by formula (IM1-2), and replace trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) with phthalic anhydride (Tokyo Chemical Industry Co., Ltd.) Stock) Manufacturing), except for this, the same procedure as in Example C-1 was carried out to obtain a compound represented by formula (Ia969).

[化137]

<Identification of the compound represented by formula (Ia969)> (mass analysis) ionization mode=ESI+: m/z=[M+H] ⁺ 555 (mass analysis) ionization mode=ESI-: m/z=[MH ] ^--553 exact mass (exact mass): 554

Example C-7 Replace the compound represented by formula (IM1-1) with the compound represented by formula (IM1-2), and replace trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) with 3-methylphthalic anhydride ( Tokyo Chemical Industry Co., Ltd. product), except that it carried out similarly to Example C-1, and obtained the compound represented by Formula (If2528).

[化138]

<Identification of the compound represented by formula (If2528)> (mass analysis) ionization mode=ESI+: m/z=[M+H] ⁺ 569 (mass analysis) ionization mode=ESI-: m/z=[MH ] ^--567 exact mass (exact mass): 568

Example C-8 Except for replacing the compound represented by formula (IM1-1) with the compound represented by formula (IM1-2), the same procedure as in Example C-1 was carried out to obtain the compound represented by formula (Ia973).

[化139]

<Identification of the compound represented by formula (Ia973)> (mass analysis) ionization mode=ESI+: m/z=[M+H] ⁺ 599 (mass analysis) ionization mode=ESI-: m/z=[MH ] ^--597 exact mass (exact mass): 598

Example C-9 Except for replacing the compound represented by formula (IM1-1) with the compound represented by formula (IM1-3), the same procedure as in Example C-1 was carried out to obtain the compound represented by formula (If1261).

[化140]

<Identification of the compound represented by the formula (If1261)> (mass analysis) ionization mode=ESI+: m/z=[M+H] ⁺ 477 (mass analysis) ionization mode=ESI-: m/z=[MH ] ^--475 exact mass (exact mass): 476

Example C-10 Replace the compound represented by formula (IM1-1) with the compound represented by formula (IM1-3), and replace trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) with tetrachlorophthalic anhydride (Tokyo Chemical Industry Co., Ltd.) Industrial Co., Ltd.), except that it carried out similarly to Example C-1, and obtained the compound represented by Formula (If5688).

[化141]

<Identification of the compound represented by formula (If5688)> (mass analysis) ionization mode=ESI+: m/z=[M+H] ⁺ 569 (mass analysis) ionization mode=ESI-: m/z=[MH ] ^--567 exact mass (exact mass): 568

Example C-11 Replace the compound represented by formula (IM1-1) with the compound represented by formula (IM1-3), and replace trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) with 2,3-naphthalenedicarboxylic anhydride (Tokyo Chemical Industry Co., Ltd.), except that it carried out similarly to Example C-1, and obtained the compound represented by Formula (If636).

[化142]

<Identification of the compound represented by the formula (If636)> (mass analysis) ionization mode=ESI+: m/z=[M+H] ⁺ 483 (mass analysis) ionization mode=ESI-: m/z=[MH ] ^--481 exact mass (exact mass): 482

Example C-12 Replace the compound represented by formula (IM1-1) with the compound represented by formula (IM1-3), and replace trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) with 1,2-naphthalenedicarboxylic anhydride (Tokyo Chemical Industry Co., Ltd.), except that it carried out similarly to Example C-1, and obtained the compound represented by Formula (If5670).

[化143]

<Identification of the compound represented by the formula (If5670)> (mass analysis) ionization mode=ESI+: m/z=[M+H] ⁺ 483 (mass analysis) ionization mode=ESI-: m/z=[MH ] ^--481 exact mass (exact mass): 482

Example C-13 Replace the compound represented by formula (IM1-1) with the compound represented by formula (IM1-3), and replace trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) with 1,8-naphthalic anhydride (Tokyo Chemical Industry Co., Ltd.), except that it carried out similarly to Example C-1, and obtained the compound represented by Formula (If5720).

[化144]

<Identification of the compound represented by the formula (If5720)> (mass analysis) ionization mode=ESI+: m/z=[M+H] ⁺ 483 (mass analysis) ionization mode=ESI-: m/z=[MH ] ^--481 exact mass (exact mass): 482

Example C-14 Except that trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with 1,8-naphthalenedicarboxylic acid anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), the same procedure as in Example C-1 was carried out to obtain the formula (Ia712) The compound represented by.

[化145]

<Identification of the compound represented by formula (Ia712)> (mass analysis) ionization mode=ESI+: m/z=[M+H] ⁺ 519 (mass analysis) ionization mode=ESI-: m/z=[MH ] ^--517 exact mass (exact mass): 518

Example C-15 Replace the compound represented by formula (IM1-1) with the compound represented by formula (IM1-4), and replace trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) with 2,3-naphthalenedicarboxylic anhydride (Tokyo Chemical Industry Co., Ltd.), except that it carried out similarly to Example C-1, and obtained the compound represented by Formula (If635).

[化146]

<Identification of the compound represented by the formula (If635)> (mass analysis) ionization mode=ESI+: m/z=[M+H] ⁺ 483 (mass analysis) ionization mode=ESI-: m/z=[MH ] ^--481 exact mass (exact mass): 482

Example C-16 Except for replacing the compound represented by formula (IM1-1) with the compound represented by formula (IM1-4), the same procedure as in Example C-1 was carried out to obtain the compound represented by formula (If1260).

[化147]

<Identification of the compound represented by the formula (If1260)> (mass analysis) ionization mode=ESI+: m/z=[M+H] ⁺ 477 (mass analysis) ionization mode=ESI-: m/z=[MH ] ^--475 exact mass (exact mass): 476

Example C-17 Replace the compound represented by formula (IM1-1) with the compound represented by formula (IM1-4), and replace trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) with pyromellitic anhydride (Tokyo Chemical Industry Co., Ltd.) Stock) Manufacturing), except for this, the same procedure as in Example C-1 was carried out to obtain the compound represented by the formula (If13040).

[化148]

<Identification of the compound represented by the formula (If13040)> (mass analysis) ionization mode=ESI+: m/z=[M+H] ⁺ 521 (mass analysis) ionization mode=ESI-: m/z=[MH ] ^--519 exact mass (exact mass): 520

Example C-18 Replace the compound represented by formula (IM1-1) with the compound represented by formula (IM1-4), and replace trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) with 4-tert-butylphthalic acid Except for acid anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), the same procedure as in Example C-1 was carried out to obtain a compound represented by the formula (If8454).

[化149]

<Identification of the compound represented by the formula (If8454)> (mass analysis) ionization mode=ESI+: m/z=[M+H] ⁺ 489 (mass analysis) ionization mode=ESI-: m/z=[MH ] ^--487 exact mass (exact mass): 488

Example C-19 Except that trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with 4-methylphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), the same procedure as in Example C-1 was carried out to obtain The compound represented by the formula (If3795).

[化150]

<Identification of the compound represented by the formula (If3795)> (mass analysis) ionization mode=ESI+: m/z=[M+H] ⁺ 483 (mass analysis) ionization mode=ESI-: m/z=[MH ] ^--481 exact mass (exact mass): 482

Example C-20 Replace the compound represented by formula (IM1-1) with the compound represented by formula (IM1-3), and replace trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) with 4-methylphthalic anhydride ( Tokyo Chemical Industry Co., Ltd. product), except that it carried out similarly to Example C-1, and obtained the compound represented by Formula (If5671).

[化151]

<Identification of the compound represented by the formula (If5671)> (mass analysis) ionization mode=ESI+: m/z=[M+H] ⁺ 447 (mass analysis) ionization mode=ESI-: m/z=[MH ] ^--445 exact mass (exact mass): 446

Example C-21 Replace the compound represented by formula (IM1-1) with the compound represented by formula (IM1-4), and replace trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) with 3-methylphthalic anhydride ( Tokyo Chemical Industry Co., Ltd. product), except that it carried out similarly to Example C-1, and obtained the compound represented by Formula (If2511).

[化152]

<Identification of the compound represented by the formula (If2511)> (mass analysis) ionization mode=ESI+: m/z=[M+H] ⁺ 447 (mass analysis) ionization mode=ESI-: m/z=[MH ] ^--445 exact mass (exact mass): 446

Example C-22 Except that trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with 4-tert-butylphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), the same procedure as in Example C-1 was carried out except that , To obtain the compound represented by the formula (If3799).

[化153]

<Identification of the compound represented by the formula (If3799)> (mass analysis) ionization mode=ESI+: m/z=[M+H] ⁺ 525 (mass analysis) ionization mode=ESI-: m/z=[MH ] ^--523 exact mass (exact mass): 524

Example C-23 Except that trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with 3-acetamide phthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), it was carried out in the same manner as in Example C-1. The compound represented by formula (If3814) was obtained.

[化154]

<Identification of the compound represented by the formula (If3814)> (mass analysis) ionization mode=ESI+: m/z=[M+H] ⁺ 526 (mass analysis) ionization mode=ESI-: m/z=[MH ] ^--524 exact mass (exact mass): 525

Example C-24 Replace the compound represented by formula (IM1-1) with the compound represented by formula (IM1-5), and replace trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) with 2,3-naphthalenedicarboxylic anhydride (Tokyo Chemical Industry Co., Ltd.), except that it carried out similarly to Example C-1, and obtained the compound represented by Formula (If654).

[化155]

<Identification of the compound represented by the formula (If654)> (mass analysis) ionization mode=ESI+: m/z=[M+H] ⁺ 526 (mass analysis) ionization mode=ESI-: m/z=[MH ] ^--524 exact mass (exact mass): 525

Example C-25 Replace the compound represented by formula (IM1-1) with the compound represented by formula (IM1-5), and replace trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) with phthalic anhydride (Tokyo Chemical Industry Co., Ltd.) Stock) Manufacturing), except for this, the same procedure as in Example C-1 was carried out to obtain the compound represented by the formula (If29).

[化156]

<Identification of the compound represented by the formula (If29)> (mass analysis) ionization mode=ESI+: m/z=[M+H] ⁺ 476 (mass analysis) ionization mode=ESI-: m/z=[MH ] ^--474 exact mass (exact mass): 475

Example C-26 Except for replacing the compound represented by formula (IM1-1) with the compound represented by formula (IM1-5), the same procedure as in Example C-1 was carried out to obtain the compound represented by formula (If1279).

[化157]

<Identification of the compound represented by the formula (If1279)> (mass analysis) ionization mode=ESI+: m/z=[M+H] ⁺ 520 (mass analysis) ionization mode=ESI-: m/z=[MH ] ^--518 exact mass (exact mass): 519

Example C-27 Replace the compound represented by formula (IM1-1) with the compound represented by formula (IM1-5), and replace trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) with the compound represented by formula (sm1), except Except for this, it carried out similarly to Example C-1, and obtained the compound represented by Formula (If1904).

[化158]

<Identification of the compound represented by the formula (If1904)> (mass analysis) ionization mode=ESI+: m/z=[M+H] ⁺ 520 (mass analysis) ionization mode=ESI-: m/z=[MH ] ^--518 exact mass (exact mass): 519

Example C-28 Except for replacing trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) with the compound represented by formula (sm1), the same procedure as in Example C-1 was carried out to obtain the compound represented by formula (Ia728).

[化159]

<Identification of the compound represented by formula (Ia728)> (mass analysis) ionization mode=ESI+: m/z=[M+H] ⁺ 513 (mass analysis) ionization mode=ESI-: m/z=[MH ] ^--511 exact mass (exact mass): 512

Example C-29 Replace the compound represented by formula (IM1-1) with the compound represented by formula (IM1-6), and replace trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) with 2,3-naphthalenedicarboxylic anhydride (Tokyo Chemical Industry Co., Ltd.), except that it carried out similarly to Example C-1, and obtained the compound represented by formula (Ia657).

[化160]

<Identification of the compound represented by formula (Ia657)> (mass analysis) ionization mode=ESI+: m/z=[M+H] ⁺ 469 (mass analysis) ionization mode=ESI-: m/z=[MH ] ^--467 exact mass (exact mass): 468

Example C-30 Replace the compound represented by formula (IM1-1) with the compound represented by formula (IM1-6), and replace trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) with 3-methylphthalic anhydride ( Tokyo Chemical Industry Co., Ltd. product), except that it carried out similarly to Example C-1, and obtained the compound represented by Formula (If3171).

[化161]

<Identification of the compound represented by the formula (If3171)> (mass analysis) ionization mode=ESI+: m/z=[M+H] ⁺ 433 (mass analysis) ionization mode=ESI-: m/z=[MH ] ^--431 exact mass (exact mass): 432

Example C-31 Replace the compound represented by formula (IM1-1) with the compound represented by formula (IM1-6), and replace trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) with 3-chlorophthalic anhydride (Tokyo Chemical Industry Co., Ltd.), except that it carried out similarly to Example C-1, and obtained the compound represented by Formula (Ia686).

[化162]

<Identification of the compound represented by formula (Ia686)> (mass analysis) ionization mode=ESI+: m/z=[M+H] ⁺ 453 (mass analysis) ionization mode=ESI-: m/z=[MH ] ^--451 exact mass (exact mass): 452

Example E-1 1.61 parts of the compound represented by the formula (Ia5) and 32.7 parts of oleum (25%) (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) were mixed while maintaining the temperature at 10°C to 20°C. The mixture was stirred for 3 hours while maintaining the temperature at 5°C to 20°C. This mixture was added dropwise to 62.2 parts of ice. The obtained mixture is filtered. Add 10% ammonia water to the obtained liquid to neutralize the obtained filtrate. The solvent of the mixture was distilled off until the volume of the mixture became half. To the obtained mixture was added methanol in a volume twice the volume of the mixture. This mixture was filtered, and the solvent of the obtained filtrate was distilled off. The obtained residue was dried under reduced pressure at 60°C to obtain a compound represented by formula (Ia5-SA1) (in which any one of the hydrogen atoms of the compound represented by formula (Ia5) was replaced with -SO ₃ NH ₄ Compound), 0.58 parts of a mixture of the compound represented by the formula (Ia5-SA2) (compound in which any two hydrogen atoms of the compound represented by the formula (Ia5) are substituted with -SO ₃ NH ₄ ).

[化163]

<Identification of formula (Ia5-SA1) of the compound represented by> (mass spectrometry) ionization mode = ESI-: m / z = [ M-NH 4 + HH] - 525 Exact mass (Exact Mass): 543

[化164]

<Formula (Ia5-SA2) identification of compounds represented by> (mass spectrometry) ionization mode = ESI-: m / z = [ M-NH 4 -NH 4 + H + HH] - 605 Exact mass (Exact Mass) : 640

Example E-2 0.30 parts of the compound represented by formula (Ia1), 3.00 parts of chloroform, and 0.55 parts of chlorosulfonic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) were mixed. The mixture was stirred for 3 hours while maintaining the temperature at 60°C. This mixture was added dropwise to 3.64 parts of ice. The obtained mixture is filtered, and the obtained residue is washed with water. The residue was washed with methanol. The residue was dried under reduced pressure at 60°C to obtain a compound containing a compound represented by formula (Ia1-SA1) (a compound in which any one of the hydrogen atoms of the compound represented by formula (Ia1) was replaced by -SO ₃ H), 0.18 parts of a mixture with the compound represented by the formula (Ia1-SA2) (a compound in which any one hydrogen atom of the compound represented by the formula (Ia1) is substituted with -SO ₂ Cl).

[化165]

<Identification of the compounds of formula (Ia1-SA1) indicated> (mass spectrometry) ionization mode = ESI-: m / z = [ MH] - 497 Exact mass (Exact Mass): 498

[化166]

<Identification of the compounds of formula (Ia1-SA2) represented> (mass spectrometry) ionization mode = ESI-: m / z = [ MH] - 515 Exact mass (Exact Mass): 516

Example E-3 1.00 part of the compound represented by formula (Ia2) and 20.6 parts of fuming sulfuric acid (30%) (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) were mixed at room temperature. The mixture was stirred at room temperature for 3 hours. This mixture was added dropwise to 208 parts of ice. The obtained mixture was mixed with 110 parts of acetonitrile. The mixture was filtered, and the obtained residue was washed with acetonitrile. The residue was dried under reduced pressure at 60°C to obtain a compound represented by formula (Ia2-SA) (a compound in which any two hydrogen atoms of the compound represented by formula (Ia2) were replaced by -SO ₃ H) 0.40 parts of the mixture.

[化167]

<Identification of the compounds of formula (Ia2-SA) represented> (mass spectrometry) ionization mode = ESI-: m / z = [ MH] - 677 Exact mass (Exact Mass): 678

Synthesis Example 1 A suitable amount of nitrogen was circulated in a flask including a reflux cooler, a dropping funnel, and a stirrer, and the atmosphere was replaced with a nitrogen atmosphere. 280 parts of propylene glycol monomethyl ether acetate was put in and heated to 80°C while stirring. Then, 38 parts of acrylic acid, acrylic acid 3,4-epoxy tricyclo [5.2.1.0 ^2,6 ] decane-8-yl ester and acrylic acid 3,4-epoxy tricyclo [5.2.1.0 ² ] were added dropwise over 5 hours. ^,6 ] A mixed solution of 289 parts of a mixture of decane-9-yl esters (contained at a molar ratio of 1:1) and 125 parts of propylene glycol monomethyl ether acetate. On the other hand, a 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 the dripping was completed, it was kept at 80°C 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 weight average molecular weight of the obtained resin B1 was 8,800, the degree of dispersion was 2.1, and the acid value in terms of solid content was 80 mg-KOH/g.

Synthesis Example 2 A suitable amount of nitrogen was circulated in a flask including a reflux cooler, a dropping funnel, and a stirrer, and the atmosphere was replaced with a nitrogen atmosphere. 340 parts of propylene glycol monomethyl ether acetate was placed and heated to 80°C while stirring. Then, 57 parts of acrylic acid, acrylic acid 3,4-epoxy tricyclo [5.2.1.0 ^2,6 ] decane-8-yl ester and acrylic acid 3,4-epoxy tricyclo [5.2.1.0 ² ] were added dropwise over 5 hours. ^,6 ] A mixed solution of 54 parts of a mixture of decane-9-yl esters (contained at a molar ratio of 1:1), 239 parts of benzyl methacrylate, and 73 parts of propylene glycol monomethyl ether acetate. On the other hand, a solution obtained by dissolving 40 parts of 2,2-azobis(2,4-dimethylvaleronitrile) in 197 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After the dripping was completed, it was kept at 80°C for 3 hours, and then cooled to room temperature to obtain a solution of a copolymer (resin B2) having a solid content of 36.8%. The weight average molecular weight of the obtained copolymer was 9,400, the degree of dispersion was 1.89, and the acid value in terms of solid content was 114 mg-KOH/g.

Example 9 The components were mixed in the following proportions, and the colorant was dispersed using a bead mill to obtain a coloring composition M1. Colorant (A): 4.50 copies of the compound represented by formula (Ia2); Coloring agent (A): the compound represented by formula (z) 0.500 copies; Dispersant solution: DISPERBYK-161 (manufactured by BYK-Chemie Japan Co., Ltd.) 16.7 copies; Resin (B): Resin B1 solution 11.4 copies; Solvent (E): Propylene glycol monomethyl ether acetate 46.9 copies; Solvent (E): ethyl lactate, 20.0 copies;

Then, each component was mixed in the following ratio, and the coloring composition 1 was obtained. Coloring composition M1 57.6 copies; Resin (B): Resin B2 solution 27.0 copies; Solvent (E): propylene glycol monomethyl ether acetate 15.4 copies; Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning (stock)) 0.00630 copies;

[化168]

On a 2-inch square glass substrate (eagle XG; manufactured by Corning), the coloring composition 1 was coated by spin coating, and then pre-baked at 100°C for 3 minutes to form a pre-baked Bake the colored coating. The film thickness of the obtained pre-baked colored coating film was measured using DektakXT (manufactured by BRUKER). A color measuring machine: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.) was used to measure the spectrum of the pre-baked colored coating film. Table 39 shows the film thickness of the prebaked colored coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the prebaked colored coating film. This pre-baked colored coating film was post-baked at 230°C for 30 minutes, thereby obtaining a post-baked colored coating film.

Example 10 Except that the compound represented by formula (Ia2) was replaced with the compound represented by formula (Ia23), the same procedure as in Example 9 was carried out to obtain a colored composition, and a pre-baked colored coating film and post-baked colored coating were obtained. Coating film. Table 39 shows the film thickness of the prebaked colored coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the prebaked colored coating film.

Example 11 Replace the compound represented by formula (Ia2) with the compound represented by formula (Ia10) obtained in Example 4, the compound represented by formula (Ia2143), the compound represented by formula (Ia850), and the compound represented by formula (Ia315) Except for this, the same procedure as in Example 9 was carried out to obtain a colored composition, and to obtain a pre-baked colored coating film and a post-baked colored coating film. Table 39 shows the film thickness of the prebaked colored coating film and the wavelength of the shoulder on the longest wavelength side of the absorption spectrum of the prebaked colored coating film.

Example 12 Except that the compound represented by formula (Ia2) was replaced with the compound represented by formula (Ia35), the same procedure as in Example 9 was carried out to obtain a colored composition, and a pre-baked colored coating film and post-baked colored coating were obtained. Coating film. Table 39 shows the film thickness of the prebaked colored coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the prebaked colored coating film.

Example 13 The components were mixed in the following proportions, and the colorant was dispersed using a bead mill to obtain a coloring composition M2. Colorant (A): 4.50 copies of the compound represented by formula (Ia1); Coloring agent (A): the compound represented by formula (z) 0.500 copies; Dispersant solution: BYK-LPN6919 (manufactured by BYK-Chemie Japan Co., Ltd.) 8.33 copies; Resin (B): Resin B1 solution 11.4 copies; Solvent (E): propylene glycol monomethyl ether acetate 55.2 copies; Solvent (E): ethyl lactate, 20.0 copies;

Then, each component was mixed in the following ratio, and the colored composition 2 was obtained. Coloring composition M2 57.6 copies; Resin (B): Resin B2 solution 27.0 copies; Solvent (E): propylene glycol monomethyl ether acetate 15.4 copies; Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning (stock)) 0.00630 copies;

On a 2-inch square glass substrate (eagle XG; manufactured by Corning), the coloring composition 2 was coated by spin coating, and then pre-baked at 100°C for 3 minutes to form a pre-baked Bake the colored coating. The film thickness of the obtained pre-baked colored coating film was measured using DektakXT (manufactured by BRUKER). A color measuring machine: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.) was used to measure the spectrum of the pre-baked colored coating film. Table 39 shows the film thickness of the prebaked colored coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the prebaked colored coating film. This pre-baked colored coating film was post-baked at 230°C for 30 minutes, thereby obtaining a post-baked colored coating film.

Example 14 The components were mixed in the following ratio, and the colorant was dispersed using a bead mill to obtain a coloring composition M3. Coloring agent (A): a mixture of the compound represented by formula (Ia10), the compound represented by formula (Ia2143), the compound represented by formula (Ia850), and the compound represented by formula (Ia315) obtained in Example 4. 5.00 Copies Dispersant solution: DISPERBYK-161 (manufactured by BYK-Chemie Japan Co., Ltd.) 16.7 copies; Resin (B): Resin B1 solution 11.4 copies; Solvent (E): Propylene glycol monomethyl ether acetate 46.9 copies; Solvent (E): ethyl lactate, 20.0 copies;

Then, each component was mixed in the following ratio, and the coloring composition 3 was obtained. Coloring composition M3 57.6 copies; Resin (B): Resin B2 solution 27.0 copies; Solvent (E): propylene glycol monomethyl ether acetate 15.4 copies; Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning (stock)) 0.00630 copies;

On a 2-inch square glass substrate (eagle XG; manufactured by Corning), the coloring composition 3 was coated by spin coating, and then pre-baked at 100°C for 3 minutes to form a pre-baked Bake the colored coating. The film thickness of the obtained pre-baked colored coating film was measured using DektakXT (manufactured by BRUKER). A color measuring machine: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.) was used to measure the spectrum of the pre-baked colored coating film. Table 39 shows the film thickness of the prebaked colored coating film and the wavelength of the shoulder on the longest wavelength side of the absorption spectrum of the prebaked colored coating film. This pre-baked colored coating film was post-baked at 230°C for 30 minutes, thereby obtaining a post-baked colored coating film.

Example 15 The mixture of the compound represented by the formula (Ia10), the compound represented by the formula (Ia2143), the compound represented by the formula (Ia850), and the compound represented by the formula (Ia315) obtained in Example 4 was replaced by the formula (Ia33) Except for the compound shown, the same procedure as in Example 14 was carried out to obtain a colored composition, and a pre-baked colored coating film and a post-baked colored coating film were obtained. Table 39 shows the film thickness of the prebaked colored coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the prebaked colored coating film.

Example 16 The components were mixed in the following proportions, and the colorant was dispersed using a bead mill to obtain a coloring composition M4. Colorant (A): 4.50 parts of the compound represented by formula (Ia22); Coloring agent (A): the compound represented by formula (z) 0.500 copies; Dispersant solution: DISPERBYK-161 (manufactured by BYK-Chemie Japan Co., Ltd.) 16.7 copies; Resin (B): Resin B1 solution 11.4 copies; Solvent (E): Propylene glycol monomethyl ether acetate 46.9 copies; Solvent (E): ethyl lactate, 20.0 copies;

Then, each component was mixed in the following ratio, and the coloring composition 4 was obtained. Coloring composition M4 48.0 copies; Resin (B): Resin B2 solution 22.5 copies; Solvent (E): Propylene glycol monomethyl ether acetate 29.5 copies; Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning (stock)) 0.00525 copies;

On a 2-inch square glass substrate (eagle XG; manufactured by Corning), the coloring composition 4 was coated by spin coating, and then pre-baked at 100°C for 3 minutes to form a pre-baked Bake the colored coating. The film thickness of the obtained pre-baked colored coating film was measured using DektakXT (manufactured by BRUKER). A color measuring machine: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.) was used to measure the spectrum of the pre-baked colored coating film. Table 39 shows the film thickness of the prebaked colored coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the prebaked colored coating film. This pre-baked colored coating film was post-baked at 230°C for 30 minutes, thereby obtaining a post-baked colored coating film.

Comparative example 1 The components were mixed in the following proportions, and the colorant was dispersed using a bead mill to obtain a coloring composition M5. Colorant (A): C.I. Pigment Yellow 138 12.0 copies; The solid content of the dispersant 4.21 copies; The solid content of the resin 5.05 copies; Solvent (E): propylene glycol monomethyl ether acetate 74.8 copies; Solvent (E): Propylene glycol monomethyl ether 3.94 copies;

Then, each component was mixed in the following ratio, and the colored composition 5 was obtained. Coloring composition M5 24.0 copies; Resin (B): Resin B2 solution 35.0 copies; Solvent (E): Propylene Glycol Monomethyl Ether Acetate 41.0 copies; Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning (stock)) 0.00630 copies;

On a 2-inch square glass substrate (eagle XG; manufactured by Corning), the coloring composition 5 was coated by spin coating, and then pre-baked at 100°C for 3 minutes to form a pre-baked Bake the colored coating. The film thickness of the obtained pre-baked colored coating film was measured using DektakXT (manufactured by BRUKER). A color measuring machine: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.) was used to measure the spectrum of the pre-baked colored coating film. Table 39 shows the film thickness of the prebaked colored coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the prebaked colored coating film. This pre-baked colored coating film was post-baked at 230°C for 30 minutes, thereby obtaining a post-baked colored coating film.

Comparative example 2 The components were mixed in the following proportions, and the colorant was dispersed using a bead mill to obtain a coloring composition M6. Colorant (A): C.I. Pigment Yellow 138 4.50 copies; Coloring agent (A): the compound represented by formula (z) 0.500 copies; Dispersant solution: DISPERBYK-161 (manufactured by BYK-Chemie Japan Co., Ltd.) 16.7 copies; Resin (B): Resin B1 solution 11.4 copies; Solvent (E): Propylene glycol monomethyl ether acetate 46.9 copies; Solvent (E): ethyl lactate, 20.0 copies;

Then, each component was mixed in the following ratio, and the coloring composition 6 was obtained. Coloring composition M6 57.6 copies; Resin (B): Resin B2 solution 27.0 copies; Solvent (E): propylene glycol monomethyl ether acetate 15.4 copies; Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning (stock)) 0.00630 copies;

On a 2-inch square glass substrate (eagle XG; manufactured by Corning), the coloring composition 6 was coated by spin coating, and then pre-baked at 100°C for 3 minutes to form a pre-baked Bake the colored coating. The film thickness of the obtained pre-baked colored coating film was measured using DektakXT (manufactured by BRUKER). A color measuring machine: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.) was used to measure the spectrum of the pre-baked colored coating film. Table 39 shows the film thickness of the prebaked colored coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the prebaked colored coating film. This pre-baked colored coating film was post-baked at 230°C for 30 minutes, thereby obtaining a post-baked colored coating film.

In Table 39, The "AAA" column indicates the maximum absorption wavelength on the longest wavelength side of the absorption spectrum, The "BBB" column indicates the wavelength of the shoulder on the longest wavelength side of the absorption spectrum.

[Table 39] Film thickness (μm) AAA (nm) BBB (nm) Example 9 2.4 487 - Example 10 2.6 468 - Example 11 2.4 - 478 Example 12 2.3 466 - Example 13 2.5 486 - Example 14 2.4 - 477 Example 15 1.7 479 - Example 16 2.4 485 - Comparative example 1 2.4 458 - Comparative example 2 2.6 458 -

Example 17 The components were mixed in the following ratio, and the colorant was dispersed using a bead mill to obtain a coloring composition M7. Coloring agent (A): The mixture containing the compound represented by formula (Ie12) obtained in Example 7; 5.00 copies; Dispersant solution: DISPERBYK-161 (manufactured by BYK-Chemie Japan Co., Ltd.) 16.7 copies; Resin (B): Resin B1 solution 11.4 copies; Solvent (E): Propylene glycol monomethyl ether acetate 46.9 copies; Solvent (E): ethyl lactate, 20.0 copies;

Then, each component was mixed in the following ratio, and the coloring composition 7 was obtained. Coloring composition M7 57.6 copies; Resin (B): Resin B2 solution 27.0 copies; Solvent (E): propylene glycol monomethyl ether acetate 15.4 copies; Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning (stock)) 0.00630 copies;

On a 2-inch square glass substrate (eagle XG; manufactured by Corning), the coloring composition 7 was coated by spin coating, and then pre-baked at 100°C for 3 minutes to form a pre-baked Bake the colored coating. This pre-baked colored coating film was post-baked at 230°C for 30 minutes, thereby obtaining a post-baked colored coating film. The film thickness of the obtained post-baking colored coating film was measured using DektakXT (manufactured by BRUKER). A color measuring machine: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.) was used to measure the spectrum of the post-baked colored coating film. Table 40 shows the film thickness of the post-baked colored coating film and the wavelength of the shoulder on the longest wavelength side of the absorption spectrum of the post-baked colored coating film.

Comparative example 3 The components were mixed in the following proportions, and the colorant was dispersed using a bead mill to obtain a coloring composition M8. Colorant (A): C.I. Pigment Yellow 138 12.0 copies; The solid content of the dispersant 4.21 copies; The solid content of the resin 5.05 copies; Solvent (E): propylene glycol monomethyl ether acetate 74.8 copies; Solvent (E): Propylene glycol monomethyl ether 3.94 copies;

Then, each component was mixed in the following ratio, and the colored composition 8 was obtained. Coloring composition M8 24.0 copies; Resin (B): Resin B2 solution 35.0 copies; Solvent (E): Propylene Glycol Monomethyl Ether Acetate 41.0 copies; Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning (stock)) 0.00630 copies;

On a 2-inch square glass substrate (eagle XG; manufactured by Corning), the coloring composition 8 was coated by spin coating, and then prebaked at 100°C for 3 minutes to form a prebaked Bake the colored coating. This pre-baked colored coating film was post-baked at 230°C for 30 minutes, thereby obtaining a post-baked colored coating film. The film thickness of the obtained post-baking colored coating film was measured using DektakXT (manufactured by BRUKER). A color measuring machine: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.) was used to measure the spectrum of the post-baked colored coating film. Table 40 shows the film thickness of the post-baked colored coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the post-baked colored coating film.

In Table 40, The "CCC" column indicates the maximum absorption wavelength on the longest wavelength side of the absorption spectrum, The "DDD" column indicates the wavelength of the shoulder on the longest wavelength side of the absorption spectrum.

[Table 40] Film thickness (μm) CCC (nm) DDD (nm) Example 17 2.0 - 467 Comparative example 3 2.0 458 -

Comparative example 4 The components were mixed in the following ratio, and the colorant was dispersed using a bead mill to obtain a coloring composition MH4. Colorant (A): C.I. Pigment Yellow 138 4.50 copies Colorant (A): the compound represented by formula (z) 0.500 copies Dispersant solution: DISPERBYK-161 (manufactured by BYK-Chemie Japan Co., Ltd.) 16.7 copies Resin (B): Resin B1 solution 11.4 copies Solvent (E): Propylene glycol monomethyl ether acetate 46.9 copies Solvent (E): ethyl lactate 20.0 copies

Then, each component was mixed in the following ratio, and the coloring composition H4 was obtained. Coloring composition MH4 57.6 copies Resin (B): Resin B2 solution 27.0 copies Solvent (E): propylene glycol monomethyl ether acetate 15.4 copies Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning (stock)) 0.00630 copies

On a 2-inch square glass substrate (eagle XG; manufactured by Corning), the coloring composition H4 was coated by spin coating, and then pre-baked at 100°C for 3 minutes to form a pre-baked Bake the colored coating. This pre-baked colored coating film was post-baked at 230°C for 30 minutes, thereby obtaining a post-baked colored coating film. The film thickness of the obtained post-baking colored coating film was measured using DektakXT (manufactured by BRUKER). A color measuring machine: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.) was used to measure the spectrum of the post-baked colored coating film. The film thickness of the post-baked colored coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the post-baked colored coating film or the shoulder wavelength on the longest wavelength side of the absorption spectrum are shown in Table AD1.

In Table AD1 ~ Table AD21, The "EEE" column indicates the maximum absorption wavelength on the longest wavelength side of the absorption spectrum, The "FFF" column indicates the wavelength of the shoulder on the longest wavelength side of the absorption spectrum.

[Table AD1] Film thickness (μm) EEE (nm) FFF (nm) Comparative example 4 2.3 458 -

Example 6-1 The components were mixed in the following proportions, and the colorant was dispersed using a bead mill to obtain a coloring composition M6-1. Coloring agent (A): Compound represented by formula (Ia51) 4.50 copies Colorant (A): the compound represented by formula (z) 0.500 copies Dispersant solution: DISPERBYK-161 (manufactured by BYK-Chemie Japan Co., Ltd.) 16.7 copies Resin (B): Resin B1 solution 11.4 copies Solvent (E): Propylene Glycol Monomethyl Ether Acetate 66.9 copies

Then, each component was mixed in the following ratio, and the coloring composition 6-1 was obtained. Coloring composition M6-1 57.6 copies Resin (B): Resin B1 solution 28.4 copies Solvent (E): propylene glycol monomethyl ether acetate 14.0 copies Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning (stock)) 0.00630 copies

On a 2-inch square glass substrate (eagle XG; manufactured by Corning), the coloring composition 6-1 was coated by spin coating, and then pre-baked at 100°C for 3 minutes to form Pre-baked colored coating film. The film thickness of the obtained pre-baked colored coating film was measured using DektakXT (manufactured by BRUKER). A color measuring machine: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.) was used to measure the spectrum of the pre-baked colored coating film. The film thickness of the prebaked colored coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the prebaked colored coating film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD2. This pre-baked colored coating film was post-baked at 230°C for 30 minutes, thereby obtaining a post-baked colored coating film.

[Table AD2] Film thickness (μm) EEE (nm) FFF (nm) Example 6-1 2.1 - 478

Example 6-2 ~ Example 6-4 The compound represented by the formula (Ia51) was replaced with the compound described in the "colorant AAA" column in Table AD3, except that it was carried out in the same manner as in Example 6-1 to obtain a colored composition and obtain a prebaked Color coating film and post-baking color coating film. The film thickness of the prebaked colored coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the prebaked colored coating film or the shoulder wavelength on the longest wavelength side of the absorption spectrum are shown in Table AD3.

[Table AD3] Colorant AAA Film thickness (μm) EEE (nm) FFF (nm) Example 6-2 Compound represented by formula (Ia3) 2.4 490 - Example 6-3 Compound represented by formula (Ia17) 2.7 475 - Example 6-4 Compound represented by formula (Ia7) 2.7 475 -

Example 7-1 The components were mixed in the following proportions, and the colorant was dispersed using a bead mill to obtain a coloring composition M7-1. Colorant (A): 4.50 parts of the compound represented by formula (Ia973); Coloring agent (A): the compound represented by formula (z) 0.500 copies; Dispersant solution: BYK-LPN6919 (manufactured by BYK-Chemie Japan Co., Ltd.) 8.33 copies; Resin (B): Resin B1 solution 11.4 copies; Solvent (E): propylene glycol monomethyl ether acetate 75.2 copies;

Then, each component was mixed in the following ratio, and the colored composition 7-1 was obtained. Coloring composition M7-1 57.6 copies; Resin (B): Resin B1 solution 28.4 copies; Solvent (E): Propylene glycol monomethyl ether acetate, 14.0 copies; Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning (stock)) 0.00630 copies;

On a 2-inch square glass substrate (eagle XG; manufactured by Corning), the coloring composition 7-1 was coated by spin coating, and then pre-baked at 100°C for 3 minutes to form Pre-baked colored coating film. The film thickness of the obtained pre-baked colored coating film was measured using DektakXT (manufactured by BRUKER). A color measuring machine: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.) was used to measure the spectrum of the pre-baked colored coating film. The film thickness of the prebaked colored coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the prebaked colored coating film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD4. This pre-baked colored coating film was post-baked at 230°C for 30 minutes, thereby obtaining a post-baked colored coating film.

[Form AD4] Film thickness (μm) EEE (nm) FFF (nm) Example 7-1 2.2 489 -

Example 7-2 ~ Example 7-6 The compound represented by the formula (Ia973) was replaced with the compound described in the "coloring agent AAA" column in Table AD5, except that the same procedure as in Example 7-1 was carried out to obtain a colored composition and obtain a prebaked Color coating film and post-baking color coating film. The film thickness of the prebaked colored coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the prebaked colored coating film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD5.

[Table AD5] Colorant AAA Film thickness (μm) EEE (nm) FFF (nm) Example 7-2 Compound represented by formula (Ia51) 2.1 - 478 Example 7-3 Compound represented by formula (Ia969) 2.5 - 465 Example 7-4 Compound represented by formula (Ia248) 2.6 - 462 Example 7-5 Compound represented by formula (Ia36) 2.0 475 - Example 7-6 Compound represented by formula (Ia19) 2.2 - 475

Example 7-7 The components were mixed in the following proportions, and the colorant was dispersed using a bead mill to obtain a coloring composition M7-7. Colorant (A): 4.50 parts of the compound represented by formula (If2528); Coloring agent (A): the compound represented by formula (z) 0.500 copies; Dispersant solution: BYK-LPN6919 (manufactured by BYK-Chemie Japan Co., Ltd.) 8.33 copies; Resin (B): Resin B1 solution 11.4 copies; Solvent (E): propylene glycol monomethyl ether acetate 75.2 copies;

Then, each component was mixed in the following ratio, and the coloring composition 7-7 was obtained. Coloring composition M7-7 57.6 copies; Resin (B): Resin B1 solution, 28.4 copies; ??????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????? Solvent (E): Propylene glycol monomethyl ether acetate, 14.0 copies; Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning (stock)) 0.00630 copies;

On a 2-inch square glass substrate (eagle XG; manufactured by Corning), the coloring composition 7-7 was coated by spin coating, and then pre-baked at 100°C for 3 minutes to form Pre-baked colored coating film. This pre-baked colored coating film was post-baked at 230°C for 30 minutes, thereby obtaining a post-baked colored coating film. The film thickness of the obtained post-baking colored coating film was measured using DektakXT (manufactured by BRUKER). A color measuring machine: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.) was used to measure the spectrum of the post-baked colored coating film. The film thickness of the post-baked colored coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the post-baked colored coating film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD6.

[Table AD6] Film thickness (μm) EEE (nm) FFF (nm) Example 7-7 1.9 - 461

Example 90-1 The components were mixed in the following proportions, and the colorant was dispersed using a bead mill to obtain a coloring composition M90-1. Coloring agent (A): 4.00 copies of the compound represented by formula (Ia5); Colorant (A): the compound represented by formula (z) 1.00 copies; Dispersant solution: BYK-LPN6919 (manufactured by BYK-Chemie Japan Co., Ltd.) 12.5 copies; Resin (B): Resin B1 solution 11.4 copies; Solvent (E): propylene glycol monomethyl ether acetate 71.1 copies;

Then, each component was mixed in the following ratio, and the colored composition 90-1 was obtained. Coloring composition M90-1 57.6 copies; Resin (B): Resin B1 solution 24.3 copies; Solvent (E): Propylene glycol monomethyl ether acetate 18.1 copies; Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning (stock)) 0.00630 copies;

On a 2-inch square glass substrate (eagle XG; manufactured by Corning), the coloring composition 90-1 was coated by spin coating, and then pre-baked at 100°C for 3 minutes to form Pre-baked colored coating film. The film thickness of the obtained pre-baked colored coating film was measured using DektakXT (manufactured by BRUKER). A color measuring machine: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.) was used to measure the spectrum of the pre-baked colored coating film. The film thickness of the prebaked colored coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the prebaked colored coating film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD7. This pre-baked colored coating film was post-baked at 230°C for 30 minutes, thereby obtaining a post-baked colored coating film.

[Form AD7] Film thickness (μm) EEE (nm) FFF (nm) Example 90-1 2.6 471 -

Example 90-2 ~ Example 90-22 The compound represented by the formula (Ia5) was replaced with the compound described in the "colorant AAA" column in Table AD8, except that the same procedure as in Example 90-1 was carried out to obtain a colored composition, and to obtain a prebaked Color coating film and post-baking color coating film. The film thickness of the prebaked colored coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the prebaked colored coating film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD8.

[Table AD8] Colorant AAA Film thickness (μm) EEE (nm) FFF (nm) Example 90-2 Compound represented by formula (Ia696) 2.1 486 - Example 90-3 The compound represented by formula (If5688) 2.2 479 - Example 90-4 Compound represented by formula (If636) 2.8 - 502 Example 90-5 Compound represented by formula (If5720) 2.2 459 - Example 90-6 Compound represented by formula (Ia712) 2.8 484 - Example 90-7 Compound represented by formula (If1260) 2.3 - 469 Example 90-8 Compound represented by formula (If13040) 2.4 - 485 Example 90-9 The compound represented by formula (If8454) 3.4 485 - Example 90-10 Compound represented by formula (If2511) 2.8 474 - Example 90-11 Compound represented by formula (If3814) 3.2 485 - Examples 90-12 Compound represented by formula (If654) 3.2 472 - Example 90-13 Compound represented by formula (If29) 3.6 467 - Examples 90-14 Compound represented by formula (If1279) 2.4 459 - Examples 90-15 Compound represented by formula (Ia970) 3.5 478 - Examples 90-16 Compound represented by formula (If3171) 2.5 479 - Examples 90-17 Compound represented by formula (Ia686) 2.9 - 489 Examples 90-18 Compound represented by formula (Ia657) 2.4 485 - Examples 90-19 Compound represented by formula (If3799) 2.2 485 - Examples 90-20 Compound represented by formula (It232) 2.7 509 - Examples 90-21 Compound represented by formula (It750) 2.6 487 - Examples 90-22 The mixture containing the compound represented by formula (Ia5-SA1) and the compound represented by formula (Ia5-SA2) obtained in Example E-1 2.2 - 465

Examples 90-23 The components were mixed in the following proportions, and the colorant was dispersed using a bead mill to obtain a coloring composition M90-23. Colorant (A): 4.00 parts of compound represented by formula (If1904); Colorant (A): the compound represented by formula (z) 1.00 copies; Dispersant solution: BYK-LPN6919 (manufactured by BYK-Chemie Japan Co., Ltd.) 12.5 copies; Resin (B): Resin B1 solution 11.4 copies; Solvent (E): propylene glycol monomethyl ether acetate 71.1 copies;

Then, each component was mixed in the following ratio, and the colored composition 90-23 was obtained. Coloring composition M90-23 57.6 copies; Resin (B): Resin B1 solution 24.3 copies; Solvent (E): Propylene glycol monomethyl ether acetate 18.1 copies; Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning (stock)) 0.00630 copies;

On a 2-inch square glass substrate (eagle XG; manufactured by Corning), the coloring composition 90-23 was coated by spin coating, and then pre-baked at 100°C for 3 minutes to form Pre-baked colored coating film. This pre-baked colored coating film was post-baked at 230°C for 30 minutes, thereby obtaining a post-baked colored coating film. The film thickness of the obtained post-baking colored coating film was measured using DektakXT (manufactured by BRUKER). A color measuring machine: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.) was used to measure the spectrum of the post-baked colored coating film. The film thickness of the post-baked colored coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the post-baked colored coating film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD9.

[Form AD9] Film thickness (μm) EEE (nm) FFF (nm) Examples 90-23 1.9 459 -

Example 91-1 The components were mixed in the following proportions, and the colorant was dispersed using a bead mill to obtain a coloring composition M91-1. Colorant (A): 4.00 parts of the compound represented by formula (If3796); Colorant (A): the compound represented by formula (z) 1.00 copies; Dispersant solution: BYK-LPN6919 (manufactured by BYK-Chemie Japan Co., Ltd.) 12.5 copies; Resin (B): Resin B1 solution 11.4 copies; Solvent (E): propylene glycol monomethyl ether acetate 71.1 copies;

Then, each component was mixed in the following ratio, and the coloring composition 91-1 was obtained. Coloring composition M91-1 51.2 copies; Resin (B): Resin B1 solution 21.6 copies; Solvent (E): Propylene glycol monomethyl ether acetate 27.2 copies; Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning (stock)) 0.00560 copies;

On a 2-inch square glass substrate (eagle XG; manufactured by Corning), the coloring composition 91-1 was coated by spin coating, and then pre-baked at 100°C for 3 minutes to form Pre-baked colored coating film. The film thickness of the obtained pre-baked colored coating film was measured using DektakXT (manufactured by BRUKER). A color measuring machine: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.) was used to measure the spectrum of the pre-baked colored coating film. The film thickness of the prebaked colored coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the prebaked colored coating film or the shoulder wavelength on the longest wavelength side of the absorption spectrum are shown in Table AD10. This pre-baked colored coating film was post-baked at 230°C for 30 minutes, thereby obtaining a post-baked colored coating film.

[Form AD10] Film thickness (μm) EEE (nm) FFF (nm) Example 91-1 1.8 484 -

Example 91-2 ~ Example 91-4 Except that the compound represented by the formula (If3796) was replaced with the compound described in the "colorant AAA" column in Table AD11, the same procedure as in Example 91-1 was carried out to obtain a colored composition and obtain a prebaked Color coating film and post-baking color coating film. The film thickness of the prebaked colored coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the prebaked colored coating film or the shoulder wavelength on the longest wavelength side of the absorption spectrum are shown in Table AD11.

[Form AD11] Colorant AAA Film thickness (μm) EEE (nm) FFF (nm) Example 91-2 Compound represented by formula (Ia699) 1.4 479 - Example 91-3 Compound represented by formula (Ia4) 1.6 479 - Example 91-4 Compound represented by formula (If635) 1.8 480 -

Example 17-1 The components were mixed in the following proportions, and the colorant was dispersed using a bead mill to obtain a coloring composition M17-1. Coloring agent (A): 3.89 parts of the mixture containing the compound represented by formula (Ia1-SA1) and the compound represented by formula (Ia1-SA2) obtained in Example E-2; Colorant (A): the compound represented by formula (z) 1.25 copies; Dispersant solution: BYK-LPN6919 (manufactured by BYK-Chemie Japan Co., Ltd.) 12.5 copies; Resin (B): Resin B1 solution 11.5 copies; Solvent (E): propylene glycol monomethyl ether acetate 70.9 parts;

Then, each component was mixed in the following ratio, and the coloring composition 17-1 was obtained. Coloring composition M17-1 57.6 copies; Resin (B): Resin B1 solution 24.3 copies; Solvent (E): Propylene glycol monomethyl ether acetate 18.1 copies; Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning (stock)) 0.00629 copies;

On a 2-inch square glass substrate (eagle XG; manufactured by Corning), the coloring composition 17-1 was applied by spin coating, and then pre-baked at 100°C for 3 minutes to form Pre-baked colored coating film. The film thickness of the obtained pre-baked colored coating film was measured using DektakXT (manufactured by BRUKER). A color measuring machine: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.) was used to measure the spectrum of the pre-baked colored coating film. The film thickness of the prebaked colored coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the prebaked colored coating film or the shoulder wavelength on the longest wavelength side of the absorption spectrum are shown in Table AD12. This pre-baked colored coating film was post-baked at 230°C for 30 minutes, thereby obtaining a post-baked colored coating film.

[Table AD12] Film thickness (μm) EEE (nm) FFF (nm) Example 17-1 2.2 - 474

Example 12-1 The components were mixed in the following proportions, and the colorant was dispersed using a bead mill to obtain a coloring composition M12-1. Colorant (A): 3.80 parts of the compound represented by formula (If1261); Colorant (A): 1.20 copies of the compound represented by formula (z); Dispersant solution: BYK-LPN6919 (manufactured by BYK-Chemie Japan Co., Ltd.) 12.5 copies; Resin (B): Resin B1 solution 11.4 copies; Solvent (E): propylene glycol monomethyl ether acetate 71.1 copies;

Then, each component was mixed in the following ratio, and the coloring composition 12-1 was obtained. Coloring composition M12-1 57.6 copies; Resin (B): Resin B1 solution 24.3 copies; Solvent (E): Propylene glycol monomethyl ether acetate 18.1 copies; Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning (stock)) 0.00630 copies;

On a 2-inch square glass substrate (eagle XG; manufactured by Corning), the coloring composition 12-1 was coated by spin coating, and then pre-baked at 100°C for 3 minutes to form Pre-baked colored coating film. This pre-baked colored coating film was post-baked at 230°C for 30 minutes, thereby obtaining a post-baked colored coating film. The film thickness of the obtained post-baking colored coating film was measured using DektakXT (manufactured by BRUKER). A color measuring machine: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.) was used to measure the spectrum of the post-baked colored coating film. The film thickness of the post-baked colored coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the post-baked colored coating film or the shoulder wavelength on the longest wavelength side of the absorption spectrum are shown in Table AD13.

[Form AD13] Film thickness (μm) EEE (nm) FFF (nm) Example 12-1 1.9 459 -

Example 13-1 The components were mixed in the following proportions, and the colorant was dispersed using a bead mill to obtain a coloring composition M13-1. Colorant (A): 5.01 copies of the compound represented by formula (Ia728); Dispersant solution: BYK-LPN6919 (manufactured by BYK-Chemie Japan Co., Ltd.) 12.5 copies; Resin (B): Resin B1 solution 11.4 copies; Solvent (E): propylene glycol monomethyl ether acetate 71.1 copies;

Then, each component was mixed in the following ratio, and the coloring composition 13-1 was obtained. Coloring composition M13-1 57.4 copies; Resin (B): Resin B1 solution 24.3 copies; Solvent (E): Propylene glycol monomethyl ether acetate 18.2 copies; Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning (stock)) 0.00636 copies;

On a 2-inch square glass substrate (eagle XG; manufactured by Corning), the coloring composition 13-1 was applied by spin coating, and then pre-baked at 100°C for 3 minutes to form Pre-baked colored coating film. The film thickness of the obtained pre-baked colored coating film was measured using DektakXT (manufactured by BRUKER). A color measuring machine: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.) was used to measure the spectrum of the pre-baked colored coating film. The film thickness of the prebaked colored coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the prebaked colored coating film or the shoulder wavelength on the longest wavelength side of the absorption spectrum are shown in Table AD14. This pre-baked colored coating film was post-baked at 230°C for 30 minutes, thereby obtaining a post-baked colored coating film.

[Form AD14] Film thickness (μm) EEE (nm) FFF (nm) Example 13-1 2.9 474 -

Example 14-1 The components were mixed in the following proportions, and the colorant was dispersed using a bead mill to obtain a coloring composition M14-1. Colorant (A): 4.66 parts of the compound represented by formula (Ia703); Colorant (A): 0.497 parts of the compound represented by formula (z); Dispersant solution: BYK-LPN6919 (manufactured by BYK-Chemie Japan Co., Ltd.) 12.5 copies; Resin (B): Resin B1 solution 11.4 copies; Solvent (E): propylene glycol monomethyl ether acetate 70.9 parts;

Then, each component was mixed in the following ratio, and the colored composition 14-1 was obtained. Coloring composition M14-1 55.5 copies; Resin (B): Resin B1 solution 24.9 copies; Solvent (E): propylene glycol monomethyl ether acetate 19.6 copies; Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning (stock)) 0.00635 copies;

On a 2-inch square glass substrate (eagle XG; manufactured by Corning), the coloring composition 14-1 was coated by spin coating, and then pre-baked at 100°C for 3 minutes to form Pre-baked colored coating film. The film thickness of the obtained pre-baked colored coating film was measured using DektakXT (manufactured by BRUKER). A color measuring machine: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.) was used to measure the spectrum of the pre-baked colored coating film. The film thickness of the prebaked colored coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the prebaked colored coating film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD15. This pre-baked colored coating film was post-baked at 230°C for 30 minutes, thereby obtaining a post-baked colored coating film.

[Table AD15] Film thickness (μm) EEE (nm) FFF (nm) Example 14-1 2.3 488 -

Example 16-1 The components were mixed in the following proportions, and the colorant was dispersed using a bead mill to obtain a coloring composition M16-1. Colorant (A): 4.13 parts of the compound represented by formula (It242); Colorant (A): 0.916 parts of the compound represented by formula (z); Dispersant solution: BYK-LPN6919 (manufactured by BYK-Chemie Japan Co., Ltd.) 12.4 copies; Resin (B): Resin B1 solution 11.4 copies; Solvent (E): propylene glycol monomethyl ether acetate 71.1 copies;

Then, each component was mixed in the following ratio, and the coloring composition 16-1 was obtained. Coloring composition M16-1 57.8 copies; Resin (B): Resin B1 solution 24.1 copies; Solvent (E): Propylene glycol monomethyl ether acetate 18.1 copies; Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning (stock)) 0.00628 copies;

On a 2-inch square glass substrate (eagle XG; manufactured by Corning), the coloring composition 16-1 was coated by spin coating, and then pre-baked at 100°C for 3 minutes to form Pre-baked colored coating film. The film thickness of the obtained pre-baked colored coating film was measured using DektakXT (manufactured by BRUKER). A color measuring machine: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.) was used to measure the spectrum of the pre-baked colored coating film. The film thickness of the prebaked colored coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the prebaked colored coating film or the shoulder wavelength on the longest wavelength side of the absorption spectrum are shown in Table AD16. This pre-baked colored coating film was post-baked at 230°C for 30 minutes, thereby obtaining a post-baked colored coating film.

[Form AD16] Film thickness (μm) EEE (nm) FFF (nm) Example 16-1 2.5 494 -

Example 51-1 The components were mixed in the following proportions, and the colorant was dispersed using a bead mill to obtain a coloring composition M51-1. Colorant (A): 2.25 parts of the compound represented by formula (Ia2); Colorant (A): 2.25 parts of the compound represented by formula (Ia5); Colorant (A): the compound represented by formula (z) 0.500 copies; Dispersant solution: DISPERBYK-161 (manufactured by BYK-Chemie Japan Co., Ltd.) 16.7 copies; Resin (B): Resin B1 solution 11.4 copies; Solvent (E): Propylene glycol monomethyl ether acetate 46.9 copies; Solvent (E): ethyl lactate, 20.0 copies;

Then, each component was mixed in the following ratio, and the colored composition 51-1 was obtained. Coloring composition M51-1 57.6 copies; Resin (B): Resin B1 solution, 28.4 copies; ??????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????????? Solvent (E): Propylene glycol monomethyl ether acetate, 14.0 copies; Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning (stock)) 0.00630 copies;

On a 2-inch square glass substrate (eagle XG; manufactured by Corning), the colored composition 51-1 was coated by spin coating, and then pre-baked at 100°C for 3 minutes to form Pre-baked colored coating film. The film thickness of the obtained pre-baked colored coating film was measured using DektakXT (manufactured by BRUKER). A color measuring machine: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.) was used to measure the spectrum of the pre-baked colored coating film. The film thickness of the prebaked colored coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the prebaked colored coating film or the shoulder wavelength on the longest wavelength side of the absorption spectrum are shown in Table AD17. This pre-baked colored coating film was post-baked at 230°C for 30 minutes, thereby obtaining a post-baked colored coating film.

[Form AD17] Film thickness (μm) EEE (nm) FFF (nm) Example 51-1 2.4 485 -

Example 571-1 The components were mixed in the following proportions, and the colorant was dispersed using a bead mill to obtain a coloring composition M571-1. Colorant (A): 2.25 parts of the compound represented by formula (Ia1); Colorant (A): 2.25 parts of the compound represented by formula (Ia5); Coloring agent (A): the compound represented by formula (z) 0.500 copies; Dispersant solution: BYK-LPN6919 (manufactured by BYK-Chemie Japan Co., Ltd.) 8.33 copies; Resin (B): Resin B1 solution 10.0 copies; Solvent (E): propylene glycol monomethyl ether acetate 76.7 copies;

Then, each component was mixed in the following ratio, and the coloring composition 571-1 was obtained. Coloring composition M571-1 57.6 copies; Resin (B): Resin B1 solution 29.2 copies; Solvent (E): Propylene glycol monomethyl ether acetate 13.2 copies; Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning (stock)) 0.00630 copies;

On a 2-inch square glass substrate (eagle XG; manufactured by Corning), the coloring composition 571-1 was applied by spin coating, and then pre-baked at 100°C for 3 minutes to form Pre-baked colored coating film. The film thickness of the obtained pre-baked colored coating film was measured using DektakXT (manufactured by BRUKER). A color measuring machine: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.) was used to measure the spectrum of the pre-baked colored coating film. The film thickness of the prebaked colored coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the prebaked colored coating film or the shoulder wavelength on the longest wavelength side of the absorption spectrum are shown in Table AD18. This pre-baked colored coating film was post-baked at 230°C for 30 minutes, thereby obtaining a post-baked colored coating film.

[Form AD18] Film thickness (μm) EEE (nm) FFF (nm) Example 571-1 2.1 477 -

Example 591-1 The components were mixed in the following proportions, and the colorant was dispersed using a bead mill to obtain a coloring composition M591-1. Colorant (A): 2.25 parts of the compound represented by formula (Ia1); Colorant (A): 2.25 parts of the compound represented by formula (Ia248); Coloring agent (A): the compound represented by formula (z) 0.500 copies; Dispersant solution: BYK-LPN6919 (manufactured by BYK-Chemie Japan Co., Ltd.) 12.5 copies; Resin (B): Resin B1 solution 11.4 copies; Solvent (E): propylene glycol monomethyl ether acetate 71.1 copies;

Then, each component was mixed in the following ratio, and the colored composition 591-1 was obtained. Coloring composition M591-1 57.6 copies; Resin (B): Resin B1 solution 24.3 copies; Solvent (E): Propylene glycol monomethyl ether acetate 18.1 copies; Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning (stock)) 0.00630 copies;

On a 2-inch square glass substrate (eagle XG; manufactured by Corning), the coloring composition 591-1 was coated by spin coating, and then pre-baked at 100°C for 3 minutes to form Pre-baked colored coating film. The film thickness of the obtained pre-baked colored coating film was measured using DektakXT (manufactured by BRUKER). A color measuring machine: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.) was used to measure the spectrum of the pre-baked colored coating film. The film thickness of the prebaked colored coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the prebaked colored coating film or the shoulder wavelength on the longest wavelength side of the absorption spectrum are shown in Table AD19. This pre-baked colored coating film was post-baked at 230°C for 30 minutes, thereby obtaining a post-baked colored coating film.

Example 591-2 In Example 591-1, instead of the compound represented by the formula (Ia1) and the compound represented by the formula (Ia248), the following coloring agent (A) was used in the following amount, except that the same as in Example 591-1 In the same manner, a colored composition is obtained, and a pre-baked colored coating film and a post-baked colored coating film are obtained. Colorant (A): a mixture of the compound represented by formula (Ia10), the compound represented by formula (Ia2143), the compound represented by formula (Ia850) and the compound represented by formula (Ia315) obtained in Example 4. 2.38 Copies Colorant (A): 2.12 parts of the compound represented by formula (Ia51); The film thickness of the prebaked colored coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the prebaked colored coating film or the shoulder wavelength on the longest wavelength side of the absorption spectrum are shown in Table AD19.

Example 591-3 In Example 591-1, instead of the compound represented by the formula (Ia1) and the compound represented by the formula (Ia248), the following coloring agent (A) was used in the following amount, except that the same as in Example 591-1 In the same manner, a colored composition is obtained, and a pre-baked colored coating film and a post-baked colored coating film are obtained. Colorant (A): 2.38 parts of the compound represented by formula (Ia248); Colorant (A): 2.12 parts of the compound represented by formula (Ia51); The film thickness of the prebaked colored coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the prebaked colored coating film or the shoulder wavelength on the longest wavelength side of the absorption spectrum are shown in Table AD19.

Example 591-4 In Example 591-1, instead of the compound represented by the formula (Ia1) and the compound represented by the formula (Ia248), the following coloring agent (A) was used in the following amount, except that the same as in Example 591-1 In the same manner, a colored composition is obtained, and a pre-baked colored coating film and a post-baked colored coating film are obtained. Colorant (A): 2.64 parts of the compound represented by formula (Ia23); Colorant (A): 1.86 parts of the compound represented by formula (Ia17); The film thickness of the prebaked colored coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the prebaked colored coating film or the shoulder wavelength on the longest wavelength side of the absorption spectrum are shown in Table AD19.

Example 591-5 In Example 591-1, instead of the compound represented by the formula (Ia1) and the compound represented by the formula (Ia248), the following coloring agent (A) was used in the following amount, except that the same as in Example 591-1 In the same manner, a colored composition is obtained, and a pre-baked colored coating film and a post-baked colored coating film are obtained. Colorant (A): 2.17 parts of the compound represented by formula (Ia19); Colorant (A): 2.33 parts of the compound represented by formula (Ia17); The film thickness of the prebaked colored coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the prebaked colored coating film or the shoulder wavelength on the longest wavelength side of the absorption spectrum are shown in Table AD19.

[Form AD19] Film thickness (μm) EEE (nm) FFF (nm) Example 591-1 2.0 480 - Example 591-2 2.1 - 467 Example 591-3 2.1 - 465 Example 591-4 2.7 - 481 Example 591-5 2.3 475 -

Example 592-1 The components were mixed in the following proportions, and the colorant was dispersed using a bead mill to obtain a coloring composition M592-1. Coloring agent (A): 4.00 copies of the compound represented by formula (Ia1); Coloring agent (A): 1.00 part of compound represented by formula (Ia248); Dispersant solution: BYK-LPN6919 (manufactured by BYK-Chemie Japan Co., Ltd.) 12.5 copies; Resin (B): Resin B1 solution 11.4 copies; Solvent (E): propylene glycol monomethyl ether acetate 71.1 copies;

Then, the components were mixed in the following proportions to obtain a colored composition 592-1. Coloring composition M592-1 57.6 copies; Resin (B): Resin B1 solution 24.3 copies; Solvent (E): Propylene glycol monomethyl ether acetate 18.1 copies; Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning (stock)) 0.00630 copies;

On a 2-inch square glass substrate (eagle XG; manufactured by Corning), the coloring composition 592-1 was coated by spin coating, and then pre-baked at 100°C for 3 minutes to form Pre-baked colored coating film. The film thickness of the obtained pre-baked colored coating film was measured using DektakXT (manufactured by BRUKER). A color measuring machine: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.) was used to measure the spectrum of the pre-baked colored coating film. The film thickness of the prebaked colored coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the prebaked colored coating film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD20. This pre-baked colored coating film was post-baked at 230°C for 30 minutes, thereby obtaining a post-baked colored coating film.

Example 592-2 In Example 592-1, instead of the compound represented by the formula (Ia1) and the compound represented by the formula (Ia248), the following coloring agent (A) was used in the following amount, except that it was the same as in Example 592-1 In the same manner, a colored composition is obtained, and a pre-baked colored coating film and a post-baked colored coating film are obtained. Coloring agent (A): 4.00 copies of the compound represented by formula (Ia5); Coloring agent (A): 1.00 part of compound represented by formula (Ia248); The film thickness of the prebaked colored coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the prebaked colored coating film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD20.

Example 592-3 In Example 592-1, instead of the compound represented by the formula (Ia1) and the compound represented by the formula (Ia248), the following coloring agent (A) was used in the following amount, except that it was the same as in Example 592-1 In the same manner, a colored composition is obtained, and a pre-baked colored coating film and a post-baked colored coating film are obtained. Colorant (A): 4.00 copies of the compound represented by formula (Ia699); Coloring agent (A): 1.00 part of compound represented by formula (Ia248); The film thickness of the prebaked colored coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the prebaked colored coating film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD20.

Example 592-4 In Example 592-1, instead of the compound represented by the formula (Ia1) and the compound represented by the formula (Ia248), the following coloring agent (A) was used in the following amount, except that it was the same as in Example 592-1 In the same manner, a colored composition is obtained, and a pre-baked colored coating film and a post-baked colored coating film are obtained. Coloring agent (A): 4.00 copies of the compound represented by formula (Ia5); Coloring agent (A): obtained in Example E-1, containing a mixture of the compound represented by formula (Ia5-SA1) and the compound represented by formula (Ia5-SA2) 1.00 part; The film thickness of the prebaked colored coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the prebaked colored coating film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD20.

[Form AD20] Film thickness (μm) EEE (nm) FFF (nm) Example 592-1 2.2 483 - Example 592-2 2.4 471 - Example 592-3 2.5 478 - Example 592-4 2.8 472 -

Example S-1 The components were mixed in the following proportions to obtain a colored composition S-1. Coloring agent (A): 2.92 parts of a mixture of the compound represented by formula (Ia5-SA1) and the compound represented by formula (Ia5-SA2) obtained in Example E-1, and N-methylpyrrolidone 97.1 A mixture of parts 51.4 parts; Resin (B): Resin B1 solution 38.5 copies; Solvent (E): propylene glycol monomethyl ether acetate, 10.1 copies; Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning (stock)) 0.00531 copies;

On a 2-inch square glass substrate (eagle XG; manufactured by Corning), the coloring composition S-1 was coated by spin coating, and then pre-baked at 100°C for 3 minutes to form Pre-baked colored coating film. This pre-baked colored coating film was post-baked at 230°C for 30 minutes, thereby obtaining a post-baked colored coating film. The film thickness of the obtained post-baking colored coating film was measured using DektakXT (manufactured by BRUKER). A color measuring machine: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.) was used to measure the spectrum of the post-baked colored coating film. The film thickness of the post-baked colored coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the post-baked colored coating film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD21.

Example S-2 The components were mixed in the following proportions to obtain a colored composition S-2. Coloring agent (A): a mixture of 1.00 part of the compound represented by the formula (If5670) and 99.0 parts of N-methylpyrrolidone 59.2 parts; Resin (B): Resin B1 solution 40.5 copies; Solvent (E): propylene glycol monomethyl ether acetate 0.278 parts; Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning (stock)) 0.00514 copies;

On a 2-inch square glass substrate (eagle XG; manufactured by Corning), the coloring composition S-2 was coated by spin coating, and then pre-baked at 100°C for 3 minutes to form Pre-baked colored coating film. This pre-baked colored coating film was post-baked at 230°C for 30 minutes, thereby obtaining a post-baked colored coating film. The film thickness of the obtained post-baking colored coating film was measured using DektakXT (manufactured by BRUKER). A color measuring machine: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.) was used to measure the spectrum of the post-baked colored coating film. The film thickness of the post-baked colored coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the post-baked colored coating film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD21.

Example S-3 The components were mixed in the following proportions to obtain a colored composition S-3. Colorant (A): The mixture containing the compound represented by the formula (Ia2-SA) obtained in Example E-3, 2.24 copies; Resin (B): Resin B1 solution 33.6 copies; Solvent (E): propylene glycol monomethyl ether acetate 0.581 copies; Solvent (E): N-methylpyrrolidone, 63.6 copies; Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning (stock)) 0.00490 copies;

On a 2-inch square glass substrate (eagle XG; manufactured by Corning), the coloring composition S-3 was coated by spin coating, and then pre-baked at 100°C for 3 minutes to form Pre-baked colored coating film. The film thickness of the obtained pre-baked colored coating film was measured using DektakXT (manufactured by BRUKER). A color measuring machine: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.) was used to measure the spectrum of the pre-baked colored coating film. The film thickness of the prebaked colored coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the prebaked colored coating film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD21. This pre-baked colored coating film was post-baked at 230°C for 30 minutes, thereby obtaining a post-baked colored coating film.

[Form AD21] Film thickness (μm) EEE (nm) FFF (nm) Example S-1 4.6 464 - Example S-2 4.0 461 - Example S-3 1.9 470 -

According to the above results, it is found that the wavelength of the maximum absorption wavelength on the longest wavelength side of the absorption spectrum or the shoulder peak on the longest wavelength side of the absorption spectrum of the colored coating film formed from the coloring composition containing the compound of the present invention is the same The colored coating film formed from the colored composition of Yellow 138 has a longer wavelength than the maximum absorption wavelength on the longest wavelength side of the absorption spectrum. [Industrial availability]

Compared with the coloring composition containing CI Pigment Yellow 138, the coloring composition and compound of the present invention can be used in the formation of a color filter with a denser color, and therefore can be suitably used for color filters, liquid crystal display devices, etc. Display device.

no

Claims (6)

A coloring composition comprising: a compound represented by the following formula (I) and a solvent,

[In formula (I), R ¹ to R ⁵ each independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, MM, a monovalent hydrocarbon group having 1 to 40 carbons, or A monovalent heterocyclic group having 1 to 40 carbon atoms, -C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -Si(-)(-)-, -CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N(-)-, and -CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group It may also be substituted with -N=, and -CH ₂ -constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -O-, -S-, -S(O) ₂ -or -CO- , The hydrogen atoms constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may also be substituted with halogen atoms, cyano groups, nitro groups, -SO ₃ M, -CO ₂ M or MM; R ¹ and R ² , R ² and R ³ , and R ³ and R ⁴ may be bonded to each other to form a ring; M represents a hydrogen atom, an alkali metal atom, a metal atom that may have a ligand, or N(Z ¹ )(Z ² )(Z ³ )(Z ⁴ ); MM represents an alkali metal atom, a metal atom that may have a ligand, or N(Z ¹ )(Z ² )(Z ³ )(Z ⁴ ); Z ¹ ～Z ⁴ each independently represent a hydrogen atom , A monovalent hydrocarbon group with 1 to 40 carbons or a monovalent heterocyclic group with 1 to 40 carbons, -C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted Is -Si(-)(-)-, -CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N(-)-, constituting the monovalent hydrocarbon group and The -CH= of the monovalent heterocyclic group may be substituted with -N=, and the -CH ₂ -constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -O-, -S-, -S(O) ₂ -or -CO-, the hydrogen atoms constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with halogen atoms, cyano groups, nitro groups, -SO ₃ M, -CO ₂ M or MM; Q ¹ and Q ² each independently represent a divalent hydrocarbon group or a divalent heterocyclic group, and -C(-)(-)- constituting the divalent hydrocarbon group and the divalent heterocyclic group may also be substituted Is -Si(-)(-)-, -CH(-)- constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted with -N(-)-, constituting the divalent hydrocarbon group and The -CH= of the divalent heterocyclic group may be substituted with -N=, and the -CH ₂ -constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted with -O-, -S-, -S(O) ₂ -or -CO-, the hydrogen atoms constituting the divalent hydrocarbon group and the divalent heterocyclic group may also be substituted with halogen atoms, cyano groups, nitro groups, -SO ₃ M, -CO ₂ M or MM; when there are a plurality of Z ¹ ˜Z ⁴ , M and MM, these may be the same or different from each other]. The coloring composition according to claim 1, which contains a resin. The coloring composition according to claim 1 or claim 2, which contains a polymerizable compound and a polymerization initiator. A color filter is formed of the coloring composition according to any one of Claims 1 to 3. A display device comprising the color filter according to claim 4. A compound represented by formula (I),

[In formula (I), R ¹ to R ⁵ each independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, MM, a monovalent hydrocarbon group having 1 to 40 carbons, or A monovalent heterocyclic group having 1 to 40 carbon atoms, -C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -Si(-)(-)-, -CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N(-)-, and -CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group It may also be substituted with -N=, and -CH ₂ -constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -O-, -S-, -S(O) ₂ -or -CO- , The hydrogen atoms constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may also be substituted with halogen atoms, cyano groups, nitro groups, -SO ₃ M, -CO ₂ M or MM; R ¹ and R ² , R ² and R ³ , and R ³ and R ⁴ may be bonded to each other to form a ring; M represents a hydrogen atom, an alkali metal atom, a metal atom that may have a ligand, or N(Z ¹ )(Z ² )(Z ³ )(Z ⁴ ); MM represents an alkali metal atom, a metal atom that may have a ligand, or N(Z ¹ )(Z ² )(Z ³ )(Z ⁴ ); Z ¹ ～Z ⁴ each independently represent a hydrogen atom , A monovalent hydrocarbon group with 1 to 40 carbons or a monovalent heterocyclic group with 1 to 40 carbons, -C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted Is -Si(-)(-)-, -CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -N(-)-, constituting the monovalent hydrocarbon group and The -CH= of the monovalent heterocyclic group may be substituted with -N=, and the -CH ₂ -constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with -O-, -S-, -S(O) ₂ -or -CO-, the hydrogen atoms constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted with halogen atoms, cyano groups, nitro groups, -SO ₃ M, -CO ₂ M or MM; Q ¹ and Q ² each independently represent a divalent hydrocarbon group or a divalent heterocyclic group, and -C(-)(-)- constituting the divalent hydrocarbon group and the divalent heterocyclic group may also be substituted Is -Si(-)(-)-, -CH(-)- constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted with -N(-)-, constituting the divalent hydrocarbon group and The -CH= of the divalent heterocyclic group may be substituted with -N=, and the -CH ₂ -constituting the divalent hydrocarbon group and the divalent heterocyclic group may be substituted with -O-, -S-, -S(O) ₂ -or -CO-, the hydrogen atoms constituting the divalent hydrocarbon group and the divalent heterocyclic group may also be substituted with halogen atoms, cyano groups, nitro groups, -SO ₃ M, -CO ₂ M or MM; when there are a plurality of Z ¹ ˜Z ⁴ , M and MM, these may be the same or different from each other].