TWI851660B - Coloring composition, compound, color filter and display device - Google Patents

Coloring composition, compound, color filter and display device Download PDF

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TWI851660B
TWI851660B TW109104792A TW109104792A TWI851660B TW I851660 B TWI851660 B TW I851660B TW 109104792 A TW109104792 A TW 109104792A TW 109104792 A TW109104792 A TW 109104792A TW I851660 B TWI851660 B TW I851660B
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織田勝成
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日商住友化學股份有限公司
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Abstract

本發明的目的在於提供一種著色組成物,其包含:於比先前已知的C.I.顏料黃138的吸收光譜的最長波長側的極大吸收波長更長的波長側具有吸收光譜的最長波長側的極大吸收波長的化合物、及/或具有吸收光譜的最長波長側的肩峰的波長的化合物。本發明是有關於一種著色組成物,其包含式(I)所表示的化合物及溶劑。 The object of the present invention is to provide a coloring composition comprising: a compound having a maximum absorption wavelength on the longest wavelength side of the absorption spectrum at a longer wavelength than the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the previously known CI Pigment Yellow 138, and/or a compound having a wavelength of a shoulder peak on the longest wavelength side of the absorption spectrum. The present invention relates to a coloring composition comprising a compound represented by formula (I) and a solvent.

Description

著色組成物、化合物、彩色濾光片及顯示裝置Coloring composition, compound, color filter and display device

本發明是有關於一種著色組成物、化合物、彩色濾光片及顯示裝置。 The present invention relates to a coloring composition, a compound, a color filter and a display device.

著色組成物可用於製造液晶顯示裝置、電致發光顯示裝置等顯示裝置中所使用的彩色濾光片。作為著色組成物中所含的著色劑,已知有C.I.顏料黃(pigment yellow)138(專利文獻1)。 The coloring composition can be used to manufacture color filters used in display devices such as liquid crystal display devices and electroluminescent display devices. As a coloring agent contained in the coloring composition, C.I. Pigment Yellow 138 is known (Patent Document 1).

Figure 109104792-A0305-02-0002-1
Figure 109104792-A0305-02-0002-1

(C.I.顏料黃138) (C.I. Pigment Yellow 138)

[現有技術文獻] [Prior art literature]

[專利文獻] [Patent Literature]

[專利文獻1]日本專利特開2013-82906號公報 [Patent document 1] Japanese Patent Publication No. 2013-82906

近年來,關於顯示顯示器,用於擴大可顯示的顏色再現區域的開發正在推進,作為其中一環,彩色濾光片亦要求顏色更濃。為了滿足該要求,需要如下著色組成物,其包含:於比先前已知的C.I.顏料黃138的吸收光譜的最長波長側的極大吸收波長更長的波長側具有吸收光譜的最長波長側的極大吸收波長的化合物、及/或具有吸收光譜的最長波長側的肩峰(shoulder peak)的波長的化合物。 In recent years, the development of display devices for expanding the color reproduction area that can be displayed has been advancing, and as one of the links, color filters are also required to have richer colors. In order to meet this requirement, the following coloring composition is required, which includes: a compound having a maximum absorption wavelength on the longest wavelength side of the absorption spectrum at a longer wavelength than the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the previously known C.I. Pigment Yellow 138, and/or a compound having a wavelength of a shoulder peak on the longest wavelength side of the absorption spectrum.

所謂所述吸收光譜的最長波長側的肩峰的波長,是指:於化合物.在比C.I.顏料黃138的吸收光譜的最長波長側的極大吸收波長更長的波長側,不具有吸收光譜的最長波長側的極大吸收波長的情況下、且.在比吸收光譜的最長波長側的極大吸收波長更長的波長側,具有兩個以上的吸收光譜的拐點的情況下,吸收光譜的最長波長側的拐點的波長、與吸收光譜的第二長的波長側的拐點的波長的平均值的波長。 The wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum refers to: for a compound, when there is no maximum absorption wavelength on the longest wavelength side of the absorption spectrum on a wavelength side longer than the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of C.I. Pigment Yellow 138, and when there are two or more inflection points of the absorption spectrum on a wavelength side longer than the maximum absorption wavelength on the longest wavelength side of the absorption spectrum, the wavelength is 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.

本發明提供以下的[1]~[6]。 The present invention provides the following [1]~[6].

[1]一種著色組成物,包含:下述式(I)所表示的化合物以及溶劑。 [1] A coloring composition comprising: a compound represented by the following formula (I) and a solvent.

[化2]

Figure 109104792-A0305-02-0004-2
[Chemistry 2]
Figure 109104792-A0305-02-0004-2

[式(I)中,R1~R5分別獨立地表示氫原子、鹵素原子、氰基、硝基、-SO3M、-CO2M、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、-SO3M、-CO2M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、-SO3M、-CO2M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、-SO3M、-CO2M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] [In formula (I), R 1 to R 5 independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, -SO 3 M, -CO 2 M, MM, a monovalent alkyl group having 1 to 40 carbon atoms, or a monovalent heterocyclic group having 1 to 40 carbon atoms; -C(-)(-)- constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by -Si(-)(-)-; -CH(-)- constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by -N(-)-; -CH= constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by -N=; -CH 2 - constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by -O-, -S-, or -S(O) 2 -or -CO-, the hydrogen atom constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by 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 may be bonded to each other to form a ring; M represents a hydrogen atom, an alkali metal atom, a metal atom which may have a ligand, or N(Z 1 )(Z 2 )(Z 3 )(Z 4 ); MM represents an alkali metal atom, a metal atom which may have a ligand, or N(Z 1 )(Z 2 )(Z 3 )(Z 4 ); Z 1 to Z 4 independently represent a hydrogen atom, a monovalent alkyl group having 1 to 40 carbon atoms, or a monovalent heterocyclic group having 1 to 40 carbon atoms; -C(-)(-)- constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by -Si(-)(-)-; -CH(-)- constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by -N(-)-; -CH= constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by -N=; -CH 2 - constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by -O-, -S-, or -S(O) 2 - or -CO-, the hydrogen atom constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by 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 alkyl group or a divalent heterocyclic group, -C(-)(-)- constituting the divalent alkyl group and the divalent heterocyclic group may be substituted by -Si(-)(-)-, -CH(-)- constituting the divalent alkyl group and the divalent heterocyclic group may be substituted by -N(-)-, -CH= constituting the divalent alkyl group and the divalent heterocyclic group may be substituted by -N=, and -CH 2 - constituting the divalent alkyl group and the divalent heterocyclic group may be substituted by -O-, -S-, -S(O) 2 - or -CO-, the hydrogen atom constituting the divalent alkyl 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; when there are plural Z 1 to Z 4 , M and MM, they may be the same or different from each other]

[2]如[1]所述的著色組成物,其包含樹脂。 [2] The coloring composition as described in [1], which contains a resin.

[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。 [3] A coloring composition as described in any one of [1] to [2], comprising a polymerizable compound and a polymerization initiator.

[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。 [4] A color filter formed from a coloring composition as described in any one of [1] to [3].

[5]一種顯示裝置,包含如[4]所述的彩色濾光片。 [5] A display device comprising the color filter described in [4].

[6]一種化合物,其由式(I)表示。 [6] A compound represented by formula (I).

Figure 109104792-A0305-02-0006-3
Figure 109104792-A0305-02-0006-3

[式(I)中,R1~R5分別獨立地表示氫原子、鹵素原子、氰基、硝基、-SO3M、-CO2M、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、-SO3M、-CO2M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、-SO3M、-CO2M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、-SO3M、-CO2M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] [In formula (I), R 1 to R 5 independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, -SO 3 M, -CO 2 M, MM, a monovalent alkyl group having 1 to 40 carbon atoms, or a monovalent heterocyclic group having 1 to 40 carbon atoms; -C(-)(-)- constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by -Si(-)(-)-; -CH(-)- constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by -N(-)-; -CH= constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by -N=; -CH 2 - constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by -O-, -S-, or -S(O) 2 -or -CO-, the hydrogen atom constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by 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 may be bonded to each other to form a ring; M represents a hydrogen atom, an alkali metal atom, a metal atom which may have a ligand, or N(Z 1 )(Z 2 )(Z 3 )(Z 4 ); MM represents an alkali metal atom, a metal atom which may have a ligand, or N(Z 1 )(Z 2 )(Z 3 )(Z 4 ); Z 1 to Z 4 independently represent a hydrogen atom, a monovalent alkyl group having 1 to 40 carbon atoms, or a monovalent heterocyclic group having 1 to 40 carbon atoms; -C(-)(-)- constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by -Si(-)(-)-; -CH(-)- constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by -N(-)-; -CH= constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by -N=; -CH 2 - constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by -O-, -S-, or -S(O) 2 - or -CO-, the hydrogen atom constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by 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 alkyl group or a divalent heterocyclic group, -C(-)(-)- constituting the divalent alkyl group and the divalent heterocyclic group may be substituted by -Si(-)(-)-, -CH(-)- constituting the divalent alkyl group and the divalent heterocyclic group may be substituted by -N(-)-, -CH= constituting the divalent alkyl group and the divalent heterocyclic group may be substituted by -N=, -CH 2 - may also be substituted with -O-, -S-, -S(O) 2 - or -CO-, and the hydrogen atoms constituting the divalent alkyl group and the divalent heterocyclic group may also 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, they may be the same or different from each other]

根據本發明,提供一種與包含C.I.顏料黃138的著色組成物相比,可於顏色更濃的彩色濾光片的形成中使用的著色組成物及化合物。 According to the present invention, a coloring composition and a compound are provided that can be used in the formation of a color filter having a darker color than a coloring composition containing C.I. Pigment Yellow 138.

[著色組成物] [Coloring composition]

本發明的著色組成物包含:式(I)所表示的化合物(以下,存在稱為化合物(I)的情況)、以及溶劑(以下,存在稱為溶劑(E)的情況)。 The coloring composition of the present invention comprises: a compound represented by formula (I) (hereinafter, sometimes referred to as compound (I)) and a solvent (hereinafter, sometimes referred to as solvent (E)).

[化4]

Figure 109104792-A0305-02-0009-4
[Chemistry 4]
Figure 109104792-A0305-02-0009-4

[式(I)中,R1~R5分別獨立地表示氫原子、鹵素原子、氰基、硝基、-SO3M、-CO2M、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、-SO3M、-CO2M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、-SO3M、-CO2M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、-SO3M、-CO2M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] [In formula (I), R 1 to R 5 independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, -SO 3 M, -CO 2 M, MM, a monovalent alkyl group having 1 to 40 carbon atoms, or a monovalent heterocyclic group having 1 to 40 carbon atoms; -C(-)(-)- constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by -Si(-)(-)-; -CH(-)- constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by -N(-)-; -CH= constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by -N=; -CH 2 - constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by -O-, -S-, or -S(O) 2 -or -CO-, the hydrogen atom constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may 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 may be bonded to each other to form a ring; M represents a hydrogen atom, an alkali metal atom, a metal atom which may have a ligand, or N(Z 1 )(Z 2 )(Z 3 )(Z 4 ); MM represents an alkali metal atom, a metal atom which may have a ligand, or N(Z 1 )(Z 2 )(Z 3 )(Z 4 ); Z 1 to Z 4 independently represent a hydrogen atom, a monovalent alkyl group having 1 to 40 carbon atoms, or a monovalent heterocyclic group having 1 to 40 carbon atoms; -C(-)(-)- constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by -Si(-)(-)-; -CH(-)- constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by -N(-)-; -CH= constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by -N=; -CH 2 - constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by -O-, -S-, or -S(O) 2 - or -CO-, the hydrogen atom constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by 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 alkyl group or a divalent heterocyclic group, -C(-)(-)- constituting the divalent alkyl group and the divalent heterocyclic group may be substituted by -Si(-)(-)-, -CH(-)- constituting the divalent alkyl group and the divalent heterocyclic group may be substituted by -N(-)-, -CH= constituting the divalent alkyl group and the divalent heterocyclic group may be substituted by -N=, and -CH 2 - constituting the divalent alkyl group and the divalent heterocyclic group may be substituted by -O-, -S-, -S(O) 2 - or -CO-, the hydrogen atom constituting the divalent alkyl 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; when there are plural Z 1 to Z 4 , M and MM, they may be the same or different from each other]

化合物(I)中亦包含其互變異構體或該些的鹽。 Compound (I) also includes its tautomers or their salts.

化合物(I)可作為著色劑來使用。 Compound (I) can be used as a coloring agent.

本發明的著色組成物中可包含一種或兩種以上的化合物(I)。 The coloring composition of the present invention may contain one or more compounds (I).

本發明的著色組成物亦可包含樹脂(以下,存在稱為樹脂(B)的情況)。 The coloring composition of the present invention may also contain a resin (hereinafter referred to as resin (B)).

本發明的著色組成物亦可包含聚合性化合物(以下,存在稱為聚合性化合物(C)的情況)。 The coloring composition of the present invention may also contain a polymerizable compound (hereinafter referred to as a polymerizable compound (C)).

本發明的著色組成物亦可包含聚合起始劑(以下,存在稱為聚合起始劑(D)的情況)。 The coloring composition of the present invention may also contain a polymerization initiator (hereinafter referred to as a polymerization initiator (D)).

本發明的著色組成物亦可包含聚合起始助劑(以下,存在稱為聚合起始助劑(D1)的情況)。 The coloring composition of the present invention may also contain a polymerization initiator (hereinafter referred to as a polymerization initiator (D1)).

本發明的著色組成物亦可包含化合物(I)以外的著色劑(以下,存在稱為著色劑(A1)的情況;而且,以下,存在將化合物(I)及著色劑(A1)總稱為「著色劑(A)」的情況)。 The coloring composition of the present invention may also contain a coloring agent other than compound (I) (hereinafter, sometimes referred to as coloring agent (A1); and, hereinafter, sometimes compound (I) and coloring agent (A1) are collectively referred to as "coloring agent (A)").

著色劑(A1)中可包含一種或兩種以上的著色劑。 The coloring agent (A1) may contain one or more coloring agents.

著色劑(A1)較佳為包含選自黃色著色劑、橙色著色劑、紅色著色劑及綠色著色劑中的一種以上。 The colorant (A1) preferably includes one or more selected from yellow colorants, orange colorants, red colorants, and green colorants.

本發明的著色組成物亦可包含調平劑(以下,存在稱為調平劑(F)的情況)。 The coloring composition of the present invention may also contain a leveling agent (hereinafter, sometimes referred to as a leveling agent (F)).

本發明的著色組成物亦可包含抗氧化劑(以下,存在稱為抗氧化劑(G)的情況)。 The coloring composition of the present invention may also contain an antioxidant (hereinafter referred to as antioxidant (G)).

[化合物(I)] [Compound (I)]

以下,列舉化合物(I)的部分結構來更具體地說明本發明, 於各部分結構中,即便僅例示鍵結於環結構的取代基在環結構的任一部位進行鍵結,於以下的例示中,亦包含該取代基於環結構的所有部位分別進行鍵結的態樣。一個或兩個以上的取代基可鍵結於環結構,於兩個以上的取代基鍵結於環結構的情況下,該取代基分別可相同,亦可不同。 The following lists partial structures of compound (I) to more specifically illustrate the present invention. In each partial structure, even if the substituent bonded to the ring structure is illustrated as being bonded to any one part of the ring structure, the following examples also include the state where the substituent is bonded to all parts of the ring structure. One 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.

作為鹵素原子,可列舉:氟原子、氯原子、溴原子及碘原子等,較佳為氟原子、氯原子及溴原子。 As the halogen atom, there can be listed: fluorine atom, chlorine atom, bromine atom and iodine atom, etc., preferably fluorine atom, chlorine atom and bromine atom.

R1~R5及Z1~Z4所表示的烴基的碳數為1~40,較佳為1~30,更佳為1~20,進而佳為1~18,尤佳為1~12。 The carbon number of the alkyl 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, further preferably 1 to 18, and particularly preferably 1 to 12.

R1~R5及Z1~Z4所表示的碳數1~40的一價烴基可為脂肪族烴基及芳香族烴基,該脂肪族烴基可為飽和或不飽和,亦可為鏈狀或環狀(脂環式烴基)。 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 or an aromatic hydrocarbon group. The aliphatic hydrocarbon group may be saturated or unsaturated and may be chain-like or cyclic (alicyclic hydrocarbon group).

作為R1~R5及Z1~Z4所表示的飽和或不飽和鏈狀烴基,可列舉:甲基、乙基、丙基、丁基、戊基、己基、庚基、辛基、壬基、癸基、十一烷基、十二烷基、十三烷基、十四烷基、十五烷基、十六烷基、十七烷基、十八烷基、十九烷基、二十烷基、二十一烷基、二十二烷基、二十三烷基、二十四烷基、二十五烷基、二十六烷基、二十七烷基、二十八烷基、二十九烷基、三十烷基、三十一烷基、三十二烷基、三十三烷基、三十四烷基、三十五烷基、三十六烷基、三十七烷基、三十八烷基、三十九烷基及四十烷基等直鏈狀烷基;異丙基、異丁基、第二丁基、第三丁基、2-乙基丁基、3,3- 二甲基丁基、1,1,3,3-四甲基丁基、1-甲基丁基、1-乙基丙基、3-甲基丁基、新戊基、1,1-二甲基丙基、2-甲基戊基、3-乙基戊基、1,3-二甲基丁基、2-丙基戊基、1-乙基-1,2-二甲基丙基、1-甲基戊基、4-甲基戊基、4-甲基己基、5-甲基己基、2-乙基己基、1-甲基己基、1-乙基戊基、1-丙基丁基、3-乙基庚基、2,2-二甲基庚基、1-甲基庚基、1-乙基己基、1-丙基戊基、1-甲基辛基、1-乙基庚基、1-丙基己基、1-丁基戊基、1-甲基壬基、1-乙基辛基、1-丙基庚基及1-丁基己基等分支鏈狀烷基;乙烯基(ethenyl)(乙烯基(vinyl))、丙烯基(例如,1-丙烯基、2-丙烯基(烯丙基))、1-甲基乙烯基、丁烯基(例如,1-丁烯基、2-丁烯基、3-丁烯基)、3-甲基-1-丁烯基、1,3-丁二烯基、1-(2-丙烯基)乙烯基、1-(1-甲基乙烯基)乙烯基、1,2-二甲基-1-丙烯基、戊烯基(例如,1-戊烯基、2-戊烯基、3-戊烯基、4-戊烯基)、1-(1,1-二甲基乙基)乙烯基、1,3-二甲基-1-丁烯基、己烯基(例如,1-己烯基、5-己烯基)、庚烯基(例如,1-庚烯基、6-庚烯基)、辛烯基(例如,1-辛烯基、7-辛烯基)、壬烯基(例如,1-壬烯基、8-壬烯基)、癸烯基(例如,1-癸烯基、9-癸烯基)、十一碳烯基、十二碳烯基、十三碳烯基、十四碳烯基、十五碳烯基、十六碳烯基、十七碳烯基、十八碳烯基、十九碳烯基、二十碳烯基、1,1-二甲基-2-丙烯基、1-乙基-2-丙烯基及1-甲基-1-丁烯基等烯基;乙炔基、丙炔基(例如,1-丙炔基、2-丙炔基)、辛炔基(例如,1-辛炔基、7-辛炔基)、丁炔基、戊炔基、己炔基、庚炔基、 壬炔基、癸炔基、十一碳炔基、十二碳炔基、十三碳炔基、十四碳炔基、十五碳炔基、十六碳炔基、十七碳炔基、十八碳炔基、十九碳炔基及二十碳炔基等炔基等。飽和或不飽和鏈狀烴基的碳數較佳為1~30,更佳為1~20,進而佳為1~18,尤佳為1~12。其中,特佳為碳數1~12的直鏈狀或分支鏈狀烷基。 Examples of the saturated or unsaturated chain alkyl groups represented by R1 to R5 and Z1 to Z4 include linear chain alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, heneicosyl, docosyl, tricosyl, tetracosyl, pentacosyl, hexacosyl, heptacosyl, octacosyl, nonacosyl, triacontyl, trineicosyl, dotriacontyl, trictriacontyl, tetratriacontyl, pentatriacontyl, hexatriacontyl, heptatriacontyl, octatriacontyl, nonacosyl, triacontyl, trineicosyl, dotriacontyl, trictriacontyl, tetratriacontyl, pentatriacontyl, hexatriacontyl, heptatriacontyl, octatriacontyl, nonacosyl and tetracontyl; linear chain alkyl groups such as isopropyl, isobutyl, sec-butyl, tert-butyl, 2-ethylbutyl, 3,3- Dimethylbutyl, 1,1,3,3-tetramethylbutyl, 1-methylbutyl, 1-ethylpropyl, 3-methylbutyl, neopentyl, 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-ethylpentyl, 1-propylbutyl, 3-ethylheptyl, 2,2-dimethylheptyl, 1-methylheptyl, branched chain alkyl groups such as 1-ethylhexyl, 1-propylpentyl, 1-methyloctyl, 1-ethylheptyl, 1-propylhexyl, 1-butylpentyl, 1-methylnonyl, 1-ethyloctyl, 1-propylheptyl and 1-butylhexyl; ethenyl (vinyl), propenyl (e.g., 1-propenyl, 2-propenyl (allyl)), 1-methylvinyl, butenyl (e.g., 1-butenyl, 2-butenyl, 3-butenyl), 3-methyl-1-butenyl, 1,3-butadienyl, 1 -(2-propenyl)vinyl, 1-(1-methylvinyl)vinyl, 1,2-dimethyl-1-propenyl, pentenyl (e.g., 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl), 1-(1,1-dimethylethyl)vinyl, 1,3-dimethyl-1-butenyl, hexenyl (e.g., 1-hexenyl, 5-hexenyl), heptenyl (e.g., 1-heptenyl, 6-heptenyl), octenyl (e.g., 1-octenyl, 7-octenyl), nonenyl (e.g., 1-nonenyl, 8-nonenyl), Alkenyl groups such as 1-decenyl, 2-decenyl, 1-hexenyl, 2-hexenyl, 3-decenyl, 4-decenyl, 5-decenyl, 6-decenyl, 7-decenyl, 8-decenyl, 10-decenyl, 15-decenyl, 16-decenyl, 17-decenyl, 18-decenyl, 10 ... The carbon number of the saturated or unsaturated chain alkyl group is preferably 1 to 30, more preferably 1 to 20, further preferably 1 to 18, and particularly preferably 1 to 12. Among them, a linear or branched chain alkyl group having 1 to 12 carbon atoms is particularly preferred.

作為R1~R5及Z1~Z4所表示的飽和或不飽和脂環式烴基,可列舉:環丙基、1-甲基環丙基、環丁基、環戊基、環己基、環庚基、1-甲基環己基、2-甲基環己基、3-甲基環己基、4-甲基環己基、1,2-二甲基環己基、1,3-二甲基環己基、1,4-二甲基環己基、2,3-二甲基環己基、2,4-二甲基環己基、2,5-二甲基環己基、2,6-二甲基環己基、3,4-二甲基環己基、3,5-二甲基環己基、2,2-二甲基環己基、3,3-二甲基環己基、4,4-二甲基環己基、環辛基、2,4,6-三甲基環己基、2,2,6,6-四甲基環己基、3,3,5,5-四甲基環己基、4-戊基環己基、4-辛基環己基及4-環己基環己基等環烷基;環己烯基(例如,環己-1-烯-1-基、環己-2-烯-1-基、環己-3-烯-1-基)、環庚烯基及環辛烯基等環烯基;降冰片基、降冰片烯基、金剛烷基及雙環[2.2.2]辛基等飽和或不飽和多環式烴基等。飽和或不飽和脂環式烴基的碳數較佳為3~30,更佳為3~20,進而佳為3~18,尤佳為3~12。其中,特佳為環戊基、環己基、環庚基、環辛基、金剛烷基。 Examples of the saturated or unsaturated alicyclic alkyl groups represented by R1 to R5 and Z1 to Z4 include cyclopropyl, 1-methylcyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, 1-methylcyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 1,2-dimethylcyclohexyl, 1,3-dimethylcyclohexyl, 1,4-dimethylcyclohexyl, 2,3-dimethylcyclohexyl, 2,4-dimethylcyclohexyl, 2,5-dimethylcyclohexyl, 2,6-dimethylcyclohexyl, 3,4-dimethylcyclohexyl, 3,5-dimethylcyclohexyl, 2,2-dimethylcyclohexyl, 3, cycloalkyl groups such as 3-dimethylcyclohexyl, 4,4-dimethylcyclohexyl, cyclooctyl, 2,4,6-trimethylcyclohexyl, 2,2,6,6-tetramethylcyclohexyl, 3,3,5,5-tetramethylcyclohexyl, 4-pentylcyclohexyl, 4-octylcyclohexyl and 4-cyclohexylcyclohexyl; cycloalkenyl groups such as cyclohexenyl (for example, cyclohex-1-en-1-yl, cyclohex-2-en-1-yl, cyclohex-3-en-1-yl), cycloheptenyl and cyclooctenyl; saturated or unsaturated polycyclic alkyl groups such as norbornyl, norbornenyl, adamantyl and bicyclo[2.2.2]octyl, and the like. The carbon number of the saturated or unsaturated alicyclic alkyl group is preferably 3 to 30, more preferably 3 to 20, further preferably 3 to 18, and particularly preferably 3 to 12. Among them, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and adamantyl are particularly preferred.

作為R1~R5及Z1~Z4所表示的芳香族烴基,可列舉:苯基、鄰甲苯基、間甲苯基、對甲苯基、2-乙基苯基、3-乙基苯基、 4-乙基苯基、2,3-二甲基苯基、2,4-二甲基苯基、2,5-二甲基苯基、2,6-二甲基苯基、3,4-二甲基苯基、3,5-二甲基苯基、4-乙烯基苯基、鄰異丙基苯基、間異丙基苯基、對異丙基苯基、鄰第三丁基苯基、間第三丁基苯基、對第三丁基苯基、3,5-二(第三丁基)苯基、3,5-二(第三丁基)-4-甲基苯基、4-丁基苯基、4-戊基苯基、2,6-雙(1-甲基乙基)苯基、2,4,6-三(1-甲基乙基)苯基、4-環己基苯基、2,4,6-三甲基苯基、4-辛基苯基、4-(1,1,3,3-四甲基丁基)苯基、1-萘基、2-萘基、6-甲基-2-萘基、5,6,7,8-四氫-1-萘基、5,6,7,8-四氫-2-萘基、芴基、菲基、蒽基、2-十二烷基苯基、3-十二烷基苯基、4-十二烷基苯基、苝基、

Figure 109104792-A0305-02-0015-355
基及芘基等芳香族烴基等。芳香族烴基的碳數較佳為6~30,更佳為6~20,進而佳為6~18,尤佳為6~12。 Examples of the aromatic hydrocarbon group represented by R1 to R5 and Z1 to Z4 include phenyl, o-tolyl, m-tolyl, p-tolyl, 2-ethylphenyl, 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-t-butylphenyl, m-t-butylphenyl, p-t-butylphenyl, 3,5-di(t-butyl)phenyl, 3,5-di(t-butyl)-4-methylphenyl, 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-naphthyl, 2-naphthyl, 6-methyl-2-naphthyl, 5,6,7,8-tetrahydro-1-naphthyl, 5,6,7,8-tetrahydro-2-naphthyl, fluorenyl, phenanthrenyl, anthracenyl, 2-dodecylphenyl, 3-dodecylphenyl, 4-dodecylphenyl, peryl,
Figure 109104792-A0305-02-0015-355
The number of carbon atoms in the aromatic alkyl group is preferably 6 to 30, more preferably 6 to 20, further preferably 6 to 18, and particularly preferably 6 to 12.

R1~R5及Z1~Z4所表示的烴基亦可為將所述列舉的烴基(例如,芳香族烴基、與鏈狀烴基及脂環式烴基的至少一個)組合而成的基,可列舉:苄基、(2-甲基苯基)甲基、(3-甲基苯基)甲基、(4-甲基苯基)甲基、(2-乙基苯基)甲基、(3-乙基苯基)甲基、(4-乙基苯基)甲基、(2-(第三丁基)苯基)甲基、(3-(第三丁基)苯基)甲基、(4-(第三丁基)苯基)甲基、(3,5-二甲基苯基)甲基、1-苯基乙基、1,1-二苯基乙基、苯乙基、1-甲基-1-苯基乙基、(1-萘基)甲基及(2-萘基)甲基等芳烷基;1-苯基乙烯基、2-苯基乙烯基(2-phenyl ethenyl)(苯基乙烯基(phenyl vinyl))、2,2-二苯基乙烯基、2-苯基-2-(1-萘基)乙烯基 等芳基烯基;苯基乙炔基等芳基炔基;聯苯基、聯三苯基等鍵結有一個以上的苯基的苯基;環己基甲基苯基、苄基苯基、(二甲基(苯基)甲基)苯基等。 The alkyl group represented by R1 to R5 and Z1 to Z4 may be a group formed by combining the alkyl groups listed above (for example, an aromatic alkyl group, and at least one of a chain alkyl group and an alicyclic alkyl group), and examples thereof 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, (4-(tert-butyl)phenyl)methyl, (3,5-dimethylphenyl)methyl, 1-phenylethyl, 1,1-diphenylethyl, phenethyl, 1-methyl-1-phenylethyl, (1-naphthyl)methyl, and (2-naphthyl)methyl; aralkyl groups such as 1-phenylethenyl, 2-phenylethenyl (phenylethenyl), ... arylalkenyl groups such as phenylethynyl and the like; phenyl groups having one or more phenyl groups bonded thereto such as biphenyl and terphenyl; cyclohexylmethylphenyl, benzylphenyl, and (dimethyl(phenyl)methyl)phenyl, and the like.

該些的碳數較佳為4~30,更佳為4~20,進而佳為4~18,尤佳為4~12。該些範圍的下限較佳為7。 The carbon number of these is preferably 4 to 30, more preferably 4 to 20, further preferably 4 to 18, and particularly preferably 4 to 12. The lower limit of these ranges is preferably 7.

關於R1~R5及Z1~Z4所表示的基,作為將所述列舉的烴基(例如,鏈狀烴基與脂環式烴基)組合而成的基,例如可為:環丙基甲基、環丙基乙基、環丁基甲基、環丁基乙基、環戊基甲基、環戊基乙基、環己基甲基、(2-甲基環己基)甲基、環己基乙基、金剛烷基甲基等鍵結有一個以上的脂環式烴基的烷基。 The groups represented by R1 to R5 and Z1 to Z4 may be groups formed by combining the above-mentioned alkyl groups (e.g., chain alkyl groups and alicyclic alkyl groups), for example, alkyl groups bonded to one or more alicyclic alkyl groups such as cyclopropylmethyl, cyclopropylethyl, cyclobutylmethyl, cyclobutylethyl, cyclopentylmethyl, cyclopentylethyl, cyclohexylmethyl, (2-methylcyclohexyl)methyl, cyclohexylethyl and adamantylmethyl.

該些的碳數較佳為4~30,更佳為4~20,進而佳為4~18,尤佳為4~12。 The carbon number of these is preferably 4 to 30, more preferably 4 to 20, further preferably 4 to 18, and particularly preferably 4 to 12.

R1~R5及Z1~Z4所表示的碳數1~40的一價雜環基是表示包含雜原子作為環的構成要素的基。作為碳數1~40的一價雜環基,可為單環,亦可為多環。作為雜原子,可列舉:氮原子、氧原子及硫原子等。 The monovalent heterocyclic group having 1 to 40 carbon atoms represented by R 1 to R 5 and Z 1 to Z 4 refers to a group containing a hetero atom as a ring constituent. The monovalent heterocyclic group having 1 to 40 carbon atoms may be a monocyclic group or a polycyclic group. Examples of the hetero atom include a nitrogen atom, an oxygen atom, and a sulfur atom.

雜環基的碳數較佳為3~30,更佳為3~20,進而佳為3~18,尤佳為3~12。 The carbon number of the heterocyclic group is preferably 3 to 30, more preferably 3 to 20, further preferably 3 to 18, and particularly preferably 3 to 12.

作為包含氮原子的雜環,可列舉:氮丙啶(aziridine)、吖丁啶(azetidine)、吡咯啶、哌啶及哌嗪等單環系飽和雜環;吡咯、1-甲基吡咯、2,5-二甲基吡咯等吡咯、吡唑、1-甲基吡 唑、2-甲基吡唑、3-甲基吡唑、4-甲基吡唑、5-甲基吡唑等吡唑、咪唑、1,2,3-三唑及1,2,4-三唑等五員環系不飽和雜環;吡啶、噠嗪、嘧啶、6-甲基嘧啶等嘧啶、吡嗪及1,3,5-三嗪等六員環系不飽和雜環;吲唑、吲哚啉、異吲哚啉、吲哚、吲哚嗪(indolizine)、苯並咪唑、喹啉、異喹啉、5,6,7,8-四氫(3-甲基)喹噁啉、3-甲基喹噁啉等喹噁啉、喹唑啉、噌啉、酞嗪、萘啶、嘌呤、喋啶、苯並吡唑、苯並哌啶等縮合二環系雜環;咔唑、吖啶及啡嗪等縮合三環系雜環等。 Examples of heterocyclic rings containing nitrogen atoms include aziridine, azetidine, pyrrolidine, piperidine, and piperazine; pyrroles such as pyrrole, 1-methylpyrrole, and 2,5-dimethylpyrrole; pyrazoles such as pyrazole, 1-methylpyrrole, 2-methylpyrrole, 3-methylpyrazole, 4-methylpyrazole, and 5-methylpyrazole; imidazole, 1,2,3-triazole, and 1,2,4-triazole; and unsaturated heterocyclic rings such as pyridine, pyrazine, Pyrimidine, 6-methylpyrimidine and other pyrimidines, pyrazine and 1,3,5-triazine and other six-membered unsaturated heterocyclic rings; indazole, indoline, isoindoline, indole, indolizine, benzimidazole, quinoline, isoquinoline, 5,6,7,8-tetrahydro(3-methyl)quinoxaline, 3-methylquinoxaline and other quinoxalines, quinazoline, cinnoline, phthalazine, naphthyridine, purine, pteridine, benzopyrazole, benzopiperidine and other condensed tricyclic heterocyclic rings such as carbazole, acridine and phenanthrazine, etc.

作為包含氧原子的雜環,可列舉:氧雜環丙烷、氧雜環丁烷、四氫呋喃、四氫吡喃、1,3-二噁烷及1,4-二噁烷、1-環戊基二氧雜環戊烷、2-環戊基二氧雜環戊烷等單環系飽和雜環;1,4-二氧雜螺環[4.5]癸烷、1,4-二氧雜螺環[4.5]壬烷、1,4-二氧雜螺環[4.4]壬烷等二環系飽和雜環;α-乙內酯、β-丙內酯、γ-丁內酯、γ-戊內酯及δ-戊內酯等內酯系雜環;呋喃、2,3-二甲基呋喃、2,5-二甲基呋喃等呋喃等五員環系不飽和雜環;2H-吡喃、4H-吡喃等六員環系不飽和雜環;1-苯並呋喃等苯並呋喃、苯並吡喃、4-甲基苯並吡喃等苯並吡喃、苯並二氧雜茂(benzodioxole)、1,3-苯並二氧雜茂、苯並二 噁烷、色原烷及異色原烷等縮合二環系雜環;氧雜蒽、二苯並呋喃等縮合三環系雜環等。 Examples of the heterocyclic ring containing an oxygen atom include: monocyclic saturated heterocyclic rings such as cyclopropane, cyclobutane, tetrahydrofuran, tetrahydropyran, 1,3-dioxane and 1,4-dioxane, 1-cyclopentyldioxacyclopentane, 2-cyclopentyldioxacyclopentane; bicyclic saturated heterocyclic rings such as 1,4-dioxaspiro[4.5]decane, 1,4-dioxaspiro[4.5]nonane, 1,4-dioxaspiro[4.4]nonane; α-acetone, β-propiolactone, γ-butyrolactone, γ-valerolactone and δ-valerolactone; esters and other lactone heterocyclic rings; furan, 2,3-dimethylfuran, 2,5-dimethylfuran and other furan and other five-membered unsaturated heterocyclic rings; 2H-pyran, 4H-pyran and other six-membered unsaturated heterocyclic rings; 1-benzofuran and other benzofurans, benzopyran, 4-methylbenzopyran and other benzopyrans, benzodioxole, 1,3-benzodioxole, benzodioxane, chromane and isochromane and other condensed bicyclic heterocyclic rings; oxanthracene, dibenzofuran and other condensed tricyclic heterocyclic rings, etc.

作為包含硫原子的雜環,可列舉:二硫戊環(dithiolane)等五員環系飽和雜環;噻烷、1,3-二噻烷、2-甲基-1,3-二噻烷等六員環系飽和雜環;噻吩、3-甲基噻吩、2-羧基噻吩等噻吩、2H-噻喃、4H-噻喃等噻喃等五員環系不飽和雜環及六員環系不飽和雜環;苯並噻喃、苯並四氫噻喃等苯並噻喃、苯並噻吩等縮合二環系雜環等;噻蒽、二苯並噻吩等縮合三環系雜環等。 Examples of heterocyclic rings containing sulfur atoms include: five-membered saturated heterocyclic rings such as dithiolane; six-membered saturated heterocyclic rings such as thioane, 1,3-dithiane, and 2-methyl-1,3-dithiane; five-membered unsaturated heterocyclic rings such as thiophene, 3-methylthiophene, and 2-carboxythiophene; 2H-thiopyran, 4H-thiopyran; condensed bicyclic heterocyclic rings such as benzothiopyran, benzotetrahydrothiopyran, and benzothiophene; and condensed tricyclic heterocyclic rings such as thianthrene and dibenzothiophene.

作為包含氮原子及氧原子的雜環,可列舉:嗎啉、2-吡咯啶酮、1-甲基-2-吡咯啶酮、2-甲基-2-吡咯啶酮、2-哌啶酮、1-甲基-2-哌啶酮及2-甲基-2-哌啶酮等單環系飽和雜環;噁唑、4-甲基噁唑等噁唑、2-甲基異噁唑、3-甲基異噁唑、4-甲基異噁唑、5-甲基異噁唑等異噁唑等單環系不飽和雜環;苯並噁唑、苯並異噁唑、苯並噁嗪、苯並二噁烷、苯並咪唑啉等縮合二環系雜環;啡噁嗪(phenoxazine)等縮合三環系雜環等。 Examples of heterocyclic rings containing nitrogen atoms and oxygen atoms include: monocyclic saturated heterocyclic rings such as morpholine, 2-pyrrolidone, 1-methyl-2-pyrrolidone, 2-methyl-2-pyrrolidone, 2-piperidone, 1-methyl-2-piperidone, and 2-methyl-2-piperidone; monocyclic unsaturated heterocyclic rings such as oxazole, 4-methyloxazole, and isoxazoles such as 2-methylisoxazole, 3-methylisoxazole, 4-methylisoxazole, and 5-methylisoxazole; condensed bicyclic heterocyclic rings such as benzoxazole, benzoisoxazole, benzoxazine, benzodioxane, and benzimidazolinone; condensed tricyclic heterocyclic rings such as phenoxazine, and the like.

作為包含氮原子及硫原子的雜環,可列舉:噻唑、2-甲基噻唑、3-甲基噻唑、4-甲基噻唑、5-甲基噻唑、2,4-二甲基噻唑等噻唑等單環系雜環;苯並噻唑等縮合二環系雜環; 啡噻嗪等縮合三環系雜環等。 Examples of heterocyclic rings containing nitrogen atoms and sulfur atoms include monocyclic heterocyclic rings such as thiazole, 2-methylthiazole, 3-methylthiazole, 4-methylthiazole, 5-methylthiazole, 2,4-dimethylthiazole, etc.; condensed bicyclic heterocyclic rings such as benzothiazole, etc.; condensed tricyclic heterocyclic rings such as phenothiazine, etc.

再者,所述雜環基的鍵結位為各雜環中所含的任意氫原子脫離的部分。 Furthermore, the bonding position of the heterocyclic group is the part from which any hydrogen atom contained in each heterocyclic ring is detached.

所述雜環基亦可為將所述列舉的雜環與所述列舉的烴基組合而成的基,例如可列舉四氫呋喃基甲基等。 The heterocyclic group may also be a group formed by combining the above-mentioned heterocyclic group and the above-mentioned alkyl group, for example, tetrahydrofuranylmethyl group may be listed.

進而,所述雜環基亦可為以下式子所表示者。※表示鍵結鍵。 Furthermore, the heterocyclic group may also be represented by the following formula. ※ represents a bond.

Figure 109104792-A0305-02-0019-5
Figure 109104792-A0305-02-0019-5

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、-SO3M、-CO2M或MM。作為此種基,可列舉以下的基。 -C(-)(-)- constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by -Si(-)(-)-, -CH(-)- constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by -N(-)-, -CH= constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by -N=, -CH 2 - constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by -O-, -S-, -S(O) 2 - or -CO-, and the hydrogen atom constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by a halogen atom, a cyano group, a nitro group, -SO 3 M, -CO 2 M or MM. Examples of such groups include the following groups.

例如,可列舉:三氯甲基、三氟甲基、2,2,2-三氟乙基、2,2-二溴乙基、2,2,3,3-四氟丙基、2-乙氧基乙基、2-丁氧基乙基、2-硝基丙基、二乙基胺基乙基、(4-甲氧基苯基)甲基、(2-甲氧基苯基)甲基、(3-甲氧基苯基)甲基、(4-硝基苯基)甲基、(2,4-二氯苯基)甲基、(4-氟苯基)甲基、(3,5-二氟苯基)甲基、2,2,2-三氟-1-三氟甲基-1-苯基乙基、(苯氧基)(苯基)甲基、(苄基氧基)(苯基)甲基、吡咯基甲基、吡咯基乙基、(4-胺基苯基)甲基、(4-氰基苯基)甲基、2-羥基-1-甲基-1-苯基乙基、2-氯-1-甲基-1-苯基乙基;-CH2CH2OCH2CH3、-CH2CH2O(CH2)3CH3、-(CH2CH2O)2CH2CH3、-(CH2CH2O)3CH2CH3、-(CH2CH2O)4CH2CH3、-(CH2CH2O)5CH2CH3、-(CH2CH2O)6CH2CH3、-(CH2CH2O)7CH2CH3、-(CH2CH2O)8CH2CH3、-(CH2CH2O)9CH2CH3、-(CH2CH2O)10CH2CH3、-(CH2CH2O)11CH2CH3、-(CH2CH2O)12CH2CH3、-(CH2CH2O)13CH3、-CH2CH2OH、-(CH2CH2O)2H、-(CH2CH2O)3H、-(CH2CH2O)4H、-(CH2CH2O)5H、-(CH2CH2O)6H、-(CH2CH2O)7H、-(CH2CH2O)8H、-(CH2CH2O)9H、-(CH2CH2O)10H、-(CH2CH2O)11H、-(CH2CH2O)12H、-(CH2CH2O)13H、-CH2CH2OCH3、-(CH2CH2O)2CH3、-(CH2CH2O)3CH3、-(CH2CH2O)4CH3、-(CH2CH2O)5CH3、-(CH2CH2O)6CH3、-(CH2CH2O)7CH3、-(CH2CH2O)8CH3、-(CH2CH2O)9CH3、-(CH2CH2O)10CH3、-(CH2CH2O)11CH3、 -(CH2CH2O)12CH3、-(CH2CH2O)13CH3等將所述一價烴基或一價雜環基的-CH2-取代為-O-而成的基等具有取代基的烷基(以下,存在將該些稱為群組A的基的情況)。 For example, there can be mentioned: 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, (benzyloxy)(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 , and an alkyl group having a substituent such as a group in which -CH 2 - of the above-mentioned monovalent hydrocarbon group or monovalent heterocyclic group is replaced by -O- (hereinafter, these may be referred to as groups of group A).

例如,可列舉:4-溴苯基、4-硝基苯基、4-甲氧基苯基、2,4-二氯苯基、五氟苯基、2-胺基苯基、2-甲基-4-氯苯基、4-羥基-1-萘基、4,5,8-三氯-2-萘基、蒽醌基、2-胺基蒽醌基等具有取代基的芳基(以下,存在將該些稱為群組B的基的情況)。 For example, there can be listed: 4-bromophenyl, 4-nitrophenyl, 4-methoxyphenyl, 2,4-dichlorophenyl, pentafluorophenyl, 2-aminophenyl, 2-methyl-4-chlorophenyl, 4-hydroxy-1-naphthyl, 4,5,8-trichloro-2-naphthyl, anthraquinone, 2-aminoanthraquinone and other aryl groups having substituents (hereinafter, these may be referred to as groups of group B).

例如,可列舉:甲醯基、乙醯基、丙醯基、丁醯基、2,2-二甲基丙醯基、戊醯基、己醯基、2-乙基己醯基、庚醯基、辛醯基、壬醯基、癸醯基、十一烷醯基、十二烷醯基、二十一烷醯基、苯甲醯基、

Figure 109104792-A0305-02-0021-6
For example, there can be mentioned: formyl, acetyl, propionyl, butyryl, 2,2-dimethylpropionyl, pentyl, hexyl, 2-ethylhexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, heneicosyl, benzoyl,
Figure 109104792-A0305-02-0021-6

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,較佳為鍵結有碳數1~30的烴基、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較佳者的羰基,更佳為鍵結有碳數1~20的烴基、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較佳者的羰基,進而佳為鍵結有碳數1~18的烴基、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較佳者的羰基,尤佳為鍵結有碳數1~12的烴基、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較佳者的羰基。 and a carbonyl group bonded to the group A to group B or the monovalent hydrocarbon group or the monovalent heterocyclic group, preferably a carbonyl group bonded to a hydrocarbon group with 1 to 30 carbon atoms, a group A to group B or the monovalent hydrocarbon group or the monovalent heterocyclic group, and more preferably a carbonyl group bonded to a hydrocarbon group with 1 to 20 carbon atoms, a group A to group B or the monovalent hydrocarbon group Preferably, the carbonyl group is a carbonyl group of a preferred 1-valent alkyl group or a monovalent heterocyclic group, and more preferably, the carbonyl group is bonded to a alkyl group having 1 to 18 carbon atoms, a group of the above group A to group B, or a preferred 1-valent alkyl group or a monovalent heterocyclic group, and more preferably, the carbonyl group is bonded to a alkyl group having 1 to 12 carbon atoms, a group of the above group A to group B, or a preferred 1-valent alkyl group or a monovalent heterocyclic group.

※表示鍵結鍵。 ※Indicates key binding.

例如,可列舉:甲氧基羰基、乙氧基羰基、丙氧基羰基、第三丁氧基羰基、丁氧基羰基、戊基氧基羰基、己基氧基羰基、(2-乙基己基)氧基羰基、庚基氧基羰基、辛基氧基羰基、壬基氧基羰基、癸基氧基羰基、十一烷基氧基羰基、十二烷基氧基羰基、苯基氧基羰基、二十烷基氧基羰基、

Figure 109104792-A0305-02-0022-7
For example, there can be mentioned methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, tert-butoxycarbonyl, butoxycarbonyl, pentyloxycarbonyl, hexyloxycarbonyl, (2-ethylhexyl)oxycarbonyl, heptyloxycarbonyl, octyloxycarbonyl, nonyloxycarbonyl, decyloxycarbonyl, undecyloxycarbonyl, dodecyloxycarbonyl, phenyloxycarbonyl, eicosyloxycarbonyl,
Figure 109104792-A0305-02-0022-7

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,較佳為鍵結有碳數1~30的烴基、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較佳者的氧基羰基,更佳為鍵結有碳數1~20的烴基、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較佳者的氧基羰基,進而佳為鍵結有碳數1~18的烴基、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較佳者的氧基羰基,尤佳為鍵結有碳數1~12的烴基、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較佳者的氧基羰基。 and an oxycarbonyl group bonded to the group A to group B or the monovalent alkyl group or the monovalent heterocyclic group, preferably an oxycarbonyl group bonded to a alkyl group with 1 to 30 carbon atoms, a group A to group B or the monovalent alkyl group or the monovalent heterocyclic group, and more preferably an oxycarbonyl group bonded to a alkyl group with 1 to 20 carbon atoms, a group A to group B or the monovalent An oxycarbonyl group of a preferred alkyl group or a monovalent heterocyclic group, further preferably an oxycarbonyl group bonded to a alkyl group having 1 to 18 carbon atoms, a group of the above group A to group B, or a preferred alkyl group or a monovalent heterocyclic group, and particularly preferably an oxycarbonyl group bonded to a alkyl group having 1 to 12 carbon atoms, a group of the above group A to group B, or a preferred alkyl group or a monovalent heterocyclic group.

※表示鍵結鍵。 ※Indicates key binding.

例如,可列舉:甲醯基氧基、乙醯氧基、丙醯基氧基、丁醯基氧基、(2,2-二甲基丙醯基)氧基、戊醯基氧基、己醯基氧基、(2-乙基己醯基)氧基、庚醯基氧基、辛醯基氧基、壬醯基氧基、癸醯基氧基、十一烷醯基氧基、十二烷醯基氧基、二十一烷醯基氧基、苯甲醯基氧基、乙烯基羰基氧基、(2-丙烯基)羰基氧基、(1-甲基乙烯基)羰基氧基、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氧基等,較佳為鍵結有碳數1~30的烴基、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較佳者的羰基氧基,更佳為鍵結有碳數1~20的烴基、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較佳者的羰基氧基,進而佳為鍵結有碳數1~18的烴基、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較佳者的羰基氧基,尤佳為鍵結有碳數1~12的烴基、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較佳者的羰基氧基。 For example, the following can be cited: formyloxy, acetyloxy, propionyloxy, butyryloxy, (2,2-dimethylpropionyl)oxy, pentyloxy, hexyloxy, (2-ethylhexyl)oxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, heneicosyloxy, benzyloxy, vinylcarbonyloxy, (2-propenyl)carbonyloxy, (1-methylvinyl)carbonyloxy, and carbonyloxy groups bonded to the groups A to B or the monovalent alkyl or monovalent heterocyclic groups, preferably bonded to A carbonyloxy group having a carbon number of 1 to 30, a group of the above group A to group B, or a preferred monovalent carbon group or monovalent heterocyclic group, more preferably a carbonyloxy group having a carbon number of 1 to 20, a group of the above group A to group B, or a preferred monovalent carbon group or monovalent heterocyclic group, further preferably a carbonyloxy group having a carbon number of 1 to 18, a group of the above group A to group B, or a preferred monovalent carbon group or monovalent heterocyclic group, and particularly preferably a carbonyloxy group having a carbon number of 1 to 12, a group of the above group A to group B, or a preferred monovalent carbon group or monovalent heterocyclic group.

例如,可列舉:羥基;甲氧基、乙氧基、丙氧基、異丙氧基、丁氧基、異丁氧基、第二丁氧基、第三丁氧基、戊基氧基、新戊基氧基、1-乙基-1,2-二甲基丙氧基、己基氧基、庚基氧基、辛基氧基、壬基氧基、癸基氧基、十一烷基氧基、十二烷基氧基、(2-乙基己基)氧基、硬脂基氧基、二十烷基氧基、1-苯基乙氧基、1-甲基-1-苯基乙氧基、苯基氧基、苄基氧基、2,3-二甲基苯基氧基、2,4-二甲基苯基氧基、2,5-二甲基苯基氧基、2,6-二甲基苯基氧基、3,4-二甲基苯基氧基、3,5-二甲基苯基氧基、2,3-二氰基苯基氧基、2,4-二氰基苯基氧基、2,5-二氰基苯基氧基、2,6-二氰基苯基氧基、3,4-二氰基苯基氧基、3,5-二氰基苯基氧基、4-甲氧基苯基氧基、2-甲氧基苯基氧基、3-甲氧基苯基氧基、4-乙氧基苯基氧基、2-乙氧基苯基氧基、3-乙氧基苯基氧基;三氯甲氧基、三氟甲氧基、2,2,2-三氟乙氧基、2,2,3,3-四氟丙氧基、3,3,3-三氟-2-三氟甲基-2-甲基丙氧基、2-丁氧基乙氧基、2-硝基丙氧基、-OCH2CH2OH、-O(CH2CH2O)4H、-OCH2CF2CF2H、-OCH2CH2O(CH2)3CH3、-OCH2CH2OCH2CH3、-O(CH2CH2O)2CH2CH3、-O(CH2CH2O)4CH2CH3、-OCH2CH2O(CH2)3CH3、[化8]

Figure 109104792-A0305-02-0025-8
For example, there can be mentioned: hydroxyl; methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, t-butoxy, pentyloxy, neopentyloxy, 1-ethyl-1,2-dimethylpropoxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, (2-ethylhexyl)oxy, stearyloxy, eicosyloxy, 1-phenylethoxy, 1-methyl-1-phenylethoxy, 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 , [Chemical 8]
Figure 109104792-A0305-02-0025-8

[化9]

Figure 109104792-A0305-02-0026-9
[Chemistry 9]
Figure 109104792-A0305-02-0026-9

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,較佳為鍵結有碳數1~30的烴基、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較佳者的氧基、或羥基,更佳為鍵結有碳數1~20的烴基、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較佳者的氧基、或羥基, 進而佳為鍵結有碳數1~18的烴基、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較佳者的氧基、或羥基,尤佳為鍵結有碳數1~12的烴基、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較佳者的氧基、或羥基。 and an oxy group bonded to the group A to group B or the monovalent alkyl group or the monovalent heterocyclic group, preferably an oxy group or a hydroxy group bonded to a alkyl group having 1 to 30 carbon atoms, a group A to group B or the monovalent alkyl group or the monovalent heterocyclic group, and more preferably a alkyl group having 1 to 20 carbon atoms, a group A to group B or the monovalent alkyl group or the monovalent heterocyclic group. Preferably, it is an oxy or hydroxyl group of a preferred monovalent heterocyclic group, and preferably, it is an oxy or hydroxyl group bonded to a alkyl group having 1 to 18 carbon atoms, a group of the above group A to group B, or a preferred monovalent alkyl group or monovalent heterocyclic group, and more preferably, it is an oxy or hydroxyl group bonded to a alkyl group having 1 to 12 carbon atoms, a group of the above group A to group B, or a preferred monovalent alkyl group or monovalent heterocyclic group.

※表示鍵結鍵。 ※Indicates key binding.

例如,可列舉:巰基;甲基硫基、乙基硫基、丙基硫基、丁基硫基、第三丁基硫基、戊基硫基、己基硫基、(2-乙基己基)硫基、庚基硫基、辛基硫基、壬基硫基、癸基硫基、十一烷基硫基、十二烷基硫基、二十烷基硫基、苯基硫基、鄰甲苯基硫基、

Figure 109104792-A0305-02-0027-10
For example, there can be mentioned: thio; methylthio, ethylthio, propylthio, butylthio, t-butylthio, pentylthio, hexylthio, (2-ethylhexyl)thio, heptylthio, octylthio, nonylthio, decylthio, undecylthio, dodecylthio, eicosylthio, phenylthio, o-tolylthio,
Figure 109104792-A0305-02-0027-10

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,較佳為將氫原子取代為碳數1~30的烴基、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較佳者而成的巰基、或巰基,更佳為將氫原子取代為碳數1~20的烴基、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較佳者而成的巰基、或巰基,進而佳為將氫原子取代為碳數1~18的烴基、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較佳者而成的巰基、或巰基,尤佳為將氫原子取代為碳數1~12的烴基、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較佳者而成的巰基、或巰基。 and a alkyl radical formed by replacing a hydrogen atom with a group of the group A to group B or a monovalent hydrocarbon group or a monovalent heterocyclic group, etc., preferably a alkyl radical formed by replacing a hydrogen atom with a alkyl radical having 1 to 30 carbon atoms, a group of the group A to group B or a monovalent hydrocarbon group or a monovalent heterocyclic group, or a alkyl radical, and more preferably a alkyl radical formed by replacing a hydrogen atom with a alkyl radical having 1 to 20 carbon atoms, a group of the group A to group B or a monovalent hydrocarbon group or a monovalent heterocyclic group. A alkyl group or alkyl group formed by a preferred monovalent heterocyclic group, further preferably a alkyl group or alkyl group formed by replacing a hydrogen atom with a carbon number of 1 to 18 alkyl group, a group of the above group A to group B, or a preferred monovalent alkyl group or monovalent heterocyclic group, and particularly preferably a alkyl group or alkyl group formed by replacing a hydrogen atom with a carbon number of 1 to 12 alkyl group, a group of the above group A to group B, or a preferred monovalent alkyl group or monovalent heterocyclic group.

※表示鍵結鍵。 ※Indicates key binding.

例如,可列舉:甲基磺醯基、乙基磺醯基、丙基磺醯基、丁基磺醯基、戊基磺醯基、己基磺醯基、(2-乙基己基)磺醯基、庚基磺醯基、辛基磺醯基、壬基磺醯基、癸基磺醯基、十一烷基磺醯基、十二烷基磺醯基、二十烷基磺醯基、苯基磺醯基、對甲苯基磺醯基、

Figure 109104792-A0305-02-0028-11
For example, there can be mentioned methylsulfonyl, ethylsulfonyl, propylsulfonyl, butylsulfonyl, pentylsulfonyl, hexylsulfonyl, (2-ethylhexyl)sulfonyl, heptylsulfonyl, octylsulfonyl, nonylsulfonyl, decylsulfonyl, undecylsulfonyl, dodecylsulfonyl, eicosylsulfonyl, phenylsulfonyl, p-tolylsulfonyl,
Figure 109104792-A0305-02-0028-11

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, 較佳為鍵結有碳數1~30的烴基、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較佳者的磺醯基,更佳為鍵結有碳數1~20的烴基、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較佳者的磺醯基,進而佳為鍵結有碳數1~18的烴基、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較佳者的磺醯基,尤佳為鍵結有碳數1~12的烴基、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較佳者的磺醯基。 and a sulfonyl group bonded to the group A~group B or the monovalent hydrocarbon group or the monovalent heterocyclic group, etc., preferably a sulfonyl group bonded to a hydrocarbon group with 1 to 30 carbon atoms, a group A~group B or the monovalent hydrocarbon group or the monovalent heterocyclic group, more preferably a sulfonyl group bonded to a hydrocarbon group with 1 to 20 carbon atoms, a group A~group B or the monovalent hydrocarbon group A sulfonyl group of a preferred alkyl group or a monovalent heterocyclic group, further preferably a sulfonyl group bonded to a alkyl group having 1 to 18 carbon atoms, a group of the above group A to group B, or a sulfonyl group of a preferred monovalent alkyl group or a monovalent heterocyclic group, and particularly preferably a sulfonyl group bonded to a alkyl group having 1 to 12 carbon atoms, a group of the above group A to group B, or a sulfonyl group of a preferred monovalent alkyl group or a monovalent heterocyclic group.

※表示鍵結鍵。 ※Indicates key binding.

例如,可列舉:胺磺醯基;N-甲基胺磺醯基、N-乙基胺磺醯基、N-丙基胺磺醯基、N-異丙基胺磺醯基、N-丁基胺磺醯基、N-異丁基胺磺醯基、N-(第二丁基)胺磺醯基、N-(第三丁基)胺磺醯基、N-戊基胺磺醯基、N-(1-乙基丙基)胺磺醯基、N-己基胺磺醯基、N-(2-乙基己基)胺磺醯基、N-庚基胺磺醯基、N-辛基胺磺醯基、N-壬基胺磺醯基、N-癸基胺磺醯基、N-十一烷基胺磺醯基、N-十二烷基胺磺醯基、N-二十烷基胺磺醯基、N-苯基胺磺醯基、-SO2NH(CH2)2N(CH2CH3)2、-SO2NHCH2CH2CH2Si(OCH2CH3)3、及所述群組A~群組B的基或者所述一價烴基或一價雜環基的一個進行取代而成的胺磺醯基等;N,N-二甲基胺磺醯基、N-乙基-N-甲基胺磺醯基、N,N- 二乙基胺磺醯基、N-丙基-N-甲基胺磺醯基、N,N-二丙基胺磺醯基、N-異丙基-N-甲基胺磺醯基、N,N-二異丙基胺磺醯基、N,N-二異丁基胺磺醯基、N,N-二(第二丁基)胺磺醯基、N-(第三丁基)-N-甲基胺磺醯基、N,N-二(第三丁基)胺磺醯基、N-丁基-N-甲基胺磺醯基、N,N-二丁基胺磺醯基、N-丁基-N-辛基胺磺醯基、N,N-二戊基胺磺醯基、N,N-雙(1-乙基丙基)胺磺醯基、N-丁基-N-己基胺磺醯基、N-己基-N-甲基胺磺醯基、N,N-二己基胺磺醯基、N-(2-乙基己基)-N-甲基胺磺醯基、N,N-雙(2-乙基己基)胺磺醯基、N,N-二庚基胺磺醯基、N-辛基-N-甲基胺磺醯基、N,N-二辛基胺磺醯基、N,N-二壬基胺磺醯基、N-癸基-N-甲基胺磺醯基、N-十一烷基-N-甲基胺磺醯基、N-十二烷基-N-甲基胺磺醯基、N-二十烷基-N-甲基胺磺醯基、N-苯基-N-甲基胺磺醯基、N,N-二苯基胺磺醯基、及選自所述群組A~群組B的基、所述一價烴基及所述一價雜環基中的兩個進行取代而成的胺磺醯基等,較佳為選自碳數1~30的烴基、所述群組A~群組B的基、所述一價烴基的較佳者及所述一價雜環基的較佳者中的一個或兩個進行取代而成的胺磺醯基、-SO2NH(CH2)2N(CH2CH3)2或胺磺醯基,更佳為選自碳數1~20的烴基、所述群組A~群組B的基、所述一價烴基的較佳者及所述一價雜環基的較佳者中的一個或兩個進行取代而成的胺磺醯基、-SO2NH(CH2)2N(CH2CH3)2或胺磺醯基, 進而佳為選自碳數1~18的烴基、所述群組A~群組B的基、所述一價烴基的較佳者及所述一價雜環基的較佳者中的一個或兩個進行取代而成的胺磺醯基、-SO2NH(CH2)2N(CH2CH3)2或胺磺醯基,尤佳為選自碳數1~12的烴基、所述群組A~群組B的基、所述一價烴基的較佳者及所述一價雜環基的較佳者中的一個或兩個進行取代而成的胺磺醯基、-SO2NH(CH2)2N(CH2CH3)2或胺磺醯基。 For example, there can be mentioned: sulfonylamine; N-methylsulfonylamine, N-ethylsulfonylamine, N-propylsulfonylamine, N-isopropylsulfonylamine, N-butylsulfonylamine, N-isobutylsulfonylamine, N-(sec-butyl)sulfonylamine, N-(tert-butyl)sulfonylamine, N-pentylsulfonylamine, N-(1-ethylpropylsulfonylamine, N-isopropyl ...(1-butylpropylsulfonylamine, N-isobutylpropylsulfonylamine, N-(1-butylpropylsulfonylamine, N-isobutylpropylsulfonylamine, N-(2-butylpropylsulfonylamine, N-isobutylpropylsulfonylamine, N-(2-butylpropylsulfonylamine, N-isobutylpropylsulfonylamine, N-(2-butylpropylsulfonylamine, N-isobutylpropylsulfonylamine, N-(2-butylpropylsulfonylamine, N-isobutylpropylsulfonylamine, N-(2-butylpropylsulfonylamine, N-isobutylpropylsulfonylamine, N-(2-butylpropylsulfonylamine, N-isobutylpropylsulfonylamine, N-(2-butylpropylsulfonylamine, amine sulfonyl, N-hexylamine sulfonyl, N-(2-ethylhexyl)amine sulfonyl, N-heptylamine sulfonyl, N-octylamine sulfonyl, N-nonylamine sulfonyl, N-decylamine sulfonyl, N-undecylamine sulfonyl, N-dodecylamine sulfonyl, N-eicosylamine sulfonyl, N-phenylamine sulfonyl, -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 an aminosulfonyl group substituted with a group of the above-mentioned group A to group B or one of the above-mentioned monovalent hydrocarbon groups or monovalent heterocyclic groups; N,N-dimethylaminosulfonyl group, N-ethyl-N-methylaminosulfonyl group, N,N- Diethylamine sulfonyl, N-propyl-N-methylamine sulfonyl, N,N-dipropylamine sulfonyl, N-isopropyl-N-methylamine sulfonyl, N,N-diisopropylamine sulfonyl, N,N-diisobutylamine sulfonyl, N,N-di(sec-butyl)amine sulfonyl, N-(tert-butyl)-N-methylamine sulfonyl, N,N-di(tert-butyl)amine sulfonyl, N-butyl-N- Methylamine sulfonyl, N,N-dibutylamine sulfonyl, N-butyl-N-octylamine sulfonyl, N,N-diamylamine sulfonyl, N,N-bis(1-ethylpropyl)amine sulfonyl, N-butyl-N-hexylamine sulfonyl, N-hexyl-N-methylamine sulfonyl, N,N-dihexylamine sulfonyl, N-(2-ethylhexyl)-N-methylamine sulfonyl, N,N-bis(2-ethylhexyl)-N-methylamine sulfonyl N,N-dihexyl)amine sulfonyl, N,N-diheptylamine sulfonyl, N-octyl-N-methylamine sulfonyl, N,N-dioctylamine sulfonyl, N,N-dinonylamine sulfonyl, N-decyl-N-methylamine sulfonyl, N-undecyl-N-methylamine sulfonyl, N-dodecyl-N-methylamine sulfonyl, N-eicosyl-N-methylamine sulfonyl, N-phenyl-N-methylamine sulfonyl The sulfonyl group is preferably an acyl group, an N,N-diphenylamine sulfonyl group, and an amine sulfonyl group formed by replacing two of the groups selected from the above group A to group B, the monovalent alkyl group and the monovalent heterocyclic group, preferably an amine sulfonyl group formed by replacing one or two of the groups selected from the above group A to group B, the monovalent alkyl group and the monovalent heterocyclic group, -SO 2 NH(CH 2 ) 2 N(CH 2 CH 3 ) 2 or an amine sulfonyl group, more preferably an amine sulfonyl group substituted with one or two selected from a alkyl group having 1 to 20 carbon atoms, a group of the aforementioned group A to group B, a preferred monovalent alkyl group, and a preferred monovalent heterocyclic group, -SO 2 NH(CH 2 ) 2 N(CH 2 CH 3 ) 2 or an amine sulfonyl group, further preferably an amine sulfonyl group substituted with one or two selected from a alkyl group having 1 to 18 carbon atoms, a group of the aforementioned group A to group B, a preferred monovalent alkyl group, and a preferred monovalent heterocyclic group, -SO 2 NH(CH 2 ) 2 N(CH 2 CH 3 ) 2 2 or sulfonamide, particularly preferably sulfonamide substituted with one or two selected from a alkyl group having 1 to 12 carbon atoms, a group of Group A to Group B, a preferred monovalent alkyl group and a preferred monovalent heterocyclic group, -SO 2 NH(CH 2 ) 2 N(CH 2 CH 3 ) 2 or sulfonamide.

例如,可列舉:胺甲醯基;N-甲基胺甲醯基、N-乙基胺甲醯基、N-丙基胺甲醯基、N-異丙基胺甲醯基、N-丁基胺甲醯基、N-異丁基胺甲醯基、N-(第二丁基)胺甲醯基、N-(第三丁基)胺甲醯基、N-戊基胺甲醯基、N-(1-乙基丙基)胺甲醯基、N-己基胺甲醯基、N-(2-乙基己基)胺甲醯基、N-庚基胺甲醯基、N-辛基胺甲醯基、N-壬基胺甲醯基、N-癸基胺甲醯基、N-十一烷基胺甲醯基、N-十二烷基胺甲醯基、N-二十烷基胺甲醯基、N-苯基胺甲醯基、-CONH(CH2)2N(CH2CH3)2、-CONHCH2CH2CH2Si(OCH2CH3)3、及所述群組A~群組B的基或所述一價烴基或一價雜環基的一個進行取代而成的胺甲醯基等;N,N-二甲基胺甲醯基、N-乙基-N-甲基胺甲醯基、N,N-二乙基胺甲醯基、N-丙基-N-甲基胺甲醯基、N,N-二丙基胺甲醯基、N-異丙基-N-甲基胺甲醯基、N,N-二異丙基胺甲醯基、N,N-二 異丁基胺甲醯基、N,N-二(第二丁基)胺甲醯基、N-(第三丁基)-N-甲基胺甲醯基、N,N-二(第三丁基)胺甲醯基、N-丁基-N-甲基胺甲醯基、N,N-二丁基胺甲醯基、N-丁基-N-辛基胺甲醯基、N,N-二戊基胺甲醯基、N,N-雙(1-乙基丙基)胺甲醯基、N-丁基-N-己基胺甲醯基、N-己基-N-甲基胺甲醯基、N,N-二己基胺甲醯基、N-(2-乙基己基)-N-甲基胺甲醯基、N,N-雙(2-乙基己基)胺甲醯基、N,N-二庚基胺甲醯基、N-辛基-N-甲基胺甲醯基、N,N-二辛基胺甲醯基、N,N-二壬基胺甲醯基、N-癸基-N-甲基胺甲醯基、N-十一烷基-N-甲基胺甲醯基、N-十二烷基-N-甲基胺甲醯基、N-二十烷基-N-甲基胺甲醯基、N-苯基-N-甲基胺甲醯基、N,N-二苯基胺甲醯基、及選自所述群組A~群組B的基、所述一價烴基及所述一價雜環基中的兩個進行取代而成的胺甲醯基等,較佳為選自碳數1~30的烴基、所述群組A~群組B的基、所述一價烴基的較佳者及所述一價雜環基的較佳者中的一個或兩個進行取代而成的胺甲醯基、或胺甲醯基,更佳為選自碳數1~20的烴基、所述群組A~群組B的基、所述一價烴基的較佳者及所述一價雜環基的較佳者中的一個或兩個進行取代而成的胺甲醯基、或胺甲醯基,進而佳為選自碳數1~18的烴基、所述群組A~群組B的基、所述一價烴基的較佳者及所述一價雜環基的較佳者中的一個或兩個進行取代而成的胺甲醯基、或胺甲醯基,尤佳為選自碳數1~12的烴基、所述群組A~群組B的基、 所述一價烴基的較佳者及所述一價雜環基的較佳者中的一個或兩個進行取代而成的胺甲醯基、或胺甲醯基。 For example, the following may be mentioned: aminoformyl; N-methylaminoformyl, N-ethylaminoformyl, N-propylaminoformyl, N-isopropylaminoformyl, N-butylaminoformyl, N-isobutylaminoformyl, N-(sec-butyl)aminoformyl, N-(tert-butyl)aminoformyl, N-pentylaminoformyl, N-(1-ethylpropyl)aminoformyl, methylaminoformyl, N-hexylaminoformyl, N-(2-ethylhexyl)aminoformyl, N-heptylaminoformyl, N-octylaminoformyl, N-nonylaminoformyl, N-decylaminoformyl, N-undecylaminoformyl, N-dodecylaminoformyl, N-eicosylaminoformyl, N-phenylaminoformyl, -CONH(CH 2 ) 2 N(CH 2 CH 3 ) 2 , -CONHCH 2 CH 2 CH 2 Si (OCH 2 CH 3 ) 3 , and aminoformyl groups substituted with the groups A to B or with one of the monovalent alkyl groups or monovalent heterocyclic groups; N,N-dimethylaminoformyl, N-ethyl-N-methylaminoformyl, N,N-diethylaminoformyl, N-propyl-N-methylaminoformyl, N,N-dipropylaminoformyl, N-isopropyl-N-methylaminoformyl, N,N-diisopropylaminoformyl, N,N-diisobutylaminoformyl, N,N-di(sec-butyl)aminoformyl, N-(tert-butyl)-N-methylaminoformyl, N,N-di(tert-butyl)aminoformyl; N-butyl-N-methylaminoformyl, N,N-dibutylaminoformyl, N-butyl-N-octylaminoformyl, N,N-dipentylaminoformyl, N,N-bis(1-ethylpropyl)aminoformyl, N-butyl-N-hexylaminoformyl, N-hexyl-N-methylaminoformyl, N,N-dihexylaminoformyl, N-(2-ethylhexyl)-N-methylaminoformyl, N,N-bis(2-ethylhexyl)aminoformyl, N,N-diheptylaminoformyl, N-octyl-N-methylaminoformyl, N,N-dioctylaminoformyl, N,N-dinonyl The present invention is preferably an aminoformyl group selected from the group A to the group B, an aminoformyl group in which two of the monovalent alkyl groups and the monovalent heterocyclic groups are substituted, and preferably one or two of the alkyl groups having 1 to 30 carbon atoms, the group selected from the group A to the group B, the preferred monovalent alkyl groups and the preferred monovalent heterocyclic groups are substituted. The aminoformyl group or aminoformyl group is preferably substituted with one or two selected from the group consisting of an alkyl group having 1 to 20 carbon atoms, a group of the group A to the group B, a preferred monovalent alkyl group, and a preferred monovalent heterocyclic group. The aminoformyl group or aminoformyl group is further preferably substituted with one or two selected from the group consisting of an alkyl group having 1 to 18 carbon atoms, a group of the group A to the group B, a preferred monovalent alkyl group, and a preferred monovalent heterocyclic group. The aminoformyl group or aminoformyl group is particularly preferably substituted with one or two selected from the group consisting of an alkyl group having 1 to 12 carbon atoms, a group of the group A to the group B, A carbamoyl group in which one or both of the preferred monovalent alkyl group and the preferred monovalent heterocyclic group are substituted, or a carbamoyl group.

例如,可列舉:胺基;N-甲基胺基、N-乙基胺基、N-丙基胺基、N-異丙基胺基、N-丁基胺基、N-異丁基胺基、N-(第二丁基)胺基、N-(第三丁基)胺基、N-戊基胺基、N-(1-乙基丙基)胺基、N-己基胺基、N-(2-乙基己基)胺基、N-庚基胺基、N-辛基胺基、N-壬基胺基、N-癸基胺基、N-十一烷基胺基、N-十二烷基胺基、N-二十烷基胺基、N-苯基胺基、及所述群組A~群組B的基或者所述一價烴基或一價雜環基的一個進行取代而成的胺基等;N,N-二甲基胺基、N-乙基-N-甲基胺基、N,N-二乙基胺基、N-丙基-N-甲基胺基、N,N-二丙基胺基、N-異丙基-N-甲基胺基、N,N-二異丙基胺基、N,N-二異丁基胺基、N,N-二(第二丁基)胺基、N-(第三丁基)-N-甲基胺基、N,N-二(第三丁基)胺基、N-丁基-N-甲基胺基、N,N-二丁基胺基、N-丁基-N-辛基胺基、N,N-二戊基胺基、N,N-雙(1-乙基丙基)胺基、N-丁基-N-己基胺基、N-己基-N-甲基胺基、N,N-二己基胺基、N-(2-乙基己基)-N-甲基胺基、N,N-雙(2-乙基己基)胺基、N,N-二庚基胺基、N-辛基-N-甲基胺基、N,N-二辛基胺基、N,N-二壬基胺基、N-癸基-N-甲基胺基、N-十一烷基-N-甲基胺基、N-十二烷基-N-甲基胺基、N-二十烷基-N-甲基胺基、N-苯基-N-甲基胺基、N,N-二苯基胺基、及 選自所述群組A~群組B的基、所述一價烴基及所述一價雜環基中的兩個進行取代而成的胺基等,較佳為選自碳數1~30的烴基、所述群組A~群組B的基、所述一價烴基的較佳者及所述一價雜環基的較佳者中的一個或兩個進行取代而成的胺基、或胺基,更佳為選自碳數1~20的烴基、所述群組A~群組B的基、所述一價烴基的較佳者及所述一價雜環基的較佳者中的一個或兩個進行取代而成的胺基、或胺基,進而佳為選自碳數1~18的烴基、所述群組A~群組B的基、所述一價烴基的較佳者及所述一價雜環基的較佳者中的一個或兩個進行取代而成的胺基、或胺基,尤佳為選自碳數1~12的烴基、所述群組A~群組B的基、所述一價烴基的較佳者及所述一價雜環基的較佳者中的一個或兩個進行取代而成的胺基、或胺基。 For example, the amino groups include: amino; N-methylamino, N-ethylamino, N-propylamino, N-isopropylamino, N-butylamino, N-isobutylamino, N-(sec-butyl)amino, N-(tert-butyl)amino, N-pentylamino, N-(1-ethylpropyl)amino, N-hexylamino, N-(2-ethylhexyl)amino, N-heptylamino, N-octylamino, N-nonylamino, N-decylamino, N-undecylamino, N-dodecylamino, N-eicosylamino, N-phenylamino, and amino groups substituted with the groups A to B or with one of the monovalent alkyl groups or monovalent heterocyclic groups; N,N-dimethylamino, N-ethylamino, N-pentylamino, N-(1-ethylpropyl)amino, N-hexylamino, N-(2-ethylhexyl)amino, N-heptylamino, N-octylamino, N-nonylamino, N-decylamino, N-undecylamino, N-dodecylamino, N-eicosylamino, N-phenylamino, and amino groups substituted with the groups A to B or with the monovalent alkyl groups or monovalent heterocyclic groups; N,N-diethylamine, N-propyl-N-methylamine, N,N-dipropylamine, N-isopropyl-N-methylamine, N,N-diisopropylamine, N,N-diisobutylamine, N,N-di(sec-butyl)amine, N-(tert-butyl)-N-methylamine, N,N-di(tert-butyl)amine, N-butyl-N-methylamine, N,N-dibutylamine, N-butyl-N-octylamine, N,N-dipentylamine, N,N-bis(1-ethylpropyl)amine, N-butyl-N-hexylamine, N-hexyl-N-methylamine, N,N-dihexylamine, N-(2-ethylhexyl)-N-methylamine , N,N-bis(2-ethylhexyl)amine, N,N-diheptylamine, N-octyl-N-methylamine, N,N-dioctylamine, N,N-dinonylamine, N-decyl-N-methylamine, N-undecyl-N-methylamine, N-dodecyl-N-methylamine, N-eicosyl-N-methylamine, N-phenyl-N-methylamine, N,N-diphenylamine, and amino groups substituted with two of the groups A to B, the monovalent alkyl groups, and the monovalent heterocyclic groups, etc., preferably alkyl groups having 1 to 30 carbon atoms, groups A to B, the preferred monovalent alkyl groups, and the preferred monovalent heterocyclic groups An amine group or an amine group substituted with one or two of them, more preferably an amine group or an amine group substituted with one or two of them selected from a alkyl group having 1 to 20 carbon atoms, a group of the group A to the group B, a preferred monovalent alkyl group and a preferred monovalent heterocyclic group, further preferably an alkyl group having 1 to 18 carbon atoms, a group of the group A to the group B The amine group or amine group is substituted by one or two of the preferred monovalent hydrocarbon group and the preferred monovalent heterocyclic group, and is particularly preferably an amine group or amine group substituted by one or two of the preferred monovalent hydrocarbon group and the preferred monovalent heterocyclic group.

例如,可列舉:甲醯基胺基、乙醯基胺基、丙醯基胺基、丁醯基胺基、(2,2-二甲基丙醯基)胺基、戊醯基胺基、己醯基胺基、(2-乙基己醯基)胺基、庚醯基胺基、辛醯基胺基、壬醯基胺基、癸醯基胺基、十一烷醯基胺基、十二烷醯基胺基、二十一烷醯基胺基、苯甲醯基胺基、[化12]

Figure 109104792-A0305-02-0035-12
For example, the following can be cited: formylamino, acetylamino, propionylamino, butyrylamino, (2,2-dimethylpropionyl)amino, pentylamino, hexylamino, (2-ethylhexyl)amino, heptylamino, octylamino, nonylamino, decylamino, undecylamino, dodecylamino, heneicosylamino, benzylamino, [Chemical 12]
Figure 109104792-A0305-02-0035-12

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,較佳為鍵結有碳數1~30的烴基、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較佳者的羰基胺基,更佳為鍵結有碳數1~20的烴基、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較佳者的羰基胺基,進而佳為鍵結有碳數1~18的烴基、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較佳者的羰基胺基,尤佳為鍵結有碳數1~12的烴基、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較佳者的羰基胺基。 and a carbonylamino group bonded to the group A to group B or the monovalent hydrocarbon group or the monovalent heterocyclic group, preferably a carbonylamino group bonded to a hydrocarbon group having 1 to 30 carbon atoms, a group A to group B or the monovalent hydrocarbon group or the monovalent heterocyclic group, and more preferably a carbonylamino group bonded to a hydrocarbon group having 1 to 20 carbon atoms, a group A to group B or the monovalent hydrocarbon group Preferably, it is a carbonylamino group that is bonded to a alkyl group having 1 to 18 carbon atoms, a group of the above group A to group B, or a carbonylamino group that is a preferred monovalent alkyl group or a monovalent heterocyclic group, and more preferably, it is a carbonylamino group that is bonded to a alkyl group having 1 to 12 carbon atoms, a group of the above group A to group B, or a carbonylamino group that is a preferred monovalent alkyl group or a monovalent heterocyclic group.

※表示鍵結鍵。 ※Indicates key binding.

例如,可列舉:-SiH3;-Si(CH3)3、-Si(CH2CH3)3、-Si((CH2)2CH3)3、-Si(CH(CH3)2)3、 -Si((CH2)3CH3)3、-Si((CH2)4CH3)3、-Si((CH2)5CH3)3、-Si((CH2)6CH3)3、-Si((CH2)7CH3)3、-Si((CH2)8CH3)3、-Si((CH2)9CH3)3、-Si((CH2)10CH3)3、-Si((CH2)11CH3)3、-Si((CH2)12CH3)3、-Si(C6H5)3、-Si(C10H7)3、-Si(CH3)2(CH2CH3)、-Si(CH3)2((CH2)2CH3)、-Si(CH3)2(CH(CH3)2)、-Si(CH3)2((CH2)3CH3)、-Si(CH3)2((CH2)5CH3)、-Si(CH3)2((CH2)7CH3)、-Si(CH3)2((CH2)9CH3)、-Si(CH3)2((CH2)11CH3)、-Si(CH3)2((CH2)13CH3)、-Si(CH3)2((CH2)15CH3)、 -Si(CH3)2((CH2)17CH3)、-Si(CH3)2((CH2)19CH3)、-Si(CH3)2((CH2)29CH3)、-Si(CH3)2(C6H5)、-Si(CH3)(C6H5)2、-Si(CH3)2(C10H7)、及選自所述群組A~群組B的基、所述一價烴基及所述一價雜環基中的一個、兩個或三個進行取代而成的-SiH3等;-Si(OH)3;-Si(OCH3)3、-Si(OCH2CH3)3、-Si(O(CH2)2CH3)3、-Si(OCH(CH3)2)3、-Si(O(CH2)3CH3)3、-Si(O(CH2)4CH3)3、-Si(O(CH2)5CH3)3、-Si(O(CH2)6CH3)3、-Si(O(CH2)7CH3)3、-Si(O(CH2)8CH3)3、-Si(O(CH2)9CH3)3、-Si(O(CH2)10CH3)3、-Si(O(CH2)11CH3)3、 -Si(OC6H5)3、-Si(OC10H7)3、-Si(OCH3)2(OCH2CH3)、-Si(OCH3)2(O(CH2)2CH3)、-Si(OCH3)2(OCH(CH3)2)、-Si(OCH3)2(O(CH2)3CH3)、-Si(OCH3)2(O(CH2)5CH3)、-Si(OCH3)2(O(CH2)7CH3)、-Si(OCH3)2(O(CH2)9CH3)、-Si(OCH3)2(O(CH2)11CH3)、-Si(OCH3)2(O(CH2)13CH3)、-Si(OCH3)2(O(CH2)15CH3)、-Si(OCH3)2(O(CH2)17CH3)、-Si(OCH3)2(O(CH2)19CH3)、-Si(OCH3)2(O(CH2)29CH3)、-Si(OCH3)2(OC6H5)、-Si(OCH3)(OC6H5)2、-Si(OCH3)2(OC10H7)、及選自所述群組A~群組B的基、所述一價烴基及所述一價雜環基中的一個、兩個或三個進行取代而成的-Si(OH)3等;-SiH(OH)2;-Si(CH3)(OCH3)2、 -Si((CH2)11CH3)(O(CH2)11CH3)2、-Si(C6H5)(OC6H5)2、-Si(CH3)(OH)2、-Si((CH2)36CH3)(OH)2、-Si(C6H5)(OH)2、及選自所述群組A~群組B的基、所述一價烴基及所述一價雜環基中的一個、兩個或三個進行取代而成的-SiH(OH)2等;-SiH2(OH);-Si(CH3)2(OCH3)、-Si((CH2)11CH3)2(O(CH2)11CH3)、-Si(C6H5)2(OC6H5)、-Si(CH3)2(OH)、-Si((CH2)17CH3)2(OH)、-Si(C6H5)2(OH)、及選自所述群組A~群組B的基、所述一價烴基及所述一價雜環基中的一個、兩個或三個進行取代而成的-SiH2(OH)等,較佳為選自碳數1~30的烴基、所述群組A~群組B的基、所述一價烴基的較佳者及所述一價雜環基的較佳者中的一個、兩個或三個進行取代而成的-SiH3、-Si(OH)3、-SiH(OH)2及-SiH2(OH)、或-Si(OH)3,更佳為選自碳數1~20的烴基、所述群組A~群組B的基、所述一價烴基的較佳者及所述一價雜環基的較佳者中的一個、兩 個或三個進行取代而成的-SiH3、-Si(OH)3、-SiH(OH)2及-SiH2(OH)、或-Si(OH)3,進而佳為選自碳數1~18的烴基、所述群組A~群組B的基、所述一價烴基的較佳者及所述一價雜環基的較佳者中的一個、兩個或三個進行取代而成的-SiH3、-Si(OH)3、-SiH(OH)2及-SiH2(OH)、或-Si(OH)3,尤佳為選自碳數1~12的烴基、所述群組A~群組B的基、所述一價烴基的較佳者及所述一價雜環基的較佳者中的一個、兩個或三個進行取代而成的-SiH3、-Si(OH)3、-SiH(OH)2及-SiH2(OH)、或-Si(OH)3For example, -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 CH3) 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 a group selected from Group A to Group B, -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 -Si(OH) 3 substituted by one, two or three of the groups selected from the groups A to B, the monovalent hydrocarbon groups and the monovalent heterocyclic groups; 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 -SiH(OH) 2 substituted by one, two or three of the groups selected from Group A to Group B, the monovalent hydrocarbon group and the monovalent heterocyclic group, etc. ; -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 -SiH 2 substituted with one, two or three of the groups selected from Group A and Group B, the monovalent hydrocarbon group and the monovalent heterocyclic group (OH), etc., preferably a alkyl group having 1 to 30 carbon atoms, a group of Group A to Group B, a preferred monovalent alkyl group, and a preferred monovalent heterocyclic group -SiH 3 , -Si(OH) 3 , -SiH(OH) 2 and -SiH 2 (OH), or -Si(OH) 3 substituted with one, two or three of them; more preferably is one or two selected from a alkyl group having 1 to 20 carbon atoms, a group of Group A to Group B, a preferred monovalent alkyl group, and a preferred monovalent heterocyclic group; or three substituted -SiH 3 , -Si(OH) 3 , -SiH(OH) 2 and -SiH 2 (OH), or -Si(OH) 3 , and preferably one selected from a alkyl group having 1 to 18 carbon atoms, a group of Group A to Group B, a preferred monovalent alkyl group, and a preferred monovalent heterocyclic group , -SiH 3 , -Si(OH) 3 , -SiH(OH) 2 and -SiH 2 (OH), or -Si(OH) 3 substituted with two or three of them, preferably selected from carbon One, two or three of the alkyl groups of 1 to 12, the groups of Group A to Group B, the preferred monovalent alkyl groups and the preferred monovalent heterocyclic groups are selected. -SiH 3 , -Si(OH) 3 , -SiH(OH) 2 , -SiH 2 (OH), or -Si(OH) 3 substituted.

例如,可列舉可具有取代基的鄰苯二甲醯亞胺甲基(C6H4(CO)2N-CH2-),作為該取代基,可列舉選自由所述鹵素原子、所述群組A~群組B的基、所述一價烴基及所述一價雜環基等所組成的群組中的至少一個。 For example, the o-xylylimidomethyl group (C 6 H 4 (CO) 2 N—CH 2 —) which may have a substituent can be exemplified, and as the substituent, at least one selected from the group consisting of the halogen atom, the group of Group A to Group B, the monovalent hydrocarbon group, and the monovalent heterocyclic group can be exemplified.

作為其他基,可列舉:-SCOCH3

Figure 109104792-A0305-02-0040-13
As other bases, we can cite: -SCOCH 3 ,
Figure 109104792-A0305-02-0040-13

等。 wait.

※表示鍵結鍵。 ※Indicates key binding.

對於該一價烴基或該一價雜環基,-SO3 -N+(C12H25)(CH3)3、-CO2 -N+(C12H25)(CH3)3、-SO3 -、-CO2 -等亦可進行取代。 The monovalent alkyl group or the monovalent heterocyclic group may be substituted by -SO 3 - N + (C 12 H 25 )(CH 3 ) 3 , -CO 2 - N + (C 12 H 25 )(CH 3 ) 3 , -SO 3 - , -CO 2 - or the like.

R1及R2、R2及R3、以及R3及R4可分別彼此鍵結而形成環。 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.

作為M及MM所表示的鹼金屬原子,可列舉:鋰原子、鈉原子及鉀原子等鹼金屬原子。 Examples of alkali metal atoms represented by M and MM include alkali metal atoms such as lithium atoms, sodium atoms, and potassium atoms.

作為M及MM所表示的可具有配位體的金屬原子的金屬原子,可列舉屬於元素週期表的2族~15族的金屬原子。作為可具有配位體的金屬原子的金屬原子,更佳為Mg、Ca、Sr、Ba、Cd、Ni、Zn、Cu、Hg、Fe、Co、Sn、Pb、Mn、Al、Cr、Rh、Ir、Pd、Ti、Zr、Hf、Si、Ge,進而佳為Mg、Ca、Sr、Ba、Ni、Zn、Cu、Fe、Co、Sn、Mn、Al、Cr,尤佳為Mg、Ca、Sr、Ba、Ni、Zn、Cu、Fe、Co、Mn、Al、Cr。 As the metal atom which may have a ligand represented by M and MM, metal atoms belonging to Group 2 to Group 15 of the periodic table of elements can be listed. As the metal atom which may have a ligand, Mg, Ca, Sr, Ba, Cd, Ni, Zn, Cu, Hg, Fe, Co, Sn, Pb, Mn, Al, Cr, Rh, Ir, Pd, Ti, Zr, Hf, Si, Ge are more preferred, Mg, Ca, Sr, Ba, Ni, Zn, Cu, Fe, Co, Sn, Mn, Al, Cr are further preferred, and Mg, Ca, Sr, Ba, Ni, Zn, Cu, Fe, Co, Mn, Al, Cr are particularly preferred.

作為可具有配位體的金屬原子的配位體,並無特別限制,例如可為鹵素原子、NO、NO3、SO4、CH3CO2、OH等,配位於該金屬原子的配位體、與同一配位體中所含的碳原子、氮原子、氧原子或硫原子等可配位於同一金屬原子,該金屬原子中,多個不同的配位體可向同一金屬原子進行配位,亦可形成寡聚物或聚合物。 The ligand of the metal atom which may have a ligand is not particularly limited, and may be, for example, a halogen atom, NO, NO 3 , SO 4 , CH 3 CO 2 , OH, etc. The ligand coordinated to the metal atom and the carbon atom, nitrogen atom, oxygen atom or sulfur atom contained in the same ligand may be coordinated to the same metal atom. In the metal atom, a plurality of different ligands may be coordinated to the same metal atom, and may form an oligomer or a polymer.

於該配位體中,在化合物(I)包含可具有配位體的金屬原子的情況下,亦可含有將可具有配位體的金屬原子除去的化合物(I)。 In the ligand, when the compound (I) contains a metal atom that can have a ligand, the compound (I) may be obtained by removing the metal atom that can have a ligand.

本發明的化合物(I)中亦含有此種寡聚物或聚合物。 The compound (I) of the present invention also contains such oligomers or polymers.

其中,化合物(I)的電荷為0。 Among them, the charge of compound (I) is 0.

作為此種化合物(I),例如可列舉下述式(EN1)~式(EN5)所表示的金屬鹽等。 Examples of such compounds (I) include metal salts represented by the following formulas (EN1) to (EN5).

其中,式(EN1)~式(EN5)中,( )內所表示的結構表示如寡聚物及聚合物般反覆進行鍵結。 Among them, in formula (EN1) to formula (EN5), the structure represented by ( ) indicates repeated bonding like oligomers and polymers.

例如,式(EN1)所表示的金屬鹽表示同一配位體配位於同一金屬原子。 For example, the metal salt represented by formula (EN1) indicates that the same ligand is coordinated to the same metal atom.

例如,式(EN2)~式(EN3)所表示的金屬鹽表示多個不同的配位體配位於同一金屬原子而形成寡聚物。 For example, the metal salts represented by formula (EN2) to (EN3) represent multiple different ligands coordinated to the same metal atom to form oligomers.

例如,式(EN4)~式(EN5)所表示的金屬鹽表示多個不同的配位體配位於同一金屬原子而形成寡聚物或聚合物。 For example, the metal salts represented by formula (EN4) to (EN5) represent multiple different ligands coordinated to the same metal atom to form oligomers or polymers.

Figure 109104792-A0305-02-0042-14
Figure 109104792-A0305-02-0042-14

Figure 109104792-A0305-02-0043-15
Figure 109104792-A0305-02-0043-15

Figure 109104792-A0305-02-0043-17
Figure 109104792-A0305-02-0043-17

[化17]

Figure 109104792-A0305-02-0044-19
[Chemistry 17]
Figure 109104792-A0305-02-0044-19

Figure 109104792-A0305-02-0044-20
Figure 109104792-A0305-02-0044-20

作為M及MM所表示的N(Z1)(Z2)(Z3)(Z4),可列舉:NH4;NH3((CH2)7CH3)、NH3((CH2)11CH3)、NH3((CH2)17CH3)等一個烷基對NH4進行取代而成的基;N(CH3)3((CH2)15CH3)、N(CH3)3((CH2)11CH3)、N(CH3)2((CH2)11CH3)2、N(CH3)2((CH2)17CH3)2等四個烷基對NH4進行取代而成的基;及選自所述群組A~群組B的基、所述一價烴基及所述一價雜環基中的一個、兩個、三個或四個進行取代而成的NH4等。 Examples of N(Z 1 )(Z 2 )(Z 3 )(Z 4 ) represented by M and MM include NH 4 ; a group formed by replacing NH 4 with an alkyl group, such as NH 3 ((CH 2 ) 7 CH 3 ), NH 3 ((CH 2 ) 11 CH 3 ), and NH 3 ((CH 2 ) 17 CH 3 ); a group formed by replacing NH 4 with four alkyl groups, such as 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 , and N(CH 3 ) 2 ((CH 2 ) 17 CH 3 ) 2 4 substituted; and NH 4 substituted by one, two, three or four of the groups selected from Group A to Group B, the monovalent hydrocarbon group and the monovalent heterocyclic group.

M較佳為:氫原子;鹼金屬原子;可具有配位體的Mg、可具有配位體的Ca、可具有配位體的Sr、可具有配位體的Ba、可具有配位體的Ni、可具有配位體的Zn、可具有配位體的Cu、可具有配位體的Fe、可具有配位體的Co、可具有配位體的Sn、可具有配位體的Mn、可具有配位體的Al、可具有配位體的Cr;NH4;NH3((CH2)7CH3)、NH3((CH2)11CH3)、NH3((CH2)17CH3)等一個烷基對NH4進行取代而成的基;N(CH3)3((CH2)15CH3)、N(CH3)3((CH2)11CH3)、 N(CH3)2((CH2)11CH3)2、N(CH3)2((CH2)17CH3)2等四個烷基對NH4進行取代而成的基,更佳為:氫原子;鈉原子、鉀原子;可具有配位體的Mg、可具有配位體的Ca、可具有配位體的Sr、可具有配位體的Ba、可具有配位體的Ni、可具有配位體的Zn、可具有配位體的Cu、可具有配位體的Fe、可具有配位體的Co、可具有配位體的Mn、可具有配位體的Al、可具有配位體的Cr;NH4;NH3((CH2)7CH3)、NH3((CH2)11CH3)、NH3((CH2)17CH3)等一個烷基對NH4進行取代而成的基;N(CH3)3((CH2)15CH3)、N(CH3)3((CH2)11CH3)、N(CH3)2((CH2)11CH3)2、N(CH3)2((CH2)17CH3)2等四個烷基對NH4進行取代而成的基。 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, Ni which may have a ligand, Zn which may have a ligand, Cu which may have a ligand, Fe which may have a ligand, Co which may have a ligand, Sn which may have a ligand, Mn which may have a ligand, Al which may have a ligand , Cr which may have a ligand; NH4 ; a group in which NH4 is substituted with an alkyl group such as NH3 (( CH2 ) 7CH3 ), NH3 (( CH2 ) 11CH3 ) , NH3 (( CH2 ) 17CH3 ) ; N( CH3 ) 3 ( ( CH2 ) 15CH3 ), N( CH3 ) 3 (( CH2 ) 11CH3 ), N(CH 3 ) 2 ((CH 2 ) 11 CH 3 ) 2 , N(CH 3 ) 2 ((CH 2 ) 17 CH 3 ) 2 , etc., which are substituted with NH 4 by four alkyl groups, and more preferably: a hydrogen atom; a sodium atom, a 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 a ligand, Cu which may have a ligand, Fe which may have a ligand, Co which may have a ligand, Mn which may have a ligand, Al which may have a ligand, Cr which may have a ligand; NH 4 ; NH 3 ((CH 2 ) 7 CH 3 ), NH 3 ((CH 2 ) 11 CH 3 ), NH 3 ((CH 2 ) 17 CH 3 ) or a group formed by replacing NH 4 with one alkyl group such as 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 , or N(CH 3 ) 2 ((CH 2 ) 17 CH 3 ) 2 .

MM較佳為:鹼金屬原子;可具有配位體的Mg、可具有配位體的Ca、可具有配位體的Sr、可具有配位體的Ba、可具有配位體的Ni、可具有配位體的Zn、可具有配位體的Cu、可具有配位體的Fe、可具有配位體的Co、可具有配位體的Sn、可具有配位體的Mn、可具有配位體的Al、可具有配位體的Cr; NH4;NH3((CH2)7CH3)、NH3((CH2)11CH3)、NH3((CH2)17CH3)等一個烷基對NH4進行取代而成的基;N(CH3)3((CH2)15CH3)、N(CH3)3((CH2)11CH3)、N(CH3)2((CH2)11CH3)2、N(CH3)2((CH2)17CH3)2等四個烷基對NH4進行取代而成的基,更佳為:鈉原子、鉀原子;可具有配位體的Mg、可具有配位體的Ca、可具有配位體的Sr、可具有配位體的Ba、可具有配位體的Ni、可具有配位體的Zn、可具有配位體的Cu、可具有配位體的Fe、可具有配位體的Co、可具有配位體的Mn、可具有配位體的Al、可具有配位體的Cr;NH4;NH3((CH2)7CH3)、NH3((CH2)11CH3)、NH3((CH2)17CH3)等一個烷基對NH4進行取代而成的基;N(CH3)3((CH2)15CH3)、N(CH3)3((CH2)11CH3)、N(CH3)2((CH2)11CH3)2、N(CH3)2((CH2)17CH3)2等四個烷基對NH4進行取代而成的基。 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 which may have a ligand, Cu which may have a ligand, Fe which may have a ligand, Co which may have a ligand, Sn which may have a ligand, Mn which may have a ligand, Al which may have a ligand, Cr which may have a ligand; NH4 ; a group formed by replacing NH4 with an alkyl group such as NH3 (( CH2 ) 7CH3 ), NH3 (( CH2 ) 11CH3 ) , NH3 (( CH2 ) 17CH3 ); N( CH3 ) 3 ( (CH2) 15CH3 ), N( CH3 ) 3 ( ( CH2 ) 11CH3 ), N(CH 3 ) 2 ((CH 2 ) 11 CH 3 ) 2 , N(CH 3 ) 2 ((CH 2 ) 17 CH 3 ) 2 , etc., which are preferably: a sodium atom, a 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 a ligand, Cu which may have a ligand, Fe which may have a ligand, Co which may have a ligand, Mn which may have a ligand, Al which may have a ligand, Cr which may have a ligand; NH 4 ; NH 3 ((CH 2 ) 7 CH 3 ), NH 3 ((CH 2 ) 11 CH 3 ), NH 3 ((CH 2 ) 17 CH 3 ) or a group formed by replacing NH 4 with one alkyl group such as 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 , or N(CH 3 ) 2 ((CH 2 ) 17 CH 3 ) 2 .

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、-SO3M、-CO2M或MM。 Q1 and Q2 each independently represent a divalent alkyl group or a divalent heterocyclic group, -C(-)(-)- constituting the divalent alkyl group and the divalent heterocyclic group may be substituted by -Si(-)(-)-, -CH(-)- constituting the divalent alkyl group and the divalent heterocyclic group may be substituted by -N(-)-, -CH= constituting the divalent alkyl group and the divalent heterocyclic group may be substituted by -N=, -CH2- constituting the divalent alkyl group and the divalent heterocyclic group may be substituted by -O-, -S-, -S(O) 2- or -CO-, and the hydrogen atom constituting the divalent alkyl group and the divalent heterocyclic group may be substituted by a halogen atom, a cyano group, a nitro group, -SO3M , -CO2 M or MM.

作為對構成該二價烴基及該二價雜環基的氫原子進行取代的基,較佳為鹵素原子、氰基、硝基、-SO3H、或-CO2H。 The group substituting the hydrogen atom constituting the divalent alkyl group and the divalent heterocyclic group is preferably a halogen atom, a cyano group, a nitro group, -SO 3 H, or -CO 2 H.

Q1及Q2可相同亦可不同,較佳為相同。 Q1 and Q2 may be the same or different, but are preferably the same.

Q1及Q2較佳為式(QQ1)~式(QQ19)所表示的基。 Q1 and Q2 are preferably groups represented by formula (QQ1) to formula (QQ19).

[化19]

Figure 109104792-A0305-02-0049-21
[Chemistry 19]
Figure 109104792-A0305-02-0049-21

[化20]

Figure 109104792-A0305-02-0050-22
[Chemistry 20]
Figure 109104792-A0305-02-0050-22

[式(QQ1)~式(QQ19)中,RQ1~RQ94分別獨立地表示氫原子、鹵素原子、氰基、硝基、-SO3M、-CO2M、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、-SO3M、-CO2M或MM;RQ1~RQ94可分別彼此與選自RQ1~RQ94中的一個以上鍵結而 形成環;M及MM表示與所述相同的含義;※表示鍵結鍵]關於為RQ1~RQ94所表示的碳數1~40的一價烴基或碳數1~40的一價雜環基、且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、-SO3M、-CO2M或MM的基,可列舉與為R1~R5及Z1~Z4所表示的碳數1~40的一價烴基或碳數1~40的一價雜環基、且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、-SO3M、-CO2M或MM的基相同者。 [In formula (QQ1) to formula (QQ19), R Q1 to R Q94 independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, -SO 3 M, -CO 2 M, MM, a monovalent alkyl group having 1 to 40 carbon atoms, or a monovalent heterocyclic group having 1 to 40 carbon atoms; -C(-)(-)- constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by -Si(-)(-)-; -CH(-)- constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by -N(-)-; -CH= constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by -N=; -CH 2 - constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by -O-, -S-, or -S(O) 2 - or -CO-, the hydrogen atom constituting the monovalent alkyl group and the monovalent heterocyclic group may 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 may be bonded to one or more selected from R Q1 to R Q94 to form a ring; M and MM have the same meanings as described above; ※ indicates a bond] For R Q1 to R The monovalent alkyl group having 1 to 40 carbon atoms or the monovalent heterocyclic group having 1 to 40 carbon atoms represented by Q94 , wherein -C(-)(-)- constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by -Si(-)(-)-, -CH(-)- constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by -N(-)-, -CH= constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by -N=, -CH 2 - constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by -O-, -S-, -S(O) 2 - or -CO-, and the hydrogen atom constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by a halogen atom, a cyano group, a nitro group, or -SO 3 The group of M, -CO 2 M or MM may be a monovalent alkyl group having 1 to 40 carbon atoms or a monovalent heterocyclic group having 1 to 40 carbon atoms represented by R 1 to R 5 and Z 1 to Z 4 , wherein -C(-)(-)- constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by -Si(-)(-)-, -CH(-)- constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by -N(-)-, -CH= constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by -N=, and -CH 2 - constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by -O-, -S-, or -S(O) 2 - or -CO-, the hydrogen atom constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted with a halogen atom, a cyano group, a nitro group, -SO 3 M, -CO 2 M or the same group as MM.

作為RQ1~RQ94的較佳者,可列舉與R1~R5及Z1~Z4的較佳者相同者。 Preferred examples of R Q1 to R Q94 include the same examples as preferred examples of R 1 to R 5 and Z 1 to Z 4 .

關於Q1及Q2,較佳為式(QQ1)~式(QQ12)所表示的基,更佳為式(QQ1)~式(QQ5)所表示的基,進而佳為式(QQ1)~式(QQ4)所表示的基,尤佳為式(QQ1)及式(QQ2)所表示的基,進而尤佳為式(QQ2)所表示的基。 Regarding Q1 and Q2 , groups represented by formula (QQ1) to (QQ12) are preferred, groups represented by formula (QQ1) to (QQ5) are more preferred, groups represented by formula (QQ1) to (QQ4) are further preferred, groups represented by formula (QQ1) and (QQ2) are particularly preferred, and groups represented by formula (QQ2) are further preferred.

作為式(QQ1)~式(QQ19),例如,可列舉下述式(Qa1)~式(Qa50);式(Qb1)~式(Qb27);式(Qc1)~式(Qc56);式(Qd1)~式(Qd41);式(Qe1)~式(Qe16);式(Qf1)~式(Qf15);式(Qg1)~式(Qg40);式(Qh1)~式(Qh40);式(Qj1)~式(Qj29);式(Qk1)~式(Qk22);式(Qm1)~式(Qm20);式(Qn1)~式(Qn16); 式(Qo1)~式(Qo15);式(Qp1)~式(Qp83);式(Qq1)~式(Qq72);式(Qr1)~式(Qr17);式(Qs1)~式(Qs26);式(Qt1)~式(Qt26);式(Qu1)~式(Qu17);式(Qv1)~式(Qv26);式(Qx1)~式(Qx2);及式(Qy1)~式(Qy10)所表示的基等。其中,※表示鍵結鍵。 As the formula (QQ1) to the formula (QQ19), for example, the following formulas (Qa1) to (Qa50); formula (Qb1) to (Qb27); formula (Qc1) to (Qc56); formula (Qd1) to (Qd41); formula (Qe1) to (Qe16); formula (Qf1) to (Qf15); formula (Qg1) to (Qg40); formula (Qh1) to (Qh40); formula (Qj1) to (Qj29); formula (Qk1) to (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 the bases represented by Formula (Qy1)~Formula (Qy10). Among them, ※ indicates a bond.

[化21]

Figure 109104792-A0305-02-0054-23
[Chemistry 21]
Figure 109104792-A0305-02-0054-23

[化22]

Figure 109104792-A0305-02-0055-26
[Chemistry 22]
Figure 109104792-A0305-02-0055-26

[化23]

Figure 109104792-A0305-02-0056-27
[Chemistry 23]
Figure 109104792-A0305-02-0056-27

[化24]

Figure 109104792-A0305-02-0057-30
[Chemistry 24]
Figure 109104792-A0305-02-0057-30

[化25]

Figure 109104792-A0305-02-0058-32
[Chemistry 25]
Figure 109104792-A0305-02-0058-32

Figure 109104792-A0305-02-0058-34
Figure 109104792-A0305-02-0058-34

[化27]

Figure 109104792-A0305-02-0059-36
[Chemistry 27]
Figure 109104792-A0305-02-0059-36

Figure 109104792-A0305-02-0059-37
Figure 109104792-A0305-02-0059-37

[化29]

Figure 109104792-A0305-02-0060-38
[Chemistry 29]
Figure 109104792-A0305-02-0060-38

Figure 109104792-A0305-02-0060-39
Figure 109104792-A0305-02-0060-39

[化31]

Figure 109104792-A0305-02-0061-40
[Chemistry 31]
Figure 109104792-A0305-02-0061-40

Figure 109104792-A0305-02-0061-42
Figure 109104792-A0305-02-0061-42

[化33]

Figure 109104792-A0305-02-0062-43
[Chemistry 33]
Figure 109104792-A0305-02-0062-43

Figure 109104792-A0305-02-0062-44
Figure 109104792-A0305-02-0062-44

Figure 109104792-A0305-02-0063-45
Figure 109104792-A0305-02-0063-45

Figure 109104792-A0305-02-0063-46
Figure 109104792-A0305-02-0063-46

Figure 109104792-A0305-02-0064-47
Figure 109104792-A0305-02-0064-47

Figure 109104792-A0305-02-0064-48
Figure 109104792-A0305-02-0064-48

[化39]

Figure 109104792-A0305-02-0065-49
[Chemistry 39]
Figure 109104792-A0305-02-0065-49

Figure 109104792-A0305-02-0065-50
Figure 109104792-A0305-02-0065-50

[化41]

Figure 109104792-A0305-02-0066-51
[Chemistry 41]
Figure 109104792-A0305-02-0066-51

[化42]

Figure 109104792-A0305-02-0067-54
[Chemistry 42]
Figure 109104792-A0305-02-0067-54

Figure 109104792-A0305-02-0067-55
Figure 109104792-A0305-02-0067-55

Figure 109104792-A0305-02-0068-56
Figure 109104792-A0305-02-0068-56

Figure 109104792-A0305-02-0069-57
Figure 109104792-A0305-02-0069-57

[化46]

Figure 109104792-A0305-02-0070-58
[Chemistry 46]
Figure 109104792-A0305-02-0070-58

Figure 109104792-A0305-02-0070-59
Figure 109104792-A0305-02-0070-59

[化48]

Figure 109104792-A0305-02-0071-60
[Chemistry 48]
Figure 109104792-A0305-02-0071-60

Figure 109104792-A0305-02-0071-61
Figure 109104792-A0305-02-0071-61

[化50]

Figure 109104792-A0305-02-0072-62
[Chemistry 50]
Figure 109104792-A0305-02-0072-62

[化51]

Figure 109104792-A0305-02-0073-63
[Chemistry 51]
Figure 109104792-A0305-02-0073-63

[化52]

Figure 109104792-A0305-02-0074-64
[Chemistry 52]
Figure 109104792-A0305-02-0074-64

[化53]

Figure 109104792-A0305-02-0075-65
[Chemistry 53]
Figure 109104792-A0305-02-0075-65

[化54]

Figure 109104792-A0305-02-0076-66
[Chemistry 54]
Figure 109104792-A0305-02-0076-66

[化55]

Figure 109104792-A0305-02-0077-68
[Chemistry 55]
Figure 109104792-A0305-02-0077-68

[化56]

Figure 109104792-A0305-02-0078-69
[Chemistry 56]
Figure 109104792-A0305-02-0078-69

[化57]

Figure 109104792-A0305-02-0079-70
[Chemistry 57]
Figure 109104792-A0305-02-0079-70

[化58]

Figure 109104792-A0305-02-0080-72
[Chemistry 58]
Figure 109104792-A0305-02-0080-72

Figure 109104792-A0305-02-0080-73
Figure 109104792-A0305-02-0080-73

[化60]

Figure 109104792-A0305-02-0081-74
[Chemistry 60]
Figure 109104792-A0305-02-0081-74

作為化合物(I),例如,可列舉下述表1~表14所示的式(Ia)所表示的化合物或其鹼金屬鹽。 As compound (I), for example, compounds represented by formula (Ia) shown in Tables 1 to 14 below or their alkali metal salts can be listed.

再者,表1~表14中的「Q1」欄及「Q2」欄中所記載的符號分別對應於所述式所表示的基。 In addition, the symbols recorded 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.

※表示鍵結鍵。 ※Indicates key binding.

Figure 109104792-A0305-02-0081-75
Figure 109104792-A0305-02-0081-75

Figure 109104792-A0305-02-0082-76
Figure 109104792-A0305-02-0082-76

[表2]

Figure 109104792-A0305-02-0083-79
[Table 2]
Figure 109104792-A0305-02-0083-79

[表3]

Figure 109104792-A0305-02-0084-80
[Table 3]
Figure 109104792-A0305-02-0084-80

[表4]

Figure 109104792-A0305-02-0085-82
[Table 4]
Figure 109104792-A0305-02-0085-82

[表5]

Figure 109104792-A0305-02-0086-83
[Table 5]
Figure 109104792-A0305-02-0086-83

[表6]

Figure 109104792-A0305-02-0087-84
[Table 6]
Figure 109104792-A0305-02-0087-84

[表7]

Figure 109104792-A0305-02-0088-85
[Table 7]
Figure 109104792-A0305-02-0088-85

[表8]

Figure 109104792-A0305-02-0089-86
[Table 8]
Figure 109104792-A0305-02-0089-86

[表9]

Figure 109104792-A0305-02-0090-87
[Table 9]
Figure 109104792-A0305-02-0090-87

[表10]

Figure 109104792-A0305-02-0091-88
[Table 10]
Figure 109104792-A0305-02-0091-88

[表11]

Figure 109104792-A0305-02-0092-89
[Table 11]
Figure 109104792-A0305-02-0092-89

[表12]

Figure 109104792-A0305-02-0093-90
[Table 12]
Figure 109104792-A0305-02-0093-90

[表13]

Figure 109104792-A0305-02-0094-91
[Table 13]
Figure 109104792-A0305-02-0094-91

[表14]

Figure 109104792-A0305-02-0095-92
[Table 14]
Figure 109104792-A0305-02-0095-92

作為化合物(I),例如,可列舉下述表15~表31所示的式(Ib)所表示的化合物或者其鹼金屬鹽。 As compound (I), for example, compounds represented by formula (Ib) shown in Tables 15 to 31 below or alkali metal salts thereof can be listed.

[化62]

Figure 109104792-A0305-02-0096-313
[Chemistry 62]
Figure 109104792-A0305-02-0096-313

式(Ib)中,RIb1~RIb5的任一個為並非氫原子的取代基(以下,存在稱為RR基的情況),其他四個為氫原子。 In formula (Ib), any one of R Ib1 to R Ib5 is a substituent other than a hydrogen atom (hereinafter referred to as an RR group in some cases), and the other four are hydrogen atoms.

表15~表31中的「Q1」欄及「Q2」欄中所記載的符號分別對應於所述式所表示的基。 The symbols recorded in the "Q 1 " column and the "Q 2 " column in Tables 15 to 31 respectively correspond to the groups represented by the above formulas.

表15~表31中的「RR」欄中所記載的符號表示RR基,分別對應於下述式(a1)~式(a69);式(b1)~式(b4);式(c1)~式(c4);式(d1)~式(d5);式(e1)~式(e20);式(f1)~式(f5);式(g1)~式(g9);式(h1)~式(h9);式(j1)~式(j9);式(k1)~式(k4);式(m1)~式(m9); 式(n1)~式(n3);式(o1)~式(o5);式(p1)~式(p23);式(q1)~式(q26);式(r1)~式(r26);式(s1)~式(s26)所表示的基,表15~表31中的「No」欄中所記載的數值分別表示RR基進行取代的位置,「1」表示RR基對RIb1進行取代,「2」表示RR基對RIb2進行取代,「3」表示RR基對RIb3進行取代,「4」表示RR基對RIb4進行取代,「5」表示RR基對RIb5進行取代。 The symbols recorded in the "RR" column in Tables 15 to 31 represent RR groups, and correspond to the following formulas (a1) to (a69); formulas (b1) to (b4); formulas (c1) to (c4); formulas (d1) to (d5); formulas (e1) to (e20); formulas (f1) to (f5); formulas (g1) to (g9); formulas (h1) to (h9); formulas (j1) to (j9); formulas (k1) to (k4); formulas (m1) to (m9); For the groups represented by formula (n1) to (n3); formula (o1) to (o5); formula (p1) to (p23); formula (q1) to (q26); formula (r1) to (r26); and formula (s1) to (s26), the values recorded in the "No" column in Tables 15 to 31 respectively indicate the positions where the RR group replaces R Ib1 , "1" indicates that the RR group replaces R Ib2 , "3" indicates that the RR group replaces R Ib3 , "4" indicates that the RR group replaces R Ib4 , and "5" indicates that the RR group replaces R Ib5 .

※表示鍵結鍵。 ※Indicates key binding.

[表15]

Figure 109104792-A0305-02-0098-93
[Table 15]
Figure 109104792-A0305-02-0098-93

[表16]

Figure 109104792-A0305-02-0099-94
[Table 16]
Figure 109104792-A0305-02-0099-94

[表17]

Figure 109104792-A0305-02-0100-95
[Table 17]
Figure 109104792-A0305-02-0100-95

[表18]

Figure 109104792-A0305-02-0101-96
[Table 18]
Figure 109104792-A0305-02-0101-96

[表19]

Figure 109104792-A0305-02-0102-98
[Table 19]
Figure 109104792-A0305-02-0102-98

[表20]

Figure 109104792-A0305-02-0103-100
[Table 20]
Figure 109104792-A0305-02-0103-100

[表21]

Figure 109104792-A0305-02-0104-101
[Table 21]
Figure 109104792-A0305-02-0104-101

[表22]

Figure 109104792-A0305-02-0105-103
[Table 22]
Figure 109104792-A0305-02-0105-103

[表23]

Figure 109104792-A0305-02-0106-104
[Table 23]
Figure 109104792-A0305-02-0106-104

[表24]

Figure 109104792-A0305-02-0107-105
[Table 24]
Figure 109104792-A0305-02-0107-105

[表25]

Figure 109104792-A0305-02-0108-106
[Table 25]
Figure 109104792-A0305-02-0108-106

[表26]

Figure 109104792-A0305-02-0109-107
[Table 26]
Figure 109104792-A0305-02-0109-107

[表27]

Figure 109104792-A0305-02-0110-108
[Table 27]
Figure 109104792-A0305-02-0110-108

[表28]

Figure 109104792-A0305-02-0111-110
[Table 28]
Figure 109104792-A0305-02-0111-110

[表29]

Figure 109104792-A0305-02-0112-111
[Table 29]
Figure 109104792-A0305-02-0112-111

[表30]

Figure 109104792-A0305-02-0113-112
[Table 30]
Figure 109104792-A0305-02-0113-112

[表31]

Figure 109104792-A0305-02-0114-113
[Table 31]
Figure 109104792-A0305-02-0114-113

[化63]

Figure 109104792-A0305-02-0115-314
[Chemistry 63]
Figure 109104792-A0305-02-0115-314

[化64]

Figure 109104792-A0305-02-0116-315
[Chemistry 64]
Figure 109104792-A0305-02-0116-315

[化65]

Figure 109104792-A0305-02-0117-316
[Chemistry 65]
Figure 109104792-A0305-02-0117-316

[化66]

Figure 109104792-A0305-02-0118-317
[Chemistry 66]
Figure 109104792-A0305-02-0118-317

[化67]

Figure 109104792-A0305-02-0119-318
[Chemistry 67]
Figure 109104792-A0305-02-0119-318

Figure 109104792-A0305-02-0119-319
Figure 109104792-A0305-02-0119-319

Figure 109104792-A0305-02-0120-320
Figure 109104792-A0305-02-0120-320

[化70]

Figure 109104792-A0305-02-0121-321
[Chemistry 70]
Figure 109104792-A0305-02-0121-321

[化71]

Figure 109104792-A0305-02-0122-322
[Chemistry 71]
Figure 109104792-A0305-02-0122-322

作為化合物(I),例如,可列舉下述表f1~表f44所示的式(If)所表示的化合物或其鹼金屬鹽。 As compound (I), for example, compounds represented by formula (If) shown in the following Table f1 to Table f44 or their alkali metal salts can be listed.

再者,表f1~表f44中的「Q1」欄及「Q2」欄中所記載的符 號分別對應於所述式所表示的基。 Furthermore, the symbols recorded in the "Q 1 " column and the "Q 2 " column in Tables f1 to f44 respectively correspond to the groups represented by the above formulas.

※表示鍵結鍵。 ※Indicates key binding.

Figure 109104792-A0305-02-0123-323
Figure 109104792-A0305-02-0123-323

[表f1]

Figure 109104792-A0305-02-0124-114
[Table f1]
Figure 109104792-A0305-02-0124-114

[表f2]

Figure 109104792-A0305-02-0125-117
[Table f2]
Figure 109104792-A0305-02-0125-117

[表f3]

Figure 109104792-A0305-02-0126-118
[Table f3]
Figure 109104792-A0305-02-0126-118

[表f4]

Figure 109104792-A0305-02-0127-356
[Table f4]
Figure 109104792-A0305-02-0127-356

[表f5]

Figure 109104792-A0305-02-0128-120
[Table f5]
Figure 109104792-A0305-02-0128-120

[表f6]

Figure 109104792-A0305-02-0129-121
[Table f6]
Figure 109104792-A0305-02-0129-121

[表f7]

Figure 109104792-A0305-02-0130-122
[Table f7]
Figure 109104792-A0305-02-0130-122

[表f8]

Figure 109104792-A0305-02-0131-123
[Table f8]
Figure 109104792-A0305-02-0131-123

[表f9]

Figure 109104792-A0305-02-0132-357
[Table f9]
Figure 109104792-A0305-02-0132-357

[表f10]

Figure 109104792-A0305-02-0133-125
[Table f10]
Figure 109104792-A0305-02-0133-125

[表f11]

Figure 109104792-A0305-02-0134-126
[Table f11]
Figure 109104792-A0305-02-0134-126

[表f12]

Figure 109104792-A0305-02-0135-127
[Table f12]
Figure 109104792-A0305-02-0135-127

[表f13]

Figure 109104792-A0305-02-0136-128
[Table f13]
Figure 109104792-A0305-02-0136-128

[表f14]

Figure 109104792-A0305-02-0137-130
[Table f14]
Figure 109104792-A0305-02-0137-130

[表f15]

Figure 109104792-A0305-02-0138-131
[Table f15]
Figure 109104792-A0305-02-0138-131

[表f16]

Figure 109104792-A0305-02-0139-132
[Table f16]
Figure 109104792-A0305-02-0139-132

[表f17]

Figure 109104792-A0305-02-0140-133
[Table f17]
Figure 109104792-A0305-02-0140-133

[表f18]

Figure 109104792-A0305-02-0141-134
[Table f18]
Figure 109104792-A0305-02-0141-134

[表f19]

Figure 109104792-A0305-02-0142-135
[Table f19]
Figure 109104792-A0305-02-0142-135

[表f20]

Figure 109104792-A0305-02-0143-136
[Table f20]
Figure 109104792-A0305-02-0143-136

[表f21]

Figure 109104792-A0305-02-0144-137
[Table f21]
Figure 109104792-A0305-02-0144-137

[表f22]

Figure 109104792-A0305-02-0145-138
[Table f22]
Figure 109104792-A0305-02-0145-138

[表f23]

Figure 109104792-A0305-02-0146-139
[Table f23]
Figure 109104792-A0305-02-0146-139

[表f24]

Figure 109104792-A0305-02-0147-140
[Table f24]
Figure 109104792-A0305-02-0147-140

[表f25]

Figure 109104792-A0305-02-0148-141
[Table f25]
Figure 109104792-A0305-02-0148-141

[表f26]

Figure 109104792-A0305-02-0149-142
[Table f26]
Figure 109104792-A0305-02-0149-142

[表f27]

Figure 109104792-A0305-02-0150-143
[Table f27]
Figure 109104792-A0305-02-0150-143

[表f28]

Figure 109104792-A0305-02-0151-144
[Table f28]
Figure 109104792-A0305-02-0151-144

[表f29]

Figure 109104792-A0305-02-0152-145
[Table f29]
Figure 109104792-A0305-02-0152-145

[表f30]

Figure 109104792-A0305-02-0153-146
[Table f30]
Figure 109104792-A0305-02-0153-146

[表f31]

Figure 109104792-A0305-02-0154-147
[Table f31]
Figure 109104792-A0305-02-0154-147

[表f32]

Figure 109104792-A0305-02-0155-149
[Table f32]
Figure 109104792-A0305-02-0155-149

[表f33]

Figure 109104792-A0305-02-0156-150
[Table f33]
Figure 109104792-A0305-02-0156-150

[表f34]

Figure 109104792-A0305-02-0157-151
[Table f34]
Figure 109104792-A0305-02-0157-151

[表f35]

Figure 109104792-A0305-02-0158-153
[Table f35]
Figure 109104792-A0305-02-0158-153

[表f36]

Figure 109104792-A0305-02-0159-154
[Table f36]
Figure 109104792-A0305-02-0159-154

[表f37]

Figure 109104792-A0305-02-0160-155
[Table f37]
Figure 109104792-A0305-02-0160-155

[表f38]

Figure 109104792-A0305-02-0161-156
[Table f38]
Figure 109104792-A0305-02-0161-156

[表f39]

Figure 109104792-A0305-02-0162-157
[Table f39]
Figure 109104792-A0305-02-0162-157

[表f40]

Figure 109104792-A0305-02-0163-158
[Table f40]
Figure 109104792-A0305-02-0163-158

[表f41]

Figure 109104792-A0305-02-0164-159
[Table f41]
Figure 109104792-A0305-02-0164-159

[表f42]

Figure 109104792-A0305-02-0165-160
[Table f42]
Figure 109104792-A0305-02-0165-160

[表f43]

Figure 109104792-A0305-02-0166-161
[Table f43]
Figure 109104792-A0305-02-0166-161

[表f44]

Figure 109104792-A0305-02-0167-162
[Table f44]
Figure 109104792-A0305-02-0167-162

作為化合物(I),例如,可列舉下述表t1~表t5所示的 式(It)所表示的化合物、及下述表u1~表u11所表示的式(Iu)所表示的化合物及該些的鹼金屬鹽。 As compound (I), for example, compounds represented by formula (It) shown in Table t1 to Table t5 below, compounds represented by formula (Iu) shown in Table u1 to Table u11 below, and alkali metal salts thereof can be listed.

再者,表t1~表t5中以及表u1~表u11中的「aq」欄、「Q1」欄、「Q2」欄以及「Qu+1」欄中所記載的符號分別對應於所述式所表示的基以及下述式(aq1)~式(aq36)所表示的基。 Furthermore, the symbols recorded in the "aq" column, "Q 1 " column, "Q 2 " column and "Q u+1 " column in Tables t1 to t5 and Tables u1 to u11 correspond to the groups represented by the above formulas and the groups represented by the following formulas (aq1) to (aq36), respectively.

表u1~表u11中的「Qu+1」欄表示式(Iu)所表示的化合物中的Q1所表示的基及Q2所表示的基為與「Qu+1」欄中所記載的符號對應的基。 The "Q u+1 " column in Tables u1 to u11 indicates that the group represented by Q 1 and the group represented by Q 2 in the compound represented by formula (Iu) are groups corresponding to the symbols described in the "Q u+1 " column.

於下述式(aq1)~式(aq36)所表示的基中,#表示與Q1的鍵結鍵,&表示與Q2的鍵結鍵。 In the groups represented by the following formulae (aq1) to (aq36), # represents a bond with Q1 , and & represents a bond with Q2 .

Figure 109104792-A0305-02-0168-324
Figure 109104792-A0305-02-0168-324

Figure 109104792-A0305-02-0168-325
Figure 109104792-A0305-02-0168-325

[化75]

Figure 109104792-A0305-02-0169-326
[Chemistry 75]
Figure 109104792-A0305-02-0169-326

[化76]

Figure 109104792-A0305-02-0170-327
[Chemistry 76]
Figure 109104792-A0305-02-0170-327

[化77]

Figure 109104792-A0305-02-0171-328
[Chemistry 77]
Figure 109104792-A0305-02-0171-328

[表t1]

Figure 109104792-A0305-02-0172-163
[Table t1]
Figure 109104792-A0305-02-0172-163

[表t2]

Figure 109104792-A0305-02-0173-164
[Table t2]
Figure 109104792-A0305-02-0173-164

[表t3]

Figure 109104792-A0305-02-0174-165
[Table t3]
Figure 109104792-A0305-02-0174-165

[表t4]

Figure 109104792-A0305-02-0175-166
[Table t4]
Figure 109104792-A0305-02-0175-166

[表t5]

Figure 109104792-A0305-02-0176-167
[Table t5]
Figure 109104792-A0305-02-0176-167

[表u1]

Figure 109104792-A0305-02-0177-168
[Table u1]
Figure 109104792-A0305-02-0177-168

[表u2]

Figure 109104792-A0305-02-0178-169
[Table u2]
Figure 109104792-A0305-02-0178-169

[表u3]

Figure 109104792-A0305-02-0179-170
[Table u3]
Figure 109104792-A0305-02-0179-170

[表u4]

Figure 109104792-A0305-02-0180-171
[Table u4]
Figure 109104792-A0305-02-0180-171

[表u5]

Figure 109104792-A0305-02-0181-174
[Table u5]
Figure 109104792-A0305-02-0181-174

[表u6]

Figure 109104792-A0305-02-0182-175
[Table u6]
Figure 109104792-A0305-02-0182-175

[表u7]

Figure 109104792-A0305-02-0183-176
[Table u7]
Figure 109104792-A0305-02-0183-176

[表u8]

Figure 109104792-A0305-02-0184-177
[Table u8]
Figure 109104792-A0305-02-0184-177

[表u9]

Figure 109104792-A0305-02-0185-178
[Table u9]
Figure 109104792-A0305-02-0185-178

[表u10]

Figure 109104792-A0305-02-0186-179
[Table u10]
Figure 109104792-A0305-02-0186-179

[表u11]

Figure 109104792-A0305-02-0187-181
[Table u11]
Figure 109104792-A0305-02-0187-181

作為化合物(I),例如,亦可列舉:於式(Ia1)~式(Ia2216)及式(Ib1)~式(Ib1312)所表示的化合物、 式(If1)~式(If13090)所表示的化合物、式(It1)~式(It900)所表示的化合物、及式(Iu1)~式(Iu3238)所表示的化合物 中取代有選自-SO3H、-CO2H、-SO3NH4、-CO2NH4、-SO2NH2、-CONH2、鄰苯二甲醯亞胺甲基(C6H4(CO)2N-CH2-)、-SO2NH(CH2)2N(CH2CH3)2、-N(CH3)((CH2)11CH3)、氟原子、氯原子及溴原子中的一個以上的化合物。 Examples of compound (I) include compounds represented by formula (Ia1) to (Ia2216) and (Ib1) to (Ib1312), compounds represented by formula (If1) to (If13090), compounds represented by formula (It1) to (It900), and compounds represented by formula (Iu1) to (Iu3238) in which a group selected from -SO 3 H, -CO 2 H , -SO 3 NH 4 , -CO 2 NH 4 , -SO 2 NH 2 , -CONH 2 , phthalimidomethyl (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 one or more of a fluorine atom, a chlorine atom and a bromine atom.

例如,於表1的式(Ia1)所表示的化合物中取代有-SO3H的化合物表示下述結構。其中,式中,-(SO3H)是指-SO3H對式(Ia1)所表示的化合物的氫原子的全部或一個以上進行取代。 For example, the compound represented by formula (Ia1) in Table 1 in which -SO 3 H is substituted has the following structure. In the formula, -(SO 3 H) means that all or one or more hydrogen atoms in the compound represented by formula (Ia1) are substituted by -SO 3 H.

Figure 109104792-A0305-02-0188-329
Figure 109104792-A0305-02-0188-329

作為該化合物,例如,亦可列舉式(Ic1)~式(Ic12)所表示的芳香族環的氫原子的全部經選自氟原子、氯原子及溴原子中的一個以上取代而成的化合物。 As such compounds, for example, compounds in which all hydrogen atoms of the aromatic rings represented by formula (Ic1) to formula (Ic12) are substituted with one or more atoms selected from fluorine atoms, chlorine atoms and bromine atoms can also be cited.

[化79]

Figure 109104792-A0305-02-0189-330
[Chemistry 79]
Figure 109104792-A0305-02-0189-330

[化80]

Figure 109104792-A0305-02-0190-331
[Chemistry 80]
Figure 109104792-A0305-02-0190-331

作為化合物(I),例如,亦可列舉:於式(Ia1)~式(Ia2216)及式(Ib1)~式(Ib1312)所表示的化合物、式(If1)~式(If13090)所表示的化合物、式(It1)~式(It900)所表示的化合物、及式(Iu1)~式(Iu3238)所表示的化合物 中取代有1個~6個選自-SO3H、-CO2H、-SO3NH4、-CO2NH4、-SO2NH2、-CONH2、鄰苯二甲醯亞胺甲基(C6H4(CO)2N-CH2-)、-SO2NH(CH2)2N(CH2CH3)2、-N(CH3)((CH2)11CH3)、氟原子、氯原 子及溴原子中的一個以上的化合物。 Examples of compound (I) include compounds represented by formula (Ia1) to (Ia2216) and (Ib1) to (Ib1312), compounds represented by formula (If1) to (If13090), compounds represented by formula (It1) to (It900), and compounds represented by formula (Iu1) to (Iu3238) substituted with 1 to 6 groups selected from -SO 3 H, -CO 2 H, -SO 3 NH 4 , -CO 2 NH 4 , -SO 2 NH 2 , -CONH 2 , phthalimidomethyl (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 one or more of a fluorine atom, a chlorine atom and a bromine atom.

例如,於表1的式(Ia1)所表示的化合物中取代有1個~6個-SO3H的化合物表示下述結構。其中,式中,-(SO3H)1~6是指-SO3H對式(Ia1)所表示的化合物的1個~6個的任一氫原子進行取代。 For example, the compound represented by formula (Ia1) in Table 1 in which 1 to 6 -SO 3 H atoms are substituted has the following structure. In the formula, -(SO 3 H) 1-6 means that -SO 3 H replaces 1 to 6 hydrogen atoms of the compound represented by formula (Ia1).

Figure 109104792-A0305-02-0191-332
Figure 109104792-A0305-02-0191-332

作為化合物(I),例如,可列舉:包含在式(Ia1)~式(Ia2216)及式(Ib1)~式(Ib1312)所表示的化合物、式(If1)~式(If13090)所表示的化合物、式(It1)~式(It900)所表示的化合物、及式(Iu1)~式(Iu3238)所表示的化合物 中取代有選自-SO3 -及-CO2 -中的一個以上的陰離子、與選自Mg2+、Ca2+、Sr2+、Ba2+、Ni2+、Zn2+、Fe2+、Co2+、Sn2+、Mn2+、Al3+、Fe3+、Cr3+、Sn4+、Mn4+、Cu2+、Li+、Na+及K+中的 一個以上的陽離子的金屬鹽。 Examples of compound (I) include compounds represented by formula (Ia1) to (Ia2216) and (Ib1) to (Ib1312), compounds represented by formula (If1) to (If13090), compounds represented by formula (It1) to (It900), and compounds represented by formula (Iu1) to (Iu3238) in which one or more anions selected from -SO 3 - and -CO 2 - and one or more anions 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 Metal salts containing one or more cations among Na + , Na + and K + .

作為化合物(I),例如,可列舉:包含下述表32~表33及表h1~表h6所示的式(Id)所表示的陰離子及式(Ih)所表示的陰離子、與選自Mg2+、Ca2+、Sr2+、Ba2+、Ni2+、Zn2+、Fe2+、Co2+、Sn2+、Mn2+、Al3+、Fe3+、Cr3+、Sn4+、Mn4+、Cu2+、Li+、Na+及K+中的一個以上的陽離子的金屬鹽。 Examples of compound (I) include metal salts comprising an anion represented by formula (Id) and an anion represented by formula (Ih) shown in Tables 32 to 33 and Tables h1 to h6 below, and a cation selected from the group consisting of 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 + .

表32~表33及表h1~表h6中的「Q1」欄以及「Q2」欄中所記載的符號分別對應於所述式所表示的基以及下述式(Qw1)~式(Qw11)所表示的基。 The symbols described in the "Q 1 " column and the "Q 2 " column in Tables 32 to 33 and Tables h1 to h6 correspond to the groups represented by the above formulas and the groups represented by the following formulas (Qw1) to (Qw11), respectively.

Figure 109104792-A0305-02-0192-333
Figure 109104792-A0305-02-0192-333

[化83]

Figure 109104792-A0305-02-0193-335
[Chemistry 83]
Figure 109104792-A0305-02-0193-335

Figure 109104792-A0305-02-0193-336
Figure 109104792-A0305-02-0193-336

Figure 109104792-A0305-02-0193-337
Figure 109104792-A0305-02-0193-337

[化86]

Figure 109104792-A0305-02-0194-338
[Chemistry 86]
Figure 109104792-A0305-02-0194-338

Figure 109104792-A0305-02-0194-182
Figure 109104792-A0305-02-0194-182

Figure 109104792-A0305-02-0195-183
Figure 109104792-A0305-02-0195-183

[表h1]

Figure 109104792-A0305-02-0196-185
[Table h1]
Figure 109104792-A0305-02-0196-185

[表h2]

Figure 109104792-A0305-02-0197-186
[Table h2]
Figure 109104792-A0305-02-0197-186

[表h3]

Figure 109104792-A0305-02-0198-187
[Table h3]
Figure 109104792-A0305-02-0198-187

[表h4]

Figure 109104792-A0305-02-0199-188
[Table h4]
Figure 109104792-A0305-02-0199-188

[表h5]

Figure 109104792-A0305-02-0200-189
[Table h5]
Figure 109104792-A0305-02-0200-189

[表h6]

Figure 109104792-A0305-02-0201-190
[Table h6]
Figure 109104792-A0305-02-0201-190

作為該金屬鹽,例如,可列舉下述表34~表38所示的式(Ie)所表示的金屬鹽及表k1~表k14所示的式(Ik)所表示 的金屬鹽。 As the metal salt, for example, the metal salt represented by the formula (Ie) shown in Tables 34 to 38 below and the metal salt represented by the formula (Ik) shown in Tables k1 to k14 can be cited.

作為表34~表38及表k1~表k14中的「Met」欄中所記載的符號,Mg2+表示Mg2+,Ca2+表示Ca2+,Sr2+表示Sr2+,Ba2+表示Ba2+,Ni2+表示Ni2+,Zn2+表示Zn2+,Fe2+表示Fe2+,Co2+表示Co2+,Sn2+表示Sn2+,Mn2+表示Mn2+,Al3+表示Al3+,Fe3+表示Fe3+,Cr3+表示Cr3+,Sn4+表示Sn4+,Mn4+表示Mn4+,Cu2+表示Cu2+,Li+表示Li+,Na+表示Na+,K+表示K+As the symbols recorded in the "Met" column in Tables 34 to 38 and Tables k1 to k14, Mg2+ represents Mg 2+ , Ca2+ represents Ca 2+ , Sr2+ represents Sr 2+ , Ba2+ represents Ba 2+ , Ni2+ represents Ni 2+ , Zn2+ represents Zn 2+ , Fe2+ represents Fe 2+ , Co2+ represents Co 2+ , Sn2+ represents Sn 2+ , Mn2+ represents Mn 2+ , Al3+ represents Al 3+ , Fe3+ represents Fe 3+ , Cr3+ represents Cr 3+ , Sn4+ represents Sn 4+ , Mn4+ represents Mn 4+ , Cu2+ represents Cu 2+ , Li+ represents Li + , Na+ represents Na + , and K+ represents K + .

表34~表38及表k1~表k14中的「Q1」欄及「Q2」欄 中所記載的符號分別對應於所述式所表示的基。 The symbols recorded in the "Q 1 " column and the "Q 2 " column in Tables 34 to 38 and Tables k1 to k14 respectively correspond to the groups represented by the above formulas.

式(Ie)及式(Ik)中的m為1以上的整數,較佳為1~20的整數,更佳為1~10的整數。 In formula (Ie) and formula (Ik), m is an integer greater than 1, preferably an integer between 1 and 20, and more preferably an integer between 1 and 10.

式(Ie)及式(Ik)中的n為1以上的整數,較佳為1~20的整數,更佳為1~10的整數。 In formula (Ie) and formula (Ik), n is an integer greater than 1, preferably an integer between 1 and 20, and more preferably an integer between 1 and 10.

其中,於本發明的化合物(I)為所述寡聚物或聚合物的情況下,m及n表示表示化合物(I)的電荷為零般的配位體的個數及金屬原子的個數的比率的最小整數,藉此,表示化合物(I)為所述寡聚物或聚合物。 Wherein, when the compound (I) of the present invention is the oligomer or polymer, m and n represent the minimum integer of the ratio of the number of ligands and the number of metal atoms such that the charge of the compound (I) is zero, thereby indicating that the compound (I) is the oligomer or polymer.

Figure 109104792-A0305-02-0203-339
Figure 109104792-A0305-02-0203-339

Figure 109104792-A0305-02-0203-340
Figure 109104792-A0305-02-0203-340

Figure 109104792-A0305-02-0204-191
Figure 109104792-A0305-02-0204-191

[表35]

Figure 109104792-A0305-02-0205-192
[Table 35]
Figure 109104792-A0305-02-0205-192

[表36]

Figure 109104792-A0305-02-0206-193
[Table 36]
Figure 109104792-A0305-02-0206-193

[表37]

Figure 109104792-A0305-02-0207-194
[Table 37]
Figure 109104792-A0305-02-0207-194

[表38]

Figure 109104792-A0305-02-0208-196
[Table 38]
Figure 109104792-A0305-02-0208-196

[表k1]

Figure 109104792-A0305-02-0209-197
[Table k1]
Figure 109104792-A0305-02-0209-197

[表k2]

Figure 109104792-A0305-02-0210-198
[Table k2]
Figure 109104792-A0305-02-0210-198

Figure 109104792-A0305-02-0211-199
Figure 109104792-A0305-02-0211-199

Figure 109104792-A0305-02-0212-200
Figure 109104792-A0305-02-0212-200

Figure 109104792-A0305-02-0213-201
Figure 109104792-A0305-02-0213-201

Figure 109104792-A0305-02-0214-202
Figure 109104792-A0305-02-0214-202

Figure 109104792-A0305-02-0215-203
Figure 109104792-A0305-02-0215-203

Figure 109104792-A0305-02-0216-204
Figure 109104792-A0305-02-0216-204

Figure 109104792-A0305-02-0217-205
Figure 109104792-A0305-02-0217-205

Figure 109104792-A0305-02-0218-206
Figure 109104792-A0305-02-0218-206

Figure 109104792-A0305-02-0219-207
Figure 109104792-A0305-02-0219-207

Figure 109104792-A0305-02-0220-208
Figure 109104792-A0305-02-0220-208

Figure 109104792-A0305-02-0221-209
Figure 109104792-A0305-02-0221-209

Figure 109104792-A0305-02-0222-210
Figure 109104792-A0305-02-0222-210

作為化合物(I),較佳為:式(Ia1)~式(Ia2216)所表示的化合物;式(If1)~式(If13090)所表示的化合物;式(It1)~式(It900)所表示的化合物;及式(Iu1)~式(Iu3238)所表示的化合物;式(Ib8)所表示的化合物;式(Ib14)所表示的化合物;於式(Ia1)~式(Ia2216)所表示的化合物、式(If1)~式(If13090)所表示的化合物、式(It1)~式(It900)所表示的化合物、式(Iu1)~式(Iu3238)所表示的化合物、式(Ib8)所表示的化合物、及式(Ib14)所表示的化合物中 取代有選自-SO3H、-CO2H、-SO3NH4、-CO2NH4、-SO2NH2、-CONH2、鄰苯二甲醯亞胺甲基(C6H4(CO)2N-CH2-)、-SO2NH(CH2)2N(CH2CH3)2、-N(CH3)((CH2)11CH3)、氟原子、氯原子及溴原子中的一個以上的化合物;以及包含在式(Ia1)~式(Ia2216)所表示的化合物、式(If1)~式(If13090)所表示的化合物、式(It1)~式(It900)所表示的化合物、式(Iu1)~式(Iu3238)所表示的化合物、式(Ib8)所表示的化合物、及 式(Ib14)所表示的化合物中 取代有選自-SO3 -及-CO2 -中的一個以上的陰離子、與選自Mg2+、Ca2+、Sr2+、Ba2+、Ni2+、Zn2+、Fe2+、Co2+、Sn2+、Mn2+、Al3+、Fe3+、Cr3+、Sn4+、Mn4+、Cu2+、Li+、Na+及K+中的一個以上的陽離子的金屬鹽,更佳為:式(Ia1)~式(Ia2216)所表示的化合物;式(If1)~式(If13090)所表示的化合物;式(It1)~式(It900)所表示的化合物;式(Iu1)~式(Iu3238)所表示的化合物;於式(Ia1)~式(Ia2216)所表示的化合物、式(If1)~式(If13090)所表示的化合物、式(It1)~式(It900)所表示的化合物、式(Iu1)~式(Iu3238)所表示的化合物、式(Ib8)所表示的化合物、及式(Ib14)所表示的化合物中 取代有選自-SO3H、-CO2H、-SO3NH4、-CO2NH4、氟原子、氯原子及溴原子中的一個以上的化合物;以及包含式(Id1)~式(Id304)所表示的陰離子及式(Ih1)~式(Ih1666)所表示的陰離子、與選自Mg2+、Ca2+、Sr2+、Ba2+、Ni2+、Zn2+、Fe2+、Co2+、Sn2+、Mn2+、Al3+、Fe3+、Cr3+、Sn4+、Mn4+、Cu2+、Li+、Na+及K+中的一個以上的陽離子的金屬鹽, 進而佳為:式(Ia1)~式(Ia2216)所表示的化合物;式(If1)~式(If13090)所表示的化合物;式(It1)~式(It900)所表示的化合物;式(Iu1)~式(Iu3238)所表示的化合物;於式(Ia1)~式(Ia2216)所表示的化合物、式(If1)~式(If13090)所表示的化合物、式(It1)~式(It900)所表示的化合物、式(Iu1)~式(Iu3238)所表示的化合物、式(Ib8)所表示的化合物、及式(Ib14)所表示的化合物中 取代有選自-SO3H、-CO2H、-SO3NH4、-CO2NH4、氯原子及溴原子中的一個以上的化合物;式(Ie1)~式(Ie76)所表示的化合物;及式(Ik1)~式(Ik114)所表示的化合物;式(Ik1615)~式(Ik1633)所表示的化合物;式(Ik1822)~式(Ik1983)所表示的化合物;式(Ie117)所表示的化合物;式(Ie123)所表示的化合物;式(Ik172)所表示的化合物;式(Ik171)所表示的化合物;式(Ik1777)所表示的化合物;式(Ik181)所表示的化合物; 式(Ik397)所表示的化合物;式(Ie273)所表示的化合物;及式(Ie116)所表示的化合物,尤佳為:式(Ia1)~式(Ia2216)所表示的化合物;式(If1)~式(If13090)所表示的化合物;式(It1)~式(It900)所表示的化合物;式(Iu1)~式(Iu3238)所表示的化合物;式(Ib8)所表示的化合物;及式(Ib14)所表示的化合物,進而尤佳為:式(Ia1)~式(Ia1241)所表示的化合物、式(It1)~式(It900)所表示的化合物,特佳為:式(Ia1)所表示的化合物、式(Ia2)所表示的化合物、式(Ia3)所表示的化合物、式(Ia10)所表示的化合物、式(Ia22)所表示的化合物、式(Ia23)所表示的化合物、式(Ia33)所表示的化合物、式(Ia35)所表示的化合物、式(Ia315)所表示的化合物、式(Ia696)所表示的化合物、式(Ia703)所表示的化合物、式(Ia973)所表示的化合物、式(It232)所表示的化合物、式(It242)所表示的化合物、及式(It750)所表示的化合物,極佳為:式(Ia1)所表示的化合物、式(Ia2)所表示的化合物、式(Ia3)所表示的化合物、式(Ia22)所表示的化合物、式(Ia23)所表示的化合物、式(Ia35)所表示的化合物、式 (Ia696)所表示的化合物、式(Ia703)所表示的化合物、式(Ia973)所表示的化合物、式(It232)所表示的化合物、式(It242)所表示的化合物、及式(It750)所表示的化合物,最佳為:式(Ia1)所表示的化合物、式(Ia2)所表示的化合物、式(Ia3)所表示的化合物、式(Ia696)所表示的化合物、式(Ia703)所表示的化合物、式(Ia973)所表示的化合物、式(It232)所表示的化合物、式(It242)所表示的化合物、及式(It750)所表示的化合物。 Preferred as compound (I) are compounds represented by formula (Ia1) to (Ia2216); compounds represented by formula (If1) to (If13090); compounds represented by formula (It1) to (It900); compounds represented by formula (Iu1) to (Iu3238); compounds represented by formula (Ib8); compounds represented by formula (Ib14); wherein the compounds represented by formula (Ia1) to (Ia2216), compounds represented by formula (If1) to (If13090), compounds represented by formula (It1) to (It900), compounds represented by formula (Iu1) to (Iu3238), compounds represented by formula (Ib8), and compounds represented by formula (Ib14) are substituted with a group selected from -SO 3 H, -CO 2 H, -SO 3 NH 4 , -CO2NH4 , -SO2NH2, -CONH2 , phthalimidomethyl ( C6H4 (CO) 2N - CH2- ) , -SO2NH (CH2) 2N (CH2CH3) 2 , -N ( CH3 )(( CH2 ) 11CH3 ), a fluorine atom, a chlorine atom and a bromine atom; and 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), a compound represented by formula (Iu1) to formula (Iu3238), a compound represented by formula (Ib8), and a compound represented by formula (Ib14) substituted with a substituted atom selected from -SO3- and -CO2 - , and one or more anions 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 + is more preferably a metal salt of one or more cations in the formula (Ia1) to (Ia2216); a compound represented by (If1) to (If13090); a compound represented by (It1) to (It900); a compound represented by (Iu1) to (Iu3238); a compound represented by (Ia1) to (Ia2216), a compound represented by (If1) to (If13090), a compound represented by (It1) to (It900), a compound represented by (Iu1) to (Iu3238), a compound represented by (Ib8), and a compound represented by (Ib14) substituted with -SO 3 H, -CO 2 H, -SO 3 NH 4 , -CO 2 NH 4 , a compound containing one or more of a fluorine atom, a chlorine atom and a bromine atom; and a metal salt containing an anion represented by formula (Id1) to formula (Id304) and an anion represented by formula (Ih1) to formula (Ih1666), and one or more cations selected from Mg2 + , Ca2 + , Sr2 + , Ba2 + , Ni2 +, Zn2 + , Fe2 + , Co2 + , Sn2+, Mn2+, Al3 +, Fe3 + , Cr3 + , Sn4 + , Mn4 + , Cu2 + , Li + , Na + and K + , Further preferred are compounds represented by formula (Ia1) to (Ia2216); compounds represented by formula (If1) to (If13090); compounds represented by formula (It1) to (It900); compounds represented by formula (Iu1) to (Iu3238); compounds represented by formula (Ia1) to (Ia2216), compounds represented by formula (If1) to (If13090), compounds represented by formula (It1) to (It900), compounds represented by formula (Iu1) to (Iu3238), compounds represented by formula (Ib8), and compounds represented by formula (Ib14) wherein -SO 3 H, -CO 2 H, -SO 3 NH 4 , -CO 2 NH 4 , a compound containing one or more of chlorine atoms and bromine atoms; a compound represented by formula (Ie1) to formula (Ie76); and a compound represented by formula (Ik1) to formula (Ik114); a compound represented by formula (Ik1615) to formula (Ik1633); a compound represented by formula (Ik1822) to formula (Ik1983); a compound represented by formula (Ie117); a compound represented by formula (Ie123); a compound represented by formula (Ik172); a compound represented by formula (Ik171); a compound represented by formula (Ik1777); a compound represented by formula (Ik181); The compound represented by formula (Ik397); the compound represented by formula (Ie273); and the compound represented by formula (Ie116), preferably: the compound represented by formula (Ia1) to formula (Ia2216); the compound represented by formula (If1) to formula (If13090); the compound represented by formula (It1) to formula (It900); the compound represented by formula (Iu1) to formula (Iu3238); the compound represented by formula (Ib8); and the compound represented by formula (Ib14), and more preferably: the compound represented by formula (Ia1) to formula (Ia124 1), a compound represented by formula (It1) to formula (It900), particularly preferably: a compound represented by formula (Ia1), a compound represented by formula (Ia2), a compound represented by formula (Ia3), a compound represented by formula (Ia10), a compound represented by formula (Ia22), a compound represented by formula (Ia23), a compound represented by formula (Ia33), a compound represented by formula (Ia35), a compound represented by formula (Ia315), a compound represented by formula (Ia696), a 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 formula (It750), and the most 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 formula (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 formula (It750) are preferably: the compound represented by formula (Ia1), the compound represented by formula (Ia2), the compound represented by formula (Ia3), 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 formula (It750).

式(I)所表示的化合物可藉由式(pt1)所表示的化合物、與式(pt2)所表示的化合物及式(pt3)所表示的化合物的反應來製造。 The compound represented by formula (I) can be produced by reacting a compound represented by formula (pt1), a compound represented by formula (pt2), and a compound represented by formula (pt3).

Figure 109104792-A0305-02-0227-341
Figure 109104792-A0305-02-0227-341

式(pt1)~式(pt3)中,R1~R5、Q1及Q2表示與所述相同的含義。 In formula (pt1) to formula (pt3), R 1 to R 5 , Q 1 and Q 2 have the same meanings as described above.

式(pt1)所表示的化合物、與式(pt2)所表示的化合物及式(pt3)所表示的化合物的反應中的、式(pt2)所表示的化 合物的使用量相對於式(pt1)所表示的化合物1莫耳而通常為0.1莫耳~30莫耳,較佳為1莫耳~20莫耳,更佳為1莫耳~16莫耳,進而佳為1莫耳~10莫耳。 In the reaction of the compound represented by formula (pt1), the compound represented by formula (pt2) and the compound represented by formula (pt3), the amount of the compound represented by formula (pt2) used is usually 0.1 mol to 30 mol, preferably 1 mol to 20 mol, more preferably 1 mol to 16 mol, and even more preferably 1 mol to 10 mol, relative to 1 mol of the compound represented by formula (pt1).

式(pt1)所表示的化合物、與式(pt2)所表示的化合物及式(pt3)所表示的化合物的反應中的、式(pt3)所表示的化合物的使用量相對於式(pt1)所表示的化合物1莫耳而通常為0.1莫耳~30莫耳,較佳為1莫耳~20莫耳,更佳為1莫耳~16莫耳,進而佳為1莫耳~10莫耳。 In the reaction of the compound represented by formula (pt1), the compound represented by formula (pt2) and the compound represented by formula (pt3), the amount of the compound represented by formula (pt3) used is usually 0.1 mol to 30 mol, preferably 1 mol to 20 mol, more preferably 1 mol to 16 mol, and even more preferably 1 mol to 10 mol, relative to 1 mol of the compound represented by formula (pt1).

反應溫度通常為-100℃~300℃,較佳為0℃~280℃,更佳為50℃~250℃,進而佳為100℃~230℃,尤佳為150℃~200℃。 The reaction temperature is usually -100℃~300℃, preferably 0℃~280℃, more preferably 50℃~250℃, further preferably 100℃~230℃, and particularly preferably 150℃~200℃.

反應時間通常為0.5小時~500小時。 The reaction time is usually 0.5 hours to 500 hours.

式(pt1)所表示的化合物、與式(pt2)所表示的化合物及式(pt3)所表示的化合物的反應通常是於溶媒的存在下實施。 The reaction of the compound represented by formula (pt1), the compound represented by formula (pt2), and the compound represented by formula (pt3) is usually carried out in the presence of a solvent.

作為溶媒,可列舉:水;乙腈等腈溶媒;甲醇、乙醇、1-丙醇、2-丙醇、1-丁醇、1-戊醇、1-己醇、1-庚醇、2-乙基-1-己醇、1-辛醇、苯酚等醇溶媒;胺溶媒;二乙基醚、四氫呋喃、二苯基醚等醚溶媒;丙酮、甲基異丁基酮等酮溶媒;乙酸乙酯、苯甲酸甲酯等酯溶媒;己烷等脂肪族烴溶媒;甲苯、三甲基苯(例如,1,3,5-三甲基苯)、十氫萘、四氫萘等芳香族烴溶媒;二氯甲烷、氯仿、1,2-二氯苯、三氯苯(例如,1,3,5-三氯苯)、1-氯萘、2-氯萘等鹵化烴溶媒;硝基苯等硝基化烴溶媒;N,N-二甲基甲醯 胺、N,N-二甲基乙醯胺、N-甲基吡咯啶酮等醯胺溶媒;二甲基亞碸等亞碸溶媒,較佳為可列舉:二苯基醚、苯甲酸甲酯、三甲基苯(例如,1,3,5-三甲基苯)、十氫萘、四氫萘、1,2-二氯苯、三氯苯(例如,1,3,5-三氯苯)、1-氯萘、2-氯萘、硝基苯、N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基吡咯啶酮、二甲基亞碸,更佳為可列舉:二苯基醚、苯甲酸甲酯、三甲基苯(例如,1,3,5-三甲基苯)、十氫萘、四氫萘、1,2-二氯苯、三氯苯(例如,1,3,5-三氯苯)、1-氯萘、2-氯萘、硝基苯、N-甲基吡咯啶酮,進而佳為可列舉苯甲酸甲酯。 As the solvent, there can be mentioned: water; nitrile solvents such as acetonitrile; alcohol solvents such as methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-octanol, phenol, etc.; amine solvents; ether solvents such as diethyl ether, tetrahydrofuran, diphenyl ether, etc.; ketone solvents such as acetone, methyl isobutyl ketone, etc.; ester solvents such as ethyl acetate, methyl benzoate, etc.; aliphatic hydrocarbon solvents such as oxane; aromatic hydrocarbon solvents such as toluene, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decahydronaphthalene, tetrahydronaphthalene; halogenated hydrocarbon solvents such as dichloromethane, chloroform, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene; nitrated hydrocarbon solvents such as nitrobenzene; N,N-dimethylformamide, N,N-dimethylacetyl amine solvents such as amine, N-methylpyrrolidone; sulfoxide solvents such as dimethyl sulfoxide, preferably diphenyl ether, methyl benzoate, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decahydronaphthalene, tetrahydronaphthalene, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N,N-dimethylformamide, N,N-di Methylacetamide, N-methylpyrrolidone, dimethyl sulfoxide, preferably diphenyl ether, methyl benzoate, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decahydronaphthalene, tetrahydronaphthalene, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N-methylpyrrolidone, and more preferably methyl benzoate.

溶媒的使用量相對於式(pt1)所表示的化合物、與式(pt2)所表示的化合物及式(pt3)所表示的化合物的反應中的、式(pt1)所表示的化合物1質量份而通常為1質量份~1000質量份。 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 compound represented by formula (pt1) in the reaction between the compound represented by formula (pt2) and the compound represented by formula (pt3).

式(pt1)所表示的化合物、與式(pt2)所表示的化合物及式(pt3)所表示的化合物的反應中,較佳為使選自酸及金屬鹽中的一種以上共存。 In the reaction of the compound represented by formula (pt1), the compound represented by formula (pt2) and the compound represented by formula (pt3), it is preferred that at least one selected from an acid and a metal salt coexists.

作為酸,可列舉:氯化氫、溴化氫、碘化氫、硫酸、硝酸、氟磺酸、磷酸等無機酸;甲磺酸、三氟甲磺酸及對甲苯磺酸等磺酸;乙酸、三氟乙酸、檸檬酸、甲酸、葡萄糖酸、乳酸、草酸、苯甲酸及酒石酸等羧酸等,較佳為可列舉:氯化氫、溴化氫、硫酸、甲磺酸、三氟甲磺酸、對甲苯磺酸及羧酸,更佳為可列舉 羧酸,進而佳為可列舉苯甲酸。 As the acid, there can be listed: inorganic acids such as hydrogen chloride, hydrogen bromide, hydrogen iodide, sulfuric acid, nitric acid, fluorosulfonic acid, phosphoric acid, etc.; 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, there can be listed: hydrogen chloride, hydrogen bromide, sulfuric acid, methanesulfonic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid and carboxylic acid, more preferably, there can be listed carboxylic acids, and more preferably, there can be listed benzoic acid.

式(pt1)所表示的化合物、與式(pt2)所表示的化合物及式(pt3)所表示的化合物的反應中的酸的使用量相對於式(pt1)所表示的化合物1莫耳而通常為1莫耳~90莫耳,較佳為1莫耳~70莫耳,更佳為1莫耳~50莫耳,進而佳為1莫耳~30莫耳。 The amount of the acid used in the reaction of the compound represented by formula (pt1), the compound represented by formula (pt2) and the compound represented by formula (pt3) is usually 1 mol to 90 mol, preferably 1 mol to 70 mol, more preferably 1 mol to 50 mol, and even more preferably 1 mol to 30 mol, relative to 1 mol of the compound represented by formula (pt1).

作為金屬鹽,可列舉氯化鋅及氯化鋁等。 Examples of metal salts include zinc chloride and aluminum chloride.

式(pt1)所表示的化合物、與式(pt2)所表示的化合物及式(pt3)所表示的化合物的反應中的金屬鹽的使用量相對於式(pt1)所表示的化合物1莫耳而通常為0.01莫耳~30莫耳,較佳為0.01莫耳~20莫耳,更佳為0.01莫耳~10莫耳,進而佳為0.01莫耳~3莫耳。 The amount of the metal salt used in the reaction of the compound represented by formula (pt1), the compound represented by formula (pt2) and the compound represented by formula (pt3) is usually 0.01 mol to 30 mol, preferably 0.01 mol to 20 mol, more preferably 0.01 mol to 10 mol, and even more preferably 0.01 mol to 3 mol, relative to 1 mol of the compound represented by formula (pt1).

自反應混合物取出化合物(I)的方法並無特別限定,可利用公知的各種方法取出。 The method for removing compound (I) from the reaction mixture is not particularly limited, and it can be removed by various known methods.

例如,反應結束後,存在反應混合物中的化合物(I)難以溶解的情況,將容易溶解化合物(I)以外的化合物的甲醇等溶媒與反應混合物充分混合後,進行過濾,藉此可取出化合物(I)。進而,可利用N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基吡咯啶酮等醯胺溶媒、二甲基亞碸等亞碸溶媒或該些的混合溶媒、氫氧化鈉水溶液等鹼性水溶液、及/或鹽酸等酸性水溶液對所獲得的殘渣進行清洗後,利用水、甲醇等低沸點醇或該些的混合溶媒進行清洗,取出化合物(I)。進而,亦可利用管柱層析法及/或再結 晶等進行精製。 For example, after the reaction is completed, if compound (I) in the reaction mixture is difficult to dissolve, a solvent such as methanol that easily dissolves compounds other than compound (I) is fully mixed with the reaction mixture, and then filtered to remove compound (I). Furthermore, the obtained residue can be washed with amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, sulfoxide solvents such as dimethyl sulfoxide, or mixed solvents thereof, alkaline aqueous solutions such as sodium hydroxide aqueous solutions, and/or acidic aqueous solutions such as hydrochloric acid, and then washed with water, low-boiling alcohols such as methanol, or mixed solvents thereof to remove compound (I). Furthermore, column chromatography and/or recrystallization can also be used for purification.

或者,反應結束後,亦可餾去反應混合物的溶媒,並利用管柱層析法及/或再結晶等對所獲得的殘渣進行精製,反應結束後,亦可利用管柱層析法及/或再結晶等對反應混合物進行精製。 Alternatively, after the reaction is completed, 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, the reaction mixture can be purified by column chromatography and/or recrystallization.

反應結束後,存在反應混合物中的化合物(I)難以溶解的情況,將容易溶解化合物(I)以外的化合物的甲醇等溶媒與反應混合物充分混合後,進行過濾,藉此可取出化合物(I)。進而,亦可利用管柱層析法及/或再結晶等進行精製。 After the reaction is completed, if compound (I) in the reaction mixture is difficult to dissolve, a solvent such as methanol that easily dissolves compounds other than compound (I) is fully mixed with the reaction mixture and then filtered to remove compound (I). Furthermore, column chromatography and/or recrystallization can also be used for purification.

式(I)所表示的化合物可藉由如下方式製造:藉由式(pt1)所表示的化合物、與式(pt2)所表示的化合物的反應來製造式(I')所表示的化合物(以下,存在稱為化合物(I')的情況),繼而,使式(I')所表示的化合物於鹼存在下進行水解,製造式(IM1)所表示的化合物(以下,存在稱為化合物(IM1)的情況),進而,進行式(IM1)所表示的化合物、與式(pt3)所表示的化合物的反應。 The compound represented by formula (I) can be produced by reacting a compound represented by formula (pt1) with a compound represented by formula (pt2) to produce a compound represented by formula (I') (hereinafter, sometimes referred to as compound (I')), then hydrolyzing the compound represented by formula (I') in the presence of a base to produce a compound represented by formula (IM1) (hereinafter, sometimes referred to as compound (IM1)), and then reacting the compound represented by formula (IM1) with a compound represented by formula (pt3).

[化90]

Figure 109104792-A0305-02-0232-343
[Chemistry 90]
Figure 109104792-A0305-02-0232-343

式(pt1)、式(pt2)、式(pt3)、式(I')及式(IM1)中,R1~R5、Q1、Q2表示與所述相同的含義。 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 meanings as described above.

式(pt1)所表示的化合物與式(pt2)所表示的化合物的反應中的、式(pt2)所表示的化合物的使用量相對於式(pt1)所表示的化合物1莫耳而通常為0.1莫耳~60莫耳,較佳為1莫耳~40莫耳,更佳為1莫耳~32莫耳,進而佳為2莫耳~20莫耳。 In the reaction between the compound represented by formula (pt1) and the compound represented by formula (pt2), the amount of the compound represented by formula (pt2) used is usually 0.1 mol to 60 mol, preferably 1 mol to 40 mol, more preferably 1 mol to 32 mol, and even more preferably 2 mol to 20 mol, relative to 1 mol of the compound represented by formula (pt1).

式(IM1)所表示的化合物與式(pt3)所表示的化合物的反應中的式(pt3)所表示的化合物的使用量相對於式(IM1)所表示的化合物1莫耳而通常為0.1莫耳~30莫耳,較佳為1莫耳~20莫耳,更佳為1莫耳~16莫耳,進而佳為1莫耳~10莫耳。 The amount of the compound represented by formula (pt3) used in the reaction between the compound represented by formula (IM1) and the compound represented by formula (pt3) is generally 0.1 mol to 30 mol, preferably 1 mol to 20 mol, more preferably 1 mol to 16 mol, and even more preferably 1 mol to 10 mol, relative to 1 mol of the compound represented by formula (IM1).

式(pt1)所表示的化合物與式(pt2)所表示的化合物的反應中的反應溫度、或式(IM1)所表示的化合物與式(pt3) 所表示的化合物的反應中的反應溫度通常為-100℃~300℃,較佳為0℃~280℃,更佳為50℃~250℃,進而佳為100℃~230℃,尤佳為150℃~200℃。 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, further preferably 100°C to 230°C, and particularly preferably 150°C to 200°C.

式(pt1)所表示的化合物與式(pt2)所表示的化合物的反應中的反應時間、或式(IM1)所表示的化合物與式(pt3)所表示的化合物的反應中的反應時間通常為0.5小時~500小時。 The reaction time of the compound represented by formula (pt1) and the compound represented by formula (pt2), or the reaction time of the compound represented by formula (IM1) and the compound represented by formula (pt3) is usually 0.5 hours to 500 hours.

式(pt1)所表示的化合物與式(pt2)所表示的化合物的反應、或式(IM1)所表示的化合物與式(pt3)所表示的化合物的反應通常是於溶媒的存在下實施。 The reaction of the compound represented by formula (pt1) with the compound represented by formula (pt2), or the reaction of the compound represented by formula (IM1) with the compound represented by formula (pt3) is usually carried out in the presence of a solvent.

作為式(pt1)所表示的化合物與式(pt2)所表示的化合物的反應、或式(IM1)所表示的化合物與式(pt3)所表示的化合物的反應中的溶媒,可列舉:水;乙腈等腈溶媒;甲醇、乙醇、1-丙醇、2-丙醇、1-丁醇、1-戊醇、1-己醇、1-庚醇、2-乙基-1-己醇、1-辛醇、苯酚等醇溶媒;胺溶媒;二乙基醚、四氫呋喃、二苯基醚等醚溶媒;丙酮、甲基異丁基酮等酮溶媒;乙酸乙酯、苯甲酸甲酯等酯溶媒;己烷等脂肪族烴溶媒;甲苯、三甲基苯(例如,1,3,5-三甲基苯)、十氫萘、四氫萘等芳香族烴溶媒;二氯甲烷、氯仿、1,2-二氯苯、三氯苯(例如,1,3,5-三氯苯)、1-氯萘、2-氯萘等鹵化烴溶媒;硝基苯等硝基化烴溶媒;N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基吡咯啶酮等醯胺溶媒;二甲基亞碸等亞碸溶媒等,較佳為可列舉:二苯基醚、苯甲酸甲酯、三甲基苯(例 如,1,3,5-三甲基苯)、十氫萘、四氫萘、1,2-二氯苯、三氯苯(例如,1,3,5-三氯苯)、1-氯萘、2-氯萘、硝基苯、N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基吡咯啶酮、二甲基亞碸,更佳為可列舉:二苯基醚、苯甲酸甲酯、三甲基苯(例如,1,3,5-三甲基苯)、十氫萘、四氫萘、1,2-二氯苯、三氯苯(例如,1,3,5-三氯苯)、1-氯萘、2-氯萘、硝基苯、N-甲基吡咯啶酮,進而佳為可列舉苯甲酸甲酯。 Examples of the solvent in 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) include: water; nitrile solvents such as acetonitrile; alcohol solvents such as methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-octanol, and phenol; amine solvents; diisocyanate; Ether solvents such as ethyl 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 (e.g., 1,3,5-trimethylbenzene), decahydronaphthalene, and tetrahydronaphthalene; halogenated hydrocarbon solvents such as dichloromethane, chloroform, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, and 2-chloronaphthalene; nitric acid solvents such as tantalum; nitrocarbon solvents such as nitrobenzene; amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone; sulfoxide solvents such as dimethyl sulfoxide, etc., preferably diphenyl ether, methyl benzoate, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decahydronaphthalene, tetrahydronaphthalene, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide, preferably diphenyl ether, methyl benzoate, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decahydronaphthalene, tetrahydronaphthalene, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N-methylpyrrolidone, and more preferably methyl benzoate.

式(pt1)所表示的化合物、與式(pt2)所表示的化合物的反應中的溶媒的使用量相對於式(pt1)所表示的化合物1質量份而通常為1質量份~1000質量份。 The amount of the solvent used in the reaction between the compound represented by formula (pt1) and the compound represented by formula (pt2) is usually 1 part by mass to 1000 parts by mass relative to 1 part by mass of the compound represented by formula (pt1).

式(IM1)所表示的化合物、與式(pt3)所表示的化合物的反應中的溶媒的使用量相對於式(IM1)所表示的化合物1質量份而通常為1質量份~1000質量份。 The amount of the solvent used in the reaction between the compound represented by formula (IM1) 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 (IM1).

式(pt1)所表示的化合物與式(pt2)所表示的化合物的反應、或式(IM1)所表示的化合物與式(pt3)所表示的化合物的反應中,較佳為使選自酸及金屬鹽中的一種以上共存。 In the reaction of the compound represented by formula (pt1) with the compound represented by formula (pt2), or the reaction of the compound represented by formula (IM1) with the compound represented by formula (pt3), it is preferred that at least one selected from an acid and a metal salt coexists.

作為式(pt1)所表示的化合物與式(pt2)所表示的化合物的反應、或式(IM1)所表示的化合物與式(pt3)所表示的化合物的反應中的酸,可列舉:氯化氫、溴化氫、碘化氫、硫酸、硝酸、氟磺酸、磷酸等無機酸;甲磺酸、三氟甲磺酸及對甲苯磺酸等磺酸;乙酸、三氟乙酸、檸檬酸、甲酸、葡萄糖酸、乳酸、草酸、苯甲酸及酒石酸等羧酸等,較佳為可列舉:氯化氫、溴化 氫、硫酸、甲磺酸、三氟甲磺酸、對甲苯磺酸及羧酸,更佳為可列舉羧酸,進而佳為可列舉苯甲酸。 The acid in 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) includes: inorganic acids such as hydrogen chloride, hydrogen bromide, hydrogen iodide, sulfuric acid, nitric acid, fluorosulfonic acid, 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 includes: hydrogen chloride, hydrogen bromide, sulfuric acid, methanesulfonic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid, and carboxylic acids, more preferably includes any carboxylic acids, and further preferably includes benzoic acid.

式(pt1)所表示的化合物與式(pt2)所表示的化合物的反應中的酸的使用量相對於式(pt1)所表示的化合物1莫耳而通常為1莫耳~90莫耳,較佳為1莫耳~70莫耳,更佳為1莫耳~50莫耳,進而佳為1莫耳~30莫耳。 The amount of the 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, preferably 1 mol to 70 mol, more preferably 1 mol to 50 mol, and even more preferably 1 mol to 30 mol, relative to 1 mol of the compound represented by formula (pt1).

式(IM1)所表示的化合物與式(pt3)所表示的化合物的反應中的酸的使用量相對於式(IM1)所表示的化合物1莫耳而通常為1莫耳~90莫耳,較佳為1莫耳~70莫耳,更佳為1莫耳~50莫耳,進而佳為1莫耳~30莫耳。 The amount of the acid used in the reaction between the compound represented by formula (IM1) and the compound represented by formula (pt3) is usually 1 mol to 90 mol, preferably 1 mol to 70 mol, more preferably 1 mol to 50 mol, and even more preferably 1 mol to 30 mol, relative to 1 mol of the compound represented by formula (IM1).

作為式(pt1)所表示的化合物與式(pt2)所表示的化合物的反應、或式(IM1)所表示的化合物與式(pt3)所表示的化合物的反應中的金屬鹽,可列舉氯化鋅及氯化鋁等。 Examples of the metal salt in 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) include zinc chloride and aluminum chloride.

式(pt1)所表示的化合物與式(pt2)所表示的化合物的反應中的金屬鹽的使用量相對於式(pt1)所表示的化合物1莫耳而通常為0.01莫耳~30莫耳,較佳為0.01莫耳~20莫耳,更佳為0.01莫耳~10莫耳,進而佳為0.01莫耳~3莫耳。 The amount of the metal salt used in the reaction between the compound represented by formula (pt1) and the compound represented by formula (pt2) is generally 0.01 mol to 30 mol, preferably 0.01 mol to 20 mol, more preferably 0.01 mol to 10 mol, and even more preferably 0.01 mol to 3 mol, relative to 1 mol of the compound represented by formula (pt1).

式(IM1)所表示的化合物與式(pt3)所表示的化合物的反應中的金屬鹽的使用量相對於式(IM1)所表示的化合物1莫耳而通常為0.01莫耳~30莫耳,較佳為0.01莫耳~20莫耳,更佳為0.01莫耳~10莫耳,進而佳為0.01莫耳~3莫耳。 The amount of the metal salt used in the reaction between the compound represented by formula (IM1) and the compound represented by formula (pt3) is generally 0.01 mol to 30 mol, preferably 0.01 mol to 20 mol, more preferably 0.01 mol to 10 mol, and even more preferably 0.01 mol to 3 mol, relative to 1 mol of the compound represented by formula (IM1).

自式(pt1)所表示的化合物與式(pt2)所表示的化合 物的反應中的反應混合物中取出式(I')所表示的化合物的方法並無特別限定,可利用公知的各種方法取出。 The method for extracting the compound represented by formula (I') from the reaction mixture in the reaction between the compound represented by formula (pt1) and the compound represented by formula (pt2) is not particularly limited, and the compound can be extracted by various known methods.

例如,反應結束後,存在反應混合物中的化合物(I')難以溶解的情況,將容易溶解化合物(I')以外的化合物的甲醇等溶媒與反應混合物充分混合後,進行過濾,藉此可取出化合物(I')。進而,可利用N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基吡咯啶酮等醯胺溶媒、二甲基亞碸等亞碸溶媒或該些的混合溶媒、氫氧化鈉水溶液等鹼性水溶液、及/或鹽酸等酸性水溶液對所獲得的殘渣進行清洗後,利用水、甲醇等低沸點醇或該些的混合溶媒進行清洗,取出化合物(I')。進而,亦可利用管柱層析法及/或再結晶等進行精製。 For example, after the reaction is completed, if compound (I') in the reaction mixture is difficult to dissolve, a solvent such as methanol that easily dissolves compounds other than compound (I') is fully mixed with the reaction mixture, and then filtered to remove compound (I'). Furthermore, the obtained residue can be washed with amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, sulfoxide solvents such as dimethyl sulfoxide, or mixed solvents thereof, alkaline aqueous solutions such as sodium hydroxide aqueous solutions, and/or acidic aqueous solutions such as hydrochloric acid, and then washed with water, low-boiling alcohols such as methanol, or mixed solvents thereof to remove compound (I'). Furthermore, column chromatography and/or recrystallization can also be used for purification.

或者,反應結束後,亦可餾去反應混合物的溶媒,並利用管柱層析法及/或再結晶等對所獲得的殘渣進行精製,反應結束後,亦可利用管柱層析法及/或再結晶等對反應混合物進行精製。 Alternatively, after the reaction is completed, 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, the reaction mixture can be purified by column chromatography and/or recrystallization.

反應結束後,存在反應混合物中的化合物(I')難以溶解的情況,將容易溶解化合物(I')以外的化合物的甲醇等溶媒與反應混合物充分混合後,進行過濾,藉此可取出化合物(I')。進而,亦可利用管柱層析法及/或再結晶等進行精製。 After the reaction is completed, if compound (I') in the reaction mixture is difficult to dissolve, a solvent such as methanol that easily dissolves compounds other than compound (I') is fully mixed with the reaction mixture, and then filtered to remove compound (I'). Furthermore, column chromatography and/or recrystallization can also be used for purification.

自式(IM1)所表示的化合物與式(pt3)所表示的化合物的反應中的反應混合物中取出式(I)所表示的化合物的方法並無特別限定,可利用公知的各種方法取出。 The method for extracting the compound represented by formula (I) from the reaction mixture in the reaction between the compound represented by formula (IM1) and the compound represented by formula (pt3) is not particularly limited, and the compound can be extracted by various known methods.

例如,反應結束後,存在反應混合物中的化合物(I)難以溶解的情況,將容易溶解化合物(I)以外的化合物的甲醇等溶媒與反應混合物充分混合後,進行過濾,藉此可取出化合物(I)。進而,可利用N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基吡咯啶酮等醯胺溶媒、二甲基亞碸等亞碸溶媒或該些的混合溶媒、氫氧化鈉水溶液等鹼性水溶液、及/或鹽酸等酸性水溶液對所獲得的殘渣進行清洗後,利用水、甲醇等低沸點醇或該些的混合溶媒進行清洗,取出化合物(I)。進而,亦可利用管柱層析法及/或再結晶等進行精製。 For example, after the reaction is completed, if compound (I) in the reaction mixture is difficult to dissolve, a solvent such as methanol that easily dissolves compounds other than compound (I) is fully mixed with the reaction mixture and filtered to remove compound (I). Furthermore, the obtained residue can be washed with amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, sulfoxide solvents such as dimethyl sulfoxide, or mixed solvents thereof, alkaline aqueous solutions such as sodium hydroxide aqueous solutions, and/or acidic aqueous solutions such as hydrochloric acid, and then washed with water, low-boiling alcohols such as methanol, or mixed solvents thereof to remove compound (I). Furthermore, column chromatography and/or recrystallization can also be used for purification.

或者,反應結束後,亦可餾去反應混合物的溶媒,並利用管柱層析法及/或再結晶等對所獲得的殘渣進行精製,反應結束後,亦可利用管柱層析法及/或再結晶等對反應混合物進行精製。 Alternatively, after the reaction is completed, 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, the reaction mixture can be purified by column chromatography and/or recrystallization.

反應結束後,存在反應混合物中的化合物(I)難以溶解的情況,將容易溶解化合物(I)以外的化合物的甲醇等溶媒與反應混合物充分混合後,進行過濾,藉此可取出化合物(I)。進而,亦可利用管柱層析法及/或再結晶等進行精製。 After the reaction is completed, if compound (I) in the reaction mixture is difficult to dissolve, a solvent such as methanol that easily dissolves compounds other than compound (I) is fully mixed with the reaction mixture and then filtered to remove compound (I). Furthermore, column chromatography and/or recrystallization can also be used for purification.

作為鹼存在下的、式(I')所表示的化合物的水解反應中的鹼,可列舉:三乙胺、4-(N,N-二甲基胺基)吡啶、吡啶、哌啶、1,8-二氮雜雙環[5.4.0]十一碳-7-烯、1,5-二氮雜雙環[4.3.0]壬-5-烯等有機鹼,甲醇鈉、乙醇鈉、第三丁醇鈉、第三丁醇鉀等金屬醇鹽,甲基鋰、丁基鋰、第三丁基鋰及苯基鋰等有機金屬化合物, 碳酸氫鈉、碳酸氫鉀、碳酸鈉、碳酸鉀、氫氧化鋰、氫氧化鈉、及氫氧化鉀等無機鹼等,較佳為無機鹼,更佳為氫氧化鋰、氫氧化鈉、及氫氧化鉀,進而佳為氫氧化鈉及氫氧化鉀,尤佳為氫氧化鉀。 Examples of the base used in the hydrolysis reaction of the compound represented by the formula (I') in the presence of a base include organic bases such as 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, sodium methoxide, sodium ethoxide, sodium tert-butoxide, sodium thiophene, sodium t-butoxide, sodium t-butylate ... Metal alkoxides such as potassium tributylate, organic metal compounds such as methyl lithium, butyl lithium, tert-butyl lithium and phenyl lithium, Inorganic bases such as sodium bicarbonate, potassium bicarbonate, sodium carbonate, potassium carbonate, lithium hydroxide, sodium hydroxide and potassium hydroxide, etc., preferably inorganic bases, more preferably lithium hydroxide, sodium hydroxide and potassium hydroxide, further preferably sodium hydroxide and potassium hydroxide, and particularly preferably potassium hydroxide.

鹼存在下的、式(I')所表示的化合物的水解反應中的鹼的使用量相對於式(I')所表示的化合物1莫耳而通常為0.1莫耳~100莫耳,較佳為1莫耳~70莫耳,更佳為2莫耳~40莫耳。 The amount of alkali used in the hydrolysis reaction of the compound represented by formula (I') in the presence of alkali is generally 0.1 mol to 100 mol, preferably 1 mol to 70 mol, and more preferably 2 mol to 40 mol, relative to 1 mol of the compound represented by formula (I').

鹼存在下的、式(I')所表示的化合物的水解反應中的水的使用量相對於式(I')所表示的化合物1質量份而通常為1質量份~1000質量份,較佳為1質量份~200質量份,更佳為1質量份~100質量份,進而佳為1質量份~50質量份。 The amount of water used in the hydrolysis reaction of the compound represented by formula (I') in the presence of an alkali is usually 1 to 1000 parts by mass, preferably 1 to 200 parts by mass, more preferably 1 to 100 parts by mass, and even more preferably 1 to 50 parts by mass, relative to 1 part by mass of the compound represented by formula (I').

鹼存在下的、式(I')所表示的化合物的水解反應中的反應溫度通常為0℃~100℃,較佳為5℃~100℃,更佳為20℃~100℃,進而佳為40℃~100℃,尤佳為60℃~100℃。 The reaction temperature in the hydrolysis reaction of the compound represented by formula (I') in the presence of an alkali is usually 0°C to 100°C, preferably 5°C to 100°C, more preferably 20°C to 100°C, further preferably 40°C to 100°C, and particularly preferably 60°C to 100°C.

鹼存在下的、式(I')所表示的化合物的水解反應中的反應時間通常為0.5小時~120小時,較佳為1小時~72小時,更佳為1小時~24小時。 The reaction time in the hydrolysis reaction of the compound represented by formula (I') in the presence of an alkali is generally 0.5 hours to 120 hours, preferably 1 hour to 72 hours, and more preferably 1 hour to 24 hours.

自鹼存在下的、式(I')所表示的化合物的水解反應中的反應混合物中取出式(IM1)所表示的化合物的方法並無特別限定,可利用公知的各種方法取出。 The method for extracting 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 an alkali is not particularly limited, and the compound can be extracted by various known methods.

例如,反應結束後,於反應混合物中加入鹽酸等酸性水溶液並進行中和後,進行過濾,藉此可取出化合物(IM1)。進而,可利用N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基吡咯啶酮等醯胺溶媒、二甲基亞碸等亞碸溶媒、丙酮等酮溶媒、甲醇等醇溶媒、乙腈等腈溶媒、水或該些的混合溶媒、氫氧化鈉水溶液等鹼性水溶液、及/或鹽酸等酸性水溶液對所獲得的殘渣進行清洗,取出化合物(IM1)。進而,亦可利用管柱層析法及/或再結晶等進行精製。 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 filtered to remove the compound (IM1). Furthermore, the obtained residue can be washed with an amide solvent such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, a sulfoxide solvent such as dimethyl sulfoxide, a ketone solvent such as acetone, an alcohol solvent such as methanol, a nitrile solvent such as acetonitrile, water or a mixed solvent thereof, an alkaline aqueous solution such as an aqueous sodium hydroxide solution, and/or an acidic aqueous solution such as hydrochloric acid to remove the compound (IM1). Furthermore, column chromatography and/or recrystallization can also be used for purification.

或者,反應結束後,亦可餾去反應混合物的溶媒,並利用管柱層析法及/或再結晶等對所獲得的殘渣進行精製,反應結束後,亦可利用管柱層析法及/或再結晶等對反應混合物進行精製。 Alternatively, after the reaction is completed, 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, the reaction mixture can be purified by column chromatography and/or recrystallization.

式(I)所表示的化合物可藉由如下方式製造:藉由式(pt1)所表示的化合物與式(pt3)所表示的化合物的反應來製造式(IM2)所表示的化合物(以下,存在稱為化合物(IM2)的情況),繼而,進行式(IM2)所表示的化合物與式(pt2)所表示的化合物的反應。 The compound represented by formula (I) can be produced by reacting a compound represented by formula (pt1) with a compound represented by formula (pt3) to produce a compound represented by formula (IM2) (hereinafter, sometimes referred to as compound (IM2)), and then reacting the compound represented by formula (IM2) with a compound represented by formula (pt2).

[化91]

Figure 109104792-A0305-02-0240-344
[Chemistry 91]
Figure 109104792-A0305-02-0240-344

式(pt1)、式(pt2)、式(pt3)、式(IM2)中,R1~R5、Q1、Q2表示與所述相同的含義。 In formula (pt1), formula (pt2), formula (pt3) and formula (IM2), R 1 to R 5 , Q 1 and Q 2 have the same meanings as described above.

式(pt1)所表示的化合物與式(pt3)所表示的化合物的反應中的、式(pt3)所表示的化合物的使用量相對於式(pt1)所表示的化合物1莫耳而通常為0.1莫耳~10莫耳,較佳為0.1莫耳~5莫耳,更佳為0.5莫耳~2莫耳,進而佳為0.8莫耳~1.5莫耳。 In the reaction between the compound represented by formula (pt1) and the compound represented by formula (pt3), the amount of the compound represented by formula (pt3) used is usually 0.1 mol to 10 mol, preferably 0.1 mol to 5 mol, more preferably 0.5 mol to 2 mol, and even more preferably 0.8 mol to 1.5 mol, relative to 1 mol of the compound represented by formula (pt1).

式(pt1)所表示的化合物與式(pt3)所表示的化合物的反應中的反應溫度通常為-100℃~300℃,較佳為0℃~280℃,更佳為50℃~250℃,進而佳為100℃~230℃,尤佳為120℃~200℃。 The reaction temperature of the compound represented by formula (pt1) and the compound represented by formula (pt3) is usually -100℃~300℃, preferably 0℃~280℃, more preferably 50℃~250℃, further preferably 100℃~230℃, and particularly preferably 120℃~200℃.

式(pt1)所表示的化合物與式(pt3)所表示的化合物的反應中的反應時間通常為0.5小時~500小時。 The reaction time of the compound represented by formula (pt1) and the compound represented by formula (pt3) is usually 0.5 hours to 500 hours.

式(pt1)所表示的化合物與式(pt3)所表示的化合物的反應通常是於溶媒的存在下實施。 The reaction between the compound represented by formula (pt1) and the compound represented by formula (pt3) is usually carried out in the presence of a solvent.

作為式(pt1)所表示的化合物與式(pt3)所表示的化合物的反應中的溶媒,可列舉:水;乙腈等腈溶媒;甲醇、乙醇、1-丙醇、2-丙醇、1-丁醇、1-戊醇、1-己醇、1-庚醇、2-乙基-1-己醇、1-辛醇、苯酚等醇溶媒;胺溶媒;二乙基醚、四氫呋喃、二苯基醚等醚溶媒;丙酮、甲基異丁基酮等酮溶媒;乙酸乙酯、苯甲酸甲酯等酯溶媒;己烷等脂肪族烴溶媒;甲苯、三甲基苯(例如,1,3,5-三甲基苯)、十氫萘、四氫萘等芳香族烴溶媒;二氯甲烷、氯仿、1,2-二氯苯、三氯苯(例如,1,3,5-三氯苯)、1-氯萘、2-氯萘等鹵化烴溶媒;硝基苯等硝基化烴溶媒;N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基吡咯啶酮等醯胺溶媒;二甲基亞碸等亞碸溶媒等,較佳為可列舉:苯酚、二苯基醚、苯甲酸甲酯、三甲基苯(例如,1,3,5-三甲基苯)、十氫萘、四氫萘、1,2-二氯苯、三氯苯(例如,1,3,5-三氯苯)、1-氯萘、2-氯萘、硝基苯、N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基吡咯啶酮、二甲基亞碸,更佳為可列舉:苯酚、二苯基醚、苯甲酸甲酯、三甲基苯(例如,1,3,5-三甲基苯)、十氫萘、四氫萘、1,2-二氯苯、三氯苯(例如,1,3,5-三氯苯)、1-氯萘、2-氯萘、硝基苯、N-甲基吡咯啶酮,進而佳為可列舉苯酚、苯甲酸甲酯,尤佳為可列舉苯酚。 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; alcohol solvents such as methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-octanol, and phenol; amine solvents; ether solvents such as diethyl ether, tetrahydrofuran, and diphenyl ether; acetone, methyl isobutyl ketone, etc. Ketone solvents; ester solvents such as ethyl acetate and methyl benzoate; aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decahydronaphthalene, and tetrahydronaphthalene; halogenated hydrocarbon solvents such as dichloromethane, chloroform, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, and 2-chloronaphthalene; nitrated hydrocarbon solvents such as nitrobenzene; N,N-dimethylformamide, N,N -dimethylacetamide, N-methylpyrrolidone and other amide solvents; dimethyl sulfoxide and other sulfoxide solvents, preferably: phenol, diphenyl ether, methyl benzoate, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decahydronaphthalene, tetrahydronaphthalene, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N,N-dimethylformamide, N,N-dimethylacetamide, Amine, N-methylpyrrolidone, dimethyl sulfoxide, preferably phenol, diphenyl ether, methyl benzoate, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decahydronaphthalene, tetrahydronaphthalene, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N-methylpyrrolidone, preferably phenol, methyl benzoate, and particularly preferably phenol.

式(pt1)所表示的化合物與式(pt3)所表示的化合物 的反應中的溶媒的使用量相對於式(pt1)所表示的化合物1質量份而通常為1質量份~1000質量份,較佳為1質量份~200質量份,更佳為1質量份~100質量份,進而佳為1質量份~50質量份。 The amount of the solvent used in the reaction of the compound represented by formula (pt1) and the compound represented by formula (pt3) is usually 1 to 1000 parts by mass, preferably 1 to 200 parts by mass, more preferably 1 to 100 parts by mass, and even more preferably 1 to 50 parts by mass, relative to 1 part by mass of the compound represented by formula (pt1).

自式(pt1)所表示的化合物與式(pt3)所表示的化合物的反應中的反應混合物中取出化合物(IM2)的方法並無特別限定,可利用公知的各種方法取出。 The method for extracting the compound (IM2) from the reaction mixture in the reaction between the compound represented by the formula (pt1) and the compound represented by the formula (pt3) is not particularly limited, and the compound (IM2) can be extracted by various known methods.

例如,反應結束後,存在反應混合物中的化合物(IM2)難以溶解的情況,將容易溶解化合物(IM2)以外的化合物的甲醇等溶媒與反應混合物充分混合後,進行過濾,藉此可取出化合物(IM2)。 For example, after the reaction is completed, if the compound (IM2) in the reaction mixture is difficult to dissolve, a solvent such as methanol that easily dissolves compounds other than the compound (IM2) is fully mixed with the reaction mixture and then filtered to remove the compound (IM2).

進而,利用N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基吡咯啶酮等醯胺溶媒、二甲基亞碸等亞碸溶媒、丙酮等酮溶媒、甲醇等醇溶媒、乙腈等腈溶媒、水或該些的混合溶媒、氫氧化鈉水溶液等鹼性水溶液、及/或鹽酸等酸性水溶液對所獲得的殘渣進行清洗,可取出化合物(IM2)。 Furthermore, the obtained residue is washed with an amide solvent such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, a sulfoxide solvent such as dimethyl sulfoxide, a ketone solvent such as acetone, an alcohol solvent such as methanol, a nitrile solvent such as acetonitrile, water or a mixed solvent thereof, an alkaline aqueous solution such as an aqueous sodium hydroxide solution, and/or an acidic aqueous solution such as hydrochloric acid, to remove the compound (IM2).

進而,亦可利用管柱層析法及/或再結晶等進行精製。 Furthermore, it can also be purified by column chromatography and/or recrystallization.

或者,反應結束後,亦可餾去反應混合物的溶媒,並利用管柱層析法及/或再結晶等對所獲得的殘渣進行精製,反應結束後,亦可利用管柱層析法及/或再結晶等對反應混合物進行精製。 Alternatively, after the reaction is completed, 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, the reaction mixture can be purified by column chromatography and/or recrystallization.

反應結束後,反應混合物中的化合物(IM2)難以溶解,在 容易溶解化合物(IM2)以外的化合物的甲醇等溶媒中加入反應混合物,充分混合後,進行過濾,藉此可取出化合物(IM2)。進而,亦可利用管柱層析法及/或再結晶等進行精製。 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), mixed thoroughly, and filtered to remove the compound (IM2). Furthermore, column chromatography and/or recrystallization can also be used for purification.

式(IM2)所表示的化合物與式(pt2)所表示的化合物的反應中的、式(pt2)所表示的化合物的使用量相對於式(IM2)所表示的化合物1莫耳而通常為0.1莫耳~30莫耳,較佳為1莫耳~20莫耳,更佳為1莫耳~16莫耳,進而佳為1莫耳~10莫耳。 In the reaction between the compound represented by formula (IM2) and the compound represented by formula (pt2), the amount of the compound represented by formula (pt2) used is usually 0.1 mol to 30 mol, preferably 1 mol to 20 mol, more preferably 1 mol to 16 mol, and even more preferably 1 mol to 10 mol, relative to 1 mol of the compound represented by formula (IM2).

式(IM2)所表示的化合物與式(pt2)所表示的化合物的反應中的反應溫度通常為-100℃~300℃,較佳為0℃~280℃,更佳為50℃~250℃,進而佳為100℃~230℃,尤佳為150℃~200℃。 The reaction temperature of the compound represented by formula (IM2) and the compound represented by formula (pt2) is usually -100℃~300℃, preferably 0℃~280℃, more preferably 50℃~250℃, further preferably 100℃~230℃, and particularly preferably 150℃~200℃.

式(IM2)所表示的化合物與式(pt2)所表示的化合物的反應中的反應時間通常為0.5小時~500小時。 The reaction time of the compound represented by formula (IM2) and the compound represented by formula (pt2) is usually 0.5 hours to 500 hours.

式(IM2)所表示的化合物與式(pt2)所表示的化合物的反應通常是於溶媒的存在下實施。 The reaction between the compound represented by formula (IM2) and the compound represented by formula (pt2) is usually carried out in the presence of a solvent.

作為式(IM2)所表示的化合物與式(pt2)所表示的化合物的反應中的溶媒,可列舉:水;乙腈等腈溶媒;甲醇、乙醇、1-丙醇、2-丙醇、1-丁醇、1-戊醇、1-己醇、1-庚醇、2-乙基-1-己醇、1-辛醇、苯酚等醇溶媒;胺溶媒;二乙基醚、四氫呋喃、二苯基醚等醚溶媒;丙酮、甲基異丁基酮等酮溶媒;乙酸乙酯、苯甲酸甲酯等酯溶媒;己烷等脂肪族烴溶媒;甲苯、三甲基苯(例如,1,3,5-三甲基苯)、十氫萘、四氫萘等芳香族烴溶媒;二氯甲 烷、氯仿、1,2-二氯苯、三氯苯(例如,1,3,5-三氯苯)、1-氯萘、2-氯萘等鹵化烴溶媒;硝基苯等硝基化烴溶媒;N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基吡咯啶酮等醯胺溶媒;二甲基亞碸等亞碸溶媒,較佳為可列舉:二苯基醚、苯甲酸甲酯、三甲基苯(例如,1,3,5-三甲基苯)、十氫萘、四氫萘、1,2-二氯苯、三氯苯(例如,1,3,5-三氯苯)、1-氯萘、2-氯萘、硝基苯、N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基吡咯啶酮、二甲基亞碸,更佳為可列舉:二苯基醚、苯甲酸甲酯、三甲基苯(例如,1,3,5-三甲基苯)、十氫萘、四氫萘、1,2-二氯苯、三氯苯(例如,1,3,5-三氯苯)、1-氯萘、2-氯萘、硝基苯、N-甲基吡咯啶酮,進而佳為可列舉苯甲酸甲酯。 Examples of the solvent in the reaction between the compound represented by formula (IM2) and the compound represented by formula (pt2) include water; nitrile solvents such as acetonitrile; alcohol solvents such as methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-octanol, and phenol; amine solvents; ether solvents such as diethyl ether, tetrahydrofuran, and diphenyl ether; acetone, methyl isocyanate, and the like. Ketone solvents such as butyl ketone; ester solvents such as ethyl acetate and methyl benzoate; aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decahydronaphthalene, and tetrahydronaphthalene; halogenated hydrocarbon solvents such as dichloromethane, chloroform, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, and 2-chloronaphthalene; nitrated hydrocarbon solvents such as nitrobenzene; N,N- Amine solvents such as dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone; sulfoxide solvents such as dimethyl sulfoxide, preferably diphenyl ether, methyl benzoate, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decahydronaphthalene, tetrahydronaphthalene, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N,N-dimethylformamide, N,N-dimethyl sulfoxide ... Amine, N,N-dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide, preferably diphenyl ether, methyl benzoate, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decahydronaphthalene, tetrahydronaphthalene, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N-methylpyrrolidone, and more preferably methyl benzoate.

式(IM2)所表示的化合物與式(pt2)所表示的化合物的反應中的溶媒的使用量相對於式(IM2)所表示的化合物1質量份而通常為1質量份~1000質量份。 The amount of the solvent used in the reaction between the compound represented by formula (IM2) and the compound represented by formula (pt2) is usually 1 part by mass to 1000 parts by mass relative to 1 part by mass of the compound represented by formula (IM2).

式(IM2)所表示的化合物與式(pt2)所表示的化合物的反應中,較佳為使選自酸及金屬鹽中的一種以上共存。 In the reaction between the compound represented by formula (IM2) and the compound represented by formula (pt2), it is preferred that at least one selected from an acid and a metal salt coexists.

作為式(IM2)所表示的化合物與式(pt2)所表示的化合物的反應中的酸,可列舉:氯化氫、溴化氫、碘化氫、硫酸、硝酸、氟磺酸、磷酸等無機酸;甲磺酸、三氟甲磺酸及對甲苯磺酸等磺酸;乙酸、三氟乙酸、檸檬酸、甲酸、葡萄糖酸、乳酸、草酸、苯甲酸及酒石酸等羧酸等,較佳為可列舉:氯化氫、溴化 氫、硫酸、甲磺酸、三氟甲磺酸、對甲苯磺酸及羧酸,更佳為可列舉羧酸,進而佳為可列舉苯甲酸。 As the acid in the reaction between the compound represented by formula (IM2) and the compound represented by formula (pt2), there can be listed: inorganic acids such as hydrogen chloride, hydrogen bromide, hydrogen iodide, sulfuric acid, nitric acid, fluorosulfonic acid, 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, there can be listed: hydrogen chloride, hydrogen bromide, sulfuric acid, methanesulfonic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid and carboxylic acid, more preferably, there can be listed carboxylic acids, and further preferably, there can be listed benzoic acid.

式(IM2)所表示的化合物與式(pt2)所表示的化合物的反應中的酸的使用量相對於式(IM2)所表示的化合物1莫耳而通常為1莫耳~90莫耳,較佳為1莫耳~70莫耳,更佳為1莫耳~50莫耳,進而佳為1莫耳~30莫耳。 The amount of the acid used in the reaction between the compound represented by formula (IM2) and the compound represented by formula (pt2) is usually 1 mol to 90 mol, preferably 1 mol to 70 mol, more preferably 1 mol to 50 mol, and even more preferably 1 mol to 30 mol, relative to 1 mol of the compound represented by formula (IM2).

作為式(IM2)所表示的化合物與式(pt2)所表示的化合物的反應中的金屬鹽,可列舉氯化鋅及氯化鋁等。 Examples of the metal salt in the reaction between the compound represented by formula (IM2) and the compound represented by formula (pt2) include zinc chloride and aluminum chloride.

式(IM2)所表示的化合物與式(pt2)所表示的化合物的反應中的金屬鹽的使用量相對於式(IM2)所表示的化合物1莫耳而通常為0.01莫耳~30莫耳,較佳為0.01莫耳~20莫耳,更佳為0.01莫耳~10莫耳,進而佳為0.01莫耳~3莫耳。 The amount of the metal salt used in the reaction between the compound represented by formula (IM2) and the compound represented by formula (pt2) is generally 0.01 mol to 30 mol, preferably 0.01 mol to 20 mol, more preferably 0.01 mol to 10 mol, and even more preferably 0.01 mol to 3 mol, relative to 1 mol of the compound represented by formula (IM2).

自式(IM2)所表示的化合物與式(pt2)所表示的化合物的反應中的反應混合物中取出式(I)所表示的化合物的方法並無特別限定,可利用公知的各種方法取出。 The method for extracting the compound represented by formula (I) from the reaction mixture in the reaction between the compound represented by formula (IM2) and the compound represented by formula (pt2) is not particularly limited, and the compound can be extracted by various known methods.

例如,反應結束後,存在反應混合物中的化合物(I)難以溶解的情況,將容易溶解化合物(I)以外的化合物的甲醇等溶媒與反應混合物充分混合後,進行過濾,藉此可取出化合物(I)。進而,可利用N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基吡咯啶酮等醯胺溶媒、二甲基亞碸等亞碸溶媒或該些的混合溶媒、氫氧化鈉水溶液等鹼性水溶液、及/或鹽酸等酸性水溶液對所獲得的殘渣進行清洗後,利用水、甲醇等低沸點醇或該些的混合溶媒進 行清洗,取出化合物(I)。進而,亦可利用管柱層析法及/或再結晶等進行精製。 For example, after the reaction is completed, if compound (I) in the reaction mixture is difficult to dissolve, a solvent such as methanol that easily dissolves compounds other than compound (I) is fully mixed with the reaction mixture and filtered to remove compound (I). Furthermore, the obtained residue can be washed with amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, sulfoxide solvents such as dimethyl sulfoxide, or mixed solvents thereof, alkaline aqueous solutions such as sodium hydroxide aqueous solutions, and/or acidic aqueous solutions such as hydrochloric acid, and then washed with water, low-boiling alcohols such as methanol, or mixed solvents thereof to remove compound (I). Furthermore, column chromatography and/or recrystallization can also be used for purification.

或者,反應結束後,亦可餾去反應混合物的溶媒,並利用管柱層析法及/或再結晶等對所獲得的殘渣進行精製,反應結束後,亦可利用管柱層析法及/或再結晶等對反應混合物進行精製。 Alternatively, after the reaction is completed, 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, the reaction mixture can be purified by column chromatography and/or recrystallization.

反應結束後,存在反應混合物中的化合物(I)難以溶解的情況,將容易溶解化合物(I)以外的化合物的甲醇等溶媒與反應混合物充分混合後,進行過濾,藉此可取出化合物(I)。進而,亦可利用管柱層析法及/或再結晶等進行精製。 After the reaction is completed, if compound (I) in the reaction mixture is difficult to dissolve, a solvent such as methanol that easily dissolves compounds other than compound (I) is fully mixed with the reaction mixture and then filtered to remove compound (I). Furthermore, column chromatography and/or recrystallization can also be used for purification.

式(I)所表示的化合物可藉由如下方式製造:藉由式(pt1)所表示的化合物與式(pt3)所表示的化合物的反應來製造式(IM2)所表示的化合物(以下,存在稱為化合物(IM2)的情況),繼而,進行式(IM2)所表示的化合物與式(pt2)所表示的化合物的反應。 The compound represented by formula (I) can be produced by reacting a compound represented by formula (pt1) with a compound represented by formula (pt3) to produce a compound represented by formula (IM2) (hereinafter, sometimes referred to as compound (IM2)), and then reacting the compound represented by formula (IM2) with a compound represented by formula (pt2).

[化92]

Figure 109104792-A0305-02-0247-345
[Chemistry 92]
Figure 109104792-A0305-02-0247-345

式(pt1)、式(pt2)、式(pt3)、式(IM2)中,R1~R5、Q1、Q2表示與所述相同的含義。 In formula (pt1), formula (pt2), formula (pt3) and formula (IM2), R 1 to R 5 , Q 1 and Q 2 have the same meanings as described above.

式(pt1)所表示的化合物與式(pt3)所表示的化合物的反應中的式(pt3)所表示的化合物的使用量相對於式(pt1)所表示的化合物1莫耳而通常為0.1莫耳~10莫耳,較佳為0.1莫耳~5莫耳,更佳為0.5莫耳~2莫耳,進而佳為0.8莫耳~1.5莫耳。 The amount of the compound represented by formula (pt3) used in the reaction between the compound represented by formula (pt1) and the compound represented by formula (pt3) is usually 0.1 mol to 10 mol, preferably 0.1 mol to 5 mol, more preferably 0.5 mol to 2 mol, and even more preferably 0.8 mol to 1.5 mol, relative to 1 mol of the compound represented by formula (pt1).

式(pt1)所表示的化合物與式(pt3)所表示的化合物的反應中的反應溫度通常為-100℃~300℃,較佳為0℃~280℃,更佳為50℃~250℃,進而佳為100℃~230℃,尤佳為120℃~200℃。 The reaction temperature of the compound represented by formula (pt1) and the compound represented by formula (pt3) is usually -100℃~300℃, preferably 0℃~280℃, more preferably 50℃~250℃, further preferably 100℃~230℃, and particularly preferably 120℃~200℃.

式(pt1)所表示的化合物與式(pt3)所表示的化合物的反應中的反應時間通常為0.5小時~500小時。 The reaction time of the compound represented by formula (pt1) and the compound represented by formula (pt3) is usually 0.5 hours to 500 hours.

式(pt1)所表示的化合物與式(pt3)所表示的化合物的反應通常是於溶媒的存在下實施。 The reaction between the compound represented by formula (pt1) and the compound represented by formula (pt3) is usually carried out in the presence of a solvent.

作為式(pt1)所表示的化合物與式(pt3)所表示的化 合物的反應中的溶媒,可列舉:水;乙腈等腈溶媒;甲醇、乙醇、1-丙醇、2-丙醇、1-丁醇、1-戊醇、1-己醇、1-庚醇、2-乙基-1-己醇、1-辛醇、苯酚等醇溶媒;胺溶媒;二乙基醚、四氫呋喃、二苯基醚等醚溶媒;丙酮、甲基異丁基酮等酮溶媒;乙酸乙酯、苯甲酸甲酯等酯溶媒;己烷等脂肪族烴溶媒;甲苯、三甲基苯(例如,1,3,5-三甲基苯)、十氫萘、四氫萘等芳香族烴溶媒;二氯甲烷、氯仿、1,2-二氯苯、三氯苯(例如,1,3,5-三氯苯)、1-氯萘、2-氯萘等鹵化烴溶媒;硝基苯等硝基化烴溶媒;N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基吡咯啶酮等醯胺溶媒;二甲基亞碸等亞碸溶媒等,較佳為可列舉:苯酚、二苯基醚、苯甲酸甲酯、三甲基苯(例如,1,3,5-三甲基苯)、十氫萘、四氫萘、1,2-二氯苯、三氯苯(例如,1,3,5-三氯苯)、1-氯萘、2-氯萘、硝基苯、N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基吡咯啶酮、二甲基亞碸,更佳為可列舉:苯酚、二苯基醚、苯甲酸甲酯、三甲基苯(例如,1,3,5-三甲基苯)、十氫萘、四氫萘、1,2-二氯苯、三氯苯(例如,1,3,5-三氯苯)、1-氯萘、2-氯萘、硝基苯、N-甲基吡咯啶酮,進而佳為可列舉苯酚、苯甲酸甲酯,尤佳為可列舉苯酚。 As the solvent in the reaction between the compound represented by formula (pt1) and the compound represented by formula (pt3), water; nitrile solvents such as acetonitrile; alcohol solvents such as methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-octanol, phenol, etc.; amine solvents; ether solvents such as diethyl ether, tetrahydrofuran, diphenyl ether, etc.; acetone, methyl isobutyl ketone, etc. Ketone solvents; ester solvents such as ethyl acetate and methyl benzoate; aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decahydronaphthalene, and tetrahydronaphthalene; halogenated hydrocarbon solvents such as dichloromethane, chloroform, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, and 2-chloronaphthalene; nitrated hydrocarbon solvents such as nitrobenzene; N,N-dimethylformamide, N,N -dimethylacetamide, N-methylpyrrolidone and other amide solvents; dimethyl sulfoxide and other sulfoxide solvents, preferably: phenol, diphenyl ether, methyl benzoate, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decahydronaphthalene, tetrahydronaphthalene, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N,N-dimethylformamide, N,N-dimethylacetamide, Amine, N-methylpyrrolidone, dimethyl sulfoxide, preferably phenol, diphenyl ether, methyl benzoate, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decahydronaphthalene, tetrahydronaphthalene, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N-methylpyrrolidone, preferably phenol, methyl benzoate, and particularly preferably phenol.

式(pt1)所表示的化合物與式(pt3)所表示的化合物的反應中的溶媒的使用量相對於式(pt1)所表示的化合物1質量 份而通常為1質量份~1000質量份,較佳為1質量份~200質量份,更佳為1質量份~100質量份,進而佳為1質量份~50質量份。 The amount of the solvent used in the reaction between the compound represented by formula (pt1) and the compound represented by formula (pt3) is usually 1 to 1000 parts by mass, preferably 1 to 200 parts by mass, more preferably 1 to 100 parts by mass, and even more preferably 1 to 50 parts by mass, relative to 1 part by mass of the compound represented by formula (pt1).

自式(pt1)所表示的化合物與式(pt3)所表示的化合物的反應中的反應混合物中取出化合物(IM2)的方法並無特別限定,可利用公知的各種方法取出。 The method for extracting the compound (IM2) from the reaction mixture in the reaction between the compound represented by the formula (pt1) and the compound represented by the formula (pt3) is not particularly limited, and the compound (IM2) can be extracted by various known methods.

例如,反應結束後,存在反應混合物中的化合物(IM2)難以溶解的情況,將容易溶解化合物(IM2)以外的化合物的甲醇等溶媒與反應混合物充分混合後,進行過濾,藉此可取出化合物(IM2)。 For example, after the reaction is completed, if the compound (IM2) in the reaction mixture is difficult to dissolve, a solvent such as methanol that easily dissolves compounds other than the compound (IM2) is fully mixed with the reaction mixture and then filtered to remove the compound (IM2).

進而,利用N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基吡咯啶酮等醯胺溶媒、二甲基亞碸等亞碸溶媒、丙酮等酮溶媒、甲醇等醇溶媒、乙腈等腈溶媒、水或該些的混合溶媒、氫氧化鈉水溶液等鹼性水溶液、及/或鹽酸等酸性水溶液對所獲得的殘渣進行清洗,可取出化合物(IM2)。 Furthermore, the obtained residue is washed with an amide solvent such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, a sulfoxide solvent such as dimethyl sulfoxide, a ketone solvent such as acetone, an alcohol solvent such as methanol, a nitrile solvent such as acetonitrile, water or a mixed solvent thereof, an alkaline aqueous solution such as an aqueous sodium hydroxide solution, and/or an acidic aqueous solution such as hydrochloric acid, to remove the compound (IM2).

進而,亦可利用管柱層析法及/或再結晶等進行精製。 Furthermore, it can also be purified by column chromatography and/or recrystallization.

或者,反應結束後,亦可餾去反應混合物的溶媒,並利用管柱層析法及/或再結晶等對所獲得的殘渣進行精製,反應結束後,亦可利用管柱層析法及/或再結晶等對反應混合物進行精製。 Alternatively, after the reaction is completed, 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, the reaction mixture can be purified by column chromatography and/or recrystallization.

反應結束後,存在反應混合物中的化合物(IM2)難以溶解的情況,將容易溶解化合物(IM2)以外的化合物的甲醇等溶媒與 反應混合物充分混合後,進行過濾,藉此可取出化合物(IM2)。進而,亦可利用管柱層析法及/或再結晶等進行精製。 After the reaction is completed, if the compound (IM2) in the reaction mixture is difficult to dissolve, a solvent such as methanol that easily dissolves compounds other than the compound (IM2) is mixed with the reaction mixture thoroughly and then filtered to remove the compound (IM2). Furthermore, column chromatography and/or recrystallization can be used for purification.

式(IM2)所表示的化合物與式(pt2)所表示的化合物的反應中的、式(pt2)所表示的化合物的使用量相對於式(IM2)所表示的化合物1莫耳而通常為0.1莫耳~30莫耳,較佳為1莫耳~20莫耳,更佳為1莫耳~16莫耳,進而佳為1莫耳~10莫耳。 In the reaction between the compound represented by formula (IM2) and the compound represented by formula (pt2), the amount of the compound represented by formula (pt2) used is usually 0.1 mol to 30 mol, preferably 1 mol to 20 mol, more preferably 1 mol to 16 mol, and even more preferably 1 mol to 10 mol, relative to 1 mol of the compound represented by formula (IM2).

式(IM2)所表示的化合物與式(pt2)所表示的化合物的反應中的反應溫度通常為-100℃~300℃,較佳為0℃~280℃,更佳為50℃~250℃,進而佳為100℃~230℃,尤佳為150℃~200℃。 The reaction temperature 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, further preferably 100°C to 230°C, and particularly preferably 150°C to 200°C.

式(IM2)所表示的化合物與式(pt2)所表示的化合物的反應中的反應時間通常為0.5小時~500小時。 The reaction time of the compound represented by formula (IM2) and the compound represented by formula (pt2) is usually 0.5 hours to 500 hours.

式(IM2)所表示的化合物與式(pt2)所表示的化合物的反應通常是於溶媒的存在下實施。 The reaction between the compound represented by formula (IM2) and the compound represented by formula (pt2) is usually carried out in the presence of a solvent.

作為式(IM2)所表示的化合物與式(pt2)所表示的化合物的反應中的溶媒,可列舉:水;乙腈等腈溶媒;甲醇、乙醇、1-丙醇、2-丙醇、1-丁醇、1-戊醇、1-己醇、1-庚醇、2-乙基-1-己醇、1-辛醇、苯酚等醇溶媒;胺溶媒;二乙基醚、四氫呋喃、二苯基醚等醚溶媒;丙酮、甲基異丁基酮等酮溶媒;乙酸乙酯、苯甲酸甲酯等酯溶媒;己烷等脂肪族烴溶媒;甲苯、三甲基苯(例如,1,3,5-三甲基苯)、十氫萘、四氫萘等芳香族烴溶媒;二氯甲烷、氯仿、1,2-二氯苯、三氯苯(例如,1,3,5-三氯苯)、1-氯萘、 2-氯萘等鹵化烴溶媒;硝基苯等硝基化烴溶媒;N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基吡咯啶酮等醯胺溶媒;二甲基亞碸等亞碸溶媒等,較佳為可列舉:二苯基醚、苯甲酸甲酯、三甲基苯(例如,1,3,5-三甲基苯)、十氫萘、四氫萘、1,2-二氯苯、三氯苯(例如,1,3,5-三氯苯)、1-氯萘、2-氯萘、硝基苯、N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基吡咯啶酮、二甲基亞碸,更佳為可列舉:二苯基醚、苯甲酸甲酯、三甲基苯(例如,1,3,5-三甲基苯)、十氫萘、四氫萘、1,2-二氯苯、三氯苯(例如,1,3,5-三氯苯)、1-氯萘、2-氯萘、硝基苯、N-甲基吡咯啶酮,進而佳為可列舉苯甲酸甲酯。 Examples of the solvent in the reaction between the compound represented by formula (IM2) and the compound represented by formula (pt2) include water; nitrile solvents such as acetonitrile; alcohol solvents such as methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-octanol, and phenol; amine solvents; ether solvents such as diethyl ether, tetrahydrofuran, and diphenyl ether; acetone, methyl isocyanate, and the like. Ketone solvents such as butyl ketone; ester solvents such as ethyl acetate and methyl benzoate; aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decahydronaphthalene, tetrahydronaphthalene; halogenated hydrocarbon solvents such as dichloromethane, chloroform, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene; nitrated hydrocarbon solvents such as nitrobenzene; N,N-dichlorobenzene; Amine solvents such as methylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone; sulfoxide solvents such as dimethyl sulfoxide, etc., preferably diphenyl ether, methyl benzoate, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decahydronaphthalene, tetrahydronaphthalene, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N,N-dimethylformamide, N,N-dimethyl sulfoxide, etc. Amine, N,N-dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide, preferably diphenyl ether, methyl benzoate, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decahydronaphthalene, tetrahydronaphthalene, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N-methylpyrrolidone, and more preferably methyl benzoate.

式(IM2)所表示的化合物與式(pt2)所表示的化合物的反應中的溶媒的使用量相對於式(IM2)所表示的化合物1質量份而通常為1質量份~1000質量份。 The amount of the solvent used in the reaction between the compound represented by formula (IM2) and the compound represented by formula (pt2) is usually 1 part by mass to 1000 parts by mass relative to 1 part by mass of the compound represented by formula (IM2).

式(IM2)所表示的化合物與式(pt2)所表示的化合物的反應中,較佳為使選自酸及金屬鹽中的一種以上共存。 In the reaction between the compound represented by formula (IM2) and the compound represented by formula (pt2), it is preferred that at least one selected from an acid and a metal salt coexists.

作為式(IM2)所表示的化合物與式(pt2)所表示的化合物的反應中的酸,可列舉:氯化氫、溴化氫、碘化氫、硫酸、硝酸、氟磺酸、磷酸等無機酸;甲磺酸、三氟甲磺酸及對甲苯磺酸等磺酸;乙酸、三氟乙酸、檸檬酸、甲酸、葡萄糖酸、乳酸、草酸、苯甲酸及酒石酸等羧酸等,較佳為可列舉:氯化氫、溴化氫、硫酸、甲磺酸、三氟甲磺酸、對甲苯磺酸及羧酸,更佳為可 列舉羧酸,進而佳為可列舉苯甲酸。 As the acid in the reaction between the compound represented by formula (IM2) and the compound represented by formula (pt2), there can be listed: inorganic acids such as hydrogen chloride, hydrogen bromide, hydrogen iodide, sulfuric acid, nitric acid, fluorosulfonic acid, 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, there can be listed: hydrogen chloride, hydrogen bromide, sulfuric acid, methanesulfonic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid and carboxylic acid, more preferably, there can be listed carboxylic acids, and further preferably, there can be listed benzoic acid.

式(IM2)所表示的化合物與式(pt2)所表示的化合物的反應中的酸的使用量相對於式(IM2)所表示的化合物1莫耳而通常為1莫耳~90莫耳,較佳為1莫耳~70莫耳,更佳為1莫耳~50莫耳,進而佳為1莫耳~30莫耳。 The amount of the acid used in the reaction between the compound represented by formula (IM2) and the compound represented by formula (pt2) is usually 1 mol to 90 mol, preferably 1 mol to 70 mol, more preferably 1 mol to 50 mol, and even more preferably 1 mol to 30 mol, relative to 1 mol of the compound represented by formula (IM2).

作為式(IM2)所表示的化合物與式(pt2)所表示的化合物的反應中的金屬鹽,可列舉氯化鋅及氯化鋁等。 Examples of the metal salt in the reaction between the compound represented by formula (IM2) and the compound represented by formula (pt2) include zinc chloride and aluminum chloride.

式(IM2)所表示的化合物與式(pt2)所表示的化合物的反應中的金屬鹽的使用量相對於式(IM2)所表示的化合物1莫耳而通常為0.01莫耳~30莫耳,較佳為0.01莫耳~20莫耳,更佳為0.01莫耳~10莫耳,進而佳為0.01莫耳~3莫耳。 The amount of the metal salt used in the reaction between the compound represented by formula (IM2) and the compound represented by formula (pt2) is generally 0.01 mol to 30 mol, preferably 0.01 mol to 20 mol, more preferably 0.01 mol to 10 mol, and even more preferably 0.01 mol to 3 mol, relative to 1 mol of the compound represented by formula (IM2).

自式(IM2)所表示的化合物與式(pt2)所表示的化合物的反應中的反應混合物中取出式(I)所表示的化合物的方法並無特別限定,可利用公知的各種方法取出。 The method for extracting the compound represented by formula (I) from the reaction mixture in the reaction between the compound represented by formula (IM2) and the compound represented by formula (pt2) is not particularly limited, and the compound can be extracted by various known methods.

例如,反應結束後,存在反應混合物中的化合物(I)難以溶解的情況,將容易溶解化合物(I)以外的化合物的甲醇等溶媒與反應混合物充分混合後,進行過濾,藉此可取出化合物(I)。進而,可利用N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基吡咯啶酮等醯胺溶媒、二甲基亞碸等亞碸溶媒或該些的混合溶媒、氫氧化鈉水溶液等鹼性水溶液、及/或鹽酸等酸性水溶液對所獲得的殘渣進行清洗後,利用水、甲醇等低沸點醇或該些的混合溶媒進行清洗,取出化合物(I)。進而,亦可利用管柱層析法及/或再結 晶等進行精製。 For example, after the reaction is completed, if compound (I) in the reaction mixture is difficult to dissolve, a solvent such as methanol that easily dissolves compounds other than compound (I) is fully mixed with the reaction mixture, and then filtered to remove compound (I). Furthermore, the obtained residue can be washed with amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, sulfoxide solvents such as dimethyl sulfoxide, or mixed solvents thereof, alkaline aqueous solutions such as sodium hydroxide aqueous solutions, and/or acidic aqueous solutions such as hydrochloric acid, and then washed with water, low-boiling alcohols such as methanol, or mixed solvents thereof to remove compound (I). Furthermore, column chromatography and/or recrystallization can also be used for purification.

或者,反應結束後,亦可餾去反應混合物的溶媒,並利用管柱層析法及/或再結晶等對所獲得的殘渣進行精製,反應結束後,亦可利用管柱層析法及/或再結晶等對反應混合物進行精製。 Alternatively, after the reaction is completed, 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, the reaction mixture can be purified by column chromatography and/or recrystallization.

反應結束後,存在反應混合物中的化合物(I)難以溶解的情況,將容易溶解化合物(I)以外的化合物的甲醇等溶媒與反應混合物充分混合後,進行過濾,藉此可取出化合物(I)。進而,亦可利用管柱層析法及/或再結晶等進行精製。 After the reaction is completed, if compound (I) in the reaction mixture is difficult to dissolve, a solvent such as methanol that easily dissolves compounds other than compound (I) is fully mixed with the reaction mixture and then filtered to remove compound (I). Furthermore, column chromatography and/or recrystallization can also be used for purification.

藉由使化合物(I)與發煙硫酸或氯磺酸等磺化劑反應,可對化合物(I)導入磺基或-SO3M。 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 into Compound (I).

對化合物(I)導入磺基或-SO3M而成的化合物(以下,存在稱為「磺化化合物(I)」的情況)亦為本發明的化合物。 A compound obtained by introducing a sulfo group or -SO 3 M into the compound (I) (hereinafter, sometimes referred to as "sulfonated compound (I)") is also a compound of the present invention.

發煙硫酸中的SO3的使用量相對於化合物(I)1莫耳而通常為1莫耳~200莫耳,較佳為2莫耳~150莫耳,更佳為3莫耳~100莫耳,進而佳為5莫耳~80莫耳。 The amount of SO 3 used in the fuming sulfuric acid is generally 1 mol to 200 mol, preferably 2 mol to 150 mol, more preferably 3 mol to 100 mol, and even more preferably 5 mol to 80 mol, relative to 1 mol of compound (I).

發煙硫酸中的SO3於發煙硫酸100質量份中通常為1質量份~90質量份,較佳為5質量份~70質量份,更佳為10質量份~60質量份,進而佳為15質量份~50質量份。 The amount of SO 3 in fuming sulfuric acid is generally 1 to 90 parts by mass, preferably 5 to 70 parts by mass, more preferably 10 to 60 parts by mass, and further preferably 15 to 50 parts by mass, based on 100 parts by mass of fuming sulfuric acid.

氯磺酸的使用量相對於化合物(I)1莫耳而通常為1莫耳~500莫耳,較佳為1莫耳~300莫耳,更佳為1莫耳~200莫耳,進而佳為1莫耳~150莫耳。 The amount of chlorosulfonic acid used is generally 1 mol to 500 mol, preferably 1 mol to 300 mol, more preferably 1 mol to 200 mol, and even more preferably 1 mol to 150 mol, relative to 1 mol of compound (I).

於使用氯磺酸對化合物(I)導入磺基或-SO3M的情況 下,可於溶媒存在下進行反應。 When chlorosulfonic acid is used to introduce a sulfo group or -SO 3 M into compound (I), the reaction may be carried out in the presence of a solvent.

作為該溶媒,可列舉:二氯甲烷、氯仿、1,2-二氯苯、三氯苯(例如,1,3,5-三氯苯)、1-氯萘、2-氯萘等鹵化烴溶媒。 Examples of the solvent include halogenated hydrocarbon solvents such as dichloromethane, chloroform, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, and 2-chloronaphthalene.

該溶媒的使用量相對於化合物(I)1質量份而通常為1質量份~1000質量份。 The amount of the solvent used is usually 1 to 1000 parts by mass relative to 1 part by mass of compound (I).

磺化的反應溫度通常為-20℃~200℃,較佳為-10℃~150℃,更佳為0℃~100℃。反應時間通常為0.5小時~300小時。 The reaction temperature of sulfonation is usually -20℃~200℃, preferably -10℃~150℃, and more preferably 0℃~100℃. The reaction time is usually 0.5 hours~300 hours.

自反應混合物中取出磺化化合物(I)的方法並無特別限定,可利用公知的各種方法取出。 The method for removing the sulfonated compound (I) from the reaction mixture is not particularly limited, and it can be removed by various known methods.

例如,反應結束後,將反應混合物滴加至冰中,對所獲得的混合物進行過濾,藉此可取出磺化化合物(I)。進而,亦可利用管柱層析法及/或再結晶等進行精製。 For example, after the reaction is completed, the reaction mixture is added dropwise to ice, and the obtained mixture is filtered to remove the sulfonated compound (I). Furthermore, it can also be purified by column chromatography and/or recrystallization.

或者,反應結束後,將反應混合物滴加至冰中,將所獲得的混合物與雖難以溶解磺化化合物(I)但容易溶解磺化化合物(I)以外的化合物的甲醇等醇溶媒、乙腈等腈溶媒及該些的混合溶媒等親水性有機溶媒混合並進行過濾,藉此可取出磺化化合物(I)。進而,亦可利用管柱層析法及/或再結晶等進行精製。 Alternatively, after the reaction is completed, the reaction mixture is added dropwise to ice, and the obtained mixture is mixed with a hydrophilic organic solvent such as methanol, an alcohol solvent such as acetonitrile, and a mixed solvent thereof, which is difficult to dissolve the sulfonated compound (I) but easy to dissolve compounds other than the sulfonated compound (I), and filtered to remove the sulfonated compound (I). Furthermore, column chromatography and/or recrystallization can also be used for purification.

或者,反應結束後,將反應混合物滴加至冰中,利用氨、水溶性胺或該些的混合物等水溶液對所獲得的混合物進行中和後,將該混合物與甲醇等醇溶媒、乙腈等腈溶媒及該些的混合溶媒等親水性有機溶媒混合,進行過濾,餾去所獲得的濾液的溶媒,藉此可取出磺化化合物(I)。進而,亦可利用管柱層析法及/或再結 晶等進行精製。 Alternatively, after the reaction is completed, the reaction mixture is added dropwise to ice, and the obtained mixture is neutralized with an aqueous solution such as ammonia, a water-soluble amine, or a mixture thereof, and then the mixture is mixed with a hydrophilic organic solvent such as an alcohol solvent such as methanol, a nitrile solvent such as acetonitrile, or a mixed solvent thereof, and filtered to remove the solvent from the obtained filtrate, thereby extracting the sulfonated compound (I). Furthermore, column chromatography and/or recrystallization can also be used for purification.

使具有-SO3H及/或-CO2H的化合物(I)(以下,存在稱為「含有酸基的化合物(I)」的情況)與具有MM的鹽進行反應,藉此可製造具有-SO3(MM)及/或-CO2(MM)的化合物(I)(以下,存在稱為「含有MM的化合物(I)」的情況)。 By reacting a compound (I) having -SO 3 H and/or -CO 2 H (hereinafter sometimes referred to as "acid group-containing compound (I)") with a salt having MM, a compound (I) having -SO 3 (MM) and/or -CO 2 (MM) (hereinafter sometimes referred to as "MM-containing compound (I)") can be produced.

具有MM的鹽的使用量相對於含有酸基的化合物(I)1莫耳而通常為0.01莫耳~100莫耳,較佳為0.02莫耳~50莫耳,更佳為0.1莫耳~30莫耳。 The amount of the salt having MM used is generally 0.01 mol to 100 mol, preferably 0.02 mol to 50 mol, and more preferably 0.1 mol to 30 mol, relative to 1 mol of the compound (I) containing an acid group.

反應溫度通常為0℃~100℃,較佳為0℃~80℃,更佳為0℃~60℃,進而佳為0℃~40℃。 The reaction temperature is usually 0℃~100℃, preferably 0℃~80℃, more preferably 0℃~60℃, and even more preferably 0℃~40℃.

反應時間通常為0.5小時~500小時。 The reaction time is usually 0.5 hours to 500 hours.

含有酸基的化合物(I)與具有MM的鹽的反應通常是於溶媒的存在下實施。 The reaction of the compound (I) containing an acid group and the salt having MM is usually carried out in the presence of a solvent.

作為該溶媒,可列舉:水;乙腈等腈溶媒;甲醇、乙醇、1-丙醇、2-丙醇、1-丁醇、1-戊醇、1-己醇、1-庚醇、2-乙基-1-己醇、1-辛醇、苯酚等醇溶媒;胺溶媒;二乙基醚、四氫呋喃、二苯基醚等醚溶媒;丙酮、甲基異丁基酮等酮溶媒;乙酸乙酯、苯甲酸甲酯等酯溶媒;己烷等脂肪族烴溶媒;甲苯、三甲基苯(例如,1,3,5-三甲基苯)、十氫萘、四氫萘等芳香族烴溶媒;二氯甲烷、氯仿、1,2-二氯苯、三氯苯(例如,1,3,5-三氯苯)、1-氯萘、2-氯萘等鹵化烴溶媒;硝基苯等硝基化烴溶媒;N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基吡咯啶酮等醯胺溶媒;二甲基亞碸等 亞碸溶媒,較佳為:水;乙腈等腈溶媒;甲醇、乙醇、1-丙醇、2-丙醇等醇溶媒;四氫呋喃等醚溶媒;丙酮等酮溶媒;N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基吡咯啶酮等醯胺溶媒;二甲基亞碸等亞碸溶媒;及該些的混合溶媒,更佳為水。 Examples of the solvent include water; nitrile solvents such as acetonitrile; alcohol solvents such as methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-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; ester solvents such as ethyl acetate and methyl benzoate; aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decahydronaphthalene, and tetrahydronaphthalene; dichloromethane, chloroform, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trimethylbenzene), and tetrahydronaphthalene; For example, halogenated hydrocarbon solvents such as 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene; nitrified hydrocarbon solvents such as nitrobenzene; amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone; dimethyl sulfoxide and other sulfoxide 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; amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone; sulfoxide solvents such as dimethyl sulfoxide; and mixed solvents thereof, preferably water.

該溶媒的使用量相對於含有酸基的化合物(I)1質量份而通常為1質量份~1000質量份,較佳為10質量份~500質量份,更佳為20質量份~300質量份。 The amount of the solvent used is generally 1 to 1000 parts by mass, preferably 10 to 500 parts by mass, and more preferably 20 to 300 parts by mass, relative to 1 part by mass of the acid group-containing compound (I).

含有酸基的化合物(I)與具有MM的鹽的反應可於鹼存在下進行。 The reaction of the compound (I) containing an acid group and the salt having MM can be carried out in the presence of a base.

作為該鹼,可列舉:三乙胺、4-(N,N-二甲基胺基)吡啶、吡啶、哌啶、1,8-二氮雜雙環[5.4.0]十一碳-7-烯、1,5-二氮雜雙環[4.3.0]壬-5-烯等有機鹼,甲醇鈉、乙醇鈉、第三丁醇鈉、第三丁醇鉀等金屬醇鹽,甲基鋰、丁基鋰、第三丁基鋰及苯基鋰等有機金屬化合物,碳酸氫鈉、碳酸氫鉀、碳酸鈉、碳酸鉀、氫氧化鋰、氫氧化鈉、及氫氧化鉀等無機鹼等,較佳為無機鹼,更佳為氫氧化鋰、氫氧化鈉、及氫氧化鉀,進而佳為氫氧化鈉及氫氧化鉀,尤佳為氫氧化鈉。 Examples of the base include organic bases such as 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, metal alkoxides such as sodium methoxide, sodium ethoxide, sodium tert-butoxide, potassium tert-butoxide, methyl Lithium, butyl lithium, tert-butyl lithium, phenyl lithium and other organic metal compounds, sodium bicarbonate, potassium bicarbonate, sodium carbonate, potassium carbonate, lithium hydroxide, sodium hydroxide, and potassium hydroxide and other inorganic bases, etc., preferably inorganic bases, more preferably lithium hydroxide, sodium hydroxide, and potassium hydroxide, further preferably sodium hydroxide and potassium hydroxide, and particularly preferably sodium hydroxide.

該鹼的使用量相對於含有酸基的化合物(I)1莫耳而通常為1莫耳~100莫耳,較佳為1莫耳~50莫耳,更佳為1莫耳 ~20莫耳,進而佳為1莫耳~10莫耳。 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, and even more preferably 1 mol to 10 mol, relative to 1 mol of the compound (I) containing an acid group.

自反應混合物中取出含有MM的化合物(I)的方法並無特別限定,可利用公知的各種方法取出。 The method for removing the MM-containing compound (I) from the reaction mixture is not particularly limited, and it can be removed by various known methods.

例如,反應結束後,對反應混合物進行過濾,藉此可取出具有-SO3(MM)及/或-CO2(MM)的化合物(I)。進而,可利用N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基吡咯啶酮等醯胺溶媒、二甲基亞碸等亞碸溶媒、丙酮等酮溶媒、甲醇等醇溶媒、乙腈等腈溶媒、水或該些的混合溶媒對所獲得的殘渣進行清洗後,利用水、甲醇等低沸點醇或該些的混合溶媒進行清洗並加以精製。 For example, after the reaction is completed, the reaction mixture is filtered to remove the compound (I) having -SO 3 (MM) and/or -CO 2 (MM). Furthermore, the obtained residue can be washed with an amide solvent such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, a sulfoxide solvent such as dimethyl sulfoxide, a ketone solvent such as acetone, an alcohol solvent such as methanol, a nitrile solvent such as acetonitrile, water, or a mixed solvent thereof, and then washed and purified with water, a low-boiling alcohol such as methanol, or a mixed solvent thereof.

[著色組成物] [Coloring composition]

本發明的著色組成物包含化合物(I)及溶劑(E)。根據本發明的著色組成物,與包含C.I.顏料黃138的著色組成物相比,可形成顏色更濃的彩色濾光片。由本發明的著色組成物形成的彩色濾光片可適宜用於液晶顯示裝置等顯示裝置中。本發明的著色組成物較佳為黃色組成物、橙色組成物、紅色組成物及綠色組成物。 The coloring composition of the present invention comprises compound (I) and solvent (E). According to the coloring composition of the present invention, a color filter with a darker color can be formed compared to a coloring composition comprising C.I. Pigment Yellow 138. The color filter formed by the coloring composition of the present invention can be suitably used in display devices such as liquid crystal display devices. The coloring composition of the present invention is preferably a yellow composition, an orange composition, a red composition and a green composition.

著色組成物中的固體成分的含有率相對於著色組成物的總量而小於100質量%,較佳為0.01質量%以上且小於100質量%,更佳為0.1質量%以上且99.9質量%以下,進而佳為0.1質量%以上且99質量%以下,尤佳為1質量%以上且90質量%以下,進而尤佳為1質量%以上且80質量%以下,特佳為1質量%以上且70質量%以下,極佳為1質量%以上且60質量%以下,最佳為1質量%以上且50質量%以下。 The content of the solid component in the coloring composition is less than 100 mass%, preferably 0.01 mass% or more and less than 100 mass%, more preferably 0.1 mass% or more and 99.9 mass% or less, further preferably 0.1 mass% or more and 99 mass% or less, particularly preferably 1 mass% or more and 90 mass% or less, further preferably 1 mass% or more and 80 mass% or less, particularly preferably 1 mass% or more and 70 mass% or less, extremely preferably 1 mass% or more and 60 mass% or less, and most preferably 1 mass% or more and 50 mass% or less.

於本說明書中,所謂「固體成分的總量」,是指自本發明的著色組成物中去除溶劑(E)後的成分的合計量。固體成分的總量及相對於其的各成分的含量可利用液相層析法或氣相層析法等公知的分析手段進行測定。 In this specification, the so-called "total amount of solid components" refers to the total amount of components after removing the solvent (E) from the coloring composition of the present invention. The total amount of solid components and the content of each component relative to it can be measured using known analytical methods such as liquid chromatography or gas chromatography.

於固體成分的總量中,著色組成物中的化合物(I)的含有率為100質量%以下,較佳為0.0001質量%以上且99.9999質量%以下,更佳為0.0001質量%以上且99質量%以下,進而佳為0.0001質量%以上且90質量%以下,尤佳為0.0001質量%以上且80質量%以下,進而尤佳為0.0001質量%以上且70質量%以下,特佳為0.0001質量%以上且60質量%以下,極佳為0.0001質量%以上且55質量%以下,最佳為0.1質量%以上且55質量%以下。 The content of compound (I) in the coloring composition in the total amount of solid components 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, further preferably 0.0001% by mass or more and 90% by mass or less, particularly preferably 0.0001% by mass or more and 80% by mass or less, further preferably 0.0001% by mass or more and 70% by mass or less, particularly preferably 0.0001% by 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.

[溶劑(E)] [Solvent (E)]

溶劑(E)並無特別限定,可使用該領域中通常所使用的溶劑。 The solvent (E) is not particularly limited, and any solvent commonly used in this field can be used.

溶劑(E)例如可列舉:酯溶劑(於分子內包含-CO-O-且不含-O-的溶劑)、醚溶劑(於分子內包含-O-且不含-CO-O-的溶劑)、醚酯溶劑(於分子內包含-CO-O-與-O-的溶劑)、酮溶劑(於分子內包含-CO-且不含-CO-O-的溶劑)、醇溶劑(於分子內包含OH且不含-O-、-CO-及-CO-O-的溶劑)、芳香族烴溶劑、醯胺溶劑及二甲基亞碸等。 Examples of solvents (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 (solvents containing OH and no -O-, -CO- and -CO-O- in the molecule), aromatic hydrocarbon solvents, amide solvents, and dimethyl sulfoxide, etc.

作為酯溶劑,可列舉:乳酸甲酯、乳酸乙酯、乳酸丁酯、2-羥基異丁酸甲酯、乙酸乙酯、乙酸正丁酯、乙酸異丁酯、甲酸 戊酯、乙酸異戊酯、丙酸丁酯、丁酸異丙酯、丁酸乙酯、丁酸丁酯、丙酮酸甲酯、丙酮酸乙酯、丙酮酸丙酯、乙醯乙酸甲酯、乙醯乙酸乙酯、環己醇乙酸酯及γ-丁內酯等。 As ester solvents, there can be listed: methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutyrate, ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, isoamyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetylacetate, ethyl acetylacetate, cyclohexanol acetate and γ-butyrolactone, etc.

作為醚溶劑,可列舉:乙二醇單甲醚、乙二醇單乙醚、乙二醇單丙醚、乙二醇單丁醚、二乙二醇單甲醚、二乙二醇單乙醚、二乙二醇單丁醚、丙二醇單甲醚、丙二醇單乙醚、丙二醇單丙醚、丙二醇單丁醚、3-甲氧基-1-丁醇、3-甲氧基-3-甲基丁醇、四氫呋喃、四氫吡喃、1,4-二噁烷、二乙二醇二甲醚、二乙二醇二乙醚、二乙二醇甲基乙醚、二乙二醇二丙醚、二乙二醇二丁醚、茴香醚、苯乙醚及甲基茴香醚等。 As ether solvents, there can be listed: ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol 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, phenethyl ether and methyl anisole, etc.

作為醚酯溶劑,可列舉:甲氧基乙酸甲酯、甲氧基乙酸乙酯、甲氧基乙酸丁酯、乙氧基乙酸甲酯、乙氧基乙酸乙酯、3-甲氧基丙酸甲酯、3-甲氧基丙酸乙酯、3-乙氧基丙酸甲酯、3-乙氧基丙酸乙酯、2-甲氧基丙酸甲酯、2-甲氧基丙酸乙酯、2-甲氧基丙酸丙酯、2-乙氧基丙酸甲酯、2-乙氧基丙酸乙酯、2-甲氧基-2-甲基丙酸甲酯、2-乙氧基-2-甲基丙酸乙酯、3-甲氧基丁基乙酸酯、3-甲基-3-甲氧基丁基乙酸酯、丙二醇單甲醚乙酸酯、丙二醇單乙醚乙酸酯、丙二醇單丙醚乙酸酯、乙二醇單甲醚乙酸酯、乙二醇單乙醚乙酸酯、二乙二醇單乙醚乙酸酯、二乙二醇單丁醚乙酸酯及二丙二醇甲醚乙酸酯等。 As the ether ester solvent, there can be mentioned: methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, 2-methoxy-2-methylpropionic acid methyl ester, 2-ethoxy-2-methylpropionic acid ethyl ester, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate and dipropylene glycol methyl ether acetate, etc.

作為酮溶劑,可列舉:4-羥基-4-甲基-2-戊酮、丙酮、2-丁酮、2-庚酮、3-庚酮、4-庚酮、4-甲基-2-戊酮、環戊酮、環己酮 及異佛爾酮等。 Ketone solvents include: 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone, and isophorone.

作為醇溶劑,可列舉:甲醇、乙醇、丙醇、丁醇、己醇、環己醇、乙二醇、丙二醇及甘油等。 As alcohol solvents, there are: methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol and glycerol, etc.

作為芳香族烴溶劑,可列舉:苯、甲苯、二甲苯及均三甲苯等。 As aromatic hydrocarbon solvents, we can cite: benzene, toluene, xylene and mesitylene, etc.

作為醯胺溶劑,可列舉:N,N-二甲基甲醯胺、N,N-二甲基乙醯胺及N-甲基吡咯啶酮等。 As amide solvents, there are: N,N-dimethylformamide, N,N-dimethylacetamide and N-methylpyrrolidone, etc.

該些溶劑亦可併用兩種以上。 Two or more of these solvents may be used in combination.

所述溶劑中,就塗佈性、乾燥性的方面而言,較佳為1atm下的沸點為120℃以上且180℃以下的有機溶劑。作為溶劑,較佳為可列舉丙二醇單甲醚乙酸酯、乳酸乙酯、丙二醇單甲醚、3-乙氧基丙酸乙酯、乙二醇單甲醚、二乙二醇單甲醚、二乙二醇單乙醚、4-羥基-4-甲基-2-戊酮、及N,N-二甲基甲醯胺,更佳為可列舉丙二醇單甲醚乙酸酯、丙二醇單甲醚、乳酸乙酯、3-乙氧基丙酸乙酯、及4-羥基-4-甲基-2-戊酮等。 Among the above solvents, organic solvents having a boiling point of 120°C or higher and 180°C or lower at 1 atm are preferred in terms of coating properties and drying properties. Preferred solvents include propylene glycol monomethyl ether acetate, ethyl lactate, propylene glycol monomethyl ether, ethyl 3-ethoxypropionate, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, 4-hydroxy-4-methyl-2-pentanone, and N,N-dimethylformamide. More preferred solvents include propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate, ethyl 3-ethoxypropionate, and 4-hydroxy-4-methyl-2-pentanone.

溶劑(E)的含有率相對於著色組成物的總量而小於100質量%,較佳為99.99質量%以下,更佳為0.1質量%以上且99.9質量%以下,進而佳為1質量%以上且99.9質量%以下,尤佳為10質量%以上且99質量%以下,進而尤佳為20質量%以上且99質量%以下,特佳為30質量%以上且99質量%以下,極佳為40質量%以上且99質量%以下,最佳為50質量%以上且99質量%以下。 The content of the solvent (E) relative to the total amount of the coloring composition is less than 100 mass%, preferably 99.99 mass% or less, more preferably 0.1 mass% or more and 99.9 mass% or less, further preferably 1 mass% or more and 99.9 mass% or less, particularly preferably 10 mass% or more and 99 mass% or less, further preferably 20 mass% or more and 99 mass% or less, particularly preferably 30 mass% or more and 99 mass% or less, extremely preferably 40 mass% or more and 99 mass% or less, and most preferably 50 mass% or more and 99 mass% or less.

[樹脂(B)] [Resin (B)]

樹脂(B)較佳為鹼可溶性樹脂,更佳為具有源自如下單量體(以下,存在稱為「單量體(a)」的情況)的結構單元的聚合物,所述單量體為選自由不飽和羧酸及不飽和羧酸酐所組成的群組中的至少一種。 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)"), wherein the monomer is at least one selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic anhydrides.

樹脂(B)較佳為具有源自含有碳數2~4的環狀醚結構與乙烯性不飽和鍵的單量體(以下,存在稱為「單量體(b)」的情況)的結構單元、以及其他結構單元的共聚物。 The resin (B) is preferably a copolymer having structural units derived from a monomer containing a cyclic ether structure having 2 to 4 carbon atoms and an ethylenic unsaturated bond (hereinafter referred to as "monomer (b)"), and other structural units.

作為其他結構單元,可列舉源自可與單量體(a)共聚的單量體(其中,與單量體(a)及單量體(b)不同;以下,存在稱為「單量體(c)」的情況)的結構單元、具有乙烯性不飽和鍵的結構單元等。 As other structural units, there can be listed structural units derived from monomers copolymerizable with monomer (a) (wherein, different from monomer (a) and monomer (b); hereinafter, there is a case where it is referred to as "monomer (c)"), structural units having ethylenic unsaturated bonds, etc.

於本說明書中,所謂「(甲基)丙烯酸」,表示選自由丙烯酸及甲基丙烯酸所組成的群組中的至少一種。「(甲基)丙烯醯基」及「(甲基)丙烯酸酯」等表述亦具有相同的含義。 In this specification, "(meth)acrylic acid" means at least one selected from the group consisting of acrylic acid and methacrylic acid. "(meth)acryl" and "(meth)acrylate" also have the same meaning.

作為單量體(a),例如,可列舉:丙烯酸、甲基丙烯酸、丁烯酸及鄰乙烯基苯甲酸、間乙烯基苯甲酸、對乙烯基苯甲酸等不飽和單羧酸;馬來酸、富馬酸、檸康酸、中康酸、衣康酸、3-乙烯基鄰苯二甲酸、4-乙烯基鄰苯二甲酸、3,4,5,6-四氫鄰苯二甲酸、1,2,3,6-四氫鄰苯二甲酸、二甲基四氫鄰苯二甲酸及1,4-環己烯二羧酸等不飽和二羧酸; 甲基-5-降冰片烯-2,3-二羧酸、5-羧基雙環[2.2.1]庚-2-烯、5,6-二羧基雙環[2.2.1]庚-2-烯、5-羧基-5-甲基雙環[2.2.1]庚-2-烯、5-羧基-5-乙基雙環[2.2.1]庚-2-烯、5-羧基-6-甲基雙環[2.2.1]庚-2-烯、5-羧基-6-乙基雙環[2.2.1]庚-2-烯等含有羧基的雙環不飽和化合物;馬來酸酐、檸康酸酐、衣康酸酐、3-乙烯基鄰苯二甲酸酐、4-乙烯基鄰苯二甲酸酐、3,4,5,6-四氫鄰苯二甲酸酐、1,2,3,6-四氫鄰苯二甲酸酐、二甲基四氫鄰苯二甲酸酐、5,6-二羧基雙環[2.2.1]庚-2-烯酐等不飽和二羧酸酐;琥珀酸單〔2-(甲基)丙烯醯基氧基乙基〕酯及鄰苯二甲酸單〔2-(甲基)丙烯醯基氧基乙基〕酯等二價以上的多元羧酸的不飽和單〔(甲基)丙烯醯基氧基烷基〕酯;α-(羥基甲基)丙烯酸等於同一分子中含有羥基及羧基的不飽和丙烯酸酯等。 Examples of the monomer (a) include acrylic acid, methacrylic acid, crotonic acid, and unsaturated monocarboxylic acids such as o-vinylbenzoic acid, m-vinylbenzoic acid, and p-vinylbenzoic acid; maleic acid, fumaric acid, citric acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyltetrahydrophthalic acid; Phthalic acid and unsaturated dicarboxylic acids such as 1,4-cyclohexenedicarboxylic 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-methyl Bicyclic unsaturated compounds containing a carboxyl group, such as bicyclo[2.2.1]hept-2-ene and 5-carboxy-6-ethylbicyclo[2.2.1]hept-2-ene; maleic anhydride, conic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5, Unsaturated dicarboxylic anhydrides such as 6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride; unsaturated mono[(meth)acryloxyalkyl] esters of polycarboxylic acids having a valency of more than two such as mono[2-(meth)acryloxyethyl] succinate and mono[2-(meth)acryloxyethyl] phthalate; unsaturated acrylic esters containing a hydroxyl group and a carboxyl group in the same molecule such as α-(hydroxymethyl)acrylic acid, etc.

該些中,就共聚反應性的方面或所獲得的樹脂於鹼性水溶液中的溶解性的方面而言,較佳為丙烯酸、甲基丙烯酸、鄰乙烯基苯甲酸、間乙烯基苯甲酸、對乙烯基苯甲酸及馬來酸酐等。 Among these, acrylic acid, methacrylic acid, o-vinylbenzoic acid, m-vinylbenzoic acid, p-vinylbenzoic acid, and maleic anhydride are preferred in terms of copolymerization reactivity or solubility of the obtained resin in alkaline aqueous solution.

單量體(b)是指具有碳數2~4的環狀醚結構(例如,選自由氧雜環丙烷環、氧雜環丁烷環及四氫呋喃環所組成的群組中的至少一種)與乙烯性不飽和鍵的聚合性化合物。 The monomer (b) refers to a polymerizable compound having a cyclic ether structure having 2 to 4 carbon atoms (for example, at least one selected from the group consisting of an oxycyclopropane ring, an oxycyclobutane ring, and a tetrahydrofuran ring) and an ethylenic unsaturated bond.

單量體(b)較佳為具有碳數2~4的環狀醚結構與(甲基)丙烯醯基氧基的單量體。 The monomer (b) is preferably a monomer having a cyclic ether structure with 2 to 4 carbon atoms and a (meth)acryloyloxy group.

作為單量體(b),例如,可列舉:具有氧雜環丙基與乙烯性不飽和鍵的單量體(以下,存在稱為「單量體(b1)」的情況)、具有氧雜環丁基與乙烯性不飽和鍵的單量體(以下,存在稱為「單量體(b2)」的情況)及具有四氫呋喃基與乙烯性不飽和鍵的單量體(以下,存在稱為「單量體(b3)」的情況)等。 Examples of monomer (b) include monomers having an oxocyclopropyl group and an ethylenic unsaturated bond (hereinafter referred to as "monomer (b1)"), monomers having an oxocyclobutyl group and an ethylenic unsaturated bond (hereinafter referred to as "monomer (b2)"), and monomers having a tetrahydrofuranyl group and an ethylenic unsaturated bond (hereinafter referred to as "monomer (b3)").

作為單量體(b1),例如,可列舉:具有直鏈狀或分支鏈狀的脂肪族不飽和烴經環氧化而成的結構的單量體(以下,存在稱為「單量體(b1-1)」的情況)及具有脂環式不飽和烴經環氧化而成的結構的單量體(以下,存在稱為「單量體(b1-2)」的情況)。 As monomer (b1), for example, there can be listed: monomers having a structure formed by epoxidation of aliphatic unsaturated hydrocarbons in a straight chain or branched chain (hereinafter, sometimes referred to as "monomer (b1-1)") and monomers having a structure formed by epoxidation of alicyclic unsaturated hydrocarbons (hereinafter, sometimes referred to as "monomer (b1-2)").

作為單量體(b1-1),較佳為具有縮水甘油基與乙烯性不飽和鍵的單量體。 As the monomer (b1-1), a monomer having a glyceryl group and an ethylenic unsaturated bond is preferred.

作為單量體(b1-1),例如,可列舉:(甲基)丙烯酸縮水甘油酯、(甲基)丙烯酸β-甲基縮水甘油酯、(甲基)丙烯酸β-乙基縮水甘油酯、縮水甘油基乙烯基醚、鄰乙烯基苄基縮水甘油醚、間乙烯基苄基縮水甘油醚、對乙烯基苄基縮水甘油醚、α-甲基-鄰乙烯基苄基縮水甘油醚、α-甲基-間乙烯基苄基縮水甘油醚、α-甲基-對乙烯基苄基縮水甘油醚、2,3-雙(縮水甘油基氧基甲基)苯乙烯、2,4-雙(縮水甘油基氧基甲基)苯乙烯、2,5-雙(縮水甘油基氧基甲基)苯乙烯、2,6-雙(縮水甘油基氧基甲基)苯乙烯、2,3,4-三(縮水甘油基氧基甲基)苯乙烯、2,3,5-三(縮水甘油基氧基甲基)苯乙烯、2,3,6-三(縮水甘油基氧基甲基)苯乙烯、3,4,5- 三(縮水甘油基氧基甲基)苯乙烯及2,4,6-三(縮水甘油基氧基甲基)苯乙烯等。 Examples of the monomer (b1-1) include glycidyl (meth)acrylate, β-methyl glycidyl (meth)acrylate, β-ethyl glycidyl (meth)acrylate, glycidyl vinyl ether, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, α-methyl-o-vinylbenzyl glycidyl ether, α-methyl-m-vinylbenzyl glycidyl ether, α-methyl-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-tri(glycidyloxymethyl)styrene, 2,3,5-tri(glycidyloxymethyl)styrene, 2,3,6-tri(glycidyloxymethyl)styrene, 3,4,5- tri(glycidyloxymethyl)styrene and 2,4,6-tri(glycidyloxymethyl)styrene, etc.

作為單量體(b1-2),例如,可列舉:乙烯基環己烯單氧化物、1,2-環氧-4-乙烯基環己烷(例如,賽羅西德(Celloxide)(註冊商標)2000;大賽璐(Daicel)(股)製造)、(甲基)丙烯酸3,4-環氧環己基甲酯(例如,沙克馬(Cyclomer)(註冊商標)A400;大賽璐(Daicel)(股)製造)、(甲基)丙烯酸3,4-環氧環己基甲酯(例如,沙克馬(Cyclomer)(註冊商標)M100;大賽璐(Daicel)(股)製造)、式(BI)所表示的化合物及式(BII)所表示的化合物等。 As monomers (b1-2), for example, vinylcyclohexene monoxide, 1,2-epoxy-4-vinylcyclohexane (e.g., Celloxide (registered trademark) 2000; manufactured by Daicel (Co., Ltd.)), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., Cyclomer (registered trademark) A400; manufactured by Daicel (Co., Ltd.)), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., Cyclomer (registered trademark) M100; manufactured by Daicel (Co., Ltd.)), compounds represented by formula (BI) and compounds represented by formula (BII), etc. can be cited.

Figure 109104792-A0305-02-0264-346
Figure 109104792-A0305-02-0264-346

[式(BI)及式(BII)中,Ra及Rb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;Xa及Xb彼此獨立地表示單鍵、*-Rc-、*-Rc-O-、*-Rc-S-或*-Rc-NH-;Rc表示碳數1~6的烷二基;*表示與O的鍵結鍵] [In formula (BI) and formula (BII), Ra and Rb independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, wherein the hydrogen atom contained in the alkyl group may be substituted by a hydroxyl group; Xa and Xb independently represent a single bond, * -Rc- , * -Rc -O-, * -Rc -S- or * -Rc -NH-; Rc represents an alkanediyl group having 1 to 6 carbon atoms; * represents a bond with O]

作為碳數1~4的烷基,例如,可列舉:甲基、乙基、 正丙基、異丙基、正丁基、第二丁基、第三丁基等。 As the alkyl group having 1 to 4 carbon atoms, for example, there can be listed: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, etc.

作為氫原子經羥基取代而成的烷基,例如,可列舉:羥基甲基、1-羥基乙基、2-羥基乙基、1-羥基丙基、2-羥基丙基、3-羥基丙基、1-羥基-1-甲基乙基、2-羥基-1-甲基乙基、1-羥基丁基、2-羥基丁基、3-羥基丁基、4-羥基丁基等。 Examples of alkyl groups formed by replacing a hydrogen atom with a hydroxyl group include hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 1-hydroxypropyl, 2-hydroxypropyl, 3-hydroxypropyl, 1-hydroxy-1-methylethyl, 2-hydroxy-1-methylethyl, 1-hydroxybutyl, 2-hydroxybutyl, 3-hydroxybutyl, 4-hydroxybutyl, etc.

作為Ra及Rb,較佳為可列舉氫原子、甲基、羥基甲基、1-羥基乙基、2-羥基乙基,更佳為可列舉氫原子、甲基。 As Ra and Rb , preferably, there can be mentioned a hydrogen atom, a methyl group, a hydroxymethyl group, a 1-hydroxyethyl group, and a 2-hydroxyethyl group, and more preferably, there can be mentioned a hydrogen atom and a methyl group.

作為烷二基,例如可列舉:亞甲基、伸乙基、丙烷-1,2-二基、丙烷-1,3-二基、丁烷-1,4-二基、戊烷-1,5-二基、己烷-1,6-二基等。 Examples of alkanediyl groups include methylene, ethylene, propane-1,2-diyl, propane-1,3-diyl, butane-1,4-diyl, pentane-1,5-diyl, hexane-1,6-diyl, etc.

作為Xa及Xb,較佳為可列舉單鍵、亞甲基、伸乙基、*-CH2-O-及*-CH2CH2-O-,更佳為可列舉單鍵、*-CH2CH2-O-(*表示與O的鍵結鍵)。 Preferred examples of Xa and Xb include a single bond, methylene, ethylidene, *-CH2-O- and *-CH2CH2-O-. More preferred examples include a single bond and *-CH2CH2 - O- ( * represents a bond with O).

作為式(BI)所表示的化合物,可列舉式(BI-1)~式(BI-15)的任一者所表示的化合物等。其中,較佳為式(BI-1)、式(BI-3)、式(BI-5)、式(BI-7)、式(BI-9)及式(BI-11)~式(BI-15)所表示的化合物,更佳為式(BI-1)、式(BI-7)、式(BI-9)及式(BI-15)所表示的化合物。 As the compound represented by formula (BI), there can be listed compounds represented by any one of formula (BI-1) to formula (BI-15). Among them, preferred are compounds represented by formula (BI-1), formula (BI-3), formula (BI-5), formula (BI-7), formula (BI-9) and formula (BI-11) to formula (BI-15), and more preferred are compounds represented by formula (BI-1), formula (BI-7), formula (BI-9) and formula (BI-15).

[化94]

Figure 109104792-A0305-02-0266-347
[Chemistry 94]
Figure 109104792-A0305-02-0266-347

[化95]

Figure 109104792-A0305-02-0267-348
[Chemistry 95]
Figure 109104792-A0305-02-0267-348

作為式(BII)所表示的化合物,可列舉式(BII-1)~式(BII-15)的任一者所表示的化合物等,其中,較佳為可列舉式(BII-1)、式(BII-3)、式(BII-5)、式(BII-7)、式(BII-9)及式(BII-11)~式(BII-15)所表示的化合物,更佳為可列舉式 (BII-1)、式(BII-7)、式(BII-9)及式(BII-15)所表示的化合物。 As the compound represented by formula (BII), there can be listed compounds represented by any one of formula (BII-1) to formula (BII-15), among which preferred are compounds represented by formula (BII-1), formula (BII-3), formula (BII-5), formula (BII-7), formula (BII-9) and formula (BII-11) to formula (BII-15), and more preferred are compounds represented by formula (BII-1), formula (BII-7), formula (BII-9) and formula (BII-15).

Figure 109104792-A0305-02-0268-349
Figure 109104792-A0305-02-0268-349

Figure 109104792-A0305-02-0269-350
Figure 109104792-A0305-02-0269-350

式(BI)所表示的化合物及式(BII)所表示的化合物 可分別單獨使用,亦可併用兩種以上。亦可併用式(BI)所表示的化合物及式(BII)所表示的化合物。於併用式(BI)所表示的化合物及式(BII)所表示的化合物的情況下,該些的含有比率〔式(BI)所表示的化合物:式(BII)所表示的化合物〕以莫耳基準計而較佳為5:95~95:5,更佳為10:90~90:10,進而佳為20:80~80:20。 The compound represented by formula (BI) and the compound represented by formula (BII) Can be used alone or in combination of two or more. The compound represented by formula (BI) and the compound represented by formula (BII) can 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 [compound represented by formula (BI): compound represented by formula (BII)] is preferably 5:95~95:5 on a molar basis, more preferably 10:90~90:10, and even more preferably 20:80~80:20.

作為單量體(b2),更佳為具有氧雜環丁基與(甲基)丙烯醯基氧基的單量體。 As the monomer (b2), a monomer having an oxacyclobutyl group and a (meth)acryloyloxy group is more preferred.

作為單量體(b2),例如,可列舉:3-甲基-3-甲基丙烯醯基氧基甲基氧雜環丁烷、3-甲基-3-丙烯醯基氧基甲基氧雜環丁烷、3-乙基-3-甲基丙烯醯基氧基甲基氧雜環丁烷、3-乙基-3-丙烯醯基氧基甲基氧雜環丁烷、3-甲基-3-甲基丙烯醯基氧基乙基氧雜環丁烷、3-甲基-3-丙烯醯基氧基乙基氧雜環丁烷、3-乙基-3-甲基丙烯醯基氧基乙基氧雜環丁烷、3-乙基-3-丙烯醯基氧基乙基氧雜環丁烷等。 As monomer (b2), for example, 3-methyl-3-methacryloyloxymethyloxycyclobutane, 3-methyl-3-acryloyloxymethyloxycyclobutane, 3-ethyl-3-methacryloyloxymethyloxycyclobutane, 3-ethyl-3-acryloyloxymethyloxycyclobutane, 3-methyl-3-methacryloyloxyethyloxycyclobutane, 3-methyl-3-acryloyloxyethyloxycyclobutane, 3-ethyl-3-methacryloyloxyethyloxycyclobutane, 3-ethyl-3-acryloyloxyethyloxycyclobutane, etc. can be cited.

作為單量體(b3),更佳為具有四氫呋喃基與(甲基)丙烯醯基氧基的單量體。 As the monomer (b3), a monomer having a tetrahydrofuranyl group and a (meth)acryloyloxy group is more preferred.

作為單量體(b3),例如可列舉:丙烯酸四氫糠基酯(例如,比斯考特(Viscoat)V#150,大阪有機化學工業(股)製造)、甲基丙烯酸四氫糠基酯等。 Examples of monomers (b3) include tetrahydrofurfuryl acrylate (e.g., Viscoat V#150, manufactured by Osaka Organic Chemical Industry Co., Ltd.), tetrahydrofurfuryl methacrylate, etc.

作為單量體(b),就可進一步提高所獲得的彩色濾光片的耐熱性、耐化學品性等的可靠性的方面而言,較佳為單量體 (b1)。進而,就著色組成物的保存穩定性優異的方面而言,更佳為單量體(b1-2)。 As the monomer (b), the monomer (b1) is preferred in terms of further improving the reliability of the obtained color filter in terms of heat resistance, chemical resistance, etc. Furthermore, the monomer (b1-2) is more preferred in terms of excellent storage stability of the coloring composition.

作為單量體(c),例如,可列舉:(甲基)丙烯酸甲酯、(甲基)丙烯酸乙酯、(甲基)丙烯酸正丁酯、(甲基)丙烯酸第二丁酯、(甲基)丙烯酸第三丁酯、(甲基)丙烯酸2-乙基己酯、(甲基)丙烯酸十二烷基酯、(甲基)丙烯酸月桂基酯、(甲基)丙烯酸硬脂基酯、(甲基)丙烯酸環戊酯、(甲基)丙烯酸環己酯、(甲基)丙烯酸2-甲基環己酯、(甲基)丙烯酸三環[5.2.1.02,6]癸烷-8-基酯、(甲基)丙烯酸三環[5.2.1.02,6]癸烷-9-基酯、(甲基)丙烯酸三環[5.2.1.02,6]癸烯-8-基酯、(甲基)丙烯酸三環[5.2.1.02,6]癸烯-9-基酯、(甲基)丙烯酸二環戊烷基氧基乙酯、(甲基)丙烯酸異冰片基酯、(甲基)丙烯酸金剛烷基酯、(甲基)丙烯酸烯丙基酯、(甲基)丙烯酸炔丙基酯、(甲基)丙烯酸苯基酯、(甲基)丙烯酸萘基酯及(甲基)丙烯酸苄基酯等(甲基)丙烯酸酯;(甲基)丙烯酸2-羥基乙酯及(甲基)丙烯酸2-羥基丙酯等含有羥基的(甲基)丙烯酸酯;(甲基)丙烯酸2,2,3,3,4,4,5,5-八氟戊酯等含有鹵素原子的(甲基)丙烯酸酯;馬來酸二乙酯、富馬酸二乙酯及衣康酸二乙酯等二羧酸二酯;雙環[2.2.1]庚-2-烯、5-甲基雙環[2.2.1]庚-2-烯、5-乙基雙環[2.2.1]庚-2-烯、5-羥基雙環[2.2.1]庚-2-烯、5-羥基甲基雙環[2.2.1]庚-2-烯、5-(2'-羥基乙基)雙環[2.2.1]庚-2-烯、5-甲氧基雙環[2.2.1] 庚-2-烯、5-乙氧基雙環[2.2.1]庚-2-烯、5,6-二羥基雙環[2.2.1]庚-2-烯、5,6-二(羥基甲基)雙環[2.2.1]庚-2-烯、5,6-二(2'-羥基乙基)雙環[2.2.1]庚-2-烯、5,6-二甲氧基雙環[2.2.1]庚-2-烯、5,6-二乙氧基雙環[2.2.1]庚-2-烯、5-羥基-5-甲基雙環[2.2.1]庚-2-烯、5-羥基-5-乙基雙環[2.2.1]庚-2-烯、5-羥基甲基-5-甲基雙環[2.2.1]庚-2-烯、5-第三丁氧基羰基雙環[2.2.1]庚-2-烯、5-環己基氧基羰基雙環[2.2.1]庚-2-烯、5-苯氧基羰基雙環[2.2.1]庚-2-烯、5,6-雙(第三丁氧基羰基)雙環[2.2.1]庚-2-烯及5,6-雙(環己基氧基羰基)雙環[2.2.1]庚-2-烯等雙環不飽和化合物;N-苯基馬來醯亞胺、N-環己基馬來醯亞胺、N-苄基馬來醯亞胺、N-琥珀醯亞胺基-3-馬來醯亞胺苯甲酸酯、N-琥珀醯亞胺基-4-馬來醯亞胺丁酸酯、N-琥珀醯亞胺基-6-馬來醯亞胺己酸酯、N-琥珀醯亞胺基-3-馬來醯亞胺丙酸酯及N-(9-吖啶基)馬來醯亞胺等二羰基醯亞胺衍生物;苯乙烯、鄰甲基苯乙烯、間甲基苯乙烯、對甲基苯乙烯、乙烯基甲苯、9-乙烯基咔唑及對甲氧基苯乙烯等含有乙烯基的芳香族化合物;(甲基)丙烯腈等含有乙烯基的腈;氯乙烯及偏二氯乙烯等鹵化烴;(甲基)丙烯醯胺等含有乙烯基的醯胺;乙酸乙烯基酯等酯;1,3-丁二烯、異戊二烯及2,3-二甲基-1,3-丁二烯等二烯等。 Examples of the monomer (c) include methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, sec-butyl (meth)acrylate, t-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, dodecyl (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-yl (meth)acrylate, tricyclo[5.2.1.0 2,6 ]decane-9-yl (meth)acrylate, tricyclo[5.2.1.0 2,6 ]decen-8-yl (meth)acrylate, tricyclo[5.2.1.0 2,6 ] (meth)acrylates such as decen-9-yl (meth)acrylate, dicyclopentyloxyethyl (meth)acrylate, isobornyl (meth)acrylate, adamantyl (meth)acrylate, allyl (meth)acrylate, propargyl (meth)acrylate, phenyl (meth)acrylate, naphthyl (meth)acrylate, and benzyl (meth)acrylate; (meth)acrylates containing a hydroxyl group such as 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate; 2,2,3,3,4,4,5,5 (meth)acrylate -octafluoropentyl esters and other halogen-containing (meth)acrylates; diethyl maleate, diethyl fumarate and diethyl itaconate and other dicarboxylic acid diesters; bicyclo[2.2.1]hept-2-ene, 5-methylbicyclo[2.2.1]hept-2-ene, 5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxybicyclo[2.2.1]hept-2-ene, 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-di(hydroxymethyl)bicyclo[2.2.1]hept-2-ene, 5,6-di(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-tert-butoxycarbonylbicyclo[2.2.1]hept-2-ene, 5-cyclohexyloxycarbonylbicyclo[2.2.1]hept-2-ene, 5-phenoxycarbonylbicyclo[2.2.1]hept-2-ene, 5,6-bis(tert-butoxycarbonyl)bicyclo[2.2.1]hept-2-ene and 5 , 6-bis(cyclohexyloxycarbonyl)bicyclo[2.2.1]hept-2-ene and other bicyclic unsaturated compounds; N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimidobenzoate, N-succinimidyl-4-maleimidobutyrate, N-succinimidyl-6-maleimidohexanoate, N-succinimidyl-3-maleimidopropionate and N-(9-acridinyl)maleimido dicarbonyl imide derivatives such as amine; aromatic compounds containing vinyl groups such as styrene, o-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, 9-vinylcarbazole and p-methoxystyrene; nitriles containing vinyl groups such as (meth)acrylonitrile; halogenated hydrocarbons such as vinyl chloride and vinylidene chloride; amides containing vinyl groups such as (meth)acrylamide; esters such as vinyl acetate; dienes such as 1,3-butadiene, isoprene and 2,3-dimethyl-1,3-butadiene, etc.

該些中,就共聚反應性及耐熱性的方面而言,較佳為:苯乙烯、乙烯基甲苯、(甲基)丙烯酸三環[5.2.1.02,6]癸烷-8-基酯、(甲基)丙烯酸三環[5.2.1.02,6]癸烷-9-基酯、(甲基)丙烯酸三環 [5.2.1.02,6]癸烯-8-基酯、(甲基)丙烯酸三環[5.2.1.02,6]癸烯-9-基酯、N-苯基馬來醯亞胺、N-環己基馬來醯亞胺、N-苄基馬來醯亞胺、雙環[2.2.1]庚-2-烯、(甲基)丙烯酸苯基酯、(甲基)丙烯酸2,2,3,3,4,4,5,5-八氟戊酯、9-乙烯基咔唑、(甲基)丙烯酸苄基酯、(甲基)丙烯酸2-羥基乙酯及(甲基)丙烯酸2-乙基己酯等。 Among them, preferred are styrene, vinyltoluene, tricyclo[5.2.1.0 2,6 ]decane-8-yl (meth)acrylate , tricyclo[5.2.1.0 2,6 ]decane-9-yl (meth)acrylate, tricyclo[5.2.1.0 2,6 ] decen-8-yl (meth)acrylate, tricyclo[5.2.1.0 2,6 ]decen-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-vinylcarbazole, benzyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate and 2-ethylhexyl (meth)acrylate, etc.

作為樹脂(B),具體可列舉:(甲基)丙烯酸3,4-環氧環己基甲酯/(甲基)丙烯酸共聚物、(甲基)丙烯酸3,4-環氧三環[5.2.1.02,6]癸酯/(甲基)丙烯酸共聚物、(甲基)丙烯酸3,4-環氧三環[5.2.1.02,6]癸酯/(甲基)丙烯酸苄基酯/(甲基)丙烯酸共聚物、(甲基)丙烯酸3,4-環氧三環[5.2.1.02,6]癸酯/9-乙烯基咔唑/(甲基)丙烯酸共聚物、(甲基)丙烯酸3,4-環氧三環[5.2.1.02,6]癸酯/(甲基)丙烯酸苯基酯/鄰乙烯基苯甲酸共聚物、(甲基)丙烯酸3,4-環氧三環[5.2.1.02,6]癸酯/(甲基)丙烯酸苯基酯/間乙烯基苯甲酸共聚物、(甲基)丙烯酸3,4-環氧三環[5.2.1.02,6]癸酯/(甲基)丙烯酸苯基酯/對乙烯基苯甲酸共聚物、(甲基)丙烯酸3,4-環氧三環[5.2.1.02,6]癸酯/(甲基)丙烯酸苯基酯/(甲基)丙烯酸共聚物、(甲基)丙烯酸3,4-環氧三環[5.2.1.02,6]癸酯/(甲基)丙烯酸2,2,3,3,4,4,5,5-八氟戊酯/(甲基)丙烯酸共聚物、(甲基)丙烯酸縮水甘油酯/(甲基)丙烯酸苄基酯/(甲基)丙烯酸共聚物、(甲基)丙烯酸縮水甘油酯/苯乙烯/(甲基)丙烯酸共聚物、(甲基)丙烯酸3,4-環氧三環[5.2.1.02,6]癸酯/(甲基)丙烯酸/N-環己基馬來醯亞胺共聚物、(甲基)丙烯酸3,4-環氧三環[5.2.1.02,6]癸酯/(甲基)丙烯酸/N-環己基馬來醯亞胺/(甲基)丙烯酸2-羥基乙 酯共聚物、(甲基)丙烯酸3,4-環氧三環[5.2.1.02,6]癸酯/(甲基)丙烯酸/乙烯基甲苯共聚物、(甲基)丙烯酸3,4-環氧三環[5.2.1.02,6]癸酯/(甲基)丙烯酸/(甲基)丙烯酸2-乙基己酯共聚物、(甲基)丙烯酸3,4-環氧三環[5.2.1.02,6]癸酯/(甲基)丙烯酸三環[5.2.1.02,6]癸烯基酯/(甲基)丙烯酸/N-環己基馬來醯亞胺共聚物、3-甲基-3-(甲基)丙烯醯基氧基甲基氧雜環丁烷/(甲基)丙烯酸/苯乙烯共聚物、(甲基)丙烯酸苄基酯/(甲基)丙烯酸共聚物、苯乙烯/(甲基)丙烯酸共聚物及日本專利特開平9-106071號公報、日本專利特開2004-29518號公報及日本專利特開2004-361455號公報各公報中記載的樹脂等。 Specific examples of the resin (B) include 3,4-epoxyhexylmethyl (meth)acrylate/(meth)acrylic acid copolymers, 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl (meth)acrylate/(meth)acrylic acid copolymers, 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl (meth)acrylate/benzyl (meth)acrylate/(meth)acrylic acid copolymers, 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl (meth)acrylate/9-vinylcarbazole/(meth)acrylic acid copolymers, 3,4-epoxytricyclo[5.2.1.0 2,6 ] decyl (meth)acrylate/phenyl (meth)acrylate/o-vinylbenzoic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl (meth)acrylate/phenyl (meth)acrylate/m-vinylbenzoic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl (meth)acrylate/phenyl (meth)acrylate/p-vinylbenzoic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] decyl (meth)acrylate/phenyl (meth)acrylate/(meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] decyl (meth)acrylate/2,2,3,3,4,4,5,5-octafluoropentyl (meth)acrylate/(meth)acrylic acid copolymer, glycidyl (meth)acrylate/benzyl (meth)acrylate/(meth)acrylic acid copolymer, glycidyl (meth)acrylate/styrene/(meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl (meth)acrylate/(meth)acrylic acid/N-cyclohexylmaleimide copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl (meth)acrylate/(meth)acrylic acid/N-cyclohexylmaleimide/2-hydroxyethyl (meth)acrylate copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] decyl ester/(meth)acrylic acid/vinyl toluene copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl (meth)acrylate/(meth)acrylic acid/2-ethylhexyl (meth)acrylate copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl (meth)acrylate/tricyclo[5.2.1.0 2,6 ] decenyl ester/(meth)acrylic acid/N-cyclohexylmaleimide copolymer, 3-methyl-3-(meth)acryloyloxymethyloxycyclobutane/(meth)acrylic acid/styrene copolymer, benzyl (meth)acrylate/(meth)acrylic acid copolymer, styrene/(meth)acrylic acid copolymer 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.

其中,作為樹脂(B),較佳為包含源自單量體(a)的結構單元及源自單量體(b)的結構單元的共聚物。 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).

樹脂(B)可組合兩種以上,該情況下,樹脂(B)至少較佳為含有至少一種包含源自單量體(a)的結構單元及源自單量體(b)的結構單元的共聚物,更佳為含有至少一種包含源自單量體(a)的結構單元及源自單量體(b1)的結構單元的共聚物,進而佳為含有至少一種包含源自單量體(a)的結構單元及源自單量體(b1-2)的結構單元的共聚物,尤佳為包含選自(甲基)丙烯酸3,4-環氧三環[5.2.1.02,6]癸酯/(甲基)丙烯酸共聚物、(甲基)丙烯酸3,4-環氧三環[5.2.1.02,6]癸酯/(甲基)丙烯酸苄基酯/(甲基)丙烯酸共聚物、(甲基)丙烯酸3,4-環氧三環[5.2.1.02,6]癸酯/(甲基)丙烯酸/N-環己基馬來醯亞胺/(甲基)丙 烯酸2-羥基乙酯共聚物、(甲基)丙烯酸3,4-環氧三環[5.2.1.02,6]癸酯/(甲基)丙烯酸/乙烯基甲苯共聚物、(甲基)丙烯酸3,4-環氧三環[5.2.1.02,6]癸酯/(甲基)丙烯酸/(甲基)丙烯酸2-乙基己酯共聚物中的一種以上。 The resin (B) may be a combination of two or more types. In this case, the resin (B) is preferably at least a copolymer containing at least one structural unit derived from the monomer (a) and a structural unit derived from the monomer (b), more preferably a copolymer containing at least one structural unit derived from the monomer (a) and a structural unit derived from the monomer (b1), further preferably a copolymer containing at least one structural unit derived from the monomer (a) and a structural unit derived from the monomer (b1-2), and particularly preferably a copolymer containing a structural unit selected from the group consisting of 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl(meth)acrylate/(meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl (meth)acrylate/benzyl (meth)acrylate/(meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl (meth)acrylate/(meth)acrylic acid/N-cyclohexylmaleimide/2-hydroxyethyl (meth)acrylate copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl (meth)acrylate/(meth)acrylic acid/vinyltoluene copolymer, and 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl (meth)acrylate/(meth)acrylic acid/2-ethylhexyl (meth)acrylate copolymer.

樹脂(B)的聚苯乙烯換算的重量平均分子量(Mw)較佳為1,000~100,000,更佳為1,000~50,000,進而佳為1,000~30,000,尤佳為3000~30000,特佳為5,000~30,000。 The polystyrene-equivalent weight average molecular weight (Mw) 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 3000 to 30000, and particularly preferably 5,000 to 30,000.

樹脂(B)的分散度[重量平均分子量(Mw)/數量平均分子量(Mn)]較佳為1~6,更佳為1~5,進而佳為1~4。 The dispersion degree of the resin (B) [weight average molecular weight (Mw)/number average molecular weight (Mn)] is preferably 1 to 6, more preferably 1 to 5, and even more preferably 1 to 4.

樹脂(B)的酸價(固體成分換算值)較佳為10mg-KOH/g~500mg-KOH/g,更佳為20mg-KOH/g~450mg-KOH/g,進而佳為20mg-KOH/g~400mg-KOH/g,進而更佳為20mg-KOH/g~370mg-KOH/g,進而尤佳為30mg-KOH/g~370mg-KOH/g,進一步更佳為30mg-KOH/g~350mg-KOH/g,特佳為30mg-KOH/g~340mg-KOH/g,最佳為30mg-KOH/g~335mg-KOH/g。此處,酸價是作為中和樹脂(B)1g所需的氫氧化鉀的量(mg)而測定的值,例如可藉由使用氫氧化鉀水溶液進行滴定來求出。 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, further preferably 20 mg-KOH/g to 400 mg-KOH/g, further more preferably 20 mg-KOH/g to 370 mg-KOH/g, further more preferably 30 mg-KOH/g to 370 mg-KOH/g, further more preferably 30 mg-KOH/g to 350 mg-KOH/g, particularly preferably 30 mg-KOH/g to 340 mg-KOH/g, and most preferably 30 mg-KOH/g to 335 mg-KOH/g. Here, the acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1g of the resin (B), and can be obtained, for example, by titration using an aqueous potassium hydroxide solution.

著色組成物中,樹脂(B)的含有率相對於固體成分的總量而小於100質量%,較佳為0.00001質量%以上且99.99999質量%以下,更佳為1質量%以上且99質量%以下,進而佳為1質量%以上且97質量%以下,尤佳為1質量%以上且95質量%以下,進而尤佳為3質量%以上且95質量%以下,特佳為5質量%以上 且95質量%以下,極佳為10質量%以上且95質量%以下。 In the coloring composition, the content of the resin (B) is less than 100 mass%, preferably 0.00001 mass% or more and 99.99999 mass% or less, more preferably 1 mass% or more and 99 mass% or less, further preferably 1 mass% or more and 97 mass% or less, particularly preferably 1 mass% or more and 95 mass% or less, further preferably 3 mass% or more and 95 mass% or less, particularly preferably 5 mass% or more and 95 mass% or less, and extremely preferably 10 mass% or more and 95 mass% or less.

[含有化合物(I)的液體的製備] [Preparation of liquid containing compound (I)]

本發明的著色組成物可於預先製備包含化合物(I)與溶劑(E)的含有化合物(I)的液體後,使用該含有化合物(I)的液體來製備著色組成物。於化合物(I)並不溶解於溶劑(E)的情況下,含有化合物(I)的液體亦可藉由使化合物(I)分散於溶劑(E)中並進行混合來製備。含有化合物(I)的液體可包含著色組成物中所含的溶劑(E)的一部分或全部。 The coloring composition of the present invention can be prepared by using a liquid containing compound (I) after pre-preparing a liquid containing compound (I) and a solvent (E). In the case where compound (I) is not dissolved in solvent (E), the liquid containing compound (I) can also be prepared by dispersing compound (I) in solvent (E) and mixing. The liquid containing compound (I) may contain a part or all of the solvent (E) contained in the coloring composition.

再者,該含有化合物(I)的液體包含於本發明的著色組成物中。 Furthermore, the liquid containing compound (I) is contained in the coloring composition of the present invention.

含有化合物(I)的液體的固體成分的含有率相對於含有化合物(I)的液體的總量而小於100質量%,較佳為0.01質量%以上且99.99質量%以下,更佳為0.1質量%以上且99.9質量%以下,進而佳為0.1質量%以上且99質量%以下,尤佳為1質量%以上且90質量%以下,進而尤佳為1質量%以上且80質量%以下,特佳為1質量%以上且70質量%以下,極佳為1質量%以上且60質量%以下,最佳為1質量%以上且50質量%以下。 The content of the solid component of the liquid containing compound (I) is less than 100 mass% relative to the total amount of the liquid containing compound (I), preferably 0.01 mass% or more and 99.99 mass% or less, more preferably 0.1 mass% or more and 99.9 mass% or less, further preferably 0.1 mass% or more and 99 mass% or less, particularly preferably 1 mass% or more and 90 mass% or less, further preferably 1 mass% or more and 80 mass% or less, particularly preferably 1 mass% or more and 70 mass% or less, extremely preferably 1 mass% or more and 60 mass% or less, and most preferably 1 mass% or more and 50 mass% or less.

於含有化合物(I)的液體中的固體成分的總量中,含有化合物(I)的液體的化合物(I)的含有率為100質量%以下,較佳為0.0001質量%以上且99.9999質量%以下,更佳為0.0001質量%以上且99質量%以下,進而佳為1質量%以上且99質量%以下,尤佳為3質量%以上且99質量%以下,進而尤佳為5質量 %以上且99質量%以下。 The content of compound (I) in the liquid containing compound (I) is 100% by mass or less in the total amount of solid components in the liquid containing compound (I), 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, further preferably 1% by mass or more and 99% by mass or less, particularly preferably 3% by mass or more and 99% by mass or less, further particularly preferably 5% by mass or more and 99% by mass or less.

化合物(I)視需要亦可實施松香處理、使用導入有酸性基或鹼性基的衍生物等的表面處理、利用高分子化合物等的對化合物(I)表面的接枝處理、利用硫酸微粒化法、鹽磨(salt milling)法等的微粒化處理、用於將雜質去除的利用有機溶劑或水等的清洗處理、離子性雜質的利用離子交換法等的去除處理等。 If necessary, compound (I) may be subjected to rosin treatment, surface treatment using derivatives that introduce acidic or alkaline groups, grafting treatment on the surface of compound (I) using polymer compounds, micronization treatment using sulfuric acid micronization method, salt milling method, etc., cleaning treatment using organic solvents or water to remove impurities, and removal treatment of ionic impurities using ion exchange method, etc.

另外,化合物(I)視需要亦可實施如下處理等:結晶結構轉換、粒子的整形及/或粒徑的大致均勻化處理;將化合物(I)與水及/或有機溶媒混合,進行攪拌及/或一邊進行加熱一邊進行攪拌,獲得懸浮液後,對該懸浮液進行過濾,獲得結晶結構發生變化的化合物(I)的處理;藉由進行再結晶而改變化合物(I)的結晶結構的處理;將化合物(I)、與水、硫酸或有機溶媒混合,進行攪拌及/或一邊進行加熱一邊進行攪拌,獲得溶液或懸浮液後,將該溶液或該懸浮液與化合物(I)的不良溶媒混合,獲得懸浮液後,對該懸浮液進行過濾,獲得結晶結構發生變化的化合物(I)的處理;將化合物(I)、與衍生物、以及水及/或有機溶媒混合,進行攪拌及/或一邊進行加熱一邊進行攪拌,獲得懸浮液後,對該懸浮液進行過濾,獲得包含結晶結構發生變化的化合物(I)的混合物的處理及/或將化合物(I)與衍生物混合的處理;藉由使化合物(I)與衍生物的混合物進行再結晶,獲得包含結晶結構發生變化的化合物(I)的混合物的處理及/或將化合物(I) 與衍生物混合的處理;將化合物(I)、與衍生物、以及水、硫酸或有機溶媒混合,進行攪拌及/或一邊進行加熱一邊進行攪拌,獲得溶液或懸浮液後,將該溶液或該懸浮液與化合物(I)的不良溶媒混合,獲得懸浮液後,對該懸浮液進行過濾,獲得包含結晶結構發生變化的化合物(I)的混合物的處理及/或將化合物(I)與衍生物混合的處理等。 In addition, compound (I) may be subjected to the following treatments as necessary: crystal structure conversion, particle shaping and/or particle size uniformization; mixing compound (I) with water and/or an organic solvent, stirring and/or stirring while heating to obtain a suspension, and filtering the suspension to obtain a compound (I) with a changed crystal structure; and changing the crystal structure of compound (I) by recrystallization. treatment; mixing compound (I) with water, sulfuric acid or an organic solvent, stirring and/or stirring while heating to obtain a solution or suspension, mixing the solution or suspension with a poor solvent for compound (I) to obtain a suspension, filtering the suspension to obtain a compound (I) with a changed crystal structure; mixing compound (I) with a derivative, and water and/or an organic solvent, stirring and / or stirring while heating to obtain a suspension, filtering the suspension to obtain a mixture containing compound (I) with a changed crystal structure and/or mixing compound (I) with a derivative; by recrystallizing the mixture of compound (I) and a derivative to obtain a mixture containing compound (I) with a changed crystal structure and/or mixing compound (I) with a derivative ; Compound (I), a derivative, and water, sulfuric acid or an organic solvent are mixed, stirred and/or stirred while heating to obtain a solution or suspension, the solution or suspension is mixed with a poor solvent for compound (I), and after obtaining a suspension, the suspension is filtered to obtain a mixture containing compound (I) with a changed crystal structure and/or a treatment of mixing compound (I) with a derivative, etc.

於使用多種化合物(I)或衍生物的情況下,可分別單獨實施該些處理,亦可混合多種來實施該些處理。 When multiple compounds (I) or derivatives are used, these treatments may be performed individually or in combination.

化合物(I)的粒徑較佳為大致均勻。 The particle size of compound (I) is preferably roughly uniform.

作為所述結晶結構轉換中所使用的有機溶媒,可列舉:乙腈等腈溶媒;甲醇、乙醇、1-丙醇、2-丙醇、1-丁醇、1-戊醇、1-己醇、1-庚醇、2-乙基-1-己醇、1-辛醇、苯酚等醇溶媒;胺溶媒;二乙基醚、四氫呋喃、二苯基醚等醚溶媒;丙酮、甲基異丁基酮等酮溶媒;乙酸乙酯、苯甲酸甲酯等酯溶媒;己烷等脂肪族烴溶媒;甲苯、三甲基苯(例如,1,3,5-三甲基苯)、十氫萘、四氫萘等芳香族烴溶媒;二氯甲烷、氯仿、1,2-二氯苯、三氯苯(例如,1,3,5-三氯苯)、1-氯萘、2-氯萘等鹵化烴溶媒;硝基苯等硝基化烴溶媒;N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基吡咯啶酮等醯胺溶媒;二甲基亞碸等亞碸溶媒等。 As the organic solvent used in the above-mentioned crystal structure transformation, there can be listed: nitrile solvents such as acetonitrile; alcohol solvents such as methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-octanol, phenol, etc.; amine solvents; ether solvents such as diethyl ether, tetrahydrofuran, diphenyl ether, etc.; ketone solvents such as acetone, methyl isobutyl ketone, etc.; ester solvents such as ethyl acetate, methyl benzoate, etc.; aliphatic hydrocarbon solvents such as hexane, etc. solvents; aromatic hydrocarbon solvents such as toluene, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decahydronaphthalene, tetrahydronaphthalene, etc.; halogenated hydrocarbon solvents such as dichloromethane, chloroform, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, etc.; nitrated hydrocarbon solvents such as nitrobenzene, etc.; amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, etc.; sulfoxide solvents such as dimethyl sulfoxide, etc., etc.

作為所述不良溶媒,可列舉:乙腈等腈溶媒;甲醇、乙醇、1-丙醇、2-丙醇、1-丁醇、1- 戊醇、1-己醇、1-庚醇、2-乙基-1-己醇、1-辛醇、苯酚等醇溶媒;胺溶媒;二乙基醚、四氫呋喃、二苯基醚等醚溶媒;丙酮、甲基異丁基酮等酮溶媒;乙酸乙酯、苯甲酸甲酯等酯溶媒;己烷等脂肪族烴溶媒;甲苯、三甲基苯(例如,1,3,5-三甲基苯)、十氫萘、四氫萘等芳香族烴溶媒;二氯甲烷、氯仿、1,2-二氯苯、三氯苯(例如,1,3,5-三氯苯)、1-氯萘、2-氯萘等鹵化烴溶媒;硝基苯等硝基化烴溶媒等。 As the bad solvents, there can be listed: nitrile solvents such as acetonitrile; alcohol solvents such as methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-octanol, phenol, etc.; amine solvents; ether solvents such as diethyl ether, tetrahydrofuran, diphenyl ether, etc.; ketone solvents such as acetone, methyl isobutyl ketone, etc.; ester solvents such as ethyl acetate, methyl benzoate, etc.; aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decahydronaphthalene, tetrahydronaphthalene, etc.; halogenated hydrocarbon solvents such as dichloromethane, chloroform, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, etc.; nitrated hydrocarbon solvents such as nitrobenzene, etc.

作為衍生物,可列舉式(z)所表示的化合物及式(z1)所表示的化合物等。 As derivatives, there can be listed compounds represented by formula (z) and compounds represented by formula (z1).

Figure 109104792-A0305-02-0279-351
Figure 109104792-A0305-02-0279-351

[化99]

Figure 109104792-A0305-02-0280-352
[Chemistry 99]
Figure 109104792-A0305-02-0280-352

於含有化合物(I)的液體含有衍生物的情況下,該衍生物的含有率相對於化合物(I)100質量份而為0.01質量份以上且100質量份以下,較佳為0.01質量份以上且70質量份以下,更佳為0.1質量份以上且50質量份以下,進而佳為0.1質量份以上且30質量份以下,尤佳為0.1質量份以上且20質量份以下。 When the liquid containing compound (I) contains a derivative, the content of the derivative is 0.01 mass parts or more and 100 mass parts or less, preferably 0.01 mass parts or more and 70 mass parts or less, more preferably 0.1 mass parts or more and 50 mass parts or less, further preferably 0.1 mass parts or more and 30 mass parts or less, and particularly preferably 0.1 mass parts or more and 20 mass parts or less, relative to 100 mass parts of compound (I).

化合物(I)藉由含有分散劑並進行分散處理,可設為化合物(I)於含有化合物(I)的液體中均勻地分散的狀態。於使用多種化合物(I)的情況下,可分別單獨進行分散處理,亦可混合多種來進行分散處理。 By containing a dispersant and performing a dispersion treatment, compound (I) can be made into a state where compound (I) is uniformly dispersed in a liquid containing compound (I). When using multiple types of compound (I), each can be dispersed individually or multiple types can be mixed and dispersed.

作為分散劑,可列舉界面活性劑等,可為陽離子系、陰離子系、非離子系以及兩性中的任一種界面活性劑。具體可列舉聚酯系、多胺系及丙烯酸系等界面活性劑等。該些分散劑可單獨使用或將兩種以上組合使用。作為分散劑,若以商品名進行表示,則可列舉:KP(信越化學工業(股)製造)、弗洛倫(Flowlen)(共榮社化學(股)製造)、索努帕斯(Solsperse)(註冊商標)(捷力康(zeneca)(股)製造)、艾夫卡(EFKA)(註冊商標)(巴斯夫 (BASF)製造)、阿吉斯帕(Ajisper)(註冊商標)(味之素精細科技(Ajinomoto Fine-Techno)(股)製造)、迪斯帕畢克(DISPERBYK)(註冊商標)(畢克化學(BYK-Chemie)(股)製造)、及畢克(BYK)(註冊商標)(畢克化學(BYK-Chemie)(股)製造)等。 As the dispersant, there can be cited surfactants, which can be any of cationic, anionic, nonionic and amphoteric surfactants. Specifically, there can be cited polyester-based, polyamine-based and acrylic-based surfactants. These dispersants can be used alone or in combination of two or more. As dispersants, if they are expressed by trade names, they include: KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Flowlen (manufactured by Kyoeisha Chemical Co., Ltd.), Solsperse (registered trademark) (manufactured by Zeneca Co., Ltd.), EFKA (registered trademark) (manufactured by BASF), Ajisper (registered trademark) (manufactured by Ajinomoto Fine Technology Co., Ltd.), and others. Fine-Techno (manufactured by) DISPERBYK (registered trademark) (manufactured by BYK-Chemie (manufactured by)), and BYK (registered trademark) (manufactured by BYK-Chemie (manufactured by) etc.

於含有化合物(I)的液體含有分散劑的情況下,該分散劑(固體成分)的使用量相對於化合物(I)100質量份而例如為0.01質量份以上且10000質量份以下,較佳為0.01質量份以上且5000質量份以下,更佳為0.01質量份以上且1000質量份以下,進而佳為0.1質量份以上且500質量份以下,尤佳為0.1質量份以上且300質量份以下,進而尤佳為1質量份以上且300質量份以下,特佳為5質量份以上且260質量份以下。 When the liquid containing compound (I) contains a dispersant, the amount of the dispersant (solid component) used is, for example, 0.01 mass parts or more and 10000 mass parts or less, preferably 0.01 mass parts or more and 5000 mass parts or less, more preferably 0.01 mass parts or more and 1000 mass parts or less, further preferably 0.1 mass parts or more and 500 mass parts or less, particularly preferably 0.1 mass parts or more and 300 mass parts or less, further preferably 1 mass parts or more and 300 mass parts or less, and particularly preferably 5 mass parts or more and 260 mass parts or less, relative to 100 mass parts of compound (I).

若該分散劑的使用量處於所述範圍內,則存在可獲得更均勻的分散狀態的含有化合物(I)的液體的傾向。 If the amount of the dispersant used is within the above range, a liquid containing compound (I) in a more uniformly dispersed state tends to be obtained.

於本發明的著色組成物包含樹脂(B)、且在預先製備包含化合物(I)與溶劑(E)的含有化合物(I)的液體後使用該含有化合物(I)的液體製備本發明的著色組成物的情況下,含有化合物(I)的液體可預先包含著色組成物中所含的樹脂(B)的一部分或全部,較佳為預先包含一部分。藉由預先包含樹脂(B),可進一步改善含有化合物(I)的液體的分散穩定性。 When the coloring composition of the present invention includes a resin (B), and a liquid containing compound (I) containing compound (I) and a solvent (E) is prepared in advance and then used to prepare the coloring composition of the present invention, the liquid containing compound (I) may pre-include a part or all of the resin (B) contained in the coloring composition, preferably a part. By pre-including the resin (B), the dispersion stability of the liquid containing compound (I) can be further improved.

於含有化合物(I)的液體含有樹脂(B)的情況下,樹脂(B)的含量相對於化合物(I)100質量份而例如為0.01質量 份以上且10000質量份以下,較佳為0.01質量份以上且5000質量份以下,更佳為0.01質量份以上且1000質量份以下,進而佳為0.1質量份以上且500質量份以下,尤佳為0.1質量份以上且300質量份以下。 When the liquid containing compound (I) contains resin (B), the content of resin (B) is, for example, 0.01 mass parts or more and 10000 mass parts or less, preferably 0.01 mass parts or more and 5000 mass parts or less, more preferably 0.01 mass parts or more and 1000 mass parts or less, further preferably 0.1 mass parts or more and 500 mass parts or less, and particularly preferably 0.1 mass parts or more and 300 mass parts or less, relative to 100 mass parts of compound (I).

[聚合性化合物(C)] [Polymerizable compound (C)]

聚合性化合物(C)為可藉由自聚合起始劑(D)產生的活性自由基及/或酸而聚合的化合物,例如為聚合性的具有乙烯性不飽和鍵的化合物等,較佳為(甲基)丙烯酸酯化合物。 The polymerizable compound (C) is a compound that can be polymerized by active free radicals and/or acids generated from the polymerization initiator (D), such as a polymerizable compound having ethylenic unsaturated bonds, etc., preferably a (meth)acrylate compound.

作為具有一個乙烯性不飽和鍵的聚合性化合物,例如,可列舉:壬基苯基卡必醇丙烯酸酯、丙烯酸2-羥基-3-苯氧基丙酯、2-乙基己基卡必醇丙烯酸酯、丙烯酸2-羥基乙酯、N-乙烯基吡咯啶酮等、以及所述單量體(a)、單量體(b)及單量體(c)。 As polymerizable compounds having one ethylenically unsaturated bond, for example, there can be listed: nonylphenyl carbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexyl carbitol acrylate, 2-hydroxyethyl acrylate, N-vinyl pyrrolidone, etc., as well as the monomer (a), monomer (b) and monomer (c).

作為具有兩個乙烯性不飽和鍵的聚合性化合物,例如,可列舉:1,6-己二醇二(甲基)丙烯酸酯、乙二醇二(甲基)丙烯酸酯、新戊二醇二(甲基)丙烯酸酯、三乙二醇二(甲基)丙烯酸酯、雙酚A的雙(丙烯醯氧基乙基)醚及3-甲基戊二醇二(甲基)丙烯酸酯等。 Examples of polymerizable compounds having two ethylenic unsaturated bonds include 1,6-hexanediol di(meth)acrylate, ethylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, bis(acryloyloxyethyl) ether of bisphenol A, and 3-methylpentanediol di(meth)acrylate.

其中,聚合性化合物(C)較佳為具有三個以上的乙烯性不飽和鍵的聚合性化合物。作為此種聚合性化合物,例如,可列舉:三羥甲基丙烷三(甲基)丙烯酸酯、季戊四醇三(甲基)丙烯酸酯、季戊四醇四(甲基)丙烯酸酯、二季戊四醇五(甲基)丙烯酸酯、二季戊四醇六(甲基)丙烯酸酯、三季戊四醇八(甲基)丙烯酸酯、三季戊四醇七(甲基)丙烯酸酯、四季戊四醇十(甲基)丙烯酸酯、四季 戊四醇九(甲基)丙烯酸酯、三(2-(甲基)丙烯醯基氧基乙基)異氰脲酸酯、乙二醇改質季戊四醇四(甲基)丙烯酸酯、乙二醇改質二季戊四醇六(甲基)丙烯酸酯、丙二醇改質季戊四醇四(甲基)丙烯酸酯、丙二醇改質二季戊四醇六(甲基)丙烯酸酯、己內酯改質季戊四醇四(甲基)丙烯酸酯及己內酯改質二季戊四醇六(甲基)丙烯酸酯等,較佳為可列舉二季戊四醇五(甲基)丙烯酸酯及二季戊四醇六(甲基)丙烯酸酯。 Among them, the polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenic unsaturated bonds. Examples of such polymerizable compounds include trihydroxymethylpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, tripentaerythritol octa(meth)acrylate, tripentaerythritol hepta(meth)acrylate, tetrapentaerythritol deca(meth)acrylate, tetrapentaerythritol nona(meth)acrylate, tri(2-(meth)acryl)propene oxyethyl) isocyanurate, ethylene glycol modified pentaerythritol tetra(meth)acrylate, ethylene glycol modified dipentaerythritol hexa(meth)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 hexa(meth)acrylate, etc., preferably dipentaerythritol penta(meth)acrylate and dipentaerythritol hexa(meth)acrylate.

聚合性化合物(C)的重量平均分子量較佳為50以上且4000以下,更佳為50以上且3500以下,進而佳為50以上且3000以下,尤佳為150以上且2,900以下,特佳為250以上且1,500以下。 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, further preferably 50 or more and 3000 or less, particularly preferably 150 or more and 2,900 or less, and particularly preferably 250 or more and 1,500 or less.

於著色組成物中,聚合性化合物(C)的含量相對於固體成分的總量而小於100質量%,較佳為0.00001質量%以上且99.99999質量%以下,更佳為1質量%以上且99質量%以下,進而佳為1質量%以上且97質量%以下,尤佳為1質量%以上且95質量%以下,進而尤佳為1質量%以上且90質量%以下,特佳為2質量%以上且80質量%以下,極佳為3質量%以上且70質量%以下。 In the coloring composition, the content of the polymerizable compound (C) is less than 100 mass%, preferably 0.00001 mass% or more and 99.99999 mass% or less, more preferably 1 mass% or more and 99 mass% or less, further preferably 1 mass% or more and 97 mass% or less, particularly preferably 1 mass% or more and 95 mass% or less, further preferably 1 mass% or more and 90 mass% or less, particularly preferably 2 mass% or more and 80 mass% or less, and extremely preferably 3 mass% or more and 70 mass% or less.

[聚合起始劑(D)] [Polymerization initiator (D)]

聚合起始劑(D)只要為可藉由光或熱的作用而產生活性自由基、酸等而使聚合開始的化合物,則並無特別限定,可使用公知的聚合起始劑。 The polymerization initiator (D) is not particularly limited as long as it is a compound that can generate active radicals, acids, etc. by the action of light or heat to initiate polymerization, and a known polymerization initiator can be used.

作為聚合起始劑(D),可列舉:肟化合物、例如O-醯基肟化合物等,苯烷基酮化合物、聯咪唑化合物、三嗪化合物及醯基氧化膦化合物等。 As polymerization initiators (D), there can be listed: oxime compounds, such as O-acyl oxime compounds, phenyl alkyl ketone compounds, biimidazole compounds, triazine compounds and acyl phosphine oxide compounds, etc.

作為O-醯基肟化合物,例如,可列舉:N-苯甲醯基氧基-1-(4-苯硫基苯基)丁烷-1-酮-2-亞胺、N-苯甲醯基氧基-1-(4-苯硫基苯基)辛烷-1-酮-2-亞胺、N-苯甲醯基氧基-1-(4-苯硫基苯基)-3-環戊基丙烷-1-酮-2-亞胺、N-乙醯氧基-1-(4-苯硫基苯基)-3-環戊基丙烷-1-酮-2-亞胺、N-乙醯氧基-1-(4-苯硫基苯基)-3-環己基丙烷-1-酮-2-亞胺、N-乙醯氧基-1-[9-乙基-6-(2-甲基苯甲醯基)-9H-咔唑-3-基]乙烷-1-亞胺、N-乙醯氧基-1-[9-乙基-6-{2-甲基-4-(3,3-二甲基-2,4-二氧雜環戊烷基甲基氧基)苯甲醯基}-9H-咔唑-3-基]乙烷-1-亞胺、N-乙醯氧基-1-[9-乙基-6-(2-甲基苯甲醯基)-9H-咔唑-3-基]-3-環戊基丙烷-1-亞胺及N-苯甲醯基氧基-1-[9-乙基-6-(2-甲基苯甲醯基)-9H-咔唑-3-基]-3-環戊基丙烷-1-酮-2-亞胺等。另外,作為O-醯基肟化合物,亦可使用豔佳固(Irgacure)OXE01、OXE02(以上,巴斯夫(BASF)製造)及N-1919(艾迪科(ADEKA)(股)製造)等市售品。其中,作為O-醯基肟化合物,較佳為選自由N-苯甲醯基氧基-1-(4-苯硫基苯基)丁烷-1-酮-2-亞胺、N-苯甲醯基氧基-1-(4-苯硫基苯基)辛烷-1-酮-2-亞胺及N-苯甲醯基氧基-1-(4-苯硫基苯基)-3-環戊基丙烷-1-酮-2-亞胺所組成的群組中的至少一種,更佳為N-苯甲醯基氧基-1-(4-苯硫基苯基)辛烷-1-酮-2-亞胺。 As the O-acyl oxime compound, for example, there can be mentioned N-benzoyloxy-1-(4-phenylthiophenyl)butane-1-one-2-imine, N-benzoyloxy-1-(4-phenylthiophenyl)octane-1-one-2-imine, N-benzoyloxy-1-(4-phenylthiophenyl)-3-cyclopentylpropane-1-one-2-imine, N-acetyloxy-1-(4-phenylthiophenyl)-3-cyclopentylpropane-1-one-2-imine, N-acetyloxy-1-(4-phenylthiophenyl)-3-cyclopentylpropane-1-one-2-imine, N-acetyloxy-1-(4-phenylthiophenyl)-3-cyclohexylpropane-1-one-2-imine, N-acetyloxy-1-[9-ethyl-6-(2 -methylbenzoyl)-9H-carbazol-3-yl]ethane-1-imine, N-acetyloxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethyl-2,4-dioxacyclopentylmethyloxy)benzoyl}-9H-carbazol-3-yl]ethane-1-imine, N-acetyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropane-1-imine and N-benzoyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropane-1-one-2-imine, etc. In addition, as the O-acyl oxime compound, commercially available products such as Irgacure OXE01 and OXE02 (both manufactured by BASF) and N-1919 (manufactured by ADEKA Co., Ltd.) can also be used. Among them, as the O-acyl oxime compound, it is preferred to be at least one selected from the group consisting of N-benzoyloxy-1-(4-phenylthiophenyl)butane-1-one-2-imine, N-benzoyloxy-1-(4-phenylthiophenyl)octane-1-one-2-imine and N-benzoyloxy-1-(4-phenylthiophenyl)-3-cyclopentylpropane-1-one-2-imine, and more preferably N-benzoyloxy-1-(4-phenylthiophenyl)octane-1-one-2-imine.

作為苯烷基酮化合物,可列舉:2-甲基-2-嗎啉基-1-(4-甲硫基苯基)丙烷-1-酮、2-二甲基胺基-1-(4-嗎啉基苯基)-2-苄基丁烷-1-酮及2-(二甲基胺基)-2-[(4-甲基苯基)甲基]-1-[4-(4-嗎啉基)苯基]丁烷-1-酮等。作為苯烷基酮化合物,亦可使用豔佳固(Irgacure)369、907、379(以上,巴斯夫(BASF)製造)等市售品。 As the alkyl phenone compound, there can be listed: 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]butane-1-one. As the alkyl phenone compound, commercially available products such as Irgacure 369, 907, and 379 (all manufactured by BASF) can also be used.

作為苯烷基酮化合物,亦可列舉:2-羥基-2-甲基-1-苯基丙烷-1-酮、2-羥基-2-甲基-1-〔4-(2-羥基乙氧基)苯基〕丙烷-1-酮、1-羥基環己基苯基酮、2-羥基-2-甲基-1-(4-異丙烯基苯基)丙烷-1-酮的寡聚物、α,α-二乙氧基苯乙酮及苄基二甲基縮酮等。 As alkyl phenone compounds, there can also be listed: 2-hydroxy-2-methyl-1-phenylpropane-1-one, 2-hydroxy-2-methyl-1-〔4-(2-hydroxyethoxy)phenyl〕propane-1-one, 1-hydroxycyclohexylphenyl ketone, oligomers of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propane-1-one, α,α-diethoxyacetophenone and benzyl dimethyl ketal, etc.

作為聯咪唑化合物,例如,可列舉:2,2'-雙(2-氯苯基)-4,4',5,5'-四苯基聯咪唑、2,2'-雙(2,3-二氯苯基)-4,4',5,5'-四苯基聯咪唑(例如,參照日本專利特開平6-75372號公報、日本專利特開平6-75373號公報等)、2,2'-雙(2-氯苯基)-4,4',5,5'-四(烷氧基苯基)聯咪唑、2,2'-雙(2-氯苯基)-4,4',5,5'-四(二烷氧基苯基)聯咪唑、2,2'-雙(2-氯苯基)-4,4',5,5'-四(三烷氧基苯基)聯咪唑(例如,參照日本專利特公昭48-38403號公報、日本專利特開昭62-174204號公報等)及4,4',5,5'-位的苯基由烷氧羰基(carboalkoxy)取代的聯咪唑化合物(例如,參照日本專利特開平7-10913號公報等)等。 Examples of the biimidazole compound include 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole (see, for example, 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(trialkoxyphenyl)biimidazole (for example, see Japanese Patent Publication No. 48-38403, Japanese Patent Publication No. 62-174204, etc.), and biimidazole compounds in which the phenyl groups at the 4,4',5,5'-positions are substituted with alkoxycarbonyl (carboalkoxy) (for example, see Japanese Patent Publication No. 7-10913, etc.).

作為三嗪化合物,可列舉:2,4-雙(三氯甲基)-6-(4-甲氧基苯基)-1,3,5-三嗪、2,4-雙(三氯甲基)-6-(4-甲氧基萘基)-1,3,5-三 嗪、2,4-雙(三氯甲基)-6-胡椒基-1,3,5-三嗪、2,4-雙(三氯甲基)-6-(4-甲氧基苯乙烯基)-1,3,5-三嗪、2,4-雙(三氯甲基)-6-〔2-(5-甲基呋喃-2-基)乙烯基〕-1,3,5-三嗪、2,4-雙(三氯甲基)-6-〔2-(呋喃-2-基)乙烯基〕-1,3,5-三嗪、2,4-雙(三氯甲基)-6-〔2-(4-二乙基胺基-2-甲基苯基)乙烯基〕-1,3,5-三嗪及2,4-雙(三氯甲基)-6-〔2-(3,4-二甲氧基苯基)乙烯基〕-1,3,5-三嗪等。 As triazine compounds, there are 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxynaphthyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-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)vinyl〕-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.

作為醯基氧化膦化合物,可列舉2,4,6-三甲基苯甲醯基二苯基氧化膦等。亦可使用豔佳固(Irgacure)(註冊商標)819(巴斯夫(BASF)製造)等市售品。 As the acylphosphine oxide compound, 2,4,6-trimethylbenzyldiphenylphosphine oxide and the like can be cited. Commercially available products such as Irgacure (registered trademark) 819 (manufactured by BASF) can also be used.

進而,作為聚合起始劑(D),可列舉:安息香、安息香甲醚、安息香乙醚、安息香異丙醚、安息香異丁醚等安息香化合物;二苯甲酮、鄰苯甲醯基苯甲酸甲酯、4-苯基二苯甲酮、4-苯甲醯基-4'-甲基二苯基硫醚、3,3',4,4'-四(第三丁基過氧化羰基)二苯甲酮及2,4,6-三甲基二苯甲酮等二苯甲酮化合物;9,10-菲醌、2-乙基蒽醌及樟腦醌等醌化合物;10-丁基-2-氯吖啶酮、苯偶醯、苯基乙醛酸甲酯及二茂鈦化合物等。 Furthermore, as the polymerization initiator (D), there can be listed: benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether; benzophenone compounds such as benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, 3,3',4,4'-tetra(tert-butylperoxycarbonyl)benzophenone, and 2,4,6-trimethylbenzophenone; quinone compounds such as 9,10-phenanthrenequinone, 2-ethylanthraquinone, and camphorquinone; 10-butyl-2-chloroacridone, benzoyl, methyl phenylglyoxylate, and titaniumocene compounds, etc.

該些較佳為與後述的聚合起始助劑(以下,存在稱為聚合起始助劑(D1)的情況)、尤其是胺類組合使用。 These are preferably used in combination with the polymerization initiator described later (hereinafter, sometimes referred to as polymerization initiator (D1)), especially amines.

聚合起始劑(D)較佳為包含選自由苯烷基酮化合物、三嗪化合物、醯基氧化膦化合物、肟化合物及聯咪唑化合物所組成的群組中的至少一種的聚合起始劑,更佳為包含肟化合物的聚合起始劑,進而佳為包含O-醯基肟化合物的聚合起始劑。 The polymerization initiator (D) is preferably a polymerization initiator comprising at least one selected from the group consisting of phenylalkyl ketone compounds, triazine compounds, acyl phosphine oxide compounds, oxime compounds and biimidazole compounds, more preferably a polymerization initiator comprising an oxime compound, and further preferably a polymerization initiator comprising an O-acyl oxime compound.

聚合起始劑(D)的含有率相對於樹脂(B)及聚合性化合物(C)的合計量而較佳為0.001質量%以上且60質量%以下,更佳為0.01質量%以上且50質量%以下。 The content of the polymerization initiator (D) is preferably 0.001 mass % or more and 60 mass % or less, and more preferably 0.01 mass % or more and 50 mass % or less, relative to the total amount of the resin (B) and the polymerizable compound (C).

[聚合起始助劑(D1)] [Polymerization initiation aid (D1)]

本發明的著色組成物亦可含有聚合起始助劑(D1)。聚合起始助劑(D1)為用於促進藉由聚合起始劑(D)而開始聚合的聚合性化合物(C)的聚合的化合物、或增感劑。於包含聚合起始助劑(D1)的情況下,通常與聚合起始劑(D)組合使用。 The coloring composition of the present invention may also contain a polymerization initiator (D1). The polymerization initiator (D1) is a compound or sensitizer used to promote the polymerization of the polymerizable compound (C) that starts polymerization by the polymerization initiator (D). When the polymerization initiator (D1) is included, it is usually used in combination with the polymerization initiator (D).

作為聚合起始助劑(D1),可列舉:胺化合物、烷氧基蒽化合物、硫雜蒽酮化合物及羧酸化合物等。 Examples of polymerization initiation aids (D1) include amine compounds, alkoxyanthracene compounds, thioanthrone compounds, and carboxylic acid compounds.

作為胺化合物,可列舉:三乙醇胺、甲基二乙醇胺、三異丙醇胺、4-二甲基胺基苯甲酸甲酯、4-二甲基胺基苯甲酸乙酯、4-二甲基胺基苯甲酸異戊酯、苯甲酸2-二甲基胺基乙酯、4-二甲基胺基苯甲酸2-乙基己酯、N,N-二甲基對甲苯胺、4,4'-雙(二甲基胺基)二苯甲酮(通稱米其勒酮(Michler's ketone))、4,4'-雙(二乙基胺基)二苯甲酮及4,4'-雙(乙基甲基胺基)二苯甲酮等,較佳為可列舉4,4'-雙(二乙基胺基)二苯甲酮。另外,作為胺化合物,亦可使用EAB-F(保土谷化學工業(股)製造)等市售品。 As the amine compound, there can be listed: triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isopentyl 4-dimethylaminobenzoate, 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, etc., preferably 4,4'-bis(diethylamino)benzophenone. In addition, as the amine compound, commercially available products such as EAB-F (manufactured by Hodogaya Chemical Industry Co., Ltd.) can also be used.

作為烷氧基蒽化合物,可列舉:9,10-二甲氧基蒽、2-乙基-9,10-二甲氧基蒽、9,10-二乙氧基蒽、2-乙基-9,10-二乙氧基蒽、9,10-二丁氧基蒽及2-乙基-9,10-二丁氧基蒽等。 As alkoxyanthracene compounds, there are: 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.

作為硫雜蒽酮化合物,可列舉:2-異丙基硫雜蒽酮、4- 異丙基硫雜蒽酮、2,4-二乙基硫雜蒽酮、2,4-二氯硫雜蒽酮及1-氯-4-丙氧基硫雜蒽酮等。 As thioxanthrone compounds, there can be listed: 2-isopropylthioxanthrone, 4- isopropylthioxanthrone, 2,4-diethylthioxanthrone, 2,4-dichlorothioxanthrone and 1-chloro-4-propoxythioxanthrone, etc.

作為羧酸化合物,可列舉:苯硫基乙酸、甲基苯硫基乙酸、乙基苯硫基乙酸、甲基乙基苯硫基乙酸、二甲基苯硫基乙酸、甲氧基苯硫基乙酸、二甲氧基苯硫基乙酸、氯苯硫基乙酸、二氯苯硫基乙酸、N-苯基甘胺酸、苯氧基乙酸、萘基硫基乙酸、N-萘基甘胺酸及萘氧基乙酸等。 As carboxylic acid compounds, there can be listed: phenylthioacetic acid, methylphenylthioacetic acid, ethylphenylthioacetic acid, methylethylphenylthioacetic acid, dimethylphenylthioacetic acid, methoxyphenylthioacetic acid, dimethoxyphenylthioacetic acid, chlorophenylthioacetic acid, dichlorophenylthioacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine and naphthoxyacetic acid, etc.

於使用該些聚合起始助劑(D1)的情況下,其含有率相對於樹脂(B)及聚合性化合物(C)的合計量而較佳為0.00001質量%以上且60質量%以下,更佳為0.0001質量%以上且50質量%以下。 When these polymerization initiation aids (D1) are used, their content is preferably 0.00001 mass % or more and 60 mass % or less, and more preferably 0.0001 mass % or more and 50 mass % or less relative to the total amount of the resin (B) and the polymerizable compound (C).

[著色劑(A1)] [Coloring agent (A1)]

本發明的著色組成物亦可包含化合物(I)以外的著色劑(以下,存在稱為著色劑(A1)的情況)。著色劑(A1)中可包含一種或兩種以上的著色劑。著色劑(A1)較佳為包含選自黃色著色劑、橙色著色劑、紅色著色劑及綠色著色劑中的一種以上,更佳為包含選自黃色著色劑及綠色著色劑中的一種以上。 The coloring composition of the present invention may also contain a coloring agent other than compound (I) (hereinafter, referred to as coloring agent (A1)). The coloring agent (A1) may contain one or more coloring agents. The coloring agent (A1) preferably contains one or more selected from yellow coloring agents, orange coloring agents, red coloring agents, and green coloring agents, and more preferably contains one or more selected from yellow coloring agents and green coloring agents.

著色劑(A1)可為染料亦可為顏料。作為染料,可使用公知的染料,例如,可列舉染料索引(Color Index)(染色與印染工作者協會(The Society of Dyers and Colourists)出版)及染色筆記(色染公司(shikisensha))中所記載的公知的染料。另外,根據化學結構,可列舉:偶氮染料、花青染料、三苯基甲烷染料、 氧雜蒽染料、蒽醌染料、萘醌染料、醌亞胺染料、次甲基染料、偶氮甲鹼染料、方酸內鎓染料、吖啶染料、苯乙烯基染料、香豆素染料、喹啉染料、硝基染料、酞菁染料、苝染料、喹酞酮染料、異吲哚啉染料等。該些染料可單獨使用或將兩種以上組合使用。 The coloring agent (A1) may be a dye or a pigment. As the dye, a known dye may be used, for example, the known dyes described in the Color Index (published by The Society of Dyers and Colourists) and the Dyeing Notes (Shikisensha) may be listed. In addition, according to the chemical structure, the following may be listed: azo dyes, cyanine dyes, triphenylmethane dyes, oxyanthracene dyes, anthraquinone dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, azoformine dyes, squarylium dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline dyes, nitro dyes, phthalocyanine dyes, perylene dyes, quinophthalone dyes, isoindoline dyes, etc. These dyes may be used alone or in combination of two or more.

具體可列舉以下般的染料索引(C.I.)編號的染料。 Specifically, the dyes with the following color index (C.I.) numbers can be listed.

C.I.溶劑黃(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;C.I.溶劑紅(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.溶劑橙(solvent orange)2、7、11、15、26、41、54、56、77、86、99;C.I.溶劑紫(solvent violet)11、13、14、26、31、36、37、38、45、47、48、51、59、60;C.I.溶劑藍(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.溶劑綠(solvent green)1、3、4、5、7、28、29、32、33、34、35等C.I.溶劑染料, C.I.酸性黃(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;C.I.酸性紅(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;C.I.酸性橙(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.酸性紫(acid violet)6B、7、9、15、16、17、19、21、23、24、25、30、34、38、49、72、102;C.I.酸性藍(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;C.I.酸性綠(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等C.I.酸性染料,C.I.直接黃(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;C.I.直接紅(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.直接橙(direct orange)26、34、39、41、46、50、52、56、57、61、64、65、68、70、96、97、106、107;C.I.直接紫(direct violet)47、52、54、59、60、65、66、79、80、81、82、84、89、90、93、95、96、103、104; C.I.直接藍(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.直接綠(direct green)25、27、31、32、34、37、63、65、66、67、68、69、72、79、82等C.I.直接染料,C.I.分散黃(disperse yellow)51、54、76;C.I.分散紫(disperse violet)26、27;C.I.分散藍(disperse blue)1、14、56、60等C.I.分散染料,C.I.鹼性紅(basic red)1、10;C.I.鹼性藍(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.鹼性紫(basic violet)2;C.I.鹼性紅9;C.I.鹼性綠(basic green)1等C.I.鹼性染料, C.I.活性黃(reactive yellow)2、76、116;C.I.活性橙(reactive orange)16;C.I.活性紅(reactive red)36等C.I.活性染料,C.I.媒染黃(mordant yellow)5、8、10、16、20、26、30、31、33、42、43、45、56、61、62、65;C.I.媒染紅(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;C.I.媒染橙(mordant orange)3、4、5、8、12、13、14、20、21、23、24、28、29、32、34、35、36、37、42、43、47、48;C.I.媒染紫(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;C.I.媒染藍(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.媒染綠(mordant green)1、3、4、5、10、13、15、19、21、23、26、29、31、33、34、35、41、43、53等C.I.媒染染料,C.I.還原綠(vat green)1等C.I.還原染料等。 C.I. 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); C.I. 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 ( 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; C.I. solvent blue (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 (solvent C.I. solvent dyes such as green)1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35, etc., C.I. 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;C.I. 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, 19 5, 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; C.I. 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; C.I. 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;C.I. Acid Green (acid C.I. acid dyes such as 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, etc., C.I. direct yellow (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; C.I. direct red (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 (direct orange)26,34,39,41,46,50,52,56,57,61,64,65,68,70,96,97,106,107; C.I. direct purple (direct violet)47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104; C.I. 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 (direct C.I. direct dyes such as blue, ... 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. alkaline dyes, C.I. reactive yellow (reactive yellow) 2, 76, 116; C.I. reactive orange (reactive orange) 16; C.I. reactive red (reactive red) 36 and other C.I. reactive dyes, C.I. mordant yellow (mordant yellow) yellow)5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65; C.I. mordant red (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; C.I. mordant orange (mordant 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; C.I. 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; C.I. mordant blue 1, 1: 1, 2, 3, 4, 5 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 (mordant green) 1, 3, 4, 5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 41, 43, 53 and other C.I. mordant dyes, C.I. vat green (vat green) 1 and other C.I. vat dyes, etc.

進而,可列舉作為巴斯夫(BASF)的製品的路摩根 (Lumogen)(註冊商標),可列舉:路摩根(Lumogen)(註冊商標)F黃083(巴斯夫(BASF)製造)、路摩根(Lumogen)(註冊商標)F黃170(巴斯夫(BASF)製造)、路摩根(Lumogen)(註冊商標)F橙240(巴斯夫(BASF)製造)及路摩根(Lumogen)(註冊商標)F紅305(巴斯夫(BASF)製造)。 Furthermore, Lumogen (registered trademark) as a product of BASF can be listed, including: Lumogen (registered trademark) F Yellow 083 (manufactured by BASF), Lumogen (registered trademark) F Yellow 170 (manufactured by BASF), Lumogen (registered trademark) F Orange 240 (manufactured by BASF), and Lumogen (registered trademark) F Red 305 (manufactured by BASF).

另外,可列舉式(z)所表示的化合物及式(z1)所表示的化合物等。 In addition, compounds represented by formula (z) and compounds represented by formula (z1) can be listed.

Figure 109104792-A0305-02-0294-353
Figure 109104792-A0305-02-0294-353

Figure 109104792-A0305-02-0294-354
Figure 109104792-A0305-02-0294-354

作為顏料,可使用公知的顏料,例如可列舉染料索引(染 色與印染工作者協會(The Society of Dyers and Colourists)出版)中分類為顏料(pigment)的顏料。可單獨使用該些,或者亦可將兩種以上組合使用。 As the pigment, known pigments 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.

具體可列舉:C.I.顏料黃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等黃色顏料;C.I.顏料橙(pigment orange)13、31、36、38、40、42、43、51、55、59、61、64、65、71、73等橙色顏料;C.I.顏料紅(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等紅色顏料;C.I.顏料藍(pigment blue)15、15:1、15:2、15:3、15:4、15:6、16、60等藍色顏料;C.I.顏料紫(pigment violet)1、19、23、29、32、36、38等紫色顏料;C.I.顏料綠(pigment green)7、36、58、59、62、63等綠色顏料;C.I.顏料棕(pigment brown)23、25等棕色顏料;C.I.顏料黑(pigment black)1、7、31、32等黑色顏料。 Specific examples include: C.I. pigment yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 129, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 185, 194, 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; C.I. pigment red Red pigments such as 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, etc.; C.I. pigment blue (pigment blue) 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 60, etc.; C.I. pigment violet (pigment violet) 1, 19, 23, 29, 32, 36, 38, etc.; C.I. pigment green (pigment Green pigments such as C.I. pigment brown (pigment brown) 23, 25, etc.; C.I. pigment black (pigment black) 1, 7, 31, 32, etc.

作為著色劑(A1),較佳為黃色染料及黃色顏料(以下, 存在將該些總稱為「黃色著色劑」的情況)、橙色染料及橙色顏料(以下,存在將該些總稱為「橙色著色劑」的情況)、紅色染料及紅色顏料(以下,存在將該些總稱為「紅色著色劑」的情況)、綠色染料及綠色顏料(以下,存在將該些總稱為「綠色著色劑」的情況),更佳為黃色著色劑及綠色著色劑,進而佳為黃色顏料及綠色顏料,尤佳為綠色顏料。 As the coloring agent (A1), yellow dyes and yellow pigments (hereinafter, these may be collectively referred to as "yellow coloring agents"), orange dyes and orange pigments (hereinafter, these may be collectively referred to as "orange coloring agents"), red dyes and red pigments (hereinafter, these may be collectively referred to as "red coloring agents"), green dyes and green pigments (hereinafter, these may be collectively referred to as "green coloring agents") are preferred, yellow coloring agents and green coloring agents are more preferred, yellow pigments and green pigments are further preferred, and green pigments are particularly preferred.

作為黃色染料,可列舉所述染料中色相被分類為黃的染料,作為黃色顏料,可列舉所述顏料中色相被分類為黃的顏料。 As yellow dyes, dyes whose hue is classified as yellow can be cited, and as yellow pigments, pigments whose hue is classified as yellow can be cited.

作為黃色著色劑,較佳為黃色染料及黃色顏料,更佳為黃色顏料,進而佳為喹酞酮顏料、含有金屬的顏料、異吲哚啉顏料,尤佳為C.I.顏料黃129、138、139、150、185、231,進而尤佳為C.I.顏料黃138、139、150、185、231。 As yellow coloring agents, yellow dyes and yellow pigments are preferred, yellow pigments are more preferred, quinophthalone pigments, metal-containing pigments, isoindoline pigments are further preferred, C.I. Pigment Yellow 129, 138, 139, 150, 185, 231 are particularly preferred, and C.I. Pigment Yellow 138, 139, 150, 185, 231 are further preferred.

作為橙色染料,可列舉所述染料中色相被分類為橙的染料,作為橙色顏料,可列舉所述顏料中色相被分類為橙的顏料。 As orange dyes, dyes whose hue is classified as orange can be cited, and as orange pigments, pigments whose hue is classified as orange can be cited.

作為橙色著色劑,較佳為橙色染料及橙色顏料,更佳為橙色顏料,進而佳為C.I.顏料橙13、31、36、38、40、42、43、51、55、59、61、64、65、71、73。 As orange coloring agents, orange dyes and orange pigments are preferred, orange pigments are more preferred, and C.I. Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73 are further preferred.

作為紅色染料,可列舉所述染料中色相被分類為紅的染料,作為紅色顏料,可列舉所述顏料中色相被分類為紅的顏料。 As red dyes, dyes whose hue is classified as red can be cited, and as red pigments, pigments whose hue is classified as red can be cited.

作為紅色著色劑,較佳為紅色染料及紅色顏料,更佳為偶氮染料、蒽醌染料、三苯基甲烷染料、氧雜蒽染料、苝染料、偶氮顏料、二酮吡咯並吡咯顏料、蒽醌顏料、三苯基甲烷染料、氧雜 蒽顏料及苝顏料,進而佳為C.I.酸性紅52、C.I.顏料紅144、177、179、242、254及269。 As the red coloring agent, red dyes and red pigments are preferred, and azo dyes, anthraquinone dyes, triphenylmethane dyes, oxyanthracene dyes, perylene dyes, azo pigments, diketopyrrolopyrrole pigments, anthraquinone pigments, triphenylmethane dyes, oxyanthracene pigments and perylene pigments are more preferred, and C.I. Acid Red 52, C.I. Pigment Red 144, 177, 179, 242, 254 and 269 are further preferred.

另外,作為黃色著色劑、橙色著色劑或紅色著色劑,亦可使用日本專利特開2013-235257號公報中記載的氧雜蒽化合物等。 In addition, as a yellow colorant, an orange colorant, or a red colorant, an oxyanthracene compound described in Japanese Patent Publication No. 2013-235257 may also be used.

作為綠色染料,可列舉所述染料中色相被分類為綠的染料,作為綠色顏料,可列舉所述顏料中色相被分類為綠的顏料。 As green dyes, dyes whose hue is classified as green can be cited, and as green pigments, pigments whose hue is classified as green can be cited.

作為綠色著色劑,較佳為綠色染料及綠色顏料,更佳為綠色顏料,進而佳為酞菁顏料,尤佳為鹵化銅酞菁顏料、鹵化鋅酞菁顏料及鹵化鋁鋅酞菁顏料,進而尤佳為C.I.顏料綠7、36、58、59、62及63。 As green colorants, green dyes and green pigments are preferred, green pigments are more preferred, phthalocyanine pigments are further preferred, copper phthalocyanine halides, zinc phthalocyanine halides and aluminum zinc phthalocyanine halides are particularly preferred, and C.I. Pigment Green 7, 36, 58, 59, 62 and 63 are further preferred.

[含有著色劑(A1)的液體的製備] [Preparation of liquid containing coloring agent (A1)]

於本發明的著色組成物包含著色劑(A1)的情況下,可在預先製備包含著色劑(A1)與溶劑(E)的含有著色劑(A1)的液體後,使用該含有著色劑(A1)的液體來製備著色組成物。於著色劑(A1)並不溶解於溶劑(E)的情況下,含有著色劑(A1)的液體亦可藉由使著色劑(A1)分散於溶劑(E)中並進行混合來製備。含有著色劑(A1)的液體可包含著色組成物中所含的溶劑(E)的一部分或全部。 When the coloring composition of the present invention contains a coloring agent (A1), a liquid containing a coloring agent (A1) and a solvent (E) may be prepared in advance, and then the coloring composition may be prepared using the liquid containing a coloring agent (A1). When the coloring agent (A1) is not dissolved in the solvent (E), the liquid containing a coloring agent (A1) may be prepared by dispersing the coloring agent (A1) in the solvent (E) and mixing the two. The liquid containing a coloring agent (A1) may contain a part or all of the solvent (E) contained in the coloring composition.

含有著色劑(A1)的液體中的固體成分的含有率相對於含有著色劑(A1)的液體的總量而小於100質量%,較佳為0.01質量%以上且99.99質量%以下,更佳為0.1質量%以上且99.9質 量%以下,進而佳為0.1質量%以上且99質量%以下,尤佳為1質量%以上且90質量%以下,進而尤佳為1質量%以上且80質量%以下,特佳為1質量%以上且70質量%以下,極佳為1質量%以上且60質量%以下,最佳為1質量%以上且50質量%以下。 The content of the solid component in the liquid containing the colorant (A1) is less than 100 mass%, preferably 0.01 mass% or more and 99.99 mass% or less, more preferably 0.1 mass% or more and 99.9 mass% or less, further preferably 0.1 mass% or more and 99 mass% or less, particularly preferably 1 mass% or more and 90 mass% or less, further preferably 1 mass% or more and 80 mass% or less, particularly preferably 1 mass% or more and 70 mass% or less, extremely preferably 1 mass% or more and 60 mass% or less, and most preferably 1 mass% or more and 50 mass% or less.

於含有著色劑(A1)的液體中的固體成分的總量中,含有著色劑(A1)的液體中的著色劑(A1)的含有率為100質量%以下,較佳為0.0001質量%以上且99.9999質量%以下,更佳為0.0001質量%以上且99質量%以下,進而佳為1質量%以上且99質量%以下,尤佳為3質量%以上且99質量%以下,進而尤佳為5質量%以上且99質量%以下。 The content of the colorant (A1) in the liquid containing the colorant (A1) is 100% by mass or less in the total amount of solid components in the liquid containing the colorant (A1), 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, further preferably 1% by mass or more and 99% by mass or less, particularly preferably 3% by mass or more and 99% by mass or less, further particularly preferably 5% by mass or more and 99% by mass or less.

著色劑(A1)視需要亦可實施松香處理、使用導入有酸性基或鹼性基的衍生物等的表面處理、利用高分子化合物等的對著色劑(A1)表面的接枝處理、利用硫酸微粒化法、鹽磨法等的微粒化處理、用於將雜質去除的利用有機溶劑或水等的清洗處理、離子性雜質的利用離子交換法等的去除處理、與化合物(I)相同的結晶結構轉換、粒子的整形及/或粒徑的大致均勻化處理等。著色劑(A1)的粒徑較佳為大致均勻。 The coloring agent (A1) may be subjected to rosin treatment, surface treatment using derivatives with acidic or alkaline groups, grafting treatment on the surface of the coloring agent (A1) using polymer compounds, micronization treatment using sulfuric acid micronization method, salt milling method, etc., cleaning treatment using organic solvents or water to remove impurities, removal treatment of ionic impurities using ion exchange method, etc., crystal structure transformation similar to compound (I), particle shaping and/or particle size roughly uniform treatment, etc. The particle size of the coloring agent (A1) is preferably roughly uniform.

著色劑(A1)藉由含有分散劑並進行分散處理,可設為著色劑(A1)於含有著色劑(A1)的液體中均勻地分散的狀態。著色劑(A1)可分別單獨進行分散處理,亦可混合多種來進行分散處理。 The colorant (A1) can be made uniformly dispersed in a liquid containing the colorant (A1) by containing a dispersant and performing a dispersion treatment. The colorant (A1) can be dispersed individually or by mixing multiple types.

作為分散劑,可列舉界面活性劑等,可為陽離子系、陰 離子系、非離子系以及兩性中的任一種界面活性劑。具體可列舉聚酯系、多胺系及丙烯酸系等界面活性劑等。該些分散劑可單獨使用或將兩種以上組合使用。作為分散劑,若以商品名進行表示,則可列舉:KP(信越化學工業(股)製造)、弗洛倫(Flowlen)(共榮社化學(股)製造)、索努帕斯(Solsperse)(註冊商標)(捷力康(zeneca)(股)製造)、艾夫卡(EFKA)(註冊商標)(巴斯夫(BASF)製造)、阿吉斯帕(Ajisper)(註冊商標)(味之素精細科技(Ajinomoto Fine-Techno)(股)製造)、迪斯帕畢克(DISPERBYK)(註冊商標)(畢克化學(BYK-Chemie)(股)製造)、及畢克(BYK)(註冊商標)(畢克化學(BYK-Chemie)(股)製造)等。 As dispersants, surfactants can be listed, and they can be any of cationic, anionic, nonionic, and amphoteric surfactants. Specifically, polyester-based, polyamine-based, and acrylic-based surfactants can be listed. These dispersants can be used alone or in combination of two or more. Dispersants that are indicated by trade names include KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Flowlen (manufactured by Kyoeisha Chemical Co., Ltd.), Solsperse (registered trademark) (manufactured by Zeneca Co., Ltd.), EFKA (registered trademark) (manufactured by BASF), Ajisper (registered trademark) (manufactured by Ajinomoto Fine-Techno Co., Ltd.), DISPERBYK (registered trademark) (manufactured by BYK-Chemie Co., Ltd.), and BYK (registered trademark) (manufactured by BYK-Chemie Co., Ltd.).

於含有著色劑(A1)的液體含有分散劑的情況下,該分散劑(固體成分)的使用量相對於著色劑(A1)100質量份而例如為0.01質量份以上且10000質量份以下,較佳為0.01質量份以上且5000質量份以下,更佳為0.01質量份以上且1000質量份以下,進而佳為0.1質量份以上且500質量份以下,尤佳為0.1質量份以上且300質量份以下,進而尤佳為1質量份以上且300質量份以下,特佳為5質量份以上且260質量份以下。 When the liquid containing the coloring agent (A1) contains a dispersant, the amount of the dispersant (solid component) used is, for example, 0.01 mass parts or more and 10000 mass parts or less, preferably 0.01 mass parts or more and 5000 mass parts or less, more preferably 0.01 mass parts or more and 1000 mass parts or less, further preferably 0.1 mass parts or more and 500 mass parts or less, particularly preferably 0.1 mass parts or more and 300 mass parts or less, further preferably 1 mass parts or more and 300 mass parts or less, and particularly preferably 5 mass parts or more and 260 mass parts or less, relative to 100 mass parts of the coloring agent (A1).

若該分散劑的使用量處於所述範圍,則存在可獲得更均勻的分散狀態的含有著色劑(A1)的液體的傾向。 If the amount of the dispersant used is within the above range, a liquid containing the colorant (A1) tends to be obtained in a more uniformly dispersed state.

於本發明的著色組成物包含樹脂(B)、且在預先製備包含著色劑(A1)與溶劑(E)的含有著色劑(A1)的液體後使用 該含有著色劑(A1)的液體製備本發明的著色組成物的情況下,含有著色劑(A1)的液體可預先包含著色組成物中所含的樹脂(B)的一部分或全部,較佳為預先包含一部分。藉由預先包含樹脂(B),可進一步改善含有著色劑(A1)的液體的分散穩定性。 The coloring composition of the present invention contains a resin (B), and a liquid containing a coloring agent (A1) containing a coloring agent (A1) and a solvent (E) is prepared in advance and then used. When the liquid containing a coloring agent (A1) is used to prepare the coloring composition of the present invention, the liquid containing a coloring agent (A1) may contain a part or all of the resin (B) contained in the coloring composition in advance, preferably a part in advance. By pre-including the resin (B), the dispersion stability of the liquid containing the coloring agent (A1) can be further improved.

於含有著色劑(A1)的液體含有樹脂(B)的情況下,樹脂(B)的含量相對於著色劑(A1)100質量份而例如為0.01質量份以上且10000質量份以下,較佳為0.01質量份以上且5000質量份以下,更佳為0.01質量份以上且1000質量份以下,進而佳為0.1質量份以上且500質量份以下,尤佳為0.1質量份以上且300質量份以下。 When the liquid containing the coloring agent (A1) contains the resin (B), the content of the resin (B) is, for example, 0.01 parts by mass or more and 10,000 parts by mass or less, preferably 0.01 parts by mass or more and 5,000 parts by mass or less, more preferably 0.01 parts by mass or more and 1,000 parts by mass or less, further preferably 0.1 parts by mass or more and 500 parts by mass or less, and particularly preferably 0.1 parts by mass or more and 300 parts by mass or less, relative to 100 parts by mass of the coloring agent (A1).

於本發明的著色組成物含有著色劑(A1)的情況下,在著色組成物中,將化合物(I)及著色劑(A1)加以合併的著色劑(A)的含有率相對於固體成分的總量而為100質量%以下,較佳為0.0001質量%以上且99.9999質量%以下,更佳為0.0001質量%以上且99質量%以下,進而佳為0.0001質量%以上且90質量%以下,尤佳為0.0001質量%以上且80質量%以下,進而尤佳為0.0001質量%以上且70質量%以下,特佳為0.0001質量%以上且60質量%以下,極佳為0.0001質量%以上且55質量%以下,最佳為0.1質量%以上且55質量%以下。 When the coloring composition of the present invention contains the coloring agent (A1), the content of the coloring agent (A) in the coloring composition, which is a combination of the compound (I) and the coloring agent (A1), 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, relative to the total amount of the solid components. The preferred range is 0.0001 mass% or more and 90 mass% or less, the particularly preferred range is 0.0001 mass% or more and 80 mass% or less, the further preferred range is 0.0001 mass% or more and 70 mass% or less, the particularly preferred range is 0.0001 mass% or more and 60 mass% or less, the extremely preferred range is 0.0001 mass% or more and 55 mass% or less, and the most preferred range is 0.1 mass% or more and 55 mass% or less.

於本發明的著色組成物含有著色劑(A1)的情況下,在著色劑(A)的總量中,化合物(I)的含有率通常為0.0001質量%以上,較佳為0.0003質量%以上,更佳為0.0005質量%以上, 進而佳為0.001質量%以上,上限小於100質量%,較佳為99.9999質量%以下,更佳為99質量%以下,進而佳為98質量%以下,尤佳為97質量%以下。 When the coloring composition of the present invention contains a coloring agent (A1), the content of compound (I) in the total amount of the coloring agent (A) is usually 0.0001 mass % or more, preferably 0.0003 mass % or more, more preferably 0.0005 mass % or more, and further 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, further preferably 98 mass % or less, and particularly preferably 97 mass % or less.

[調平劑(F)] [Leveling agent (F)]

作為調平劑(F),可列舉矽酮系界面活性劑、氟系界面活性劑及具有氟原子的矽酮系界面活性劑等。該些亦可於側鏈具有聚合性基。 As leveling agents (F), silicone-based surfactants, fluorine-based surfactants, and silicone-based surfactants having fluorine atoms can be listed. These may also have polymerizable groups in the side chains.

作為矽酮系界面活性劑,可列舉於分子內具有矽氧烷鍵的界面活性劑等。具體可列舉:東麗矽酮(Toray Silicone)DC3PA、東麗矽酮(Toray Silicone)SH7PA、東麗矽酮(Toray Silicone)DC11PA、東麗矽酮(Toray Silicone)SH21PA、東麗矽酮(Toray Silicone)SH28PA、東麗矽酮(Toray Silicone)SH29PA、東麗矽酮(Toray Silicone)SH30PA、東麗矽酮(Toray Silicone)SH8400(商品名:東麗道康寧(Toray Dow Corning)(股)製造),KP321、KP322、KP323、KP324、KP326、KP340、KP341(信越化學工業(股)製造),TSF400、TSF401、TSF410、TSF4300、TSF4440、TSF4445、TSF4446、TSF4452及TSF4460(日本邁圖高新材料(Momentive Performance Materials Japan)有限責任公司製造)等。 Examples of silicone-based surfactants include surfactants having siloxane bonds in the molecule. Specifically, they include: Toray Silicone DC3PA, Toray Silicone SH7PA, Toray Silicone DC11PA, Toray Silicone SH21PA, Toray Silicone SH28PA, Toray Silicone SH29PA, Toray Silicone SH30PA, Toray Silicone SH8400 (trade name: Toray Dow Corning) Corning (manufactured by), KP321, KP322, KP323, KP324, KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452 and TSF4460 (manufactured by Momentive Performance Materials Japan Co., Ltd.), etc.

作為氟系界面活性劑,可列舉於分子內具有氟碳鏈的界面活性劑等。具體可列舉:弗拉德(Fluorad)(註冊商標)FC430、弗拉德(Fluorad)FC431(住友3M(股)製造),美佳法(Megafac)(註冊商標)F142D、美佳法(Megafac)F171、美佳法(Megafac) F172、美佳法(Megafac)F173、美佳法(Megafac)F177、美佳法(Megafac)F183、美佳法(Megafac)F554、美佳法(Megafac)R30、美佳法(Megafac)RS-718-K(迪愛生(DIC)(股)製造),艾福拓(Eftop)(註冊商標)EF301、艾福拓(Eftop)EF303、艾福拓(Eftop)EF351、艾福拓(Eftop)EF352(三菱材料電子化成(股)製造),沙福隆(Surflon)(註冊商標)S381、沙福隆(Surflon)S382、沙福隆(Surflon)SC101、沙福隆(Surflon)SC105(旭硝子(股)製造)及E5844(大金精細化學(Daikin Fine Chemical)研究所(股)製造)等。 As fluorine-based surfactants, surfactants having fluorine-carbon chains in the molecule can be cited. Specifically, they include: Fluorad (registered trademark) FC430, Fluorad (Fluorad) FC431 (manufactured by Sumitomo 3M Co., Ltd.), Megafac (registered trademark) F142D, Megafac F171, Megafac F172, Megafac F173, Megafac F177, Megafac F183, Megafac F554, Megafac R30, Megafac RS-718-K (manufactured by DIC Corporation), Eftop (registered trademark) EF301, Eftop EF303, Eftop EF351, Eftop EF352 (manufactured by Mitsubishi Materials Corporation), Surflon (registered trademark) S381, Surflon S382, Surflon SC101, Surflon SC105 (manufactured by Asahi Glass Corporation) and E5844 (manufactured by Daikin Fine Chemical Laboratories, Ltd.), etc.

作為具有氟原子的矽酮系界面活性劑,可列舉於分子內具有矽氧烷鍵及氟碳鏈的界面活性劑等。具體可列舉:美佳法(Megafac)(註冊商標)R08、美佳法(Megafac)BL20、美佳法(Megafac)F475、美佳法(Megafac)F477及美佳法(Megafac)F443(迪愛生(DIC)(股)製造)等。 As silicone-based surfactants having fluorine atoms, surfactants having siloxane bonds and fluorocarbon chains in the molecule can be cited. Specifically, Megafac (registered trademark) R08, Megafac BL20, Megafac F475, Megafac F477 and Megafac F443 (manufactured by DIC Corporation) can be cited.

於含有調平劑(F)的情況下,其含量相對於著色組成物的總量而通常為0.00001質量%以上且5質量%以下,較佳為0.00001質量%以上且3質量%以下,更佳為0.0001質量%以上且2質量%以下,進而佳為0.0001質量%以上且1質量%以下。 When a leveling agent (F) is contained, its content is generally 0.00001 mass % or more and 5 mass % or less, preferably 0.00001 mass % or more and 3 mass % or less, more preferably 0.0001 mass % or more and 2 mass % or less, and even more preferably 0.0001 mass % or more and 1 mass % or less, relative to the total amount of the coloring composition.

若調平劑(F)的含量處於所述範圍內,則可使彩色濾光片的平坦性良好。 If the content of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.

[抗氧化劑(G)] [Antioxidant (G)]

就提高著色劑的耐熱性及耐光性的觀點而言,較佳為將抗氧 化劑單獨使用或組合使用兩種以上。作為抗氧化劑,若為工業上通常所使用的抗氧化劑則並無特別限定,可使用酚系抗氧化劑、磷系抗氧化劑及硫系抗氧化劑等。 From the perspective of improving the heat resistance and light resistance of the coloring agent, it is preferred to use an antioxidant alone or in combination of two or more. As an antioxidant, there is no particular limitation as long as it is an antioxidant commonly used in industry, and phenolic antioxidants, phosphorus antioxidants, sulfur antioxidants, etc. can be used.

作為所述酚系抗氧化劑,例如,可列舉:易璐諾斯1010(Irganox 1010:季戊四醇四[3-(3,5-二-第三丁基-4-羥基苯基)丙酸酯],巴斯夫(BASF)製造)、易璐諾斯1076(Irganox 1076:十八烷基-3-(3,5-二-第三丁基-4-羥基苯基)丙酸酯,巴斯夫(BASF)製造)、易璐諾斯1330(Irganox 1330:3,3',3",5,5',5"-六-第三丁基-a,a',a"-(均三甲苯-2,4,6-甲苯甲醯基)三-對甲酚,巴斯夫(BASF)製造)、易璐諾斯3114(Irganox 3114:1,3,5-三(3,5-二-第三丁基-4-羥基苄基)-1,3,5-三嗪-2,4,6(1H,3H,5H)-三酮,巴斯夫(BASF)製造)、易璐諾斯3790(Irganox 3790:1,3,5-三((4-第三丁基-3-羥基-2,6-二甲苯基)甲基)-1,3,5-三嗪-2,4,6(1H,3H,5H)-三酮,巴斯夫(BASF)製造)、易璐諾斯1035(Irganox 1035:硫代二伸乙基雙[3-(3,5-二-第三丁基-4-羥基苯基)丙酸酯],巴斯夫(BASF)製造)、易璐諾斯1135(Irganox 1135:苯丙酸、3,5-雙(1,1-二甲基乙基)-4-羥基、C7-C9側鏈烷基酯,巴斯夫(BASF)製造)、易璐諾斯1520L(Irganox 1520L:4,6-雙(辛基硫基甲基)-鄰甲酚,巴斯夫(BASF)製造)、易璐諾斯3125(Irganox 3125,巴斯夫(BASF)製造)、易璐諾斯565(Irganox 565:2,4-雙(正辛基硫基)-6-(4-羥基-3',5'-二-第三丁基苯胺基)-1,3,5-三嗪,巴斯夫(BASF)製造)、艾迪科斯塔波AO-80(Adekastab AO-80:3,9-雙(2-(3-(3-第三丁基-4-羥基 -5-甲基苯基)丙醯基氧基)-1,1-二甲基乙基)-2,4,8,10-四氧雜螺環(5,5)十一烷、艾迪科(ADEKA)(股)製造)、蘇米萊澤BHT(Sumilizer BHT,住友化學(股)製造)、蘇米萊澤GA-80(Sumilizer GA-80,住友化學(股)製造)、蘇米萊澤GS(Sumilizer GS,住友化學(股)製造)、夏諾克斯1790(Cyanox 1790,氰特(Cytec)(股)製造)及維他命(Vitamin)E(衛材(Eisai)(股)製造)等。 As the phenolic antioxidant, for example, there can be cited: Irganox 1010 (Irganox 1010: pentaerythritol tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl) propionate], manufactured by BASF), Irganox 1076 (Irganox 1076: octadecyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl) propionate, manufactured by BASF), Irganox 1330 (Irganox 1330: 3,3',3",5,5',5"-hexa-tert-butyl-a,a',a"-(mesitylene-2,4,6-toluyl) tri-p-cresol, manufactured by BASF), Irganox 3114 (Irganox 3114: 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione, manufactured by BASF), Irganox 3790 (Irganox 3790: 1,3,5-tris((4-tert-butyl-3-hydroxy-2,6-xylyl)methyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione, manufactured by BASF), Irganox 1035 (Irganox 1035: thiodiethylenebis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], manufactured by 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(octylthiomethyl)-o-cresol, manufactured by BASF), Irganox 3125 (Irganox 3125, manufactured by BASF), Irganox 565 (Irganox 565: 2,4-bis(n-octylthio)-6-(4-hydroxy-3',5'-di-tert-butylanilino)-1,3,5-triazine, manufactured by BASF), Adekastab AO-80 (Adekastab AO-80: 3,9-bis(2-(3-(3-tert-butyl-4-hydroxyl -5-methylphenyl)propionyloxy)-1,1-dimethylethyl)-2,4,8,10-tetraoxahyspiro(5,5)undecane, manufactured by ADEKA Co., Ltd.), Sumilizer BHT (manufactured by Sumitomo Chemical Co., Ltd.), Sumilizer GA-80 (manufactured by Sumitomo Chemical Co., Ltd.), Sumilizer GS (manufactured by Sumitomo Chemical Co., Ltd.), Cyanox 1790 (manufactured by Cytec Co., Ltd.) and Vitamin E (manufactured by Eisai Co., Ltd.), etc.

作為所述磷系抗氧化劑,例如,可列舉:易璐佛斯168(Irgafos 168:三(2,4-二-第三丁基苯基)亞磷酸酯,巴斯夫(BASF)製造)、易璐佛斯12(Irgafos 12:三[2-[[2,4,8,10-四-第三丁基二苯並[d,f][1,3,2]二氧雜膦-6-基]氧基]乙基]胺,巴斯夫(BASF)製造)、易璐佛斯38(Irgafos 38:雙(2,4-雙(1,1-二甲基乙基)-6-甲基苯基)乙基酯亞磷酸,巴斯夫(BASF)製造)、艾迪科斯塔波(Adekastab)329K(艾迪科(ADEKA)(股)製造)、艾迪科斯塔波(Adekastab)PEP36(艾迪科(ADEKA)(股)製造)、艾迪科斯塔波(Adekastab)PEP-8(艾迪科(ADEKA)(股)製造)、桑得斯塔波(Sandstab)P-EPQ(科萊恩(Clariant)公司製造)、韋斯頓618(Weston 618,GE公司製造)、韋斯頓619G(Weston 619G,GE公司製造)、烏特拉諾克斯626(Ultranox 626,GE公司製造)及蘇米萊澤GP(Sumilizer GP:6-[3-(3-第三丁基-4-羥基-5-甲基苯基)丙氧基]-2,4,8,10-四-第三丁基二苯並[d,f][1.3.2]二氧雜磷雜庚英)(住友化學(股)製造)等。 As the phosphorus-based antioxidant, for example, there can be cited: Irgafos 168 (Irgafos 168: tris (2,4-di-tert-butylphenyl) phosphite, manufactured by BASF), Irgafos 12 (Irgafos 12: tris [2- [[2,4,8,10-tetra-tert-butyl dibenzo [d, f] [1,3,2] dioxaphosphin-6-yl] oxy] ethyl] amine, manufactured by BASF), Irgafos 38 (Irgafos 38: Bis(2,4-bis(1,1-dimethylethyl)-6-methylphenyl)ethyl phosphite, manufactured by BASF), Adekastab 329K (manufactured by ADEKA), Adekastab PEP36 (manufactured by ADEKA), Adekastab PEP-8 (manufactured by ADEKA), Sandstab P-EPQ (manufactured by Clariant), Weston 618 (manufactured by GE), Weston 619G (manufactured by GE), Ultranox 626 (manufactured by 626, manufactured by GE) and Sumilizer GP (Sumilizer GP: 6-[3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propoxy]-2,4,8,10-tetra-tert-butyldibenzo[d,f][1.3.2]dioxophosphin) (manufactured by Sumitomo Chemical Co., Ltd.), etc.

作為所述硫系抗氧化劑,例如,可列舉:硫代二丙酸二月桂基酯、硫代二丙酸二豆蔻基酯或硫代二丙酸二硬脂基酯等硫代二丙酸二烷基酯化合物及四[亞甲基(3-十二烷基硫基)丙酸酯]甲烷等多元醇的β-烷基巰基丙酸酯化合物等。 As the sulfur-based antioxidant, for example, there can be listed: dialkyl thiodipropionate compounds such as dilauryl thiodipropionate, dimyristyl thiodipropionate or distearyl thiodipropionate, and β-alkyl propionate compounds of polyols such as tetrakis[methylene(3-dodecylthio)propionate]methane, etc.

[其他成分] [Other ingredients]

本發明的著色組成物視需要亦可包含填充劑、其他高分子化合物、密接促進劑、光穩定劑、鏈轉移劑等該技術領域中公知的添加劑。 The coloring composition of the present invention may also contain fillers, other polymer compounds, adhesion promoters, light stabilizers, chain transfer agents and other additives known in the technical field as needed.

作為密接促進劑,例如,可列舉:乙烯基三甲氧基矽烷、乙烯基三乙氧基矽烷、乙烯基三(2-甲氧基乙氧基)矽烷、3-縮水甘油基氧基丙基三甲氧基矽烷、3-縮水甘油氧基丙基甲基二甲氧基矽烷、3-縮水甘油氧基丙基甲基二乙氧基矽烷、2-(3,4-環氧環己基)乙基三甲氧基矽烷、3-氯丙基甲基二甲氧基矽烷、3-氯丙基三甲氧基矽烷、3-甲基丙烯醯基氧基丙基三甲氧基矽烷、3-巰基丙基三甲氧基矽烷、3-硫基丙基三甲氧基矽烷、3-異氰酸酯基丙基三乙氧基矽烷、N-2-(胺基乙基)-3-胺基丙基甲基二甲氧基矽烷、N-2-(胺基乙基)-3-胺基丙基甲基二乙氧基矽烷、N-2-(胺基乙基)-3-胺基丙基三甲氧基矽烷、N-2-(胺基乙基)-3-胺基丙基甲基二乙氧基矽烷、3-胺基丙基三甲氧基矽烷、3-胺基丙基三乙氧基矽烷、N-苯基-3-胺基丙基三甲氧基矽烷及N-苯基-3-胺基丙基三乙氧基矽烷等。 Examples of the adhesion promoter include vinyl trimethoxysilane, vinyl triethoxysilane, vinyl tri(2-methoxyethoxy)silane, 3-glycidyloxypropyl trimethoxysilane, 3-glycidyloxypropyl methyl dimethoxysilane, 3-glycidyloxypropyl methyl diethoxysilane, 2-(3,4-epoxycyclohexyl)ethyl trimethoxysilane, 3-chloropropyl methyl dimethoxysilane, 3-chloropropyl trimethoxysilane, 3-methacryloyloxypropyl trimethoxysilane, 3-butyl propyl trimethoxysilane, 3-thiophene propyl trimethoxysilane, 3-isocyanate propyl triethoxysilane, N-2-(aminoethyl)-3-aminopropyl methyl dimethoxysilane, N-2-(aminoethyl)-3-aminopropyl methyl diethoxysilane, N-2-(aminoethyl)-3-aminopropyl trimethoxysilane, N-2-(aminoethyl)-3-aminopropyl methyl diethoxysilane, 3-aminopropyl trimethoxysilane, 3-aminopropyl triethoxysilane, N-phenyl-3-aminopropyl trimethoxysilane and N-phenyl-3-aminopropyl triethoxysilane, etc.

[著色組成物的製造方法] [Method for producing coloring composition]

本發明的著色組成物例如可藉由將化合物(I)、溶劑(E)、 及視需要的樹脂(B)、聚合性化合物(C)、聚合起始劑(D)、聚合起始助劑(D1)、著色劑(A1)、調平劑(F)、抗氧化劑(G)及/或其他成分混合來製備。混合可藉由公知或慣用的裝置或條件來進行。 The coloring composition of the present invention can be prepared by mixing, for example, compound (I), solvent (E), and, if necessary, resin (B), polymerizable compound (C), polymerization initiator (D), polymerization initiator aid (D1), coloring agent (A1), leveling agent (F), antioxidant (G) and/or other components. The mixing can be performed by known or conventional devices or conditions.

化合物(I)較佳為以含有化合物(I)的液體的狀態使用,所述含有化合物(I)的液體是將化合物(I)預先與溶劑(E)的一部分或全部混合,並使用珠磨機等分散至化合物(I)的平均粒子徑為0.2μm以下左右而成。此時,視需要可調配所述分散劑、樹脂(B)的一部分或全部。 Compound (I) is preferably used in the form of a liquid containing compound (I), wherein the liquid containing compound (I) is prepared by mixing compound (I) with a part or all of solvent (E) in advance and dispersing compound (I) using a bead mill or the like until the average particle size of compound (I) is about 0.2 μm or less. At this time, part or all of the dispersant and resin (B) may be prepared as needed.

著色劑(A1)較佳為以含有著色劑(A1)的液體的狀態使用,所述含有著色劑(A1)的液體是將著色劑(A1)預先與溶劑(E)的一部分或全部混合,並使用珠磨機等分散至著色劑(A1)的平均粒子徑為0.2μm以下左右而成。此時,視需要可調配所述分散劑、樹脂(B)的一部分或全部。 The colorant (A1) is preferably used in the form of a liquid containing the colorant (A1), wherein the liquid containing the colorant (A1) is prepared by pre-mixing the colorant (A1) with a part or all of the solvent (E), and dispersing the colorant (A1) using a bead mill or the like until the average particle size of the colorant (A1) is about 0.2 μm or less. At this time, a part or all of the dispersant and the resin (B) may be prepared as needed.

化合物(I)較佳為以預先溶解於溶劑(E)的一部分或全部中而成的溶液(該溶液包含於含有化合物(I)的液體中)的狀態使用。進而,較佳為利用孔徑0.01μm以上且1μm以下左右的過濾器對該含有化合物(I)的液體進行過濾。 The compound (I) is preferably used in the form of a solution pre-dissolved in a part or all of the solvent (E) (the solution is contained in the liquid containing the compound (I)). Furthermore, it is preferred to filter the liquid containing the compound (I) using a filter having a pore size of about 0.01 μm or more and about 1 μm or less.

著色劑(A1)較佳為以預先溶解於溶劑(E)的一部分或全部中而成的溶液(該溶液包含於含有著色劑(A1)的液體中)的狀態使用。進而,較佳為利用孔徑0.01μm以上且1μm以下左右的過濾器對該含有著色劑(A1)的液體進行過濾。 The coloring agent (A1) is preferably used in the form of a solution pre-dissolved in a part or all of the solvent (E) (the solution is contained in the liquid containing the coloring agent (A1)). Furthermore, it is preferred to filter the liquid containing the coloring agent (A1) using a filter with a pore size of about 0.01 μm or more and about 1 μm or less.

較佳為利用孔徑0.01μm以上且10μm以下左右的過濾器對混合後的著色組成物進行過濾。 It is preferred to filter the mixed coloring composition using a filter with a pore size of about 0.01 μm or more and about 10 μm or less.

[彩色濾光片] [Color filter]

可由本發明的著色組成物形成彩色濾光片。 A color filter can be formed from the coloring composition of the present invention.

將著色組成物塗佈於基板上,去除溶劑等揮發成分並加以乾燥,藉此可形成著色塗膜。如此形成的著色塗膜包含於本發明的彩色濾光片中。 The coloring composition is applied on a substrate, volatile components such as solvents are removed and dried to form a coloring film. The coloring film thus formed is included in the color filter of the present invention.

作為形成著色圖案的方法,可列舉光微影法、噴墨法、印刷法等。其中,較佳為光微影法。光微影法是於基板上塗佈所述著色組成物,使其乾燥而形成著色組成物層,並介隔光罩對該著色組成物層進行曝光且進行顯影的方法。於光微影法中,藉由在曝光時不使用光罩、及/或不進行顯影,可形成作為所述著色組成物層的硬化物的著色塗膜。如此形成的著色圖案或著色塗膜為本發明的彩色濾光片。 As methods for forming a coloring pattern, photolithography, inkjet, printing, etc. can be cited. Among them, photolithography is preferred. Photolithography is a method of coating the coloring composition on a substrate, drying it to form a coloring composition layer, and exposing and developing the coloring composition layer through a photomask. In photolithography, by not using a photomask during exposure and/or not developing, a coloring film can be formed as a cured product of the coloring composition layer. The coloring pattern or coloring film formed in this way is the color filter of the present invention.

製作的彩色濾光片的膜厚並無特別限定,可根據目的或用途等適宜調整,例如為0.1μm~30μm,較佳為0.1μm~20μm,進而佳為0.5μm~6μm。 The film thickness of the produced color filter is not particularly limited and can be appropriately adjusted according to the purpose or use, for example, 0.1μm~30μm, preferably 0.1μm~20μm, and more preferably 0.5μm~6μm.

作為基板,可使用石英玻璃、硼矽酸玻璃、氧化鋁矽酸鹽玻璃、對表面進行二氧化矽塗佈而成的鈉鈣玻璃等玻璃板、或聚碳酸酯、聚甲基丙烯酸甲酯、聚對苯二甲酸乙二酯等樹脂板、矽、於所述基板上形成有鋁、銀、銀/銅/鈀合金薄膜等者。於該些基底上亦可形成其他彩色濾光片層、樹脂層、電晶體及電路等。 As the substrate, quartz glass, borosilicate glass, alumina silicate glass, sodium calcium glass with silicon dioxide coated on the surface, or resin plates such as polycarbonate, polymethyl methacrylate, polyethylene terephthalate, silicon, and aluminum, silver, silver/copper/palladium alloy thin films formed on the substrate can be used. Other color filter layers, resin layers, transistors, circuits, etc. can also be formed on these substrates.

利用光微影法進行的各色畫素的形成可藉由公知或慣用的裝置或條件來進行。例如,可以如下方式來製作。 The formation of pixels of various colors by photolithography can be performed by known or conventional devices or conditions. For example, it can be produced in the following manner.

首先,將著色組成物塗佈於基板上,藉由進行加熱乾燥(預烘烤)及/或減壓乾燥來去除溶劑等揮發成分並使其乾燥,獲得平滑的著色組成物層。 First, the coloring composition is applied to the substrate, and then volatile components such as solvents are removed and dried by heat drying (pre-baking) and/or reduced pressure drying to obtain a smooth coloring composition layer.

作為塗佈方法,可列舉旋塗法、狹縫塗佈法以及狹縫與旋塗法等。 As coating methods, there are rotary coating, slit coating, and slit and rotary coating.

進行加熱乾燥時的溫度較佳為30℃~120℃,更佳為50℃~110℃。另外,作為加熱時間,較佳為10秒~60分鐘,更佳為30秒~30分鐘。於進行減壓乾燥的情況下,較佳為於50Pa~150Pa壓力下、20℃~25℃的溫度範圍內進行。著色組成物層的膜厚並無特別限定,只要根據目標彩色濾光片的膜厚適宜選擇即可。 The temperature for heating and drying is preferably 30℃~120℃, more preferably 50℃~110℃. In addition, the heating time is preferably 10 seconds~60 minutes, more preferably 30 seconds~30 minutes. When performing reduced pressure drying, it is preferably carried out at a pressure of 50Pa~150Pa and a temperature range of 20℃~25℃. The film thickness of the coloring composition layer is not particularly limited, as long as it is appropriately selected according to the film thickness of the target color filter.

其次,對著色組成物層介隔用於形成目標著色圖案的光罩進行曝光。 Secondly, the coloring composition layer is interposed with a photomask for forming a target coloring pattern.

該光罩上的圖案並無特別限定,可使用與目標用途相應的圖案。作為曝光中所使用的光源,較佳為產生250nm~450nm的波長的光的光源。例如,可對於小於350nm的光,使用截止該波長區域的濾光片進行截止,或者對於436nm附近、408nm附近、365nm附近的光,使用取出該些波長區域的帶通濾光片進行選擇性取出。作為光源的具體例,可列舉水銀燈、發光二極體、金屬鹵化物燈及鹵素燈。 The pattern on the mask is not particularly limited, and a pattern corresponding to the target application can be used. As the light source used in the exposure, it is preferably a light source that generates light with a wavelength of 250nm~450nm. For example, for light less than 350nm, a filter that cuts off the wavelength region can be used to cut off, or for light near 436nm, near 408nm, and near 365nm, a bandpass filter that takes out these wavelength regions can be used to selectively take out. As specific examples of light sources, mercury lamps, light-emitting diodes, metal halide lamps, and halogen lamps can be listed.

為了對曝光面整體均勻地照射平行光線、或者可進行光罩與 形成有著色組成物層的基板的準確的位置對準,較佳為使用遮罩對準器及步進機等曝光裝置。 In order to evenly irradiate the entire exposure surface with parallel light or to accurately align the position of the mask and the substrate on which the colored component layer is formed, it is preferable to use an exposure device such as a mask aligner and a stepper.

藉由使曝光後的著色組成物層接觸顯影液來進行顯影,而於基板上形成著色圖案。藉由顯影,著色組成物層的未曝光部溶解於顯影液中而被去除。 The exposed coloring composition layer is brought into contact with a developer to form a coloring pattern on the substrate. By developing, the unexposed portion of the coloring composition layer is dissolved in the developer and removed.

作為顯影液,例如較佳為氫氧化鉀、碳酸氫鈉、碳酸鈉及氫氧化四甲基銨等鹼性化合物的水溶液。 As a developer, preferably, an aqueous solution of an alkaline compound such as potassium hydroxide, sodium bicarbonate, sodium carbonate, and tetramethylammonium hydroxide is used.

鹼性化合物的濃度較佳為0.01質量%~10質量%,更佳為0.02質量%~5質量%。顯影液可包含界面活性劑。 The concentration of the alkaline compound is preferably 0.01 mass% to 10 mass%, and more preferably 0.02 mass% to 5 mass%. The developer may contain a surfactant.

顯影方法可為覆液法、浸漬法及噴霧法等的任一種。進而,顯影時,可使基板以任意角度傾斜。 The developing method can be any of the liquid coating method, immersion method and spray method. Furthermore, during the development, the substrate can be tilted at any angle.

顯影後的基板較佳為經水洗。 The substrate is preferably washed with water after development.

進而,較佳為對所獲得的著色圖案進行後烘烤。 Furthermore, it is preferred to post-bake the obtained colored pattern.

後烘烤溫度較佳為150℃~250℃,更佳為160℃~235℃。後烘烤時間較佳為1分鐘~120分鐘,更佳為10分鐘~60分鐘。如此所獲得的著色圖案或著色塗膜即彩色濾光片為了賦予各種特性亦可進而供於表面塗佈處理中。 The post-baking temperature is preferably 150℃~250℃, more preferably 160℃~235℃. The post-baking time is preferably 1 minute~120 minutes, more preferably 10 minutes~60 minutes. The colored pattern or colored coating film obtained in this way, i.e., the color filter, can also be used in surface coating treatment in order to impart various properties.

所述彩色濾光片作為顯示裝置(例如,液晶顯示裝置、有機電致發光(electroluminescence,EL)裝置、電子紙等)以及固體攝像元件中所使用的彩色濾光片、尤其是作為液晶顯示裝置中所使用的彩色濾光片而有用。 The color filter is useful as a color filter used in display devices (e.g., liquid crystal display devices, organic electroluminescence (EL) devices, electronic paper, etc.) and solid-state imaging elements, and is particularly useful as a color filter used in liquid crystal display devices.

本申請案主張基於在2019年2月18日提出申請的日本 專利申請案第2019-026911號的優先權的利益。將在2019年2月18日提出申請的日本專利申請案第2019-026911號的說明書的全部內容引用至本申請案,以進行參考。 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 herein by reference.

[實施例] [Implementation example]

以下,列舉實施例來更具體地說明本發明,但本發明根本不受下述實施例的限制,當然亦能夠於可適合所述及後述主旨的範圍內適當施加變更而實施,該些均包含於本發明的技術範圍內。再者,以下,只要無特別說明,則「份」是指「質量份」,「%」是指「質量%」。 The following examples are given to more specifically illustrate the present invention, but the present invention is not limited to the following examples at all, and can of course be implemented with appropriate changes within the scope of the above and the following subject matter, all of which are included in the technical scope of the present invention. Furthermore, below, unless otherwise specified, "parts" means "parts by mass" and "%" means "% by mass".

以下的合成例中,化合物的結構是藉由質量分析(LC;安捷倫(Agilent)製造的1200型、MASS;安捷倫(Agilent)製造的LC/MSD6130型)來確認。 In the following synthesis examples, the structures of the compounds were confirmed by mass analysis (LC; Model 1200 manufactured by Agilent, MASS; Model LC/MSD6130 manufactured by Agilent).

樹脂的聚苯乙烯換算的重量平均分子量(Mw)及數量平均分子量(Mn)的測定是藉由凝膠滲透層析法(Gel Permeation Chromatography,GPC)並利用以下條件進行。 The polystyrene-equivalent weight average molecular weight (Mw) and number average molecular weight (Mn) of the resin were determined by gel permeation chromatography (GPC) under the following conditions.

裝置:HLC-8120GPC(東曹(Tosoh)(股)製造) Device: HLC-8120GPC (manufactured by Tosoh Co., Ltd.)

管柱:TSK-GELG2000HXL Column: TSK-GELG2000HXL

管柱溫度:40℃ Column temperature: 40℃

溶媒:四氫呋喃 Solvent: Tetrahydrofuran

流速:1.0mL/分鐘 Flow rate: 1.0mL/min

分析試樣的固體成分濃度:0.001質量%~0.01質量% Solid content concentration of the analyzed sample: 0.001 mass%~0.01 mass%

注入量:50μL Injection volume: 50μL

檢測器:RI Detector: RI

校正用標準物質:TSK標準聚苯乙烯(TSK STANDARD POLYSTYRENE)F-40、F-4、F-288、A-2500、A-500(東曹(Tosoh)(股)製造) Standard materials for calibration: TSK standard polystyrene F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Co., Ltd.)

將所述所獲得的聚苯乙烯換算的重量平均分子量(Mw)及數量平均分子量(Mn)的比(Mw/Mn)設為分散度。 The ratio (Mw/Mn) of the obtained polystyrene-converted weight average molecular weight (Mw) and number average molecular weight (Mn) is defined as the dispersion degree.

實施例1 Implementation Example 1

將4-胺基-2-甲基喹啉(東京化成工業(股)製造)3.02份、2,3-萘二羧酸酐(東京化成工業(股)製造)8.33份、苯甲酸(東京化成工業(股)製造)11.7份及苯甲酸甲酯(東京化成工業(股)製造)66.7份混合。 Mix 3.02 parts of 4-amino-2-methylquinoline (manufactured by Tokyo Chemical Industry Co., Ltd.), 8.33 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 66.7 parts of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.).

將該混合物一邊保持為170℃一邊攪拌9小時。 The mixture was stirred for 9 hours while being maintained at 170°C.

於該混合物中加入2,3-萘二羧酸酐(東京化成工業(股)製造)13.6份、苯甲酸(東京化成工業(股)製造)22.9份及苯甲酸甲酯(東京化成工業(股)製造)66.4份。 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 66.4 parts of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.) were added to the mixture.

將該混合物一邊保持為170℃一邊攪拌49小時。 The mixture was stirred for 49 hours while being maintained at 170°C.

於該混合物中加入2,3-萘二羧酸酐(東京化成工業(股)製造)8.32份、苯甲酸(東京化成工業(股)製造)11.7份及苯甲酸甲酯(東京化成工業(股)製造)43.5份。 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 43.5 parts of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.) were added to the mixture.

將該混合物一邊保持為170℃一邊攪拌28小時。 The mixture was stirred for 28 hours while being maintained at 170°C.

將該混合物冷卻至室溫,於該混合物中加入甲醇1300份。 The mixture was cooled to room temperature and 1300 parts of methanol were added to the mixture.

對該混合物於室溫下進行攪拌後,進行過濾,並利用甲醇400 份對所獲得的殘渣進行7次清洗。 The mixture was stirred at room temperature, filtered, and the obtained residue was washed 7 times with 400 parts of methanol.

於60℃下對所獲得的殘渣進行減壓乾燥。 The obtained residue was dried under reduced pressure at 60°C.

於該殘渣中加入N,N-二甲基甲醯胺875份。 Add 875 parts of N,N-dimethylformamide to the residue.

對該混合物於室溫下進行攪拌後,進行過濾,並利用與所獲得的殘渣為相同體積的N,N-二甲基甲醯胺對所獲得的殘渣進行3次清洗。 After the mixture was stirred at room temperature, it was filtered and the residue was washed three times with the same volume of N,N-dimethylformamide as the residue.

利用甲醇200份對該殘渣進行3次清洗。 The residue was washed three times with 200 parts of methanol.

於60℃下對所獲得的殘渣進行減壓乾燥,獲得式(Ia2)所表示的化合物7.25份。 The obtained residue was dried under reduced pressure at 60°C to obtain 7.25 parts of the compound represented by formula (Ia2).

Figure 109104792-A0305-02-0312-211
Figure 109104792-A0305-02-0312-211

<式(Ia2)所表示的化合物的鑑定> <Identification of the compound represented by formula (Ia2)>

(質量分析)離子化模式=ESI+:m/z=[M+H]+519 (Mass analysis) Ionization mode = ESI+: m/z = [M+H] + 519

(質量分析)離子化模式=ESI-:m/z=[M-H]-517 (Mass analysis) Ionization mode = ESI-: m/z = [MH] - 517

精確質量(Exact Mass):518 Exact Mass: 518

實施例2 Example 2

將4-胺基-2-甲基喹啉(東京化成工業(股)製造)2.05份、四氯鄰苯二甲酸酐(東京化成工業(股)製造)8.16份、苯甲酸(東京化成工業(股)製造)8.05份及苯甲酸甲酯(東京化成工業(股)製造)58.6份混合。 Mix 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.), 8.05 parts of benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.), and 58.6 parts of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.).

將該混合物一邊保持為170℃一邊攪拌5小時。 The mixture was stirred for 5 hours while being maintained at 170°C.

於該混合物中加入四氯鄰苯二甲酸酐(東京化成工業(股)製造)3.72份、苯甲酸(東京化成工業(股)製造)8.00份及苯甲酸甲酯(東京化成工業(股)製造)18.0份。 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 18.0 parts of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.) were added to the mixture.

將該混合物一邊保持為170℃一邊攪拌6小時。 The mixture was stirred for 6 hours while being maintained at 170°C.

於該混合物中加入四氯鄰苯二甲酸酐(東京化成工業(股)製造)1.89份、苯甲酸(東京化成工業(股)製造)4.09份及苯甲酸甲酯(東京化成工業(股)製造)54.5份。 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 54.5 parts of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.) were added to the mixture.

將該混合物一邊保持為170℃一邊攪拌6小時。 The mixture was stirred for 6 hours while being maintained at 170°C.

於該混合物中加入四氯鄰苯二甲酸酐(東京化成工業(股)製造)11.4份、苯甲酸(東京化成工業(股)製造)12.6份及苯甲酸甲酯(東京化成工業(股)製造)18.4份。 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 18.4 parts of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.) were added to the mixture.

將該混合物一邊保持為170℃一邊攪拌16小時。 The mixture was stirred for 16 hours while being maintained at 170°C.

將該混合物冷卻至室溫,於該混合物中加入甲醇1200份。 The mixture was cooled to room temperature and 1200 parts of methanol were added to the mixture.

對該混合物於室溫下進行攪拌後,進行過濾,並利用甲醇400份對所獲得的殘渣進行8次清洗。 The mixture was stirred at room temperature, filtered, and the obtained residue was washed 8 times with 400 parts of methanol.

於60℃下對所獲得的殘渣進行減壓乾燥,獲得式(Ia23)所表示的化合物8.88份。 The obtained residue was dried under reduced pressure at 60°C to obtain 8.88 parts of the compound represented by formula (Ia23).

Figure 109104792-A0305-02-0314-212
Figure 109104792-A0305-02-0314-212

<式(Ia23)所表示的化合物的鑑定> <Identification of the compound represented by formula (Ia23)>

(質量分析)離子化模式=ESI+:m/z=[M+H]+691 (Mass analysis) Ionization mode = ESI+: m/z = [M+H] + 691

(質量分析)離子化模式=ESI-:m/z=[M-H]-689 (Mass analysis) Ionization mode = ESI-: m/z = [MH] - 689

精確質量(Exact Mass):690 Exact Mass: 690

實施例3 Implementation Example 3

將4-胺基-2-甲基喹啉(東京化成工業(股)製造)1.01份、4-苯基乙炔基鄰苯二甲酸酐(東京化成工業(股)製造)3.49份、苯甲酸(東京化成工業(股)製造)3.95份及苯甲酸甲酯(東京化成工業(股)製造)28.7份混合。 Mix 1.01 parts of 4-amino-2-methylquinoline (manufactured by Tokyo Chemical Industry Co., Ltd.), 3.49 parts of 4-phenylethynylphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 3.95 parts of benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.), and 28.7 parts of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.).

將該混合物一邊保持為170℃一邊攪拌20小時。 The mixture was stirred for 20 hours while being maintained at 170°C.

於該混合物中加入4-苯基乙炔基鄰苯二甲酸酐(東京化成工業(股)製造)0.476份、苯甲酸(東京化成工業(股)製造)1.32份及苯甲酸甲酯(東京化成工業(股)製造)3.3份。 0.476 parts of 4-phenylethynylphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 1.32 parts of benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) and 3.3 parts of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.) were added to the mixture.

將該混合物一邊保持為170℃一邊攪拌10小時。 The mixture was stirred for 10 hours while being maintained at 170°C.

於該混合物中加入4-苯基乙炔基鄰苯二甲酸酐(東京化成工業(股)製造)0.801份、苯甲酸(東京化成工業(股)製造)2.90份及苯甲酸甲酯(東京化成工業(股)製造)9.13份。 0.801 parts of 4-phenylethynylphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 2.90 parts of benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) and 9.13 parts of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.) were added to the mixture.

將該混合物一邊保持為170℃一邊攪拌29小時。 The mixture was stirred for 29 hours while being maintained at 170°C.

將該混合物冷卻至室溫,於該混合物中加入甲醇400份並攪拌1小時。 The mixture was cooled to room temperature, 400 parts of methanol was added to the mixture and stirred for 1 hour.

對該混合物進行過濾,並利用甲醇140份對所獲得的殘渣進行6次清洗。 The mixture was filtered and the obtained residue was washed 6 times with 140 parts of methanol.

於60℃下對所獲得的殘渣進行減壓乾燥,獲得式(Ia22)所表示的化合物3.12份。 The obtained residue was dried under reduced pressure at 60°C to obtain 3.12 parts of the compound represented by formula (Ia22).

Figure 109104792-A0305-02-0315-213
Figure 109104792-A0305-02-0315-213

<式(Ia22)所表示的化合物的鑑定> <Identification of the compound represented by formula (Ia22)>

(質量分析)離子化模式=ESI+:m/z=[M+H]+619 (Mass analysis) Ionization mode = ESI+: m/z = [M+H] + 619

(質量分析)離子化模式=ESI-:m/z=[M-H]-617 (Mass analysis) Ionization mode = ESI-: m/z = [MH] - 617

精確質量(Exact Mass):618 Exact Mass: 618

實施例4 Example 4

將4-胺基-2-甲基喹啉(東京化成工業(股)製造)4.04份、偏苯三甲酸酐(東京化成工業(股)製造)10.8份、苯甲酸(東京化成工業(股)製造)15.6份及苯甲酸甲酯(東京化成工業(股)製造)92.3份混合。 Mix 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.), 15.6 parts of benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.), and 92.3 parts of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.).

將該混合物一邊保持為167℃一邊攪拌5小時。 The mixture was stirred for 5 hours while being maintained at 167°C.

於該混合物中加入苯甲酸甲酯(東京化成工業(股)製造)40.2份。 40.2 parts of methyl benzoate (produced by Tokyo Chemical Industry Co., Ltd.) were added to the mixture.

將該混合物一邊保持為167℃一邊攪拌9小時。 The mixture was stirred for 9 hours while being maintained at 167°C.

於該混合物中加入苯甲酸甲酯(東京化成工業(股)製造)28.0份。 28.0 parts of methyl benzoate (produced by Tokyo Chemical Industry Co., Ltd.) was added to the mixture.

將該混合物一邊保持為170℃一邊攪拌11小時。 The mixture was stirred for 11 hours while being maintained at 170°C.

將該混合物冷卻至室溫,於該混合物中加入甲醇2000份。 The mixture was cooled to room temperature and 2000 parts of methanol were added to the mixture.

於室溫下對該混合物進行攪拌。 The mixture was stirred at room temperature.

於所獲得的混合物中加入甲醇173份。 173 parts of methanol were added to the obtained mixture.

對該混合物進行過濾,並對所獲得的殘渣利用甲醇124份進行1次清洗、利用甲醇160份進行1次清洗、利用甲醇400份進行1次清洗。 The 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.

於60℃下對所獲得的殘渣進行減壓乾燥,獲得式(Ia10)所 表示的化合物、式(Ia2143)所表示的化合物、式(Ia850)所表示的化合物及式(Ia315)所表示的化合物的混合物9.91份。 The obtained residue was dried under reduced pressure at 60°C to obtain 9.91 parts of a mixture of 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).

Figure 109104792-A0305-02-0317-214
Figure 109104792-A0305-02-0317-214

<式(Ia10)所表示的化合物的鑑定> <Identification of the compound represented by formula (Ia10)>

(質量分析)離子化模式=ESI+:m/z=[M+H]+507 (Mass analysis) Ionization mode = ESI+: m/z = [M+H] + 507

(質量分析)離子化模式=ESI-:m/z=[M-H]-505 (Mass analysis) Ionization mode = ESI-: m/z = [MH] - 505

精確質量(Exact Mass):506 Exact Mass: 506

[化106]

Figure 109104792-A0305-02-0318-215
[Chemistry 106]
Figure 109104792-A0305-02-0318-215

<式(Ia2143)所表示的化合物的鑑定> <Identification of the compound represented by formula (Ia2143)>

(質量分析)離子化模式=ESI+:m/z=[M+H]+521 (Mass analysis) Ionization mode = ESI+: m/z = [M+H] + 521

(質量分析)離子化模式=ESI-:m/z=[M-H]-519 (Mass analysis) Ionization mode = ESI-: m/z = [MH] - 519

精確質量(Exact Mass):520 Exact Mass: 520

Figure 109104792-A0305-02-0318-216
Figure 109104792-A0305-02-0318-216

<式(Ia850)所表示的化合物的鑑定> <Identification of the compound represented by formula (Ia850)>

(質量分析)離子化模式=ESI+:m/z=[M+H]+521 (Mass analysis) Ionization mode = ESI+: m/z = [M+H] + 521

(質量分析)離子化模式=ESI-:m/z=[M-H]-519 (Mass analysis) Ionization mode = ESI-: m/z = [MH] - 519

精確質量(Exact Mass):520 Exact Mass: 520

Figure 109104792-A0305-02-0319-217
Figure 109104792-A0305-02-0319-217

<式(Ia315)所表示的化合物的鑑定> <Identification of the compound represented by formula (Ia315)>

(質量分析)離子化模式=ESI+:m/z=[M+H]+535 (Mass analysis) Ionization mode = ESI+: m/z = [M+H] + 535

(質量分析)離子化模式=ESI-:m/z=[M-H]-533 (Mass analysis) Ionization mode = ESI-: m/z = [MH] - 533

精確質量(Exact Mass):534 Exact Mass: 534

實施例5 Example 5

將4-胺基-2-甲基喹啉(東京化成工業(股)製造)5.23份、3-硝基鄰苯二甲酸酐(東京化成工業(股)製造)14.2份、苯甲酸(東京化成工業(股)製造)20.2份及苯甲酸甲酯(東京化成工業(股)製造)119份混合。 Mix 5.23 parts of 4-amino-2-methylquinoline (manufactured by Tokyo Chemical Industry Co., Ltd.), 14.2 parts of 3-nitrophthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 20.2 parts of benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.), and 119 parts of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.).

將該混合物一邊保持為168℃一邊攪拌12小時。 The mixture was stirred for 12 hours while being maintained at 168°C.

於該混合物中加入3-硝基鄰苯二甲酸酐(東京化成工業(股)製造)7.12份、苯甲酸(東京化成工業(股)製造)10.3份及苯甲酸甲酯(東京化成工業(股)製造)16.0份。 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 16.0 parts of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.) were added to the mixture.

將該混合物一邊保持為170℃一邊攪拌26小時。 The mixture was stirred for 26 hours while being maintained at 170°C.

將該混合物冷卻至室溫,於該混合物中加入甲醇2400份。 The mixture was cooled to room temperature and 2400 parts of methanol were added to the mixture.

於室溫下對所獲得的混合物進行攪拌後,進行過濾。 The obtained mixture was stirred at room temperature and then filtered.

利用甲醇400份對所獲得的殘渣進行5次清洗。 The obtained residue was washed five times with 400 parts of methanol.

於60℃下對所獲得的殘渣進行減壓乾燥,獲得式(Ia35)所表示的化合物13.0份。 The obtained residue was dried under reduced pressure at 60°C to obtain 13.0 parts of the compound represented by formula (Ia35).

Figure 109104792-A0305-02-0320-218
Figure 109104792-A0305-02-0320-218

<式(Ia35)所表示的化合物的鑑定> <Identification of the compound represented by formula (Ia35)>

(質量分析)離子化模式=ESI+:m/z=[M+H]+509 (Mass analysis) Ionization mode = ESI+: m/z = [M+H] + 509

(質量分析)離子化模式=ESI-:m/z=[M-H]-507 (Mass analysis) Ionization mode = ESI-: m/z = [MH] - 507

精確質量(Exact Mass):508 Exact Mass: 508

實施例6 Example 6

將4-胺基-2-甲基喹啉(東京化成工業(股)製造)3.67份、鄰苯二甲酸酐(東京化成工業(股)製造)7.59份、苯甲酸(東京化成工業(股)製造)14.4份及苯甲酸甲酯(東京化成工業(股)製造)84.3份混合。 Mix 3.67 parts of 4-amino-2-methylquinoline (manufactured by Tokyo Chemical Industry Co., Ltd.), 7.59 parts of phthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 14.4 parts of benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.), and 84.3 parts of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.).

將該混合物一邊保持為170℃一邊攪拌10小時。 The mixture was stirred for 10 hours while being maintained at 170°C.

於該混合物中加入鄰苯二甲酸酐(東京化成工業(股)製造)7.92份、苯甲酸(東京化成工業(股)製造)15.5份及苯甲酸甲酯(東京化成工業(股)製造)45份。 Add 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 45 parts of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.) to the mixture.

將該混合物一邊保持為170℃一邊攪拌9小時。 The mixture was stirred for 9 hours while being maintained at 170°C.

於該混合物中加入苯甲酸甲酯(東京化成工業(股)製造)9份。 Add 9 parts of methyl benzoate (produced by Tokyo Chemical Industry Co., Ltd.) to the mixture.

將該混合物一邊保持為170℃一邊攪拌18小時。 The mixture was stirred for 18 hours while being maintained at 170°C.

於該混合物中加入鄰苯二甲酸酐(東京化成工業(股)製造)7.77份、苯甲酸(東京化成工業(股)製造)14.6份及苯甲酸甲酯(東京化成工業(股)製造)11.1份。 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.) were added to the mixture.

將該混合物一邊保持為170℃一邊攪拌27小時。 The mixture was stirred for 27 hours while being maintained at 170°C.

於該混合物中加入鄰苯二甲酸酐(東京化成工業(股)製造)3.88份、苯甲酸(東京化成工業(股)製造)7.33份及苯甲酸甲酯(東京化成工業(股)製造)12.3份。 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.) were added to the mixture.

將該混合物一邊保持為170℃一邊攪拌8小時。 The mixture was stirred for 8 hours while being maintained at 170°C.

將該混合物冷卻至室溫,於該混合物中加入甲醇2800份。 The mixture was cooled to room temperature and 2800 parts of methanol were added to the mixture.

於室溫下對所獲得的混合物進行攪拌後,進行過濾。 The obtained mixture was stirred at room temperature and then filtered.

對所獲得的殘渣,利用甲醇400份進行2次清洗,利用甲醇800份進行1次清洗。 The obtained residue was washed twice with 400 parts of methanol and once with 800 parts of methanol.

於60℃下對所獲得的殘渣進行減壓乾燥,獲得式(Ia1)所表示的化合物7.67份。 The obtained residue was dried under reduced pressure at 60°C to obtain 7.67 parts of the compound represented by formula (Ia1).

Figure 109104792-A0305-02-0322-219
Figure 109104792-A0305-02-0322-219

<式(Ia1)所表示的化合物的鑑定> <Identification of the compound represented by formula (Ia1)>

(質量分析)離子化模式=ESI+:m/z=[M+H]+419 (Mass analysis) Ionization mode = ESI+: m/z = [M+H] + 419

(質量分析)離子化模式=ESI-:m/z=[M-H]-417 (Mass analysis) Ionization mode = ESI-: m/z = [MH] - 417

精確質量(Exact Mass):418 Exact Mass: 418

實施例7 Example 7

將實施例4中獲得的式(Ia10)所表示的化合物、式(Ia2143)所表示的化合物、式(Ia850)所表示的化合物及式(Ia315)所表示的化合物的混合物1.05份與水106份混合。 1.05 parts of a mixture of 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) were mixed with 106 parts of water.

於室溫下,在該混合物中加入1%氫氧化鈉水溶液22.1份。 At room temperature, add 22.1 parts of 1% sodium hydroxide aqueous solution to the mixture.

於室溫下,在所獲得的混合物中加入硝酸鐵(III)九水合物(和光純藥工業(股)製造)3.23份與水29.1份的混合物8.19份。 At room temperature, 8.19 parts of a mixture of 3.23 parts of iron nitrate (III) nonahydrate (produced by Wako Pure Chemical Industries, Ltd.) and 29.1 parts of water were added to the obtained mixture.

對所獲得的混合物進行過濾,並利用與所獲得的殘渣為相同體積的水對所獲得的殘渣進行2次清洗。 The obtained mixture was filtered and the obtained residue was washed twice with water having the same volume as the obtained residue.

於60℃下對所獲得的殘渣進行減壓乾燥,獲得包含式(Ie12) 所表示的化合物的混合物1.17份。 The obtained residue was dried under reduced pressure at 60°C to obtain 1.17 parts of a mixture containing a compound represented by formula (Ie12).

Figure 109104792-A0305-02-0323-220
Figure 109104792-A0305-02-0323-220

實施例8 Example 8

將4-胺基-2-甲基喹啉(東京化成工業(股)製造)5.03份、4-硝基鄰苯二甲酸酐(東京化成工業(股)製造)13.6份、苯甲酸(東京化成工業(股)製造)19.5份及苯甲酸甲酯(東京化成工業(股)製造)116份混合。 Mix 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.), 19.5 parts of benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.), and 116 parts of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.).

將該混合物一邊保持為170℃一邊攪拌4小時。 The mixture was stirred for 4 hours while being maintained at 170°C.

於該混合物中加入4-硝基鄰苯二甲酸酐(東京化成工業(股)製造)7.12份、苯甲酸(東京化成工業(股)製造)10.5份及苯甲酸甲酯(東京化成工業(股)製造)30.1份。 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 30.1 parts of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.) were added to the mixture.

將該混合物一邊保持為170℃一邊攪拌18小時。 The mixture was stirred for 18 hours while being maintained at 170°C.

於該混合物中加入4-硝基鄰苯二甲酸酐(東京化成工業(股)製造)13.6份、苯甲酸(東京化成工業(股)製造)19.9份及苯甲酸甲酯(東京化成工業(股)製造)29.1份。 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 29.1 parts of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.) were added to the mixture.

將該混合物一邊保持為170℃一邊攪拌27小時。 The mixture was stirred for 27 hours while being maintained at 170°C.

將該混合物冷卻至室溫,於該混合物中加入甲醇2800份。 The mixture was cooled to room temperature and 2800 parts of methanol were added to the mixture.

於室溫下對所獲得的混合物進行攪拌後,進行過濾。 The obtained mixture was stirred at room temperature and then filtered.

利用甲醇400份對所獲得的殘渣進行4次清洗。 The obtained residue was washed 4 times with 400 parts of methanol.

於60℃下對所獲得的殘渣進行減壓乾燥,獲得式(Ia33)所表示的化合物14.8份。 The obtained residue was dried under reduced pressure at 60°C to obtain 14.8 parts of the compound represented by formula (Ia33).

Figure 109104792-A0305-02-0324-221
Figure 109104792-A0305-02-0324-221

<式(Ia33)所表示的化合物的鑑定> <Identification of the compound represented by formula (Ia33)>

(質量分析)離子化模式=ESI+:m/z=[M+H]+509 (Mass analysis) Ionization mode = ESI+: m/z = [M+H] + 509

(質量分析)離子化模式=ESI-:m/z=[M-H]-507 (Mass analysis) Ionization mode = ESI-: m/z = [MH] - 507

精確質量(Exact Mass):508 Exact Mass: 508

實施例A-1 Example A-1

將4-胺基-2-甲基喹啉(東京化成工業(股)製造)1莫耳、3-甲基鄰苯二甲酸酐(東京化成工業(股)製造)8莫耳、苯甲酸(東京化成工業(股)製造)21莫耳及 4-胺基-2-甲基喹啉(東京化成工業(股)製造)1莫耳的重量的73倍的重量的苯甲酸甲酯(東京化成工業(股)製造)混合。 Mix 1 mol of 4-amino-2-methylquinoline (manufactured by Tokyo Chemical Industry Co., Ltd.), 8 mol of 3-methylphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 21 mol of benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.), and methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.) in an amount 73 times the weight of 1 mol of 4-amino-2-methylquinoline (manufactured by Tokyo Chemical Industry Co., Ltd.).

將該混合物一邊保持為170℃一邊攪拌120小時。 The mixture was stirred for 120 hours while being maintained at 170°C.

將該混合物冷卻至室溫,於該混合物中加入該混合物的重量的13倍的重量的甲醇。 The mixture was cooled to room temperature, and methanol in an amount 13 times the weight of the mixture was added to the mixture.

於室溫下對所獲得的混合物進行攪拌後,進行過濾。 The obtained mixture was stirred at room temperature and then filtered.

利用甲醇對所獲得的殘渣進行清洗。 The obtained residue is washed with methanol.

利用管柱層析法對所獲得的殘渣進行精製,獲得式(Ia5)所表示的化合物。 The obtained residue is purified by column chromatography to obtain the compound represented by formula (Ia5).

Figure 109104792-A0305-02-0325-223
Figure 109104792-A0305-02-0325-223

<式(Ia5)所表示的化合物的鑑定> <Identification of the compound represented by formula (Ia5)>

(質量分析)離子化模式=ESI+:m/z=[M+H]+447 (Mass analysis) Ionization mode = ESI+: m/z = [M+H] + 447

(質量分析)離子化模式=ESI-:m/z=[M-H]-445 (Mass analysis) Ionization mode = ESI-: m/z = [MH] - 445

精確質量(Exact Mass):446 Exact Mass: 446

實施例A-2 Example A-2

將3-甲基鄰苯二甲酸酐(東京化成工業(股)製造)替換為1,2-萘二甲酸酐(東京化成工業(股)製造),除此以外,與實施例A-1同樣地實施,獲得式(Ia3)所表示的化合物。 The same method as Example A-1 was followed except that 3-methylphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with 1,2-naphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) to obtain a compound represented by formula (Ia3).

Figure 109104792-A0305-02-0326-224
Figure 109104792-A0305-02-0326-224

<式(Ia3)所表示的化合物的鑑定> <Identification of the compound represented by formula (Ia3)>

(質量分析)離子化模式=ESI+:m/z=[M+H]+519 (Mass analysis) Ionization mode = ESI+: m/z = [M+H] + 519

(質量分析)離子化模式=ESI-:m/z=[M-H]-517 (Mass analysis) Ionization mode = ESI-: m/z = [MH] - 517

精確質量(Exact Mass):518 Exact Mass: 518

實施例A-3 Example A-3

將3-甲基鄰苯二甲酸酐(東京化成工業(股)製造)替換為3-氯鄰苯二甲酸酐(東京化成工業(股)製造),除此以外,與實施例A-1同樣地實施,獲得式(Ia17)所表示的化合物。 The same method as Example A-1 was followed except that 3-methylphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was used to replace 3-chlorophthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) to obtain a compound represented by formula (Ia17).

[化115]

Figure 109104792-A0305-02-0327-225
[Chemistry 115]
Figure 109104792-A0305-02-0327-225

<式(Ia17)所表示的化合物的鑑定> <Identification of the compound represented by formula (Ia17)>

(質量分析)離子化模式=ESI+:m/z=[M+H]+487 (Mass analysis) Ionization mode = ESI+: m/z = [M+H] + 487

(質量分析)離子化模式=ESI-:m/z=[M-H]-485 (Mass analysis) Ionization mode = ESI-: m/z = [MH] - 485

精確質量(Exact Mass):486 Exact Mass: 486

實施例A-4 Example A-4

將3-甲基鄰苯二甲酸酐(東京化成工業(股)製造)替換為4-氯鄰苯二甲酸酐(東京化成工業(股)製造),除此以外,與實施例A-1同樣地實施,獲得式(Ia7)所表示的化合物。 The same method as Example A-1 was followed 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.) to obtain a compound represented by formula (Ia7).

Figure 109104792-A0305-02-0327-226
Figure 109104792-A0305-02-0327-226

<式(Ia7)所表示的化合物的鑑定> <Identification of the compound represented by formula (Ia7)>

(質量分析)離子化模式=ESI+:m/z=[M+H]+487 (Mass analysis) Ionization mode = ESI+: m/z = [M+H] + 487

(質量分析)離子化模式=ESI-:m/z=[M-H]-485 (Mass analysis) Ionization mode = ESI-: m/z = [MH] - 485

精確質量(Exact Mass):486 Exact Mass: 486

實施例A-5 Example A-5

將3-甲基鄰苯二甲酸酐(東京化成工業(股)製造)替換為3-乙醯胺鄰苯二甲酸酐(東京化成工業(股)製造),除此以外,與實施例A-1同樣地實施,獲得式(Ia36)所表示的化合物。 The same method as Example A-1 was followed except that 3-methylphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was used to replace 3-acetamidophthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) to obtain a compound represented by formula (Ia36).

Figure 109104792-A0305-02-0328-227
Figure 109104792-A0305-02-0328-227

<式(Ia36)所表示的化合物的鑑定> <Identification of the compound represented by formula (Ia36)>

(質量分析)離子化模式=ESI+:m/z=[M+H]+533 (Mass analysis) Ionization mode = ESI+: m/z = [M+H] + 533

(質量分析)離子化模式=ESI-:m/z=[M-H]-531 (Mass analysis) Ionization mode = ESI-: m/z = [MH] - 531

精確質量(Exact Mass):532 Exact Mass: 532

實施例A-6 Example A-6

將3-甲基鄰苯二甲酸酐(東京化成工業(股)製造)替換為3-羥基鄰苯二甲酸酐(日本西格瑪奧德里奇(Sigma-Aldrich Japan) 有限責任公司製造),除此以外,與實施例A-1同樣地實施,獲得式(Ia51)所表示的化合物。 The same method as Example A-1 was followed except that 3-methylphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was used to replace 3-hydroxyphthalic anhydride (manufactured by Sigma-Aldrich Japan Co., Ltd.) to obtain a compound represented by formula (Ia51).

Figure 109104792-A0305-02-0329-228
Figure 109104792-A0305-02-0329-228

<式(Ia51)所表示的化合物的鑑定> <Identification of the compound represented by formula (Ia51)>

(質量分析)離子化模式=ESI+:m/z=[M+H]+451 (Mass analysis) Ionization mode = ESI+: m/z = [M+H] + 451

(質量分析)離子化模式=ESI-:m/z=[M-H]-449 (Mass analysis) Ionization mode = ESI-: m/z = [MH] - 449

精確質量(Exact Mass):450 Exact Mass: 450

實施例A-7 Example A-7

將3-甲基鄰苯二甲酸酐(東京化成工業(股)製造)替換為3-氟鄰苯二甲酸酐(東京化成工業(股)製造),除此以外,與實施例A-1同樣地實施,獲得式(Ia19)所表示的化合物。 The same method as Example A-1 was followed except that 3-methylphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with 3-fluorophthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) to obtain a compound represented by formula (Ia19).

[化119]

Figure 109104792-A0305-02-0330-229
[Chemistry 119]
Figure 109104792-A0305-02-0330-229

<式(Ia19)所表示的化合物的鑑定> <Identification of the compound represented by formula (Ia19)>

(質量分析)離子化模式=ESI+:m/z=[M+H]+455 (Mass analysis) Ionization mode = ESI+: m/z = [M+H] + 455

(質量分析)離子化模式=ESI-:m/z=[M-H]-453 (Mass analysis) Ionization mode = ESI-: m/z = [MH] - 453

精確質量(Exact Mass):454 Exact Mass: 454

實施例A-8 Example A-8

將3-甲基鄰苯二甲酸酐(東京化成工業(股)製造)替換為式(sm1)所表示的化合物,除此以外,與實施例A-1同樣地實施,獲得式(Ia248)所表示的化合物。 The same method as Example A-1 was followed except that 3-methylphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with the compound represented by formula (sm1) to obtain the compound represented by formula (Ia248).

Figure 109104792-A0305-02-0330-230
Figure 109104792-A0305-02-0330-230

[化121]

Figure 109104792-A0305-02-0331-231
[Chemistry 121]
Figure 109104792-A0305-02-0331-231

<式(Ia248)所表示的化合物的鑑定> <Identification of the compound represented by formula (Ia248)>

(質量分析)離子化模式=ESI+:m/z=[M+H]+507 (Mass analysis) Ionization mode = ESI+: m/z = [M+H] + 507

(質量分析)離子化模式=ESI-:m/z=[M-H]-505 (Mass analysis) Ionization mode = ESI-: m/z = [MH] - 505

精確質量(Exact Mass):506 Exact Mass: 506

實施例A-9 Example A-9

將3-甲基鄰苯二甲酸酐(東京化成工業(股)製造)替換為4-甲基鄰苯二甲酸酐(東京化成工業(股)製造),除此以外,與實施例A-1同樣地實施,獲得式(Ia4)所表示的化合物。 The same method as Example A-1 was followed except that 3-methylphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with 4-methylphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) to obtain a compound represented by formula (Ia4).

Figure 109104792-A0305-02-0331-232
Figure 109104792-A0305-02-0331-232

<式(Ia4)所表示的化合物的鑑定> <Identification of the compound represented by formula (Ia4)>

(質量分析)離子化模式=ESI+:m/z=[M+H]+447 (Mass analysis) Ionization mode = ESI+: m/z = [M+H] + 447

(質量分析)離子化模式=ESI-:m/z=[M-H]-445 (Mass analysis) Ionization mode = ESI-: m/z = [MH] - 445

精確質量(Exact Mass):446 Exact Mass: 446

實施例A-10 Example A-10

將4-胺基-2-甲基喹啉(東京化成工業(股)製造)替換為4-胺基-6-氟-2-甲基喹啉(日本西格瑪奧德里奇(Sigma-Aldrich Japan)有限責任公司製造),將3-甲基鄰苯二甲酸酐(東京化成工業(股)製造)替換為2,3-萘二羧酸酐(東京化成工業(股)製造),除此以外,與實施例A-1同樣地實施,獲得式(It242)所表示的化合物。 The same method as in Example A-1 was followed except that 4-amino-2-methylquinoline (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced by 4-amino-6-fluoro-2-methylquinoline (manufactured by Sigma-Aldrich Japan Co., Ltd.), and 3-methylphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced by 2,3-naphthalene dicarboxylic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.). The compound represented by formula (It242) was obtained.

Figure 109104792-A0305-02-0332-233
Figure 109104792-A0305-02-0332-233

<式(It242)所表示的化合物的鑑定> <Identification of the compound represented by formula (It242)>

(質量分析)離子化模式=ESI+:m/z=[M+H]+537 (Mass analysis) Ionization mode = ESI+: m/z = [M+H] + 537

(質量分析)離子化模式=ESI-:m/z=[M-H]-535 (Mass analysis) Ionization mode = ESI-: m/z = [MH] - 535

精確質量(Exact Mass):536 Exact Mass: 536

實施例A-11 Example A-11

將4-胺基-2-甲基喹啉(東京化成工業(股)製造)替換為4-胺基-6-甲氧基-2-甲基喹啉(日本西格瑪奧德里奇(Sigma-Aldrich Japan)有限責任公司製造),將3-甲基鄰苯二甲酸酐(東京化成工業(股)製造)替換為2,3-萘二羧酸酐(東京化成工業(股)製造),除此以外,與實施例A-1同樣地實施,獲得式(It232)所表示的化合物。 The same method as in Example A-1 was followed except that 4-amino-2-methylquinoline (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced by 4-amino-6-methoxy-2-methylquinoline (manufactured by Sigma-Aldrich Japan Co., Ltd.), and 3-methylphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced by 2,3-naphthalene dicarboxylic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.). The compound represented by formula (It232) was obtained.

Figure 109104792-A0305-02-0333-234
Figure 109104792-A0305-02-0333-234

<式(It232)所表示的化合物的鑑定> <Identification of the compound represented by formula (It232)>

(質量分析)離子化模式=ESI+:m/z=[M+H]+549 (Mass analysis) Ionization mode = ESI+: m/z = [M+H] + 549

(質量分析)離子化模式=ESI-:m/z=[M-H]-547 (Mass analysis) Ionization mode = ESI-: m/z = [MH] - 547

精確質量(Exact Mass):548 Exact Mass: 548

實施例A-12 Example A-12

將4-胺基-2-甲基喹啉(東京化成工業(股)製造)替換為4- 胺基-6-溴-2-甲基喹啉(日本西格瑪奧德里奇(Sigma-Aldrich Japan)有限責任公司製造),除此以外,與實施例A-1同樣地實施,獲得式(It750)所表示的化合物。 The same method as Example A-1 was followed except that 4-amino-2-methylquinoline (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with 4-amino-6-bromo-2-methylquinoline (manufactured by Sigma-Aldrich Japan Co., Ltd.) to obtain a compound represented by formula (It750).

Figure 109104792-A0305-02-0334-235
Figure 109104792-A0305-02-0334-235

<式(It750)所表示的化合物的鑑定> <Identification of the compound represented by formula (It750)>

(質量分析)離子化模式=ESI+:m/z=[M+H]+525 (Mass analysis) Ionization mode = ESI+: m/z = [M+H] + 525

(質量分析)離子化模式=ESI-:m/z=[M-H]-523 (Mass analysis) Ionization mode = ESI-: m/z = [MH] - 523

精確質量(Exact Mass):524 Exact Mass: 524

合成例B-1 Synthesis Example B-1

將式(Ia2)所表示的化合物1莫耳、及氫氧化鉀20莫耳與式(Ia2)所表示的化合物1莫耳的重量的10倍的重量的水的混合物混合。 Mix 1 mol of the compound represented by formula (Ia2), 20 mol of potassium hydroxide, and a mixture of water 10 times the weight of 1 mol of the compound represented by formula (Ia2).

將該混合物一邊保持為90℃一邊進行攪拌直至式(Ia2)所表示的化合物消失為止。 The mixture was stirred while being maintained at 90°C until the compound represented by formula (Ia2) disappeared.

將該混合物與36%鹽酸混合,進行中和。 Neutralize the mixture by mixing it with 36% hydrochloric acid.

對該混合物進行過濾。 The mixture was filtered.

利用水對所獲得的殘渣進行清洗。 The obtained residue is washed with water.

利用管柱層析法對該殘渣進行精製,獲得式(IM1-1)所表示的化合物。 The residue was purified by column chromatography to obtain the compound represented by formula (IM1-1).

Figure 109104792-A0305-02-0335-236
Figure 109104792-A0305-02-0335-236

<式(IM1-1)所表示的化合物的鑑定> <Identification of the compound represented by formula (IM1-1)>

(質量分析)離子化模式=ESI+:m/z=[M+H]+339 (Mass analysis) Ionization mode = ESI+: m/z = [M+H] + 339

(質量分析)離子化模式=ESI-:m/z=[M-H]-337 (Mass analysis) Ionization mode = ESI-: m/z = [MH] - 337

精確質量(Exact Mass):338 Exact Mass: 338

合成例B-2 Synthesis Example B-2

將式(Ia2)所表示的化合物替換為式(Ia23)所表示的化合物,除此以外,與合成例B-1同樣地實施,獲得式(IM1-2)所表示的化合物。 The compound represented by formula (IM1-2) was obtained in the same manner as in Synthesis Example B-1 except that the compound represented by formula (Ia2) was replaced by the compound represented by formula (Ia23).

[化127]

Figure 109104792-A0305-02-0336-238
[Chemistry 127]
Figure 109104792-A0305-02-0336-238

<式(IM1-2)所表示的化合物的鑑定> <Identification of the compound represented by formula (IM1-2)>

(質量分析)離子化模式=ESI+:m/z=[M+H]+425 (Mass analysis) Ionization mode = ESI+: m/z = [M+H] + 425

(質量分析)離子化模式=ESI-:m/z=[M-H]-423 (Mass analysis) Ionization mode = ESI-: m/z = [MH] - 423

精確質量(Exact Mass):424 Exact Mass: 424

合成例B-3 Synthesis Example B-3

將式(Ia2)所表示的化合物替換為式(Ia5)所表示的化合物,除此以外,與合成例B-1同樣地實施,獲得式(IM1-3)所表示的化合物。 The compound represented by formula (IM1-3) was obtained by performing the same method as in Synthesis Example B-1 except that the compound represented by formula (Ia2) was replaced by the compound represented by formula (Ia5).

Figure 109104792-A0305-02-0336-239
Figure 109104792-A0305-02-0336-239

<式(IM1-3)所表示的化合物的鑑定> <Identification of the compound represented by formula (IM1-3)>

(質量分析)離子化模式=ESI+:m/z=[M+H]+303 (Mass analysis) Ionization mode = ESI+: m/z = [M+H] + 303

(質量分析)離子化模式=ESI-:m/z=[M-H]-301 (Mass analysis) Ionization mode = ESI-: m/z = [MH] - 301

精確質量(Exact Mass):302 Exact Mass: 302

合成例B-4 Synthesis Example B-4

將式(Ia2)所表示的化合物替換為式(Ia4)所表示的化合物,除此以外,與合成例B-1同樣地實施,獲得式(IM1-4)所表示的化合物。 The compound represented by formula (IM1-4) was obtained by performing the same method as in Synthesis Example B-1 except that the compound represented by formula (Ia2) was replaced by the compound represented by formula (Ia4).

Figure 109104792-A0305-02-0337-240
Figure 109104792-A0305-02-0337-240

<式(IM1-4)所表示的化合物的鑑定> <Identification of the compound represented by formula (IM1-4)>

(質量分析)離子化模式=ESI+:m/z=[M+H]+303 (Mass analysis) Ionization mode = ESI+: m/z = [M+H] + 303

(質量分析)離子化模式=ESI-:m/z=[M-H]-301 (Mass analysis) Ionization mode = ESI-: m/z = [MH] - 301

精確質量(Exact Mass):302 Exact Mass: 302

合成例B-5 Synthesis Example B-5

將式(Ia2)所表示的化合物替換為式(Ia36)所表示的化合物,除此以外,與合成例B-1同樣地實施,獲得式(IM1-5)所表示的化合物。 The compound represented by formula (IM1-5) was obtained by performing the same method as in Synthesis Example B-1 except that the compound represented by formula (Ia2) was replaced by the compound represented by formula (Ia36).

[化130]

Figure 109104792-A0305-02-0338-241
[Chemistry 130]
Figure 109104792-A0305-02-0338-241

<式(IM1-5)所表示的化合物的鑑定> <Identification of the compound represented by formula (IM1-5)>

(質量分析)離子化模式=ESI+:m/z=[M+H]+346 (Mass analysis) Ionization mode = ESI+: m/z = [M+H] + 346

(質量分析)離子化模式=ESI-:m/z=[M-H]-344 (Mass analysis) Ionization mode = ESI-: m/z = [MH] - 344

精確質量(Exact Mass):345 Exact Mass: 345

合成例B-6 Synthesis Example B-6

將式(Ia2)所表示的化合物替換為式(Ia1)所表示的化合物,除此以外,與合成例B-1同樣地實施,獲得式(IM1-6)所表示的化合物。 The compound represented by formula (IM1-6) was obtained by performing the same method as in Synthesis Example B-1 except that the compound represented by formula (Ia2) was replaced by the compound represented by formula (Ia1).

Figure 109104792-A0305-02-0338-242
Figure 109104792-A0305-02-0338-242

<式(IM1-6)所表示的化合物的鑑定> <Identification of the compound represented by formula (IM1-6)>

(質量分析)離子化模式=ESI+:m/z=[M+H]+289 (Mass analysis) Ionization mode = ESI+: m/z = [M+H] + 289

(質量分析)離子化模式=ESI-:m/z=[M-H]-287 (Mass analysis) Ionization mode = ESI-: m/z = [MH] - 287

精確質量(Exact Mass):288 Exact Mass: 288

實施例C-1 Example C-1

將式(IM1-1)所表示的化合物1莫耳、偏苯三甲酸酐(東京化成工業(股)製造)8莫耳、苯甲酸(東京化成工業(股)製造)21莫耳及式(IM1-1)所表示的化合物1莫耳的重量的73倍的重量的苯甲酸甲酯(東京化成工業(股)製造)混合。 Mix 1 mol of the compound represented by formula (IM1-1), 8 mol of trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 21 mol of benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.), and methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.) in an amount 73 times the weight of 1 mol of the compound represented by formula (IM1-1).

將該混合物一邊保持為170℃一邊攪拌120小時。 The mixture was stirred for 120 hours while being maintained at 170°C.

將該混合物冷卻至室溫,於該混合物中加入該混合物的重量的13倍的重量的甲醇。 The mixture was cooled to room temperature, and methanol in an amount 13 times the weight of the mixture was added to the mixture.

於室溫下對所獲得的混合物進行攪拌後,進行過濾。 The obtained mixture was stirred at room temperature and then filtered.

利用甲醇對所獲得的殘渣進行清洗。 The obtained residue is washed with methanol.

利用管柱層析法對所獲得的殘渣進行精製,獲得式(Ia699)所表示的化合物。 The obtained residue is purified by column chromatography to obtain the compound represented by formula (Ia699).

Figure 109104792-A0305-02-0339-244
Figure 109104792-A0305-02-0339-244

<式(Ia699)所表示的化合物的鑑定> <Identification of the compound represented by formula (Ia699)>

(質量分析)離子化模式=ESI+:m/z=[M+H]+513 (Mass analysis) Ionization mode = ESI+: m/z = [M+H] + 513

(質量分析)離子化模式=ESI-:m/z=[M-H]-511 (Mass analysis) Ionization mode = ESI-: m/z = [MH] - 511

精確質量(Exact Mass):512 Exact Mass: 512

實施例C-2 Example C-2

將式(IM1-1)所表示的化合物替換為式(IM1-2)所表示的化合物,將偏苯三甲酸酐(東京化成工業(股)製造)替換為2,3-萘二羧酸酐(東京化成工業(股)製造),除此以外,與實施例C-1同樣地實施,獲得式(Ia970)所表示的化合物。 The compound represented by formula (Ia970) was obtained in the same manner as Example C-1 except that the compound represented by formula (IM1-1) was replaced by the compound represented by formula (IM1-2) and trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced by 2,3-naphthalene dicarboxylic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.).

Figure 109104792-A0305-02-0340-245
Figure 109104792-A0305-02-0340-245

<式(Ia970)所表示的化合物的鑑定> <Identification of the compound represented by formula (Ia970)>

(質量分析)離子化模式=ESI+:m/z=[M+H]+605 (Mass analysis) Ionization mode = ESI+: m/z = [M+H] + 605

(質量分析)離子化模式=ESI-:m/z=[M-H]-603 (Mass analysis) Ionization mode = ESI-: m/z = [MH] - 603

精確質量(Exact Mass):604 Exact Mass: 604

實施例C-3 Example C-3

將偏苯三甲酸酐(東京化成工業(股)製造)替換為四氯鄰苯二甲酸酐(東京化成工業(股)製造),除此以外,與實施例C-1同樣地實施,獲得式(Ia703)所表示的化合物。 The same method as Example C-1 was followed except that trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with tetrachlorophthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) to obtain a compound represented by formula (Ia703).

Figure 109104792-A0305-02-0341-246
Figure 109104792-A0305-02-0341-246

<式(Ia703)所表示的化合物的鑑定> <Identification of the compound represented by formula (Ia703)>

(質量分析)離子化模式=ESI+:m/z=[M+H]+605 (Mass analysis) Ionization mode = ESI+: m/z = [M+H] + 605

(質量分析)離子化模式=ESI-:m/z=[M-H]-603 (Mass analysis) Ionization mode = ESI-: m/z = [MH] - 603

精確質量(Exact Mass):604 Exact Mass: 604

實施例C-4 Example C-4

將偏苯三甲酸酐(東京化成工業(股)製造)替換為3-甲基鄰苯二甲酸酐(東京化成工業(股)製造),除此以外,與實施例C-1同樣地實施,獲得式(If3796)所表示的化合物。 The same method as Example C-1 was followed except that trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with 3-methylphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) to obtain a compound represented by formula (If3796).

[化135]

Figure 109104792-A0305-02-0342-247
[Chemistry 135]
Figure 109104792-A0305-02-0342-247

<式(If3796)所表示的化合物的鑑定> <Identification of the compound represented by formula (If3796)>

(質量分析)離子化模式=ESI+:m/z=[M+H]+483 (Mass analysis) Ionization mode = ESI+: m/z = [M+H] + 483

(質量分析)離子化模式=ESI-:m/z=[M-H]-481 (Mass analysis) Ionization mode = ESI-: m/z = [MH] - 481

精確質量(Exact Mass):482 Exact Mass: 482

實施例C-5 Example C-5

將偏苯三甲酸酐(東京化成工業(股)製造)替換為鄰苯二甲酸酐(東京化成工業(股)製造),除此以外,與實施例C-1同樣地實施,獲得式(Ia696)所表示的化合物。 The same method as Example C-1 was followed except that trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with phthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) to obtain a compound represented by formula (Ia696).

Figure 109104792-A0305-02-0342-248
Figure 109104792-A0305-02-0342-248

<式(Ia696)所表示的化合物的鑑定> <Identification of the compound represented by formula (Ia696)>

(質量分析)離子化模式=ESI+:m/z=[M+H]+469 (Mass analysis) Ionization mode = ESI+: m/z = [M+H] + 469

(質量分析)離子化模式=ESI-:m/z=[M-H]-467 (Mass analysis) Ionization mode = ESI-: m/z = [MH] - 467

精確質量(Exact Mass):468 Exact Mass: 468

實施例C-6 Example C-6

將式(IM1-1)所表示的化合物替換為式(IM1-2)所表示的化合物,將偏苯三甲酸酐(東京化成工業(股)製造)替換為鄰苯二甲酸酐(東京化成工業(股)製造),除此以外,與實施例C-1同樣地實施,獲得式(Ia969)所表示的化合物。 The compound represented by formula (Ia969) was obtained by carrying out the same method as Example C-1 except that the compound represented by formula (IM1-1) was replaced by the compound represented by formula (IM1-2) and trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced by phthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.).

Figure 109104792-A0305-02-0343-249
Figure 109104792-A0305-02-0343-249

<式(Ia969)所表示的化合物的鑑定> <Identification of the compound represented by formula (Ia969)>

(質量分析)離子化模式=ESI+:m/z=[M+H]+555 (Mass analysis) Ionization mode = ESI+: m/z = [M+H] + 555

(質量分析)離子化模式=ESI-:m/z=[M-H]-553 (Mass analysis) Ionization mode = ESI-: m/z = [MH] - 553

精確質量(Exact Mass):554 Exact Mass: 554

實施例C-7 Example C-7

將式(IM1-1)所表示的化合物替換為式(IM1-2)所表示的化合物,將偏苯三甲酸酐(東京化成工業(股)製造)替換為3-甲基鄰苯二甲酸酐(東京化成工業(股)製造),除此以外,與實施例C-1同樣地實施,獲得式(If2528)所表示的化合物。 The compound represented by formula (If2528) was obtained by carrying out the same method as Example C-1 except that the compound represented by formula (IM1-1) was replaced by the compound represented by formula (IM1-2) and trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced by 3-methylphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.).

Figure 109104792-A0305-02-0344-250
Figure 109104792-A0305-02-0344-250

<式(If2528)所表示的化合物的鑑定> <Identification of the compound represented by formula (If2528)>

(質量分析)離子化模式=ESI+:m/z=[M+H]+569 (Mass analysis) Ionization mode = ESI+: m/z = [M+H] + 569

(質量分析)離子化模式=ESI-:m/z=[M-H]-567 (Mass analysis) Ionization mode = ESI-: m/z = [MH] - 567

精確質量(Exact Mass):568 Exact Mass: 568

實施例C-8 Example C-8

將式(IM1-1)所表示的化合物替換為式(IM1-2)所表示的化合物,除此以外,與實施例C-1同樣地實施,獲得式(Ia973)所表示的化合物。 The compound represented by formula (Ia973) was obtained by carrying out the same method as Example C-1 except that the compound represented by formula (IM1-1) was replaced by the compound represented by formula (IM1-2).

[化139]

Figure 109104792-A0305-02-0345-251
[Chemistry 139]
Figure 109104792-A0305-02-0345-251

<式(Ia973)所表示的化合物的鑑定> <Identification of the compound represented by formula (Ia973)>

(質量分析)離子化模式=ESI+:m/z=[M+H]+599 (Mass analysis) Ionization mode = ESI+: m/z = [M+H] + 599

(質量分析)離子化模式=ESI-:m/z=[M-H]-597 (Mass analysis) Ionization mode = ESI-: m/z = [MH] - 597

精確質量(Exact Mass):598 Exact Mass: 598

實施例C-9 Example C-9

將式(IM1-1)所表示的化合物替換為式(IM1-3)所表示的化合物,除此以外,與實施例C-1同樣地實施,獲得式(If1261)所表示的化合物。 The compound represented by formula (If1261) is obtained by performing the same method as Example C-1 except that the compound represented by formula (IM1-1) is replaced by the compound represented by formula (IM1-3).

[化140]

Figure 109104792-A0305-02-0346-252
[Chemistry 140]
Figure 109104792-A0305-02-0346-252

<式(If1 261)所表示的化合物的鑑定> <Identification of the compound represented by formula (If1 261)>

(質量分析)離子化模式=ESI+:m/z=[M+H]+477 (Mass analysis) Ionization mode = ESI+: m/z = [M+H] + 477

(質量分析)離子化模式=ESI-:m/z=[M-H]-475 (Mass analysis) Ionization mode = ESI-: m/z = [MH] - 475

精確質量(Exact Mass):476 Exact Mass: 476

實施例C-10 Example C-10

將式(IM1-1)所表示的化合物替換為式(IM1-3)所表示的化合物,將偏苯三甲酸酐(東京化成工業(股)製造)替換為四氯鄰苯二甲酸酐(東京化成工業(股)製造),除此以外,與實施例C-1同樣地實施,獲得式(If5688)所表示的化合物。 The same method as Example C-1 was followed except that the compound represented by Formula (IM1-1) was replaced by the compound represented by Formula (IM1-3) and trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced by tetrachlorophthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), to obtain the compound represented by Formula (If5688).

Figure 109104792-A0305-02-0346-253
Figure 109104792-A0305-02-0346-253

<式(If5688)所表示的化合物的鑑定> <Identification of the compound represented by formula (If5688)>

(質量分析)離子化模式=ESI+:m/z=[M+H]+569 (Mass analysis) Ionization mode = ESI+: m/z = [M+H] + 569

(質量分析)離子化模式=ESI-:m/z=[M-H]-567 (Mass analysis) Ionization mode = ESI-: m/z = [MH] - 567

精確質量(Exact Mass):568 Exact Mass: 568

實施例C-11 Example C-11

將式(IM1-1)所表示的化合物替換為式(IM1-3)所表示的化合物,將偏苯三甲酸酐(東京化成工業(股)製造)替換為2,3-萘二羧酸酐(東京化成工業(股)製造),除此以外,與實施例C-1同樣地實施,獲得式(If636)所表示的化合物。 The compound represented by formula (If636) was obtained in the same manner as Example C-1 except that the compound represented by formula (IM1-1) was replaced by the compound represented by formula (IM1-3) and trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced by 2,3-naphthalene dicarboxylic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.).

Figure 109104792-A0305-02-0347-254
Figure 109104792-A0305-02-0347-254

<式(If636)所表示的化合物的鑑定> <Identification of the compound represented by formula (If636)>

(質量分析)離子化模式=ESI+:m/z=[M+H]+483 (Mass analysis) Ionization mode = ESI+: m/z = [M+H] + 483

(質量分析)離子化模式=ESI-:m/z=[M-H]-481 (Mass analysis) Ionization mode = ESI-: m/z = [MH] - 481

精確質量(Exact Mass):482 Exact Mass: 482

實施例C-12 Example C-12

將式(IM1-1)所表示的化合物替換為式(IM1-3)所表示的化合物,將偏苯三甲酸酐(東京化成工業(股)製造)替換為1,2-萘二甲酸酐(東京化成工業(股)製造),除此以外,與實施例C-1同樣地實施,獲得式(If5670)所表示的化合物。 The compound represented by formula (If5670) was obtained in the same manner as Example C-1 except that the compound represented by formula (IM1-1) was replaced by the compound represented by formula (IM1-3) and trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced by 1,2-naphthalene dicarboxylic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.).

Figure 109104792-A0305-02-0348-255
Figure 109104792-A0305-02-0348-255

<式(If5670)所表示的化合物的鑑定> <Identification of the compound represented by formula (If5670)>

(質量分析)離子化模式=ESI+:m/z=[M+H]+483 (Mass analysis) Ionization mode = ESI+: m/z = [M+H] + 483

(質量分析)離子化模式=ESI-:m/z=[M-H]-481 (Mass analysis) Ionization mode = ESI-: m/z = [MH] - 481

精確質量(Exact Mass):482 Exact Mass: 482

實施例C-13 Example C-13

將式(IM1-1)所表示的化合物替換為式(IM1-3)所表示的化合物,將偏苯三甲酸酐(東京化成工業(股)製造)替換為1,8-萘二甲酸酐(東京化成工業(股)製造),除此以外,與實施例C-1同樣地實施,獲得式(If5720)所表示的化合物。 The compound represented by formula (If5720) was obtained in the same manner as Example C-1 except that the compound represented by formula (IM1-1) was replaced by the compound represented by formula (IM1-3) and trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced by 1,8-naphthalene dicarboxylic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.).

Figure 109104792-A0305-02-0349-256
Figure 109104792-A0305-02-0349-256

<式(If5720)所表示的化合物的鑑定> <Identification of the compound represented by formula (If5720)>

(質量分析)離子化模式=ESI+:m/z=[M+H]+483 (Mass analysis) Ionization mode = ESI+: m/z = [M+H] + 483

(質量分析)離子化模式=ESI-:m/z=[M-H]-481 (Mass analysis) Ionization mode = ESI-: m/z = [MH] - 481

精確質量(Exact Mass):482 Exact Mass: 482

實施例C-14 Example C-14

將偏苯三甲酸酐(東京化成工業(股)製造)替換為1,8-萘二甲酸酐(東京化成工業(股)製造),除此以外,與實施例C-1同樣地實施,獲得式(Ia712)所表示的化合物。 The same method as Example C-1 was followed except that trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with 1,8-naphthalene dicarboxylic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) to obtain a compound represented by formula (Ia712).

Figure 109104792-A0305-02-0349-257
Figure 109104792-A0305-02-0349-257

<式(Ia712)所表示的化合物的鑑定> <Identification of the compound represented by formula (Ia712)>

(質量分析)離子化模式=ESI+:m/z=[M+H]+519 (Mass analysis) Ionization mode = ESI+: m/z = [M+H] + 519

(質量分析)離子化模式=ESI-:m/z=[M-H]-517 (Mass analysis) Ionization mode = ESI-: m/z = [MH] - 517

精確質量(Exact Mass):518 Exact Mass: 518

實施例C-15 Example C-15

將式(IM1-1)所表示的化合物替換為式(IM1-4)所表示的化合物,將偏苯三甲酸酐(東京化成工業(股)製造)替換為2,3-萘二羧酸酐(東京化成工業(股)製造),除此以外,與實施例C-1同樣地實施,獲得式(If635)所表示的化合物。 The compound represented by formula (If635) was obtained in the same manner as Example C-1 except that the compound represented by formula (IM1-1) was replaced by the compound represented by formula (IM1-4) and trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced by 2,3-naphthalene dicarboxylic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.).

Figure 109104792-A0305-02-0350-258
Figure 109104792-A0305-02-0350-258

<式(If635)所表示的化合物的鑑定> <Identification of the compound represented by formula (If635)>

(質量分析)離子化模式=ESI+:m/z=[M+H]+483 (Mass analysis) Ionization mode = ESI+: m/z = [M+H] + 483

(質量分析)離子化模式=ESI-:m/z=[M-H]-481 (Mass analysis) Ionization mode = ESI-: m/z = [MH] - 481

精確質量(Exact Mass):482 Exact Mass: 482

實施例C-16 Example C-16

將式(IM1-1)所表示的化合物替換為式(IM1-4)所表示的化合物,除此以外,與實施例C-1同樣地實施,獲得式(If1260)所表示的化合物。 The compound represented by formula (If1260) is obtained by performing the same method as Example C-1 except that the compound represented by formula (IM1-1) is replaced by the compound represented by formula (IM1-4).

Figure 109104792-A0305-02-0351-259
Figure 109104792-A0305-02-0351-259

<式(If1260)所表示的化合物的鑑定> <Identification of the compound represented by formula (If1260)>

(質量分析)離子化模式=ESI+:m/z=[M+H]+477 (Mass analysis) Ionization mode = ESI+: m/z = [M+H] + 477

(質量分析)離子化模式=ESI-:m/z=[M-H]-475 (Mass analysis) Ionization mode = ESI-: m/z = [MH] - 475

精確質量(Exact Mass):476 Exact Mass: 476

實施例C-17 Example C-17

將式(IM1-1)所表示的化合物替換為式(IM1-4)所表示的化合物,將偏苯三甲酸酐(東京化成工業(股)製造)替換為均苯四甲酸酐(東京化成工業(股)製造),除此以外,與實施例C-1同樣地實施,獲得式(If13040)所表示的化合物。 The compound represented by formula (If13040) was obtained by carrying out the same method as Example C-1 except that the compound represented by formula (IM1-1) was replaced by the compound represented by formula (IM1-4) and trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced by pyromellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.).

[化148]

Figure 109104792-A0305-02-0352-260
[Chemistry 148]
Figure 109104792-A0305-02-0352-260

<式(If1 3040)所表示的化合物的鑑定> <Identification of the compound represented by formula (If1 3040)>

(質量分析)離子化模式=ESI+:m/z=[M+H]+521 (Mass analysis) Ionization mode = ESI+: m/z = [M+H] + 521

(質量分析)離子化模式=ESI-:m/z=[M-H]-519 (Mass analysis) Ionization mode = ESI-: m/z = [MH] - 519

精確質量(Exact Mass):520 Exact Mass: 520

實施例C-18 Example C-18

將式(IM1-1)所表示的化合物替換為式(IM1-4)所表示的化合物,將偏苯三甲酸酐(東京化成工業(股)製造)替換為4-第三丁基鄰苯二甲酸酐(東京化成工業(股)製造),除此以外,與實施例C-1同樣地實施,獲得式(If8454)所表示的化合物。 The compound represented by formula (If8454) was obtained by carrying out the same method as Example C-1 except that the compound represented by formula (IM1-1) was replaced by the compound represented by formula (IM1-4) and trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced by 4-tert-butylphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.).

Figure 109104792-A0305-02-0352-261
Figure 109104792-A0305-02-0352-261

<式(If8454)所表示的化合物的鑑定> <Identification of the compound represented by formula (If8454)>

(質量分析)離子化模式=ESI+:m/z=[M+H]+489 (Mass analysis) Ionization mode = ESI+: m/z = [M+H] + 489

(質量分析)離子化模式=ESI-:m/z=[M-H]-487 (Mass analysis) Ionization mode = ESI-: m/z = [MH] - 487

精確質量(Exact Mass):488 Exact Mass: 488

實施例C-19 Example C-19

將偏苯三甲酸酐(東京化成工業(股)製造)替換為4-甲基鄰苯二甲酸酐(東京化成工業(股)製造),除此以外,與實施例C-1同樣地實施,獲得式(If3795)所表示的化合物。 The same method as Example C-1 was followed except that trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with 4-methylphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) to obtain a compound represented by formula (If3795).

Figure 109104792-A0305-02-0353-262
Figure 109104792-A0305-02-0353-262

<式(If3795)所表示的化合物的鑑定> <Identification of the compound represented by formula (If3795)>

(質量分析)離子化模式=ESI+:m/z=[M+H]+483 (Mass analysis) Ionization mode = ESI+: m/z = [M+H] + 483

(質量分析)離子化模式=ESI-:m/z=[M-H]-481 (Mass analysis) Ionization mode = ESI-: m/z = [MH] - 481

精確質量(Exact Mass):482 Exact Mass: 482

實施例C-20 Example C-20

將式(IM1-1)所表示的化合物替換為式(IM1-3)所表示的化合物,將偏苯三甲酸酐(東京化成工業(股)製造)替換為4-甲基鄰苯二甲酸酐(東京化成工業(股)製造),除此以外,與實施例C-1同樣地實施,獲得式(If5671)所表示的化合物。 The same method as Example C-1 was followed except that the compound represented by Formula (IM1-1) was replaced by the compound represented by Formula (IM1-3) and trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced by 4-methylphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) to obtain the compound represented by Formula (If5671).

Figure 109104792-A0305-02-0354-263
Figure 109104792-A0305-02-0354-263

<式(If5671)所表示的化合物的鑑定> <Identification of the compound represented by formula (If5671)>

(質量分析)離子化模式=ESI+:m/z=[M+H]+447 (Mass analysis) Ionization mode = ESI+: m/z = [M+H] + 447

(質量分析)離子化模式=ESI-:m/z=[M-H]-445 (Mass analysis) Ionization mode = ESI-: m/z = [MH] - 445

精確質量(Exact Mass):446 Exact Mass: 446

實施例C-21 Example C-21

將式(IM1-1)所表示的化合物替換為式(IM1-4)所表示的化合物,將偏苯三甲酸酐(東京化成工業(股)製造)替換為3-甲基鄰苯二甲酸酐(東京化成工業(股)製造),除此以外,與實施例C-1同樣地實施,獲得式(If2511)所表示的化合物。 The compound represented by formula (If2511) was obtained in the same manner as Example C-1 except that the compound represented by formula (IM1-1) was replaced by the compound represented by formula (IM1-4) and trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced by 3-methylphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.).

[化152]

Figure 109104792-A0305-02-0355-264
[Chemistry 152]
Figure 109104792-A0305-02-0355-264

<式(If2511)所表示的化合物的鑑定> <Identification of the compound represented by formula (If2511)>

(質量分析)離子化模式=ESI+:m/z=[M+H]+447 (Mass analysis) Ionization mode = ESI+: m/z = [M+H] + 447

(質量分析)離子化模式=ESI-:m/z=[M-H]-445 (Mass analysis) Ionization mode = ESI-: m/z = [MH] - 445

精確質量(Exact Mass):446 Exact Mass: 446

實施例C-22 Example C-22

將偏苯三甲酸酐(東京化成工業(股)製造)替換為4-第三丁基鄰苯二甲酸酐(東京化成工業(股)製造),除此以外,與實施例C-1同樣地實施,獲得式(If3799)所表示的化合物。 The same method as Example C-1 was followed 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.) to obtain a compound represented by formula (If3799).

Figure 109104792-A0305-02-0355-266
Figure 109104792-A0305-02-0355-266

<式(If3799)所表示的化合物的鑑定> <Identification of the compound represented by formula (If3799)>

(質量分析)離子化模式=ESI+:m/z=[M+H]+525 (Mass analysis) Ionization mode = ESI+: m/z = [M+H] + 525

(質量分析)離子化模式=ESI-:m/z=[M-H]-523 (Mass analysis) Ionization mode = ESI-: m/z = [MH] - 523

精確質量(Exact Mass):524 Exact Mass: 524

實施例C-23 Example C-23

將偏苯三甲酸酐(東京化成工業(股)製造)替換為3-乙醯胺鄰苯二甲酸酐(東京化成工業(股)製造),除此以外,與實施例C-1同樣地實施,獲得式(If3814)所表示的化合物。 The same method as Example C-1 was followed except that trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with 3-acetamidophthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) to obtain a compound represented by formula (If3814).

Figure 109104792-A0305-02-0356-267
Figure 109104792-A0305-02-0356-267

<式(If3814)所表示的化合物的鑑定> <Identification of the compound represented by formula (If3814)>

(質量分析)離子化模式=ESI+:m/z=[M+H]+526 (Mass analysis) Ionization mode = ESI+: m/z = [M+H] + 526

(質量分析)離子化模式=ESI-:m/z=[M-H]-524 (Mass analysis) Ionization mode = ESI-: m/z = [MH] - 524

精確質量(Exact Mass):525 Exact Mass: 525

實施例C-24 Example C-24

將式(IM1-1)所表示的化合物替換為式(IM1-5)所表示的化合物,將偏苯三甲酸酐(東京化成工業(股)製造)替換為2,3-萘二羧酸酐(東京化成工業(股)製造),除此以外,與實施例C-1同樣地實施,獲得式(If654)所表示的化合物。 The compound represented by formula (If654) was obtained by carrying out the same method as Example C-1 except that the compound represented by formula (IM1-1) was replaced by the compound represented by formula (IM1-5) and trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced by 2,3-naphthalene dicarboxylic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.).

Figure 109104792-A0305-02-0357-268
Figure 109104792-A0305-02-0357-268

<式(If654)所表示的化合物的鑑定> <Identification of the compound represented by formula (If654)>

(質量分析)離子化模式=ESI+:m/z=[M+H]+526 (Mass analysis) Ionization mode = ESI+: m/z = [M+H] + 526

(質量分析)離子化模式=ESI-:m/z=[M-H]-524 (Mass analysis) Ionization mode = ESI-: m/z = [MH] - 524

精確質量(Exact Mass):525 Exact Mass: 525

實施例C-25 Example C-25

將式(IM1-1)所表示的化合物替換為式(IM1-5)所表示的化合物,將偏苯三甲酸酐(東京化成工業(股)製造)替換為鄰苯二甲酸酐(東京化成工業(股)製造),除此以外,與實施例C-1同樣地實施,獲得式(If29)所表示的化合物。 The same method as Example C-1 was followed except that the compound represented by Formula (IM1-1) was replaced by the compound represented by Formula (IM1-5) and trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced by phthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), to obtain the compound represented by Formula (If29).

[化156]

Figure 109104792-A0305-02-0358-269
[Chemistry 156]
Figure 109104792-A0305-02-0358-269

<式(If29)所表示的化合物的鑑定> <Identification of the compound represented by formula (If29)>

(質量分析)離子化模式=ESI+:m/z=[M+H]+476 (Mass analysis) Ionization mode = ESI+: m/z = [M+H] + 476

(質量分析)離子化模式=ESI-:m/z=[M-H]-474 (Mass analysis) Ionization mode = ESI-: m/z = [MH] - 474

精確質量(Exact Mass):475 Exact Mass: 475

實施例C-26 Example C-26

將式(IM1-1)所表示的化合物替換為式(IM1-5)所表示的化合物,除此以外,與實施例C-1同樣地實施,獲得式(If1279)所表示的化合物。 The compound represented by formula (If1279) is obtained by performing the same method as Example C-1 except that the compound represented by formula (IM1-1) is replaced by the compound represented by formula (IM1-5).

Figure 109104792-A0305-02-0358-270
Figure 109104792-A0305-02-0358-270

<式(If1 279)所表示的化合物的鑑定> <Identification of the compound represented by formula (If1 279)>

(質量分析)離子化模式=ESI+:m/z=[M+H]+520 (Mass analysis) Ionization mode = ESI+: m/z = [M+H] + 520

(質量分析)離子化模式=ESI-:m/z=[M-H]-518 (Mass analysis) Ionization mode = ESI-: m/z = [MH] - 518

精確質量(Exact Mass):519 Exact Mass: 519

實施例C-27 Example C-27

將式(IM1-1)所表示的化合物替換為式(IM1-5)所表示的化合物,將偏苯三甲酸酐(東京化成工業(股)製造)替換為式(sm1)所表示的化合物,除此以外,與實施例C-1同樣地實施,獲得式(If1904)所表示的化合物。 The compound represented by formula (If1904) was obtained by carrying out the same process as Example C-1 except that the compound represented by formula (IM1-1) was replaced by the compound represented by formula (IM1-5) and trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced by the compound represented by formula (sm1).

Figure 109104792-A0305-02-0359-271
Figure 109104792-A0305-02-0359-271

<式(If1904)所表示的化合物的鑑定> <Identification of the compound represented by formula (If1904)>

(質量分析)離子化模式=ESI+:m/z=[M+H]+520 (Mass analysis) Ionization mode = ESI+: m/z = [M+H] + 520

(質量分析)離子化模式=ESI-:m/z=[M-H]-518 (Mass analysis) Ionization mode = ESI-: m/z = [MH] - 518

精確質量(Exact Mass):519 Exact Mass: 519

實施例C-28 Example C-28

將偏苯三甲酸酐(東京化成工業(股)製造)替換為式(sm1)所表示的化合物,除此以外,與實施例C-1同樣地實施,獲得式(Ia728)所表示的化合物。 The same method as Example C-1 was followed except that trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with the compound represented by formula (sm1) to obtain the compound represented by formula (Ia728).

Figure 109104792-A0305-02-0360-272
Figure 109104792-A0305-02-0360-272

<式(Ia728)所表示的化合物的鑑定> <Identification of the compound represented by formula (Ia728)>

(質量分析)離子化模式=ESI+:m/z=[M+H]+513 (Mass analysis) Ionization mode = ESI+: m/z = [M+H] + 513

(質量分析)離子化模式=ESI-:m/z=[M-H]-511 (Mass analysis) Ionization mode = ESI-: m/z = [MH] - 511

精確質量(Exact Mass):512 Exact Mass: 512

實施例C-29 Example C-29

將式(IM1-1)所表示的化合物替換為式(IM1-6)所表示的化合物,將偏苯三甲酸酐(東京化成工業(股)製造)替換為2,3-萘二羧酸酐(東京化成工業(股)製造),除此以外,與實施例C-1同樣地實施,獲得式(Ia657)所表示的化合物。 The compound represented by formula (Ia657) was obtained in the same manner as Example C-1 except that the compound represented by formula (IM1-1) was replaced by the compound represented by formula (IM1-6) and trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced by 2,3-naphthalene dicarboxylic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.).

[化160]

Figure 109104792-A0305-02-0361-273
[Chemistry 160]
Figure 109104792-A0305-02-0361-273

<式(Ia657)所表示的化合物的鑑定> <Identification of the compound represented by formula (Ia657)>

(質量分析)離子化模式=ESI+:m/z=[M+H]+469 (Mass analysis) Ionization mode = ESI+: m/z = [M+H] + 469

(質量分析)離子化模式=ESI-:m/z=[M-H]-467 (Mass analysis) Ionization mode = ESI-: m/z = [MH] - 467

精確質量(Exact Mass):468 Exact Mass: 468

實施例C-30 Example C-30

將式(IM1-1)所表示的化合物替換為式(IM1-6)所表示的化合物,將偏苯三甲酸酐(東京化成工業(股)製造)替換為3-甲基鄰苯二甲酸酐(東京化成工業(股)製造),除此以外,與實施例C-1同樣地實施,獲得式(If3171)所表示的化合物。 The compound represented by formula (If3171) was obtained in the same manner as Example C-1 except that the compound represented by formula (IM1-1) was replaced by the compound represented by formula (IM1-6) and trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced by 3-methylphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.).

Figure 109104792-A0305-02-0361-274
Figure 109104792-A0305-02-0361-274

<式(If3171)所表示的化合物的鑑定> <Identification of the compound represented by formula (If3171)>

(質量分析)離子化模式=ESI+:m/z=[M+H]+433 (Mass analysis) Ionization mode = ESI+: m/z = [M+H] + 433

(質量分析)離子化模式=ESI-:m/z=[M-H]-431 (Mass analysis) Ionization mode = ESI-: m/z = [MH] - 431

精確質量(Exact Mass):432 Exact Mass: 432

實施例C-31 Example C-31

將式(IM1-1)所表示的化合物替換為式(IM1-6)所表示的化合物,將偏苯三甲酸酐(東京化成工業(股)製造)替換為3-氯鄰苯二甲酸酐(東京化成工業(股)製造),除此以外,與實施例C-1同樣地實施,獲得式(Ia686)所表示的化合物。 The same method as Example C-1 was followed except that the compound represented by Formula (IM1-1) was replaced by the compound represented by Formula (IM1-6) and trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced by 3-chlorophthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) to obtain the compound represented by Formula (Ia686).

Figure 109104792-A0305-02-0362-275
Figure 109104792-A0305-02-0362-275

<式(Ia686)所表示的化合物的鑑定> <Identification of the compound represented by formula (Ia686)>

(質量分析)離子化模式=ESI+:m/z=[M+H]+453 (Mass analysis) Ionization mode = ESI+: m/z = [M+H] + 453

(質量分析)離子化模式=ESI-:m/z=[M-H]-451 (Mass analysis) Ionization mode = ESI-: m/z = [MH] - 451

精確質量(Exact Mass):452 Exact Mass: 452

實施例E-1 Example E-1

將式(Ia5)所表示的化合物1.61份與發煙硫酸(25%)(富 士軟片和光純藥(股)製造)32.7份一邊保持為10℃~20℃一邊加以混合。 1.61 parts of the compound represented by formula (Ia5) and 32.7 parts of fuming sulfuric acid (25%) (manufactured by Fuji Films and Wako Pure Chemical Industries, Ltd.) were mixed while maintaining the temperature at 10°C to 20°C.

將該混合物一邊保持為5℃~20℃一邊攪拌3小時。 The mixture was stirred for 3 hours while being kept at 5℃~20℃.

將該混合物滴加至62.2份的冰中。 The mixture was added dropwise to 62.2 parts of ice.

對所獲得的混合物進行過濾。 The obtained mixture was filtered.

於所獲得的液體中加入10%氨水,中和所獲得的濾液。 Add 10% ammonia water to the obtained liquid to neutralize the obtained filter liquid.

餾去該混合物的溶媒直至該混合物的體積變為一半為止。 Distill the solvent from the mixture until the volume of the mixture is reduced to half.

於所獲得的混合物中加入該混合物的體積的2倍的體積的甲醇。 To the obtained mixture, methanol in a volume twice the volume of the mixture was added.

對該混合物進行過濾,並餾去所獲得的濾液的溶媒。 The mixture is filtered, and the solvent is distilled off from the obtained filtrate.

於60℃下對所獲得的殘渣進行減壓乾燥,獲得包含式(Ia5-SA1)所表示的化合物(將式(Ia5)所表示的化合物的一個任一氫原子取代為-SO3NH4的化合物)、與式(Ia5-SA2)所表示的化合物(將式(Ia5)所表示的化合物的兩個任一氫原子取代為-SO3NH4的化合物)的混合物0.58份。 The obtained residue was dried under reduced pressure at 60°C to obtain 0.58 parts of a mixture of a compound represented by formula (Ia5-SA1) (a compound in which one hydrogen atom of the compound represented by formula (Ia5) is replaced by -SO 3 NH 4 ) and a compound represented by formula (Ia5-SA2) (a compound in which two hydrogen atoms of the compound represented by formula (Ia5) are replaced by -SO 3 NH 4 ).

Figure 109104792-A0305-02-0363-276
Figure 109104792-A0305-02-0363-276

<式(Ia5-SA1)所表示的化合物的鑑定> <Identification of compounds represented by formula (Ia5-SA1)>

(質量分析)離子化模式=ESI-:m/z=[M-NH4+H-H]-525 (Mass analysis) Ionization mode = ESI-: m/z = [M-NH 4 +HH] - 525

精確質量(Exact Mass):543 Exact Mass: 543

Figure 109104792-A0305-02-0364-277
Figure 109104792-A0305-02-0364-277

<式(Ia5-SA2)所表示的化合物的鑑定> <Identification of compounds represented by formula (Ia5-SA2)>

(質量分析)離子化模式=ESI-:m/z=[M-NH4-NH4+H+H-H]-605 (Mass analysis) Ionization mode = ESI-: m/z = [M-NH 4 -NH 4 +H+HH] - 605

精確質量(Exact Mass):640 Exact Mass: 640

實施例E-2 Example E-2

將式(Ia1)所表示的化合物0.30份、氯仿3.00份及氯磺酸(東京化成工業(股)製造)0.55份混合。 Mix 0.30 parts of the compound represented by formula (Ia1), 3.00 parts of chloroform, and 0.55 parts of chlorosulfonic acid (produced by Tokyo Chemical Industry Co., Ltd.).

將該混合物一邊保持為60℃一邊攪拌3小時。 The mixture was stirred for 3 hours while being maintained at 60°C.

將該混合物滴加至3.64份的冰中。 The mixture was added dropwise to 3.64 parts of ice.

對所獲得的混合物進行過濾,並利用水對所獲得的殘渣進行清洗。 The obtained mixture is filtered and the obtained residue is washed with water.

利用甲醇對該殘渣進行清洗。 The residue is washed with methanol.

於60℃下對該殘渣進行減壓乾燥,獲得包含式(Ia1-SA1)所表示的化合物(將式(Ia1)所表示的化合物的一個任一氫原子取代為-SO3H的化合物)、與式(Ia1-SA2)所表示的化合物(將式(Ia1)所表示的化合物的一個任一氫原子取代為-SO2Cl的化合物)的混合物0.18份。 The residue was dried under reduced pressure at 60°C to obtain 0.18 parts of a mixture containing a compound represented by formula (Ia1-SA1) (a compound in which one hydrogen atom of the compound represented by formula (Ia1) is substituted with -SO3H ) and a compound represented by formula (Ia1-SA2) (a compound in which one hydrogen atom of the compound represented by formula (Ia1) is substituted with -SO2Cl ).

Figure 109104792-A0305-02-0365-278
Figure 109104792-A0305-02-0365-278

<式(Ia1-SA1)所表示的化合物的鑑定> <Identification of compounds represented by formula (Ia1-SA1)>

(質量分析)離子化模式=ESI-:m/z=[M-H]-497 (Mass analysis) Ionization mode = ESI-: m/z = [MH] - 497

精確質量(Exact Mass):498 Exact Mass: 498

Figure 109104792-A0305-02-0365-279
Figure 109104792-A0305-02-0365-279

<式(Ia1-SA2)所表示的化合物的鑑定> <Identification of compounds represented by formula (Ia1-SA2)>

(質量分析)離子化模式=ESI-:m/z=[M-H]-515 (Mass analysis) Ionization mode = ESI-: m/z = [MH] - 515

精確質量(Exact Mass):516 Exact Mass: 516

實施例E-3 Example E-3

將式(Ia2)所表示的化合物1.00份與發煙硫酸(30%)(富士軟片和光純藥(股)製造)20.6份於室溫下混合。 1.00 parts of the compound represented by formula (Ia2) and 20.6 parts of fuming sulfuric acid (30%) (manufactured by Fuji Films and Wako Pure Chemical Industries, Ltd.) were mixed at room temperature.

於室溫下將該混合物攪拌3小時。 The mixture was stirred at room temperature for 3 hours.

將該混合物滴加至208份的冰中。 The mixture was added dropwise to 208 parts of ice.

將所獲得的混合物與乙腈110份混合。 The obtained mixture was mixed with 110 parts of acetonitrile.

對該混合物進行過濾,並利用乙腈對所獲得的殘渣進行清洗。 The mixture was filtered and the resulting residue was washed with acetonitrile.

於60℃下對該殘渣進行減壓乾燥,獲得包含式(Ia2-SA)所表示的化合物(將式(Ia2)所表示的化合物的兩個任一氫原子取代為-SO3H的化合物)的混合物0.40份。 The residue was dried under reduced pressure at 60°C to obtain 0.40 parts of a mixture containing a compound represented by formula (Ia2-SA) (a compound in which any two hydrogen atoms of the compound represented by formula (Ia2) are replaced by -SO 3 H).

Figure 109104792-A0305-02-0366-280
Figure 109104792-A0305-02-0366-280

<式(Ia2-SA)所表示的化合物的鑑定> <Identification of compounds represented by formula (Ia2-SA)>

(質量分析)離子化模式=ESI-:m/z=[M-H]-677 (Mass analysis) Ionization mode = ESI-: m/z = [MH] - 677

精確質量(Exact Mass):678 Exact Mass: 678

合成例1 Synthesis Example 1

於包括回流冷卻器、滴加漏斗及攪拌機的燒瓶內流通適量氮氣,置換為氮氣環境,放入丙二醇單甲醚乙酸酯280份,一邊進行攪拌一邊加熱至80℃。繼而,歷時5小時滴加丙烯酸38份、丙烯酸3,4-環氧三環[5.2.1.02,6]癸烷-8-基酯及丙烯酸3,4-環氧三環[5.2.1.02,6]癸烷-9-基酯的混合物(含有比以莫耳比計為1:1)289份、丙二醇單甲醚乙酸酯125份的混合溶液。另一方面,歷時6小時滴加使2,2-偶氮雙(2,4-二甲基戊腈)33份溶解於丙二醇單甲醚乙酸酯235份中而成的溶液。滴加結束後,於80℃下保持4小時,之後冷卻至室溫,獲得固體成分為35.0%的共聚物(樹脂B1)的溶液。所獲得的樹脂B1的重量平均分子量為8800,分散度為2.1,固體成分換算的酸價為80mg-KOH/g。 A suitable amount of nitrogen was passed through a flask including a reflux cooler, a dropping funnel and a stirrer to replace the atmosphere with a nitrogen atmosphere, and 280 parts of propylene glycol monomethyl ether acetate was added and heated to 80°C while stirring. Subsequently, a mixed solution of 38 parts of acrylic acid, 289 parts of a mixture of 3,4-epoxytricyclo[5.2.1.0 2,6 ]decane-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 2,6 ]decane-9-yl acrylate (containing ratio of 1:1 in molar ratio) and 125 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. On the other hand, a solution prepared 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 addition was completed, the mixture 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 8800, the degree of dispersion was 2.1, and the acid value converted to solid content was 80 mg-KOH/g.

合成例2 Synthesis Example 2

於包括回流冷卻器、滴加漏斗及攪拌機的燒瓶內流通適量氮氣,置換為氮氣環境,放入丙二醇單甲醚乙酸酯340份,一邊進行攪拌一邊加熱至80℃。繼而,歷時5小時滴加丙烯酸57份、丙烯酸3,4-環氧三環[5.2.1.02,6]癸烷-8-基酯及丙烯酸3,4-環氧三環[5.2.1.02,6]癸烷-9-基酯的混合物(含有比以莫耳比計為1:1)54份、甲基丙烯酸苄基酯239份、丙二醇單甲醚乙酸酯73份的混合 溶液。另一方面,歷時6小時滴加使2,2-偶氮雙(2,4-二甲基戊腈)40份溶解於丙二醇單甲醚乙酸酯197份中而成的溶液。滴加結束後,於80℃下保持3小時,之後冷卻至室溫,獲得固體成分為36.8%的共聚物(樹脂B2)的溶液。所獲得的共聚物的重量平均分子量為9400,分散度為1.89,固體成分換算的酸價為114mg-KOH/g。 A suitable amount of nitrogen was passed through a flask including a reflux cooler, a dropping funnel and a stirrer to replace the atmosphere with a nitrogen atmosphere, and 340 parts of propylene glycol monomethyl ether acetate was added and heated to 80°C while stirring. Subsequently, a mixed solution of 57 parts of acrylic acid, 54 parts of a mixture of 3,4-epoxytricyclo[5.2.1.0 2,6 ]decane-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 2,6 ]decane-9-yl acrylate (containing ratio of 1:1 in terms of molar ratio), 239 parts of benzyl methacrylate and 73 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. On the other hand, a solution prepared 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 addition was completed, the mixture 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 9400, the degree of dispersion was 1.89, and the acid value calculated as solid content was 114 mg-KOH/g.

實施例9 Example 9

按照以下比例將各成分混合,使用珠磨機使著色劑分散,獲得著色組成物M1。 Mix the components in the following proportions and disperse the colorant using a bead mill to obtain a coloring composition M1.

著色劑(A):式(Ia2)所表示的化合物 4.50份;著色劑(A):式(z)所表示的化合物 0.500份;分散劑溶液:迪斯帕畢克(DISPERBYK)-161(日本畢克化學(BYK-Chemie Japan)股份有限公司製造) 16.7份;樹脂(B):樹脂B1溶液 11.4份;溶劑(E):丙二醇單甲醚乙酸酯 46.9份;溶劑(E):乳酸乙酯 20.0份;繼而,按照以下比例將各成分混合,獲得著色組成物1。 Colorant (A): 4.50 parts of the compound represented by formula (Ia2); Colorant (A): 0.500 parts of the compound represented by formula (z); Dispersant solution: 16.7 parts of DISPERBYK-161 (manufactured by BYK-Chemie Japan Co., Ltd.); Resin (B): 11.4 parts of resin B1 solution; Solvent (E): 46.9 parts of propylene glycol monomethyl ether acetate; Solvent (E): 20.0 parts of ethyl lactate; Then, the components were mixed in the following proportions to obtain a coloring composition 1.

著色組成物M1 57.6份;樹脂(B):樹脂B2溶液 27.0份;溶劑(E):丙二醇單甲醚乙酸酯 15.4份;調平劑(F):東麗矽酮(Toray Silicone)SH8400(東麗道康寧(Toray Dow Corning)(股)製造) 0.00630份;[化168]

Figure 109104792-A0305-02-0369-281
Coloring composition M1 57.6 parts; Resin (B): Resin B2 solution 27.0 parts; Solvent (E): Propylene glycol monomethyl ether acetate 15.4 parts; Leveling agent (F): Toray Silicone SH8400 (Toray Dow Corning Co., Ltd.) 0.00630 parts; [Chemical 168]
Figure 109104792-A0305-02-0369-281

於2英吋見方的玻璃基板(益格(eagle)XG;康寧(Corning)製造)上,利用旋塗法塗佈著色組成物1,之後,在100℃下預烘烤3分鐘,形成預烘烤著色塗膜。 The coloring composition 1 was applied on a 2-inch square glass substrate (Eagle XG; manufactured by Corning) by spin coating, and then pre-baked at 100°C for 3 minutes to form a pre-baked coloring film.

使用DektakXT(布魯克(BRUKER)製造)測定所獲得的預烘烤著色塗膜的膜厚。 The film thickness of the obtained pre-baked pigmented coating film was measured using DektakXT (manufactured by BRUKER).

使用測色機:LVmicroZ(蘭木達比森(lambda-vision)股份有限公司製造)測定該預烘烤著色塗膜的光譜。 The spectrum of the pre-baked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.).

將該預烘烤著色塗膜的膜厚、及該預烘烤著色塗膜的吸收光譜的最長波長側的極大吸收波長示於表39中。 The film thickness of the pre-baked color coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked color coating film are shown in Table 39.

對該預烘烤著色塗膜於230℃下進行30分鐘後烘烤,藉此獲得後烘烤著色塗膜。 The pre-baked colored coating film was post-baked at 230°C for 30 minutes to obtain a post-baked colored coating film.

實施例10 Example 10

將式(Ia2)所表示的化合物替換為式(Ia23)所表示的化合物,除此以外,與實施例9同樣地進行,獲得著色組成物,並獲得預烘烤著色塗膜及後烘烤著色塗膜。 The compound represented by formula (Ia2) is replaced by the compound represented by formula (Ia23). The same procedure as in Example 9 is followed to obtain a coloring composition, a pre-baked coloring film, and a post-baked coloring film.

將該預烘烤著色塗膜的膜厚、及該預烘烤著色塗膜的吸收光譜的最長波長側的極大吸收波長示於表39中。 The film thickness of the pre-baked color coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked color coating film are shown in Table 39.

實施例11 Example 11

將式(Ia2)所表示的化合物替換為實施例4中獲得的式(Ia10)所表示的化合物、式(Ia2143)所表示的化合物、式(Ia850)所表示的化合物及式(Ia315)所表示的化合物的混合物,除此以外,與實施例9同樣地進行,獲得著色組成物,並獲得預烘烤著色塗膜及後烘烤著色塗膜。 The same process as in Example 9 was performed except that the compound represented by formula (Ia2) was replaced by the compound represented by formula (Ia10) obtained in Example 4, the compound represented by formula (Ia2143), the compound represented by formula (Ia850) and the mixture of the compound represented by formula (Ia315), to obtain a coloring composition, a pre-baked coloring film and a post-baked coloring film.

將該預烘烤著色塗膜的膜厚、及該預烘烤著色塗膜的吸收光譜的最長波長側的肩峰的波長示於表39中。 The film thickness of the pre-baked color coating film and the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum of the pre-baked color coating film are shown in Table 39.

實施例12 Example 12

將式(Ia2)所表示的化合物替換為式(Ia35)所表示的化合物,除此以外,與實施例9同樣地進行,獲得著色組成物,並獲得預烘烤著色塗膜及後烘烤著色塗膜。 The compound represented by formula (Ia2) is replaced by the compound represented by formula (Ia35). The same method as in Example 9 is followed to obtain a coloring composition, a pre-baked coloring film, and a post-baked coloring film.

將該預烘烤著色塗膜的膜厚、及該預烘烤著色塗膜的吸收光譜的最長波長側的極大吸收波長示於表39中。 The film thickness of the pre-baked color coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked color coating film are shown in Table 39.

實施例13 Example 13

按照以下比例將各成分混合,使用珠磨機使著色劑分散,獲得著色組成物M2。 Mix the components in the following proportions, and use a bead mill to disperse the colorant to obtain a coloring composition M2.

著色劑(A):式(Ia1)所表示的化合物 4.50份;著色劑(A):式(z)所表示的化合物 0.500份;分散劑溶液:畢克(BYK)-LPN6919(日本畢克化學 (BYK-Chemie Japan)股份有限公司製造) 8.33份;樹脂(B):樹脂B1溶液 11.4份;溶劑(E):丙二醇單甲醚乙酸酯 55.2份;溶劑(E):乳酸乙酯 20.0份;繼而,按照以下比例將各成分混合,獲得著色組成物2。 Colorant (A): 4.50 parts of the compound represented by formula (Ia1); Colorant (A): 0.500 parts of the compound represented by formula (z); Dispersant solution: 8.33 parts of BYK-LPN6919 (manufactured by BYK-Chemie Japan Co., Ltd.); Resin (B): 11.4 parts of resin B1 solution; Solvent (E): 55.2 parts of propylene glycol monomethyl ether acetate; Solvent (E): 20.0 parts of ethyl lactate; Then, the components were mixed in the following proportions to obtain a coloring composition 2.

著色組成物M2 57.6份;樹脂(B):樹脂B2溶液 27.0份;溶劑(E):丙二醇單甲醚乙酸酯 15.4份;調平劑(F):東麗矽酮(Toray Silicone)SH8400(東麗道康寧(Toray Dow Corning)(股)製造) 0.00630份;於2英吋見方的玻璃基板(益格(eagle)XG;康寧(Corning)製造)上,利用旋塗法塗佈著色組成物2,之後,在100℃下預烘烤3分鐘,形成預烘烤著色塗膜。 Coloring composition M2 57.6 parts; Resin (B): Resin B2 solution 27.0 parts; Solvent (E): Propylene glycol monomethyl ether acetate 15.4 parts; Leveling agent (F): Toray Silicone SH8400 (Toray Dow Corning Co., Ltd.) 0.00630 parts; Coloring composition 2 was applied by spin coating on a 2-inch square glass substrate (Eagle XG; Corning), and then pre-baked at 100°C for 3 minutes to form a pre-baked coloring film.

使用DektakXT(布魯克(BRUKER)製造)測定所獲得的預烘烤著色塗膜的膜厚。 The film thickness of the obtained pre-baked pigmented coating film was measured using DektakXT (manufactured by BRUKER).

使用測色機:LVmicroZ(蘭木達比森(lambda-vision)股份有限公司製造)測定該預烘烤著色塗膜的光譜。 The spectrum of the pre-baked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.).

將該預烘烤著色塗膜的膜厚、及該預烘烤著色塗膜的吸收光譜的最長波長側的極大吸收波長示於表39中。 The film thickness of the pre-baked color coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked color coating film are shown in Table 39.

對該預烘烤著色塗膜於230℃下進行30分鐘後烘烤,藉此獲得後烘烤著色塗膜。 The pre-baked colored coating film was post-baked at 230°C for 30 minutes to obtain a post-baked colored coating film.

實施例14 Example 14

按照以下比例將各成分混合,使用珠磨機使著色劑分散,獲得著色組成物M3。 Mix the components in the following proportions, and use a bead mill to disperse the colorant to obtain a coloring composition M3.

著色劑(A):實施例4中獲得的式(Ia10)所表示的化合物、式(Ia2143)所表示的化合物、式(Ia850)所表示的化合物及式(Ia315)所表示的化合物的混合物 5.00份;分散劑溶液:迪斯帕畢克(DISPERBYK)-161(日本畢克化學(BYK-Chemie Japan)股份有限公司製造) 16.7份;樹脂(B):樹脂B1溶液 11.4份;溶劑(E):丙二醇單甲醚乙酸酯 46.9份;溶劑(E):乳酸乙酯 20.0份;繼而,按照以下比例將各成分混合,獲得著色組成物3。 Coloring agent (A): 5.00 parts of 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; Dispersant solution: 16.7 parts of DISPERBYK-161 (manufactured by BYK-Chemie Japan Co., Ltd.); Resin (B): 11.4 parts of resin B1 solution; Solvent (E): 46.9 parts of propylene glycol monomethyl ether acetate; Solvent (E): 20.0 parts of ethyl lactate; Then, the components were mixed in the following proportions to obtain a coloring composition 3.

著色組成物M3 57.6份;樹脂(B):樹脂B2溶液 27.0份;溶劑(E):丙二醇單甲醚乙酸酯 15.4份;調平劑(F):東麗矽酮(Toray Silicone)SH8400(東麗道康寧(Toray Dow Corning)(股)製造) 0.00630份;於2英吋見方的玻璃基板(益格(eagle)XG;康寧(Corning)製造)上,利用旋塗法塗佈著色組成物3,之後,在100℃下預烘烤3分鐘,形成預烘烤著色塗膜。 Coloring composition M3 57.6 parts; Resin (B): Resin B2 solution 27.0 parts; Solvent (E): Propylene glycol monomethyl ether acetate 15.4 parts; Leveling agent (F): Toray Silicone SH8400 (Toray Dow Corning) (co., Ltd.) 0.00630 parts; Coloring composition 3 was applied by spin coating on a 2-inch square glass substrate (Eagle XG; Corning), and then pre-baked at 100°C for 3 minutes to form a pre-baked coloring film.

使用DektakXT(布魯克(BRUKER)製造)測定所獲得的預烘烤著色塗膜的膜厚。 The film thickness of the obtained pre-baked pigmented coating film was measured using DektakXT (manufactured by BRUKER).

使用測色機:LVmicroZ(蘭木達比森(lambda-vision)股份 有限公司製造)測定該預烘烤著色塗膜的光譜。 The spectrum of the pre-baked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.).

將該預烘烤著色塗膜的膜厚、及該預烘烤著色塗膜的吸收光譜的最長波長側的肩峰的波長示於表39中。 The film thickness of the pre-baked color coating film and the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum of the pre-baked color coating film are shown in Table 39.

對該預烘烤著色塗膜於230℃下進行30分鐘後烘烤,藉此獲得後烘烤著色塗膜。 The pre-baked colored coating film was post-baked at 230°C for 30 minutes to obtain a post-baked colored coating film.

實施例15 Example 15

將實施例4中獲得的式(Ia10)所表示的化合物、式(Ia2143)所表示的化合物、式(Ia850)所表示的化合物及式(Ia315)所表示的化合物的混合物替換為式(Ia33)所表示的化合物,除此以外,與實施例14同樣地進行,獲得著色組成物,並獲得預烘烤著色塗膜及後烘烤著色塗膜。 The same process as in Example 14 was performed except that the compound represented by formula (Ia10), the compound represented by formula (Ia2143), the compound represented by formula (Ia850) and the mixture of the compound represented by formula (Ia315) obtained in Example 4 were replaced by the compound represented by formula (Ia33) to obtain a coloring composition, a pre-baked coloring film and a post-baked coloring film.

將該預烘烤著色塗膜的膜厚、及該預烘烤著色塗膜的吸收光譜的最長波長側的極大吸收波長示於表39中。 The film thickness of the pre-baked color coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked color coating film are shown in Table 39.

實施例16 Example 16

按照以下比例將各成分混合,使用珠磨機使著色劑分散,獲得著色組成物M4。 Mix the components in the following proportions and disperse the colorant using a bead mill to obtain coloring composition M4.

著色劑(A):式(Ia22)所表示的化合物 4.50份;著色劑(A):式(z)所表示的化合物 0.500份;分散劑溶液:迪斯帕畢克(DISPERBYK)-161(日本畢克化學(BYK-Chemie Japan)股份有限公司製造) 16.7份;樹脂(B):樹脂B1溶液 11.4份;溶劑(E):丙二醇單甲醚乙酸酯 46.9份; 溶劑(E):乳酸乙酯 20.0份;繼而,按照以下比例將各成分混合,獲得著色組成物4。 Colorant (A): 4.50 parts of the compound represented by formula (Ia22); Colorant (A): 0.500 parts of the compound represented by formula (z); Dispersant solution: 16.7 parts of DISPERBYK-161 (manufactured by BYK-Chemie Japan Co., Ltd.); Resin (B): 11.4 parts of resin B1 solution; Solvent (E): 46.9 parts of propylene glycol monomethyl ether acetate; Solvent (E): 20.0 parts of ethyl lactate; Then, the components were mixed in the following proportions to obtain a coloring composition 4.

著色組成物M4 48.0份;樹脂(B):樹脂B2溶液 22.5份;溶劑(E):丙二醇單甲醚乙酸酯 29.5份;調平劑(F):東麗矽酮(Toray Silicone)SH8400(東麗道康寧(Toray Dow Corning)(股)製造) 0.00525份;於2英吋見方的玻璃基板(益格(eagle)XG;康寧(Corning)製造)上,利用旋塗法塗佈著色組成物4,之後,在100℃下預烘烤3分鐘,形成預烘烤著色塗膜。 Coloring composition M4 48.0 parts; Resin (B): Resin B2 solution 22.5 parts; Solvent (E): Propylene glycol monomethyl ether acetate 29.5 parts; Leveling agent (F): Toray Silicone SH8400 (Toray Dow Corning Co., Ltd.) 0.00525 parts; Coloring composition 4 was applied by spin coating on a 2-inch square glass substrate (Eagle XG; Corning), and then pre-baked at 100°C for 3 minutes to form a pre-baked coloring film.

使用DektakXT(布魯克(BRUKER)製造)測定所獲得的預烘烤著色塗膜的膜厚。 The film thickness of the obtained pre-baked pigmented coating film was measured using DektakXT (manufactured by BRUKER).

使用測色機:LVmicroZ(蘭木達比森(lambda-vision)股份有限公司製造)測定該預烘烤著色塗膜的光譜。 The spectrum of the pre-baked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.).

將該預烘烤著色塗膜的膜厚、及該預烘烤著色塗膜的吸收光譜的最長波長側的極大吸收波長示於表39中。 The film thickness of the pre-baked color coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked color coating film are shown in Table 39.

對該預烘烤著色塗膜於230℃下進行30分鐘後烘烤,藉此獲得後烘烤著色塗膜。 The pre-baked colored coating film was post-baked at 230°C for 30 minutes to obtain a post-baked colored coating film.

比較例1 Comparison Example 1

按照以下比例將各成分混合,使用珠磨機使著色劑分散,獲得著色組成物M5。 Mix the components in the following proportions and disperse the colorant using a bead mill to obtain coloring composition M5.

著色劑(A):C.I.顏料黃138 12.0份; 分散劑的固體成分 4.21份;樹脂的固體成分 5.05份;溶劑(E):丙二醇單甲醚乙酸酯 74.8份;溶劑(E):丙二醇單甲醚 3.94份;繼而,按照以下比例將各成分混合,獲得著色組成物5。 Colorant (A): C.I. Pigment Yellow 138 12.0 parts; Dispersant solid content 4.21 parts; Resin solid content 5.05 parts; Solvent (E): Propylene glycol monomethyl ether acetate 74.8 parts; Solvent (E): Propylene glycol monomethyl ether 3.94 parts; Then, the components were mixed in the following proportions to obtain a coloring composition 5.

著色組成物M5 24.0份;樹脂(B):樹脂B2溶液 35.0份;溶劑(E):丙二醇單甲醚乙酸酯 41.0份;調平劑(F):東麗矽酮(Toray Silicone)SH8400(東麗道康寧(Toray Dow Corning)(股)製造) 0.00630份;於2英吋見方的玻璃基板(益格(eagle)XG;康寧(Corning)製造)上,利用旋塗法塗佈著色組成物5,之後,在100℃下預烘烤3分鐘,形成預烘烤著色塗膜。 Coloring composition M5 24.0 parts; Resin (B): Resin B2 solution 35.0 parts; Solvent (E): Propylene glycol monomethyl ether acetate 41.0 parts; Leveling agent (F): Toray Silicone SH8400 (Toray Dow Corning Co., Ltd.) 0.00630 parts; Coloring composition 5 was applied by spin coating on a 2-inch square glass substrate (Eagle XG; Corning), and then pre-baked at 100°C for 3 minutes to form a pre-baked coloring film.

使用DektakXT(布魯克(BRUKER)製造)測定所獲得的預烘烤著色塗膜的膜厚。 The film thickness of the obtained pre-baked pigmented coating film was measured using DektakXT (manufactured by BRUKER).

使用測色機:LVmicroZ(蘭木達比森(lambda-vision)股份有限公司製造)測定該預烘烤著色塗膜的光譜。 The spectrum of the pre-baked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.).

將該預烘烤著色塗膜的膜厚、及該預烘烤著色塗膜的吸收光譜的最長波長側的極大吸收波長示於表39中。 The film thickness of the pre-baked color coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked color coating film are shown in Table 39.

對該預烘烤著色塗膜於230℃下進行30分鐘後烘烤,藉此獲得後烘烤著色塗膜。 The pre-baked colored coating film was post-baked at 230°C for 30 minutes to obtain a post-baked colored coating film.

比較例2 Comparison Example 2

按照以下比例將各成分混合,使用珠磨機使著色劑分散,獲得著色組成物M6。 Mix the components in the following proportions and disperse the colorant using a bead mill to obtain coloring composition M6.

著色劑(A):C.I.顏料黃138 4.50份;著色劑(A):式(z)所表示的化合物 0.500份;分散劑溶液:迪斯帕畢克(DISPERBYK)-161(日本畢克化學(BYK-Chemie Japan)股份有限公司製造) 16.7份;樹脂(B):樹脂B1溶液 11.4份;溶劑(E):丙二醇單甲醚乙酸酯 46.9份;溶劑(E):乳酸乙酯 20.0份;繼而,按照以下比例將各成分混合,獲得著色組成物6。 Colorant (A): C.I. Pigment Yellow 138 4.50 parts; Colorant (A): Compound represented by formula (z) 0.500 parts; Dispersant solution: DISPERBYK-161 (manufactured by BYK-Chemie Japan Co., Ltd.) 16.7 parts; Resin (B): Resin B1 solution 11.4 parts; Solvent (E): Propylene glycol monomethyl ether acetate 46.9 parts; Solvent (E): Ethyl lactate 20.0 parts; Then, the components were mixed in the following proportions to obtain a coloring composition 6.

著色組成物M6 57.6份;樹脂(B):樹脂B2溶液 27.0份;溶劑(E):丙二醇單甲醚乙酸酯 15.4份;調平劑(F):東麗矽酮(Toray Silicone)SH8400(東麗道康寧(Toray Dow Corning)(股)製造) 0.00630份;於2英吋見方的玻璃基板(益格(eagle)XG;康寧(Corning)製造)上,利用旋塗法塗佈著色組成物6,之後,在100℃下預烘烤3分鐘,形成預烘烤著色塗膜。 Coloring composition M6 57.6 parts; Resin (B): Resin B2 solution 27.0 parts; Solvent (E): Propylene glycol monomethyl ether acetate 15.4 parts; Leveling agent (F): Toray Silicone SH8400 (Toray Dow Corning) (co., Ltd.) 0.00630 parts; Coloring composition 6 was applied by spin coating on a 2-inch square glass substrate (Eagle XG; Corning), and then pre-baked at 100°C for 3 minutes to form a pre-baked coloring film.

使用DektakXT(布魯克(BRUKER)製造)測定所獲得的預烘烤著色塗膜的膜厚。 The film thickness of the obtained pre-baked pigmented coating film was measured using DektakXT (manufactured by BRUKER).

使用測色機:LVmicroZ(蘭木達比森(lambda-vision)股份有限公司製造)測定該預烘烤著色塗膜的光譜。 The spectrum of the pre-baked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.).

將該預烘烤著色塗膜的膜厚、及該預烘烤著色塗膜的吸收光譜的最長波長側的極大吸收波長示於表39中。 The film thickness of the pre-baked color coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked color coating film are shown in Table 39.

對該預烘烤著色塗膜於230℃下進行30分鐘後烘烤,藉此獲得後烘烤著色塗膜。 The pre-baked colored coating film was post-baked at 230°C for 30 minutes to obtain a post-baked colored coating film.

於表39中,「AAA」欄表示吸收光譜的最長波長側的極大吸收波長,「BBB」欄表示吸收光譜的最長波長側的肩峰的波長。 In Table 39, the "AAA" column indicates the maximum absorption wavelength on the longest wavelength side of the absorption spectrum, and the "BBB" column indicates the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum.

Figure 109104792-A0305-02-0377-282
Figure 109104792-A0305-02-0377-282

實施例17 Example 17

按照以下比例將各成分混合,使用珠磨機使著色劑分散,獲得著色組成物M7。 Mix the components in the following proportions and disperse the colorant using a bead mill to obtain coloring composition M7.

著色劑(A):實施例7中獲得的包含式(Ie12)所表示的化合物的混合物 5.00份;分散劑溶液:迪斯帕畢克(DISPERBYK)-161(日本畢克化 學(BYK-Chemie Japan)股份有限公司製造) 16.7份;樹脂(B):樹脂B1溶液 11.4份;溶劑(E):丙二醇單甲醚乙酸酯 46.9份;溶劑(E):乳酸乙酯 20.0份;繼而,按照以下比例將各成分混合,獲得著色組成物7。 Colorant (A): 5.00 parts of the mixture containing the compound represented by formula (Ie12) obtained in Example 7; Dispersant solution: 16.7 parts of DISPERBYK-161 (manufactured by BYK-Chemie Japan Co., Ltd.); Resin (B): 11.4 parts of resin B1 solution; Solvent (E): 46.9 parts of propylene glycol monomethyl ether acetate; Solvent (E): 20.0 parts of ethyl lactate; Then, the components were mixed in the following proportions to obtain a coloring composition 7.

著色組成物M7 57.6份;樹脂(B):樹脂B2溶液 27.0份;溶劑(E):丙二醇單甲醚乙酸酯 15.4份;調平劑(F):東麗矽酮(Toray Silicone)SH8400(東麗道康寧(Toray Dow Corning)(股)製造) 0.00630份;於2英吋見方的玻璃基板(益格(eagle)XG;康寧(Corning)製造)上,利用旋塗法塗佈著色組成物7,之後,在100℃下預烘烤3分鐘,形成預烘烤著色塗膜。 Coloring composition M7 57.6 parts; Resin (B): Resin B2 solution 27.0 parts; Solvent (E): Propylene glycol monomethyl ether acetate 15.4 parts; Leveling agent (F): Toray Silicone SH8400 (Toray Dow Corning) (co., Ltd.) 0.00630 parts; Coloring composition 7 was applied by spin coating on a 2-inch square glass substrate (Eagle XG; Corning), and then pre-baked at 100°C for 3 minutes to form a pre-baked coloring film.

對該預烘烤著色塗膜於230℃下進行30分鐘後烘烤,藉此獲得後烘烤著色塗膜。 The pre-baked colored coating film was post-baked at 230°C for 30 minutes to obtain a post-baked colored coating film.

使用DektakXT(布魯克(BRUKER)製造)測定所獲得的後烘烤著色塗膜的膜厚。 The film thickness of the obtained post-baking colored coating film was measured using DektakXT (manufactured by BRUKER).

使用測色機:LVmicroZ(蘭木達比森(lambda-vision)股份有限公司製造)測定該後烘烤著色塗膜的光譜。 The spectrum of the post-baked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.).

將該後烘烤著色塗膜的膜厚、及該後烘烤著色塗膜的吸收光譜的最長波長側的肩峰的波長示於表40中。 The film thickness of the post-baked paint film and the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum of the post-baked paint film are shown in Table 40.

比較例3 Comparison Example 3

按照以下比例將各成分混合,使用珠磨機使著色劑分散,獲得著色組成物M8。 Mix the ingredients in the following proportions and disperse the colorant using a bead mill to obtain coloring composition M8.

著色劑(A):C.I.顏料黃138 12.0份;分散劑的固體成分 4.21份;樹脂的固體成分 5.05份;溶劑(E):丙二醇單甲醚乙酸酯 74.8份;溶劑(E):丙二醇單甲醚 3.94份;繼而,按照以下比例將各成分混合,獲得著色組成物8。 Colorant (A): 12.0 parts of C.I. Pigment Yellow 138; 4.21 parts of solid content of dispersant; 5.05 parts of solid content of resin; Solvent (E): 74.8 parts of propylene glycol monomethyl ether acetate; Solvent (E): 3.94 parts of propylene glycol monomethyl ether; Then, the components were mixed in the following proportions to obtain a coloring composition 8.

著色組成物M8 24.0份;樹脂(B):樹脂B2溶液 35.0份;溶劑(E):丙二醇單甲醚乙酸酯 41.0份;調平劑(F):東麗矽酮(Toray Silicone)SH8400(東麗道康寧(Toray Dow Corning)(股)製造) 0.00630份;於2英吋見方的玻璃基板(益格(eagle)XG;康寧(Corning)製造)上,利用旋塗法塗佈著色組成物8,之後,在100℃下預烘烤3分鐘,形成預烘烤著色塗膜。 Coloring composition M8 24.0 parts; Resin (B): Resin B2 solution 35.0 parts; Solvent (E): Propylene glycol monomethyl ether acetate 41.0 parts; Leveling agent (F): Toray Silicone SH8400 (Toray Dow Corning Co., Ltd.) 0.00630 parts; Coloring composition 8 was applied by spin coating on a 2-inch square glass substrate (Eagle XG; Corning), and then pre-baked at 100°C for 3 minutes to form a pre-baked coloring film.

對該預烘烤著色塗膜於230℃下進行30分鐘後烘烤,藉此獲得後烘烤著色塗膜。 The pre-baked colored coating film was post-baked at 230°C for 30 minutes to obtain a post-baked colored coating film.

使用DektakXT(布魯克(BRUKER)製造)測定所獲得的後烘烤著色塗膜的膜厚。 The film thickness of the obtained post-baking colored coating film was measured using DektakXT (manufactured by BRUKER).

使用測色機:LVmicroZ(蘭木達比森(lambda-vision)股份有限公司製造)測定該後烘烤著色塗膜的光譜。 The spectrum of the post-baked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.).

將該後烘烤著色塗膜的膜厚、及該後烘烤著色塗膜的吸收光譜的最長波長側的極大吸收波長示於表40中。 The film thickness of the post-baked paint film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the post-baked paint film are shown in Table 40.

於表40中,「CCC」欄表示吸收光譜的最長波長側的極大吸收波長,「DDD」欄表示吸收光譜的最長波長側的肩峰的波長。 In Table 40, the "CCC" column indicates the maximum absorption wavelength on the longest wavelength side of the absorption spectrum, and the "DDD" column indicates the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum.

Figure 109104792-A0305-02-0380-283
Figure 109104792-A0305-02-0380-283

比較例4 Comparison Example 4

按照以下比例將各成分混合,使用珠磨機使著色劑分散,獲得著色組成物MH4。 Mix the ingredients in the following proportions and disperse the colorant using a bead mill to obtain a coloring composition MH4.

著色劑(A):C.I.顏料黃138 4.50份 Colorant (A): C.I. Pigment Yellow 138 4.50 parts

著色劑(A):式(z)所表示的化合物 0.500份 Coloring agent (A): 0.500 parts of the compound represented by formula (z)

分散劑溶液:迪斯帕畢克(DISPERBYK)-161(日本畢克化學(BYK-Chemie Japan)股份有限公司製造) 16.7份 Dispersant solution: DISPERBYK-161 (manufactured by BYK-Chemie Japan Co., Ltd.) 16.7 parts

樹脂(B):樹脂B1溶液 11.4份 Resin (B): 11.4 parts of Resin B1 solution

溶劑(E):丙二醇單甲醚乙酸酯 46.9份 Solvent (E): 46.9 parts of propylene glycol monomethyl ether acetate

溶劑(E):乳酸乙酯 20.0份 Solvent (E): 20.0 parts of ethyl lactate

繼而,按照以下比例將各成分混合,獲得著色組成物H4。 Then, the components were mixed in the following proportions to obtain a coloring composition H4.

著色組成物MH4 57.6份 Coloring composition MH4 57.6 parts

樹脂(B):樹脂B2溶液 27.0份 Resin (B): 27.0 parts of Resin B2 solution

溶劑(E):丙二醇單甲醚乙酸酯 15.4份 Solvent (E): 15.4 parts of propylene glycol monomethyl ether acetate

調平劑(F):東麗矽酮(Toray Silicone)SH8400(東麗道康寧(Toray Dow Corning)(股)製造) 0.00630份 Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning Co., Ltd.) 0.00630 parts

於2英吋見方的玻璃基板(益格(eagle)XG;康寧(Corning)製造)上,利用旋塗法塗佈著色組成物H4,之後,在100℃下預烘烤3分鐘,形成預烘烤著色塗膜。對該預烘烤著色塗膜於230℃下進行30分鐘後烘烤,藉此獲得後烘烤著色塗膜。使用DektakXT(布魯克(BRUKER)製造)測定所獲得的後烘烤著色塗膜的膜厚。使用測色機:LVmicroZ(蘭木達比森(lambda-vision)股份有限公司製造)測定該後烘烤著色塗膜的光譜。 The coloring composition H4 was applied by spin coating on a 2-inch square glass substrate (Eagle XG; manufactured by Corning), and then pre-baked at 100°C for 3 minutes to form a pre-baked coloring film. The pre-baked coloring film was post-baked at 230°C for 30 minutes to obtain a post-baked coloring film. The film thickness of the obtained post-baked coloring film was measured using DektakXT (manufactured by BRUKER). The spectrum of the post-baked coloring film was measured using a colorimeter: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.).

將該後烘烤著色塗膜的膜厚、及該後烘烤著色塗膜的吸收光譜的最長波長側的極大吸收波長或吸收光譜的最長波長側的肩峰的波長示於表AD1中。 The film thickness of the post-baked paint film, and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the post-baked paint film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD1.

於表AD1~表AD21中,「EEE」欄表示吸收光譜的最長波長側的極大吸收波長,「FFF」欄表示吸收光譜的最長波長側的肩峰的波長。 In Tables AD1 to AD21, the "EEE" column indicates the maximum absorption wavelength on the longest wavelength side of the absorption spectrum, and the "FFF" column indicates the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum.

Figure 109104792-A0305-02-0381-284
Figure 109104792-A0305-02-0381-284
Figure 109104792-A0305-02-0382-285
Figure 109104792-A0305-02-0382-285

實施例6-1 Implementation Example 6-1

按照以下比例將各成分混合,使用珠磨機使著色劑分散,獲得著色組成物M6-1。 Mix the components in the following proportions, and use a bead mill to disperse the colorant to obtain a coloring composition M6-1.

著色劑(A):式(Ia51)所表示的化合物 4.50份 Coloring agent (A): 4.50 parts of the compound represented by formula (Ia51)

著色劑(A):式(z)所表示的化合物 0.500份 Coloring agent (A): 0.500 parts of the compound represented by formula (z)

分散劑溶液:迪斯帕畢克(DISPERBYK)-161(日本畢克化學(BYK-Chemie Japan)股份有限公司製造) 16.7份 Dispersant solution: DISPERBYK-161 (manufactured by BYK-Chemie Japan Co., Ltd.) 16.7 parts

樹脂(B):樹脂B1溶液 11.4份 Resin (B): 11.4 parts of Resin B1 solution

溶劑(E):丙二醇單甲醚乙酸酯 66.9份 Solvent (E): 66.9 parts of propylene glycol monomethyl ether acetate

繼而,按照以下比例將各成分混合,獲得著色組成物6-1。 Then, the components are mixed in the following proportions to obtain a coloring composition 6-1.

著色組成物M6-1 57.6份 Coloring composition M6-1 57.6 parts

樹脂(B):樹脂B1溶液 28.4份 Resin (B): 28.4 parts of Resin B1 solution

溶劑(E):丙二醇單甲醚乙酸酯 14.0份 Solvent (E): 14.0 parts of propylene glycol monomethyl ether acetate

調平劑(F):東麗矽酮(Toray Silicone)SH8400(東麗道康寧(Toray Dow Corning)(股)製造) 0.00630份 Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning Co., Ltd.) 0.00630 parts

於2英吋見方的玻璃基板(益格(eagle)XG;康寧(Corning)製造)上,利用旋塗法塗佈著色組成物6-1,之後,在100℃下預烘烤3分鐘,形成預烘烤著色塗膜。 The coloring composition 6-1 was applied on a 2-inch square glass substrate (Eagle XG; manufactured by Corning) by spin coating, and then pre-baked at 100°C for 3 minutes to form a pre-baked coloring film.

使用DektakXT(布魯克(BRUKER)製造)測定所獲得的預 烘烤著色塗膜的膜厚。使用測色機:LVmicroZ(蘭木達比森(lambda-vision)股份有限公司製造)測定該預烘烤著色塗膜的光譜。 The film thickness of the obtained pre-baked colored coating film was measured using DektakXT (manufactured by BRUKER). The spectrum of the pre-baked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.).

將該預烘烤著色塗膜的膜厚、及該預烘烤著色塗膜的吸收光譜的最長波長側的極大吸收波長或吸收光譜的最長波長側的肩峰的波長示於表AD2中。 The film thickness of the pre-baked paint film, and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked paint film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD2.

對該預烘烤著色塗膜於230℃下進行30分鐘後烘烤,藉此獲得後烘烤著色塗膜。 The pre-baked colored coating film was post-baked at 230°C for 30 minutes to obtain a post-baked colored coating film.

Figure 109104792-A0305-02-0383-286
Figure 109104792-A0305-02-0383-286

實施例6-2~實施例6-4 Example 6-2~Example 6-4

將式(Ia51)所表示的化合物替換為表AD3中的「著色劑AAA」欄中記載的化合物,除此以外,與實施例6-1同樣地進行,獲得著色組成物,並獲得預烘烤著色塗膜及後烘烤著色塗膜。 The compound represented by formula (Ia51) is replaced with the compound listed in the "Colorant AAA" column in Table AD3. The same method as in Example 6-1 is followed to obtain a coloring composition, a pre-baked coloring film, and a post-baked coloring film.

將該預烘烤著色塗膜的膜厚、及該預烘烤著色塗膜的吸收光譜的最長波長側的極大吸收波長或吸收光譜的最長波長側的肩峰的波長示於表AD3中。 The film thickness of the pre-baked paint film, and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked paint film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD3.

Figure 109104792-A0305-02-0383-287
Figure 109104792-A0305-02-0383-287
Figure 109104792-A0305-02-0384-288
Figure 109104792-A0305-02-0384-288

實施例7-1 Implementation Example 7-1

按照以下比例將各成分混合,使用珠磨機使著色劑分散,獲得著色組成物M7-1。 Mix the components in the following proportions, and use a bead mill to disperse the colorant to obtain the coloring composition M7-1.

著色劑(A):式(Ia973)所表示的化合物 4.50份;著色劑(A):式(z)所表示的化合物 0.500份;分散劑溶液:畢克(BYK)-LPN6919(日本畢克化學(BYK-Chemie Japan)股份有限公司製造) 8.33份;樹脂(B):樹脂B1溶液 11.4份;溶劑(E):丙二醇單甲醚乙酸酯 75.2份;繼而,按照以下比例將各成分混合,獲得著色組成物7-1。 Colorant (A): 4.50 parts of the compound represented by formula (Ia973); Colorant (A): 0.500 parts of the compound represented by formula (z); Dispersant solution: 8.33 parts of BYK-LPN6919 (manufactured by BYK-Chemie Japan Co., Ltd.); Resin (B): 11.4 parts of resin B1 solution; Solvent (E): 75.2 parts of propylene glycol monomethyl ether acetate; Then, the components were mixed in the following proportions to obtain a coloring composition 7-1.

著色組成物M7-1 57.6份;樹脂(B):樹脂B1溶液 28.4份;溶劑(E):丙二醇單甲醚乙酸酯 14.0份;調平劑(F):東麗矽酮(Toray Silicone)SH8400(東麗道康寧(Toray Dow Corning)(股)製造) 0.00630份;於2英吋見方的玻璃基板(益格(eagle)XG;康寧(Corning)製造)上,利用旋塗法塗佈著色組成物7-1,之後,在100℃下預烘烤3分鐘,形成預烘烤著色塗膜。 Coloring composition M7-1 57.6 parts; Resin (B): Resin B1 solution 28.4 parts; Solvent (E): Propylene glycol monomethyl ether acetate 14.0 parts; Leveling agent (F): Toray Silicone SH8400 (Toray Dow Corning) (co., Ltd.) 0.00630 parts; Coloring composition 7-1 was applied by spin coating on a 2-inch square glass substrate (Eagle XG; Corning), and then pre-baked at 100°C for 3 minutes to form a pre-baked coloring film.

使用DektakXT(布魯克(BRUKER)製造)測定所獲得的預烘烤著色塗膜的膜厚。使用測色機:LVmicroZ(蘭木達比森(lambda-vision)股份有限公司製造)測定該預烘烤著色塗膜的光譜。 The film thickness of the obtained pre-baked colored coating film was measured using DektakXT (manufactured by BRUKER). The spectrum of the pre-baked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.).

將該預烘烤著色塗膜的膜厚、及該預烘烤著色塗膜的吸收光譜的最長波長側的極大吸收波長或吸收光譜的最長波長側的肩峰的波長示於表AD4中。 The film thickness of the pre-baked color coating film, and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked color coating film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD4.

對該預烘烤著色塗膜於230℃下進行30分鐘後烘烤,藉此獲得後烘烤著色塗膜。 The pre-baked colored coating film was post-baked at 230°C for 30 minutes to obtain a post-baked colored coating film.

Figure 109104792-A0305-02-0385-289
Figure 109104792-A0305-02-0385-289

實施例7-2~實施例7-6 Example 7-2~Example 7-6

將式(Ia973)所表示的化合物替換為表AD5中的「著色劑AAA」欄中記載的化合物,除此以外,與實施例7-1同樣地進行,獲得著色組成物,並獲得預烘烤著色塗膜及後烘烤著色塗膜。 The compound represented by formula (Ia973) is replaced with the compound listed in the "Colorant AAA" column in Table AD5. The same method as Example 7-1 is followed to obtain a coloring composition, a pre-baked coloring film, and a post-baked coloring film.

將該預烘烤著色塗膜的膜厚、及該預烘烤著色塗膜的吸收光譜的最長波長側的極大吸收波長或吸收光譜的最長波長側的肩峰的波長示於表AD5中。 The film thickness of the pre-baked paint film, and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked paint film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD5.

[表AD5]

Figure 109104792-A0305-02-0386-290
[Table AD5]
Figure 109104792-A0305-02-0386-290

實施例7-7 Implementation Example 7-7

按照以下比例將各成分混合,使用珠磨機使著色劑分散,獲得著色組成物M7-7。 Mix the ingredients in the following proportions, disperse the colorant using a bead mill, and obtain the coloring composition M7-7.

著色劑(A):式(If2528)所表示的化合物 4.50份;著色劑(A):式(z)所表示的化合物 0.500份;分散劑溶液:畢克(BYK)-LPN6919(日本畢克化學(BYK-Chemie Japan)股份有限公司製造) 8.33份;樹脂(B):樹脂B1溶液 11.4份;溶劑(E):丙二醇單甲醚乙酸酯 75.2份;繼而,按照以下比例將各成分混合,獲得著色組成物7-7。 Colorant (A): 4.50 parts of the compound represented by formula (If2528); Colorant (A): 0.500 parts of the compound represented by formula (z); Dispersant solution: 8.33 parts of BYK-LPN6919 (manufactured by BYK-Chemie Japan Co., Ltd.); Resin (B): 11.4 parts of resin B1 solution; Solvent (E): 75.2 parts of propylene glycol monomethyl ether acetate; Then, the components were mixed in the following proportions to obtain a coloring composition 7-7.

著色組成物M7-7 57.6份;樹脂(B):樹脂B1溶液 28.4份;溶劑(E):丙二醇單甲醚乙酸酯 14.0份;調平劑(F):東麗矽酮(Toray Silicone)SH8400(東麗道康寧(Toray Dow Corning)(股)製造) 0.00630份; 於2英吋見方的玻璃基板(益格(eagle)XG;康寧(Corning)製造)上,利用旋塗法塗佈著色組成物7-7,之後,在100℃下預烘烤3分鐘,形成預烘烤著色塗膜。 Coloring composition M7-7 57.6 parts; Resin (B): Resin B1 solution 28.4 parts; Solvent (E): Propylene glycol monomethyl ether acetate 14.0 parts; Leveling agent (F): Toray Silicone SH8400 (Toray Dow Corning Co., Ltd.) 0.00630 parts; Coloring composition 7-7 was applied by spin coating on a 2-inch square glass substrate (Eagle XG; Corning), and then pre-baked at 100°C for 3 minutes to form a pre-baked coloring film.

對該預烘烤著色塗膜於230℃下進行30分鐘後烘烤,藉此獲得後烘烤著色塗膜。使用DektakXT(布魯克(BRUKER)製造)測定所獲得的後烘烤著色塗膜的膜厚。使用測色機:LVmicroZ(蘭木達比森(lambda-vision)股份有限公司製造)測定該後烘烤著色塗膜的光譜。 The pre-baked color coating film was post-baked at 230°C for 30 minutes to obtain a post-baked color coating film. The film thickness of the post-baked color coating film was measured using DektakXT (manufactured by BRUKER). The spectrum of the post-baked color coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.).

將該後烘烤著色塗膜的膜厚、及該後烘烤著色塗膜的吸收光譜的最長波長側的極大吸收波長或吸收光譜的最長波長側的肩峰的波長示於表AD6中。 The film thickness of the post-baked paint film, and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the post-baked paint film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD6.

Figure 109104792-A0305-02-0387-291
Figure 109104792-A0305-02-0387-291

實施例90-1 Implementation Example 90-1

按照以下比例將各成分混合,使用珠磨機使著色劑分散,獲得著色組成物M90-1。 Mix the ingredients in the following proportions, and use a bead mill to disperse the colorant to obtain the coloring composition M90-1.

著色劑(A):式(Ia5)所表示的化合物 4.00份;著色劑(A):式(z)所表示的化合物 1.00份;分散劑溶液:畢克(BYK)-LPN6919(日本畢克化學 (BYK-Chemie Japan)股份有限公司製造) 12.5份;樹脂(B):樹脂B1溶液 11.4份;溶劑(E):丙二醇單甲醚乙酸酯 71.1份;繼而,按照以下比例將各成分混合,獲得著色組成物90-1。 Colorant (A): 4.00 parts of the compound represented by formula (Ia5); Colorant (A): 1.00 parts of the compound represented by formula (z); Dispersant solution: 12.5 parts of BYK-LPN6919 (manufactured by BYK-Chemie Japan Co., Ltd.); Resin (B): 11.4 parts of resin B1 solution; Solvent (E): 71.1 parts of propylene glycol monomethyl ether acetate; Then, the components were mixed in the following proportions to obtain a coloring composition 90-1.

著色組成物M90-1 57.6份;樹脂(B):樹脂B1溶液 24.3份;溶劑(E):丙二醇單甲醚乙酸酯 18.1份;調平劑(F):東麗矽酮(Toray Silicone)SH8400(東麗道康寧(Toray Dow Corning)(股)製造) 0.00630份;於2英吋見方的玻璃基板(益格(eagle)XG;康寧(Corning)製造)上,利用旋塗法塗佈著色組成物90-1,之後,在100℃下預烘烤3分鐘,形成預烘烤著色塗膜。使用DektakXT(布魯克(BRUKER)製造)測定所獲得的預烘烤著色塗膜的膜厚。使用測色機:LVmicroZ(蘭木達比森(lambda-vision)股份有限公司製造)測定該預烘烤著色塗膜的光譜。 Coloring composition M90-1 57.6 parts; Resin (B): Resin B1 solution 24.3 parts; Solvent (E): Propylene glycol monomethyl ether acetate 18.1 parts; Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning Co., Ltd.) 0.00630 parts; Coloring composition 90-1 was applied by spin coating on a 2-inch square glass substrate (Eagle XG; manufactured by Corning), and then pre-baked at 100°C for 3 minutes to form a pre-baked coloring film. The film thickness of the obtained pre-baked coloring film was measured using DektakXT (manufactured by BRUKER). The spectrum of the pre-baked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.).

將該預烘烤著色塗膜的膜厚、及該預烘烤著色塗膜的吸收光譜的最長波長側的極大吸收波長或吸收光譜的最長波長側的肩峰的波長示於表AD7中。 The film thickness of the pre-baked paint film, and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked paint film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD7.

對該預烘烤著色塗膜於230℃下進行30分鐘後烘烤,藉此獲得後烘烤著色塗膜。 The pre-baked colored coating film was post-baked at 230°C for 30 minutes to obtain a post-baked colored coating film.

[表AD7]

Figure 109104792-A0305-02-0389-292
[Table AD7]
Figure 109104792-A0305-02-0389-292

實施例90-2~實施例90-22 Example 90-2~Example 90-22

將式(Ia5)所表示的化合物替換為表AD8中的「著色劑AAA」欄中記載的化合物,除此以外,與實施例90-1同樣地進行,獲得著色組成物,並獲得預烘烤著色塗膜及後烘烤著色塗膜。 The compound represented by formula (Ia5) is replaced with the compound listed in the "Colorant AAA" column in Table AD8. The same method as Example 90-1 is followed to obtain a coloring composition, a pre-baked coloring film, and a post-baked coloring film.

將該預烘烤著色塗膜的膜厚、及該預烘烤著色塗膜的吸收光譜的最長波長側的極大吸收波長或吸收光譜的最長波長側的肩峰的波長示於表AD8中。 The film thickness of the pre-baked paint film, and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked paint film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD8.

Figure 109104792-A0305-02-0389-293
Figure 109104792-A0305-02-0389-293
Figure 109104792-A0305-02-0390-294
Figure 109104792-A0305-02-0390-294

實施例90-23 Example 90-23

按照以下比例將各成分混合,使用珠磨機使著色劑分散,獲得著色組成物M90-23。 Mix the ingredients in the following proportions, and use a bead mill to disperse the colorant to obtain the coloring composition M90-23.

著色劑(A):式(If1904)所表示的化合物 4.00份;著色劑(A):式(z)所表示的化合物 1.00份;分散劑溶液:畢克(BYK)-LPN6919(日本畢克化學(BYK-Chemie Japan)股份有限公司製造) 12.5份;樹脂(B):樹脂B1溶液 11.4份;溶劑(E):丙二醇單甲醚乙酸酯 71.1份;繼而,按照以下比例將各成分混合,獲得著色組成物90-23。 Colorant (A): 4.00 parts of the compound represented by formula (If1904); Colorant (A): 1.00 parts of the compound represented by formula (z); Dispersant solution: 12.5 parts of BYK-LPN6919 (manufactured by BYK-Chemie Japan Co., Ltd.); Resin (B): 11.4 parts of resin B1 solution; Solvent (E): 71.1 parts of propylene glycol monomethyl ether acetate; Then, the components were mixed in the following proportions to obtain a coloring composition 90-23.

著色組成物M90-23 57.6份;樹脂(B):樹脂B1溶液 24.3份;溶劑(E):丙二醇單甲醚乙酸酯 18.1份;調平劑(F):東麗矽酮(Toray Silicone)SH8400(東麗道康寧(Toray Dow Corning)(股)製造) 0.00630份;於2英吋見方的玻璃基板(益格(eagle)XG;康寧 (Corning)製造)上,利用旋塗法塗佈著色組成物90-23,之後,在100℃下預烘烤3分鐘,形成預烘烤著色塗膜。對該預烘烤著色塗膜於230℃下進行30分鐘後烘烤,藉此獲得後烘烤著色塗膜。使用DektakXT(布魯克(BRUKER)製造)測定所獲得的後烘烤著色塗膜的膜厚。使用測色機:LVmicroZ(蘭木達比森(lambda-vision)股份有限公司製造)測定該後烘烤著色塗膜的光譜。 Coloring composition M90-23 57.6 parts; Resin (B): Resin B1 solution 24.3 parts; Solvent (E): Propylene glycol monomethyl ether acetate 18.1 parts; Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning Co., Ltd.) 0.00630 parts; Coloring composition 90-23 was applied by spin coating on a 2-inch square glass substrate (Eagle XG; manufactured by Corning) and then pre-baked at 100°C for 3 minutes to form a pre-baked coloring film. The pre-baked coloring film was post-baked at 230°C for 30 minutes to obtain a post-baked coloring film. The film thickness of the obtained post-baking color coating film was measured using DektakXT (manufactured by BRUKER). The spectrum of the post-baking color coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.).

將該後烘烤著色塗膜的膜厚、及該後烘烤著色塗膜的吸收光譜的最長波長側的極大吸收波長或吸收光譜的最長波長側的肩峰的波長示於表AD9中。 The film thickness of the post-baked painted film, and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the post-baked painted film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD9.

Figure 109104792-A0305-02-0391-295
Figure 109104792-A0305-02-0391-295

實施例91-1 Implementation Example 91-1

按照以下比例將各成分混合,使用珠磨機使著色劑分散,獲得著色組成物M91-1。 Mix the ingredients in the following proportions, and use a bead mill to disperse the colorant to obtain the coloring composition M91-1.

著色劑(A):式(If3796)所表示的化合物 4.00份;著色劑(A):式(z)所表示的化合物 1.00份;分散劑溶液:畢克(BYK)-LPN6919(日本畢克化學(BYK-Chemie Japan)股份有限公司製造) 12.5份; 樹脂(B):樹脂B1溶液 11.4份;溶劑(E):丙二醇單甲醚乙酸酯 71.1份;繼而,按照以下比例將各成分混合,獲得著色組成物91-1。 Colorant (A): 4.00 parts of the compound represented by formula (If3796); Colorant (A): 1.00 parts of the compound represented by formula (z); Dispersant solution: 12.5 parts of BYK-LPN6919 (manufactured by BYK-Chemie Japan Co., Ltd.); Resin (B): 11.4 parts of resin B1 solution; Solvent (E): 71.1 parts of propylene glycol monomethyl ether acetate; Then, the components were mixed in the following proportions to obtain a coloring composition 91-1.

著色組成物M91-1 51.2份;樹脂(B):樹脂B1溶液 21.6份;溶劑(E):丙二醇單甲醚乙酸酯 27.2份;調平劑(F):東麗矽酮(Toray Silicone)SH8400(東麗道康寧(Toray Dow Corning)(股)製造) 0.00560份;於2英吋見方的玻璃基板(益格(eagle)XG;康寧(Corning)製造)上,利用旋塗法塗佈著色組成物91-1,之後,在100℃下預烘烤3分鐘,形成預烘烤著色塗膜。使用DektakXT(布魯克(BRUKER)製造)測定所獲得的預烘烤著色塗膜的膜厚。使用測色機:LVmicroZ(蘭木達比森(lambda-vision)股份有限公司製造)測定該預烘烤著色塗膜的光譜。 Coloring composition M91-1 51.2 parts; Resin (B): Resin B1 solution 21.6 parts; Solvent (E): Propylene glycol monomethyl ether acetate 27.2 parts; Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning Co., Ltd.) 0.00560 parts; Coloring composition 91-1 was applied by spin coating on a 2-inch square glass substrate (Eagle XG; manufactured by Corning), and then pre-baked at 100°C for 3 minutes to form a pre-baked coloring film. The film thickness of the obtained pre-baked coloring film was measured using DektakXT (manufactured by BRUKER). The spectrum of the pre-baked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.).

將該預烘烤著色塗膜的膜厚、及該預烘烤著色塗膜的吸收光譜的最長波長側的極大吸收波長或吸收光譜的最長波長側的肩峰的波長示於表AD10中。 The film thickness of the pre-baked paint film, and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked paint film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD10.

對該預烘烤著色塗膜於230℃下進行30分鐘後烘烤,藉此獲得後烘烤著色塗膜。 The pre-baked colored coating film was post-baked at 230°C for 30 minutes to obtain a post-baked colored coating film.

[表AD10]

Figure 109104792-A0305-02-0393-296
[Table AD10]
Figure 109104792-A0305-02-0393-296

實施例91-2~實施例91-4 Example 91-2~Example 91-4

將式(If3796)所表示的化合物替換為表AD11中的「著色劑AAA」欄中記載的化合物,除此以外,與實施例91-1同樣地進行,獲得著色組成物,並獲得預烘烤著色塗膜及後烘烤著色塗膜。 The compound represented by formula (If3796) is replaced with the compound listed in the "Colorant AAA" column in Table AD11. The same method as Example 91-1 is followed to obtain a coloring composition, a pre-baked coloring film, and a post-baked coloring film.

將該預烘烤著色塗膜的膜厚、及該預烘烤著色塗膜的吸收光譜的最長波長側的極大吸收波長或吸收光譜的最長波長側的肩峰的波長示於表AD11中。 The film thickness of the pre-baked color coating film, and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked color coating film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD11.

Figure 109104792-A0305-02-0393-297
Figure 109104792-A0305-02-0393-297

實施例17-1 Implementation Example 17-1

按照以下比例將各成分混合,使用珠磨機使著色劑分散,獲得著色組成物M17-1。 Mix the components in the following proportions and disperse the colorant using a bead mill to obtain the coloring composition M17-1.

著色劑(A):實施例E-2中獲得的包含式(Ia1-SA1)所表示的化合物與式(Ia1-SA2)所表示的化合物的混合物 3.89份;著色劑(A):式(z)所表示的化合物 1.25份;分散劑溶液:畢克(BYK)-LPN6919(日本畢克化學 (BYK-Chemie Japan)股份有限公司製造) 12.5份;樹脂(B):樹脂B1溶液 11.5份;溶劑(E):丙二醇單甲醚乙酸酯 70.9份;繼而,按照以下比例將各成分混合,獲得著色組成物17-1。 Colorant (A): 3.89 parts of a mixture of a compound represented by formula (Ia1-SA1) and a compound represented by formula (Ia1-SA2) obtained in Example E-2; Colorant (A): 1.25 parts of a compound represented by formula (z); Dispersant solution: 12.5 parts of BYK-LPN6919 (manufactured by BYK-Chemie Japan Co., Ltd.); Resin (B): 11.5 parts of resin B1 solution; Solvent (E): 70.9 parts of propylene glycol monomethyl ether acetate; Then, the components were mixed in the following proportions to obtain a coloring composition 17-1.

著色組成物M17-1 57.6份;樹脂(B):樹脂B1溶液 24.3份;溶劑(E):丙二醇單甲醚乙酸酯 18.1份;調平劑(F):東麗矽酮(Toray Silicone)SH8400(東麗道康寧(Toray Dow Corning)(股)製造) 0.00629份;於2英吋見方的玻璃基板(益格(eagle)XG;康寧(Corning)製造)上,利用旋塗法塗佈著色組成物17-1,之後,在100℃下預烘烤3分鐘,形成預烘烤著色塗膜。 Coloring composition M17-1 57.6 parts; Resin (B): Resin B1 solution 24.3 parts; Solvent (E): Propylene glycol monomethyl ether acetate 18.1 parts; Leveling agent (F): Toray Silicone SH8400 (Toray Dow Corning) (co., Ltd.) 0.00629 parts; Coloring composition 17-1 was applied by spin coating on a 2-inch square glass substrate (Eagle XG; Corning), and then pre-baked at 100°C for 3 minutes to form a pre-baked coloring film.

使用DektakXT(布魯克(BRUKER)製造)測定所獲得的預烘烤著色塗膜的膜厚。 The film thickness of the obtained pre-baked pigmented coating film was measured using DektakXT (manufactured by BRUKER).

使用測色機:LVmicroZ(蘭木達比森(lambda-vision)股份有限公司製造)測定該預烘烤著色塗膜的光譜。 The spectrum of the pre-baked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.).

將該預烘烤著色塗膜的膜厚、及該預烘烤著色塗膜的吸收光譜的最長波長側的極大吸收波長或吸收光譜的最長波長側的肩峰的波長示於表AD12中。 The film thickness of the pre-baked paint film, and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked paint film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD12.

對該預烘烤著色塗膜於230℃下進行30分鐘後烘烤,藉此獲得後烘烤著色塗膜。 The pre-baked colored coating film was post-baked at 230°C for 30 minutes to obtain a post-baked colored coating film.

Figure 109104792-A0305-02-0395-298
Figure 109104792-A0305-02-0395-298

實施例12-1 Implementation Example 12-1

按照以下比例將各成分混合,使用珠磨機使著色劑分散,獲得著色組成物M12-1。 Mix the components in the following proportions, and use a bead mill to disperse the colorant to obtain a coloring composition M12-1.

著色劑(A):式(If1261)所表示的化合物 3.80份;著色劑(A):式(z)所表示的化合物 1.20份;分散劑溶液:畢克(BYK)-LPN6919(日本畢克化學(BYK-Chemie Japan)股份有限公司製造) 12.5份;樹脂(B):樹脂B1溶液 11.4份;溶劑(E):丙二醇單甲醚乙酸酯 71.1份;繼而,按照以下比例將各成分混合,獲得著色組成物12-1。 Colorant (A): 3.80 parts of the compound represented by formula (If1261); Colorant (A): 1.20 parts of the compound represented by formula (z); Dispersant solution: 12.5 parts of BYK-LPN6919 (manufactured by BYK-Chemie Japan Co., Ltd.); Resin (B): 11.4 parts of resin B1 solution; Solvent (E): 71.1 parts of propylene glycol monomethyl ether acetate; Then, the components were mixed in the following proportions to obtain a coloring composition 12-1.

著色組成物M12-1 57.6份;樹脂(B):樹脂B1溶液 24.3份;溶劑(E):丙二醇單甲醚乙酸酯 18.1份;調平劑(F):東麗矽酮(Toray Silicone)SH8400(東麗道康寧(Toray Dow Corning)(股)製造) 0.00630份;於2英吋見方的玻璃基板(益格(eagle)XG;康寧 (Corning)製造)上,利用旋塗法塗佈著色組成物12-1,之後,在100℃下預烘烤3分鐘,形成預烘烤著色塗膜。對該預烘烤著色塗膜於230℃下進行30分鐘後烘烤,藉此獲得後烘烤著色塗膜。使用DektakXT(布魯克(BRUKER)製造)測定所獲得的後烘烤著色塗膜的膜厚。 Coloring composition M12-1 57.6 parts; Resin (B): Resin B1 solution 24.3 parts; Solvent (E): Propylene glycol monomethyl ether acetate 18.1 parts; Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning Co., Ltd.) 0.00630 parts; Coloring composition 12-1 was applied by spin coating on a 2-inch square glass substrate (Eagle XG; manufactured by Corning) and then pre-baked at 100°C for 3 minutes to form a pre-baked coloring film. The pre-baked coloring film was post-baked at 230°C for 30 minutes to obtain a post-baked coloring film. The film thickness of the obtained post-baking colored coating film was measured using DektakXT (manufactured by BRUKER).

使用測色機:LVmicroZ(蘭木達比森(lambda-vision)股份有限公司製造)測定該後烘烤著色塗膜的光譜。 The spectrum of the post-baked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.).

將該後烘烤著色塗膜的膜厚、及該後烘烤著色塗膜的吸收光譜的最長波長側的極大吸收波長或吸收光譜的最長波長側的肩峰的波長示於表AD13中。 The film thickness of the post-baked painted film, and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the post-baked painted film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD13.

Figure 109104792-A0305-02-0396-299
Figure 109104792-A0305-02-0396-299

實施例13-1 Implementation Example 13-1

按照以下比例將各成分混合,使用珠磨機使著色劑分散,獲得著色組成物M13-1。 Mix the components in the following proportions, and use a bead mill to disperse the colorant to obtain the coloring composition M13-1.

著色劑(A):式(Ia728)所表示的化合物 5.01份;分散劑溶液:畢克(BYK)-LPN6919(日本畢克化學(BYK-Chemie Japan)股份有限公司製造) 12.5份;樹脂(B):樹脂B1溶液 11.4份; 溶劑(E):丙二醇單甲醚乙酸酯 71.1份;繼而,按照以下比例將各成分混合,獲得著色組成物13-1。 Colorant (A): 5.01 parts of the compound represented by formula (Ia728); Dispersant solution: 12.5 parts of BYK-LPN6919 (manufactured by BYK-Chemie Japan Co., Ltd.); Resin (B): 11.4 parts of resin B1 solution; Solvent (E): 71.1 parts of propylene glycol monomethyl ether acetate; Then, the components were mixed in the following proportions to obtain a coloring composition 13-1.

著色組成物M13-1 57.4份;樹脂(B):樹脂B1溶液 24.3份;溶劑(E):丙二醇單甲醚乙酸酯 18.2份;調平劑(F):東麗矽酮(Toray Silicone)SH8400(東麗道康寧(Toray Dow Corning)(股)製造) 0.00636份;於2英吋見方的玻璃基板(益格(eagle)XG;康寧(Corning)製造)上,利用旋塗法塗佈著色組成物13-1,之後,在100℃下預烘烤3分鐘,形成預烘烤著色塗膜。使用DektakXT(布魯克(BRUKER)製造)測定所獲得的預烘烤著色塗膜的膜厚。使用測色機:LVmicroZ(蘭木達比森(lambda-vision)股份有限公司製造)測定該預烘烤著色塗膜的光譜。 Coloring composition M13-1 57.4 parts; Resin (B): Resin B1 solution 24.3 parts; Solvent (E): Propylene glycol monomethyl ether acetate 18.2 parts; Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning Co., Ltd.) 0.00636 parts; Coloring composition 13-1 was applied by spin coating on a 2-inch square glass substrate (Eagle XG; manufactured by Corning), and then pre-baked at 100°C for 3 minutes to form a pre-baked coloring film. The film thickness of the obtained pre-baked coloring film was measured using DektakXT (manufactured by BRUKER). The spectrum of the pre-baked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.).

將該預烘烤著色塗膜的膜厚、及該預烘烤著色塗膜的吸收光譜的最長波長側的極大吸收波長或吸收光譜的最長波長側的肩峰的波長示於表AD14中。 The film thickness of the pre-baked color coating film, and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked color coating film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD14.

對該預烘烤著色塗膜於230℃下進行30分鐘後烘烤,藉此獲得後烘烤著色塗膜。 The pre-baked colored coating film was post-baked at 230°C for 30 minutes to obtain a post-baked colored coating film.

Figure 109104792-A0305-02-0397-300
Figure 109104792-A0305-02-0397-300
Figure 109104792-A0305-02-0398-301
Figure 109104792-A0305-02-0398-301

實施例14-1 Implementation Example 14-1

按照以下比例將各成分混合,使用珠磨機使著色劑分散,獲得著色組成物M14-1。 Mix the components in the following proportions and disperse the colorant using a bead mill to obtain the coloring composition M14-1.

著色劑(A):式(Ia703)所表示的化合物 4.66份;著色劑(A):式(z)所表示的化合物 0.497份;分散劑溶液:畢克(BYK)-LPN6919(日本畢克化學(BYK-Chemie Japan)股份有限公司製造) 12.5份;樹脂(B):樹脂B1溶液 11.4份;溶劑(E):丙二醇單甲醚乙酸酯 70.9份;繼而,按照以下比例將各成分混合,獲得著色組成物14-1。 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: 12.5 parts of BYK-LPN6919 (manufactured by BYK-Chemie Japan Co., Ltd.); Resin (B): 11.4 parts of resin B1 solution; Solvent (E): 70.9 parts of propylene glycol monomethyl ether acetate; Then, the components were mixed in the following proportions to obtain a coloring composition 14-1.

著色組成物M14-1 55.5份;樹脂(B):樹脂B1溶液 24.9份;溶劑(E):丙二醇單甲醚乙酸酯 19.6份;調平劑(F):東麗矽酮(Toray Silicone)SH8400(東麗道康寧(Toray Dow Corning)(股)製造) 0.00635份;於2英吋見方的玻璃基板(益格(eagle)XG;康寧(Corning)製造)上,利用旋塗法塗佈著色組成物14-1,之後,在100℃下預烘烤3分鐘,形成預烘烤著色塗膜。使用DektakXT(布魯克(BRUKER)製造)測定所獲得的預烘烤著色塗膜的膜 厚。使用測色機:LVmicroZ(蘭木達比森(lambda-vision)股份有限公司製造)測定該預烘烤著色塗膜的光譜。 Coloring composition M14-1 55.5 parts; Resin (B): Resin B1 solution 24.9 parts; Solvent (E): Propylene glycol monomethyl ether acetate 19.6 parts; Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning Co., Ltd.) 0.00635 parts; Coloring composition 14-1 was applied by spin coating on a 2-inch square glass substrate (Eagle XG; manufactured by Corning), and then pre-baked at 100°C for 3 minutes to form a pre-baked coloring film. The film thickness of the obtained pre-baked coloring film was measured using DektakXT (manufactured by BRUKER). The spectrum of the pre-baked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.).

將該預烘烤著色塗膜的膜厚、及該預烘烤著色塗膜的吸收光譜的最長波長側的極大吸收波長或吸收光譜的最長波長側的肩峰的波長示於表AD15中。 The film thickness of the pre-baked paint film, and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked paint film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD15.

對該預烘烤著色塗膜於230℃下進行30分鐘後烘烤,藉此獲得後烘烤著色塗膜。 The pre-baked colored coating film was post-baked at 230°C for 30 minutes to obtain a post-baked colored coating film.

Figure 109104792-A0305-02-0399-302
Figure 109104792-A0305-02-0399-302

實施例16-1 Implementation Example 16-1

按照以下比例將各成分混合,使用珠磨機使著色劑分散,獲得著色組成物M16-1。 Mix the components in the following proportions and disperse the colorant using a bead mill to obtain the coloring composition M16-1.

著色劑(A):式(It242)所表示的化合物 4.13份;著色劑(A):式(z)所表示的化合物 0.916份;分散劑溶液:畢克(BYK)-LPN6919(日本畢克化學(BYK-Chemie Japan)股份有限公司製造) 12.4份;樹脂(B):樹脂B1溶液 11.4份;溶劑(E):丙二醇單甲醚乙酸酯 71.1份;繼而,按照以下比例將各成分混合,獲得著色組成物 16-1。 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: 12.4 parts of BYK-LPN6919 (manufactured by BYK-Chemie Japan Co., Ltd.); Resin (B): 11.4 parts of resin B1 solution; Solvent (E): 71.1 parts of propylene glycol monomethyl ether acetate; Then, the components were mixed in the following proportions to obtain a coloring composition 16-1.

著色組成物M16-1 57.8份;樹脂(B):樹脂B1溶液 24.1份;溶劑(E):丙二醇單甲醚乙酸酯 18.1份;調平劑(F):東麗矽酮(Toray Silicone)SH8400(東麗道康寧(Toray Dow Corning)(股)製造) 0.00628份;於2英吋見方的玻璃基板(益格(eagle)XG;康寧(Corning)製造)上,利用旋塗法塗佈著色組成物16-1,之後,在100℃下預烘烤3分鐘,形成預烘烤著色塗膜。使用DektakXT(布魯克(BRUKER)製造)測定所獲得的預烘烤著色塗膜的膜厚。使用測色機:LVmicroZ(蘭木達比森(lambda-vision)股份有限公司製造)測定該預烘烤著色塗膜的光譜。 Coloring composition M16-1 57.8 parts; Resin (B): Resin B1 solution 24.1 parts; Solvent (E): Propylene glycol monomethyl ether acetate 18.1 parts; Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning Co., Ltd.) 0.00628 parts; Coloring composition 16-1 was applied by spin coating on a 2-inch square glass substrate (Eagle XG; manufactured by Corning), and then pre-baked at 100°C for 3 minutes to form a pre-baked coloring film. The film thickness of the obtained pre-baked coloring film was measured using DektakXT (manufactured by BRUKER). The spectrum of the pre-baked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.).

將該預烘烤著色塗膜的膜厚、及該預烘烤著色塗膜的吸收光譜的最長波長側的極大吸收波長或吸收光譜的最長波長側的肩峰的波長示於表AD16中。 The film thickness of the pre-baked paint film, and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked paint film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD16.

對該預烘烤著色塗膜於230℃下進行30分鐘後烘烤,藉此獲得後烘烤著色塗膜。 The pre-baked colored coating film was post-baked at 230°C for 30 minutes to obtain a post-baked colored coating film.

Figure 109104792-A0305-02-0400-303
Figure 109104792-A0305-02-0400-303

實施例51-1 Implementation Example 51-1

按照以下比例將各成分混合,使用珠磨機使著色劑分散,獲得著色組成物M51-1。 Mix the ingredients in the following proportions, and use a bead mill to disperse the colorant to obtain the coloring composition M51-1.

著色劑(A):式(Ia2)所表示的化合物 2.25份;著色劑(A):式(Ia5)所表示的化合物 2.25份;著色劑(A):式(z)所表示的化合物 0.500份;分散劑溶液:迪斯帕畢克(DISPERBYK)-161(日本畢克化學(BYK-Chemie Japan)股份有限公司製造) 16.7份;樹脂(B):樹脂B1溶液 11.4份;溶劑(E):丙二醇單甲醚乙酸酯 46.9份;溶劑(E):乳酸乙酯 20.0份;繼而,按照以下比例將各成分混合,獲得著色組成物51-1。 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): 0.500 parts of the compound represented by formula (z); Dispersant solution: 16.7 parts of DISPERBYK-161 (manufactured by BYK-Chemie Japan Co., Ltd.); Resin (B): 11.4 parts of resin B1 solution; Solvent (E): 46.9 parts of propylene glycol monomethyl ether acetate; Solvent (E): 20.0 parts of ethyl lactate; Then, the components were mixed in the following proportions to obtain a coloring composition 51-1.

著色組成物M51-1 57.6份;樹脂(B):樹脂B1溶液 28.4份;溶劑(E):丙二醇單甲醚乙酸酯 14.0份;調平劑(F):東麗矽酮(Toray Silicone)SH8400(東麗道康寧(Toray Dow Corning)(股)製造) 0.00630份;於2英吋見方的玻璃基板(益格(eagle)XG;康寧(Corning)製造)上,利用旋塗法塗佈著色組成物51-1,之後,在100℃下預烘烤3分鐘,形成預烘烤著色塗膜。使用DektakXT(布魯克(BRUKER)製造)測定所獲得的預烘烤著色塗膜的膜 厚。使用測色機:LVmicroZ(蘭木達比森(lambda-vision)股份有限公司製造)測定該預烘烤著色塗膜的光譜。 Coloring composition M51-1 57.6 parts; Resin (B): Resin B1 solution 28.4 parts; Solvent (E): Propylene glycol monomethyl ether acetate 14.0 parts; Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning Co., Ltd.) 0.00630 parts; Coloring composition 51-1 was applied by spin coating on a 2-inch square glass substrate (Eagle XG; manufactured by Corning), and then pre-baked at 100°C for 3 minutes to form a pre-baked coloring film. The film thickness of the obtained pre-baked coloring film was measured using DektakXT (manufactured by BRUKER). The spectrum of the pre-baked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.).

將該預烘烤著色塗膜的膜厚、及該預烘烤著色塗膜的吸收光譜的最長波長側的極大吸收波長或吸收光譜的最長波長側的肩峰的波長示於表AD17中。 The film thickness of the pre-baked color coating film, and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked color coating film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD17.

對該預烘烤著色塗膜於230℃下進行30分鐘後烘烤,藉此獲得後烘烤著色塗膜。 The pre-baked colored coating film was post-baked at 230°C for 30 minutes to obtain a post-baked colored coating film.

Figure 109104792-A0305-02-0402-304
Figure 109104792-A0305-02-0402-304

實施例571-1 Implementation Example 571-1

按照以下比例將各成分混合,使用珠磨機使著色劑分散,獲得著色組成物M571-1。 Mix the ingredients in the following proportions and disperse the colorant using a bead mill to obtain the coloring composition M571-1.

著色劑(A):式(Ia1)所表示的化合物 2.25份;著色劑(A):式(Ia5)所表示的化合物 2.25份;著色劑(A):式(z)所表示的化合物 0.500份;分散劑溶液:畢克(BYK)-LPN6919(日本畢克化學(BYK-Chemie Japan)股份有限公司製造) 8.33份;樹脂(B):樹脂B1溶液 10.0份;溶劑(E):丙二醇單甲醚乙酸酯 76.7份; 繼而,按照以下比例將各成分混合,獲得著色組成物571-1。 Colorant (A): 2.25 parts of the compound represented by formula (Ia1); Colorant (A): 2.25 parts of the compound represented by formula (Ia5); Colorant (A): 0.500 parts of the compound represented by formula (z); Dispersant solution: 8.33 parts of BYK-LPN6919 (manufactured by BYK-Chemie Japan Co., Ltd.); Resin (B): 10.0 parts of resin B1 solution; Solvent (E): 76.7 parts of propylene glycol monomethyl ether acetate; Then, the components were mixed in the following proportions to obtain a coloring composition 571-1.

著色組成物M571-1 57.6份;樹脂(B):樹脂B1溶液 29.2份;溶劑(E):丙二醇單甲醚乙酸酯 13.2份;調平劑(F):東麗矽酮(Toray Silicone)SH8400(東麗道康寧(Toray Dow Corning)(股)製造) 0.00630份;於2英吋見方的玻璃基板(益格(eagle)XG;康寧(Corning)製造)上,利用旋塗法塗佈著色組成物571-1,之後,在100℃下預烘烤3分鐘,形成預烘烤著色塗膜。使用DektakXT(布魯克(BRUKER)製造)測定所獲得的預烘烤著色塗膜的膜厚。使用測色機:LVmicroZ(蘭木達比森(lambda-vision)股份有限公司製造)測定該預烘烤著色塗膜的光譜。 Coloring composition M571-1 57.6 parts; Resin (B): Resin B1 solution 29.2 parts; Solvent (E): Propylene glycol monomethyl ether acetate 13.2 parts; Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning Co., Ltd.) 0.00630 parts; Coloring composition 571-1 was applied by spin coating on a 2-inch square glass substrate (Eagle XG; manufactured by Corning), and then pre-baked at 100°C for 3 minutes to form a pre-baked coloring film. The film thickness of the obtained pre-baked coloring film was measured using DektakXT (manufactured by BRUKER). The spectrum of the pre-baked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.).

將該預烘烤著色塗膜的膜厚、及該預烘烤著色塗膜的吸收光譜的最長波長側的極大吸收波長或吸收光譜的最長波長側的肩峰的波長示於表AD18中。 The film thickness of the pre-baked paint film, and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked paint film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD18.

對該預烘烤著色塗膜於230℃下進行30分鐘後烘烤,藉此獲得後烘烤著色塗膜。 The pre-baked colored coating film was post-baked at 230°C for 30 minutes to obtain a post-baked colored coating film.

Figure 109104792-A0305-02-0403-305
Figure 109104792-A0305-02-0403-305

實施例591-1 Example 591-1

按照以下比例將各成分混合,使用珠磨機使著色劑分散,獲得著色組成物M591-1。 Mix the ingredients in the following proportions and disperse the colorant using a bead mill to obtain the coloring composition M591-1.

著色劑(A):式(Ia1)所表示的化合物 2.25份;著色劑(A):式(Ia248)所表示的化合物 2.25份;著色劑(A):式(z)所表示的化合物 0.500份;分散劑溶液:畢克(BYK)-LPN6919(日本畢克化學(BYK-Chemie Japan)股份有限公司製造) 12.5份;樹脂(B):樹脂B1溶液 11.4份;溶劑(E):丙二醇單甲醚乙酸酯 71.1份;繼而,按照以下比例將各成分混合,獲得著色組成物591-1。 Colorant (A): 2.25 parts of the compound represented by formula (Ia1); Colorant (A): 2.25 parts of the compound represented by formula (Ia248); Colorant (A): 0.500 parts of the compound represented by formula (z); Dispersant solution: 12.5 parts of BYK-LPN6919 (manufactured by BYK-Chemie Japan Co., Ltd.); Resin (B): 11.4 parts of resin B1 solution; Solvent (E): 71.1 parts of propylene glycol monomethyl ether acetate; Then, the components were mixed in the following proportions to obtain a coloring composition 591-1.

著色組成物M591-1 57.6份;樹脂(B):樹脂B1溶液 24.3份;溶劑(E):丙二醇單甲醚乙酸酯 18.1份;調平劑(F):東麗矽酮(Toray Silicone)SH8400(東麗道康寧(Toray Dow Corning)(股)製造) 0.00630份;於2英吋見方的玻璃基板(益格(eagle)XG;康寧(Corning)製造)上,利用旋塗法塗佈著色組成物591-1,之後,在100℃下預烘烤3分鐘,形成預烘烤著色塗膜。使用DektakXT(布魯克(BRUKER)製造)測定所獲得的預烘烤著色塗膜的膜 厚。使用測色機:LVmicroZ(蘭木達比森(lambda-vision)股份有限公司製造)測定該預烘烤著色塗膜的光譜。 Coloring composition M591-1 57.6 parts; Resin (B): Resin B1 solution 24.3 parts; Solvent (E): Propylene glycol monomethyl ether acetate 18.1 parts; Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning Co., Ltd.) 0.00630 parts; Coloring composition 591-1 was applied by spin coating on a 2-inch square glass substrate (Eagle XG; manufactured by Corning), and then pre-baked at 100°C for 3 minutes to form a pre-baked coloring film. The film thickness of the obtained pre-baked coloring film was measured using DektakXT (manufactured by BRUKER). The spectrum of the pre-baked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.).

將該預烘烤著色塗膜的膜厚、及該預烘烤著色塗膜的吸收光譜的最長波長側的極大吸收波長或吸收光譜的最長波長側的肩峰的波長示於表AD19中。 The film thickness of the pre-baked paint film, and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked paint film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD19.

對該預烘烤著色塗膜於230℃下進行30分鐘後烘烤,藉此獲得後烘烤著色塗膜。 The pre-baked colored coating film was post-baked at 230°C for 30 minutes to obtain a post-baked colored coating film.

實施例591-2 Example 591-2

於實施例591-1中,代替式(Ia1)所表示的化合物及式(Ia248)所表示的化合物而使用下述量的以下的著色劑(A),除此以外,與實施例591-1同樣地進行,獲得著色組成物,並獲得預烘烤著色塗膜及後烘烤著色塗膜。 In Example 591-1, the following coloring agent (A) in the following amount is used instead of the compound represented by formula (Ia1) and the compound represented by formula (Ia248). The same method as in Example 591-1 is followed to obtain a coloring composition, a pre-baked coloring film, and a post-baked coloring film.

著色劑(A):實施例4中獲得的式(Ia10)所表示的化合物、式(Ia2143)所表示的化合物、式(Ia850)所表示的化合物及式(Ia315)所表示的化合物的混合物 2.38份;著色劑(A):式(Ia51)所表示的化合物 2.12份;將該預烘烤著色塗膜的膜厚、及該預烘烤著色塗膜的吸收光譜的最長波長側的極大吸收波長或吸收光譜的最長波長側的肩峰的波長示於表AD19中。 Colorant (A): 2.38 parts of 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; Colorant (A): 2.12 parts of the compound represented by formula (Ia51); The film thickness of the pre-baked color coating film, and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked color coating film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD19.

實施例591-3 Example 591-3

於實施例591-1中,代替式(Ia1)所表示的化合物及式(Ia248)所表示的化合物而使用下述量的以下的著色劑(A),除此以外, 與實施例591-1同樣地進行,獲得著色組成物,並獲得預烘烤著色塗膜及後烘烤著色塗膜。 In Example 591-1, the following coloring agent (A) is used in the following amount instead of the compound represented by formula (Ia1) and the compound represented by formula (Ia248). The same method as in Example 591-1 is followed to obtain a coloring composition, a pre-baked coloring film, and a post-baked coloring film.

著色劑(A):式(Ia248)所表示的化合物 2.38份;著色劑(A):式(Ia51)所表示的化合物 2.12份;將該預烘烤著色塗膜的膜厚、及該預烘烤著色塗膜的吸收光譜的最長波長側的極大吸收波長或吸收光譜的最長波長側的肩峰的波長示於表AD19中。 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 pre-baked color coating film, and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked color coating film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD19.

實施例591-4 Example 591-4

於實施例591-1中,代替式(Ia1)所表示的化合物及式(Ia248)所表示的化合物而使用下述量的以下的著色劑(A),除此以外,與實施例591-1同樣地進行,獲得著色組成物,並獲得預烘烤著色塗膜及後烘烤著色塗膜。 In Example 591-1, the following coloring agent (A) in the following amount is used instead of the compound represented by formula (Ia1) and the compound represented by formula (Ia248). The same method as in Example 591-1 is followed to obtain a coloring composition, a pre-baked coloring film, and a post-baked coloring film.

著色劑(A):式(Ia23)所表示的化合物 2.64份;著色劑(A):式(Ia17)所表示的化合物 1.86份;將該預烘烤著色塗膜的膜厚、及該預烘烤著色塗膜的吸收光譜的最長波長側的極大吸收波長或吸收光譜的最長波長側的肩峰的波長示於表AD19中。 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 pre-baked color coating film, and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked color coating film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD19.

實施例591-5 Example 591-5

於實施例591-1中,代替式(Ia1)所表示的化合物及式(Ia248)所表示的化合物而使用下述量的以下的著色劑(A),除此以外,與實施例591-1同樣地進行,獲得著色組成物,並獲得預烘烤著色塗膜及後烘烤著色塗膜。 In Example 591-1, the following coloring agent (A) in the following amount is used instead of the compound represented by formula (Ia1) and the compound represented by formula (Ia248). The same method as in Example 591-1 is followed to obtain a coloring composition, a pre-baked coloring film, and a post-baked coloring film.

著色劑(A):式(Ia19)所表示的化合物 2.17份;著色劑(A):式(Ia17)所表示的化合物 2.33份;將該預烘烤著色塗膜的膜厚、及該預烘烤著色塗膜的吸收光譜的最長波長側的極大吸收波長或吸收光譜的最長波長側的肩峰的波長示於表AD19中。 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 pre-baked color coating film, and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked color coating film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD19.

Figure 109104792-A0305-02-0407-306
Figure 109104792-A0305-02-0407-306

實施例592-1 Example 592-1

按照以下比例將各成分混合,使用珠磨機使著色劑分散,獲得著色組成物M592-1。 Mix the ingredients in the following proportions, and use a bead mill to disperse the colorant to obtain the coloring composition M592-1.

著色劑(A):式(Ia1)所表示的化合物 4.00份;著色劑(A):式(Ia248)所表示的化合物 1.00份;分散劑溶液:畢克(BYK)-LPN6919(日本畢克化學(BYK-Chemie Japan)股份有限公司製造) 12.5份;樹脂(B):樹脂B1溶液 11.4份;溶劑(E):丙二醇單甲醚乙酸酯 71.1份;繼而,按照以下比例將各成分混合,獲得著色組成物 592-1。 Colorant (A): 4.00 parts of the compound represented by formula (Ia1); Colorant (A): 1.00 parts of the compound represented by formula (Ia248); Dispersant solution: 12.5 parts of BYK-LPN6919 (manufactured by BYK-Chemie Japan Co., Ltd.); Resin (B): 11.4 parts of resin B1 solution; Solvent (E): 71.1 parts of propylene glycol monomethyl ether acetate; Then, the components were mixed in the following proportions to obtain a coloring composition 592-1.

著色組成物M592-1 57.6份;樹脂(B):樹脂B1溶液 24.3份;溶劑(E):丙二醇單甲醚乙酸酯 18.1份;調平劑(F):東麗矽酮(Toray Silicone)SH8400(東麗道康寧(Toray Dow Corning)(股)製造) 0.00630份;於2英吋見方的玻璃基板(益格(eagle)XG;康寧(Corning)製造)上,利用旋塗法塗佈著色組成物592-1,之後,在100℃下預烘烤3分鐘,形成預烘烤著色塗膜。使用DektakXT(布魯克(BRUKER)製造)測定所獲得的預烘烤著色塗膜的膜厚。使用測色機:LVmicroZ(蘭木達比森(lambda-vision)股份有限公司製造)測定該預烘烤著色塗膜的光譜。 Coloring composition M592-1 57.6 parts; Resin (B): Resin B1 solution 24.3 parts; Solvent (E): Propylene glycol monomethyl ether acetate 18.1 parts; Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning Co., Ltd.) 0.00630 parts; Coloring composition 592-1 was applied by spin coating on a 2-inch square glass substrate (Eagle XG; manufactured by Corning), and then pre-baked at 100°C for 3 minutes to form a pre-baked coloring film. The film thickness of the obtained pre-baked coloring film was measured using DektakXT (manufactured by BRUKER). The spectrum of the pre-baked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.).

將該預烘烤著色塗膜的膜厚、及該預烘烤著色塗膜的吸收光譜的最長波長側的極大吸收波長或吸收光譜的最長波長側的肩峰的波長示於表AD20中。 The film thickness of the pre-baked color coating film, and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked color coating film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD20.

對該預烘烤著色塗膜於230℃下進行30分鐘後烘烤,藉此獲得後烘烤著色塗膜。 The pre-baked colored coating film was post-baked at 230°C for 30 minutes to obtain a post-baked colored coating film.

實施例592-2 Example 592-2

於實施例592-1中,代替式(Ia1)所表示的化合物及式(Ia248)所表示的化合物而使用下述量的以下的著色劑(A),除此以外,與實施例592-1同樣地進行,獲得著色組成物,並獲得預烘烤著色塗膜及後烘烤著色塗膜。 In Example 592-1, the following coloring agent (A) in the following amount is used instead of the compound represented by formula (Ia1) and the compound represented by formula (Ia248). The same method as in Example 592-1 is followed to obtain a coloring composition, a pre-baked coloring film, and a post-baked coloring film.

著色劑(A):式(Ia5)所表示的化合物 4.00份;著色劑(A):式(Ia248)所表示的化合物 1.00份;將該預烘烤著色塗膜的膜厚、及該預烘烤著色塗膜的吸收光譜的最長波長側的極大吸收波長或吸收光譜的最長波長側的肩峰的波長示於表AD20中。 Colorant (A): 4.00 parts of the compound represented by formula (Ia5); Colorant (A): 1.00 parts of the compound represented by formula (Ia248); The film thickness of the pre-baked color coating film, and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked color coating film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD20.

實施例592-3 Example 592-3

於實施例592-1中,代替式(Ia1)所表示的化合物及式(Ia248)所表示的化合物而使用下述量的以下的著色劑(A),除此以外,與實施例592-1同樣地進行,獲得著色組成物,並獲得預烘烤著色塗膜及後烘烤著色塗膜。 In Example 592-1, the following coloring agent (A) in the following amount is used instead of the compound represented by formula (Ia1) and the compound represented by formula (Ia248). The same method as in Example 592-1 is followed to obtain a coloring composition, a pre-baked coloring film, and a post-baked coloring film.

著色劑(A):式(Ia699)所表示的化合物 4.00份;著色劑(A):式(Ia248)所表示的化合物 1.00份;將該預烘烤著色塗膜的膜厚、及該預烘烤著色塗膜的吸收光譜的最長波長側的極大吸收波長或吸收光譜的最長波長側的肩峰的波長示於表AD20中。 Colorant (A): 4.00 parts of the compound represented by formula (Ia699); Colorant (A): 1.00 parts of the compound represented by formula (Ia248); The film thickness of the pre-baked color coating film, and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked color coating film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD20.

實施例592-4 Example 592-4

於實施例592-1中,代替式(Ia1)所表示的化合物及式(Ia248)所表示的化合物而使用下述量的以下的著色劑(A),除此以外,與實施例592-1同樣地進行,獲得著色組成物,並獲得預烘烤著色塗膜及後烘烤著色塗膜。 In Example 592-1, the following coloring agent (A) in the following amount is used instead of the compound represented by formula (Ia1) and the compound represented by formula (Ia248). The same method as in Example 592-1 is followed to obtain a coloring composition, a pre-baked coloring film, and a post-baked coloring film.

著色劑(A):式(Ia5)所表示的化合物 4.00份;著色劑(A):實施例E-1中獲得的、包含式(Ia5-SA1)所表 示的化合物與式(Ia5-SA2)所表示的化合物的混合物 1.00份;將該預烘烤著色塗膜的膜厚、及該預烘烤著色塗膜的吸收光譜的最長波長側的極大吸收波長或吸收光譜的最長波長側的肩峰的波長示於表AD20中。 Colorant (A): 4.00 parts of the compound represented by formula (Ia5); Colorant (A): 1.00 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; The film thickness of the pre-baked color coating film, and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked color coating film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD20.

Figure 109104792-A0305-02-0410-307
Figure 109104792-A0305-02-0410-307

實施例S-1 Example S-1

按照以下比例將各成分混合,獲得著色組成物S-1。 The ingredients were mixed in the following proportions to obtain the coloring composition S-1.

著色劑(A):實施例E-1中獲得的包含式(Ia5-SA1)所表示的化合物與式(Ia5-SA2)所表示的化合物的混合物2.92份、和N-甲基吡咯啶酮97.1份的混合物 51.4份;樹脂(B):樹脂B1溶液 38.5份;溶劑(E):丙二醇單甲醚乙酸酯 10.1份;調平劑(F):東麗矽酮(Toray Silicone)SH8400(東麗道康寧(Toray Dow Corning)(股)製造) 0.00531份;於2英吋見方的玻璃基板(益格(eagle)XG;康寧(Corning)製造)上,利用旋塗法塗佈著色組成物S-1,之後,在100℃下預烘烤3分鐘,形成預烘烤著色塗膜。 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 51.4 parts of a mixture of 97.1 parts of N-methylpyrrolidone; Resin (B): 38.5 parts of resin B1 solution; Solvent (E): 10.1 parts of propylene glycol monomethyl ether acetate; Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning Co., Ltd.) 0.00531 parts; on a 2-inch square glass substrate (Eagle XG; manufactured by Corning), the coloring composition S-1 was applied by spin coating, and then pre-baked at 100°C for 3 minutes to form a pre-baked coloring film.

對該預烘烤著色塗膜於230℃下進行30分鐘後烘烤,藉此獲得後烘烤著色塗膜。 The pre-baked colored coating film was post-baked at 230°C for 30 minutes to obtain a post-baked colored coating film.

使用DektakXT(布魯克(BRUKER)製造)測定所獲得的後烘烤著色塗膜的膜厚。 The film thickness of the obtained post-baking colored coating film was measured using DektakXT (manufactured by BRUKER).

使用測色機:LVmicroZ(蘭木達比森(lambda-vision)股份有限公司製造)測定該後烘烤著色塗膜的光譜。 The spectrum of the post-baked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.).

將該後烘烤著色塗膜的膜厚、及該後烘烤著色塗膜的吸收光譜的最長波長側的極大吸收波長或吸收光譜的最長波長側的肩峰的波長示於表AD21中。 The film thickness of the post-baked painted film, and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the post-baked painted film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD21.

實施例S-2 Example S-2

按照以下比例將各成分混合,獲得著色組成物S-2。 The ingredients were mixed in the following proportions to obtain the coloring composition S-2.

著色劑(A):式(If5670)所表示的化合物1.00份、與N-甲基吡咯啶酮99.0份的混合物 59.2份;樹脂(B):樹脂B1溶液 40.5份;溶劑(E):丙二醇單甲醚乙酸酯 0.278份;調平劑(F):東麗矽酮(Toray Silicone)SH8400(東麗道康寧(Toray Dow Corning)(股)製造) 0.00514份;於2英吋見方的玻璃基板(益格(eagle)XG;康寧(Corning)製造)上,利用旋塗法塗佈著色組成物S-2,之後,在100℃下預烘烤3分鐘,形成預烘烤著色塗膜。對該預烘烤著色塗膜於230℃下進行30分鐘後烘烤,藉此獲得後烘烤著色塗膜。使用DektakXT(布魯克(BRUKER)製造)測定所獲得的後烘烤 著色塗膜的膜厚。使用測色機:LVmicroZ(蘭木達比森(lambda-vision)股份有限公司製造)測定該後烘烤著色塗膜的光譜。 Colorant (A): 59.2 parts of a mixture of 1.00 parts of a compound represented by the formula (If5670) and 99.0 parts of N-methylpyrrolidone; Resin (B): 40.5 parts of a resin B1 solution; Solvent (E): 0.278 parts of propylene glycol monomethyl ether acetate; Leveling agent (F): 0.00514 parts of Toray Silicone SH8400 (manufactured by Toray Dow Corning Co., Ltd.); The coloring composition S-2 was applied by spin coating on a 2-inch square glass substrate (Eagle XG; manufactured by Corning) and then pre-baked at 100°C for 3 minutes to form a pre-baked coloring film. The pre-baked color coating film was post-baked at 230°C for 30 minutes to obtain a post-baked color coating film. The film thickness of the post-baked color coating film was measured using DektakXT (manufactured by BRUKER). The spectrum of the post-baked color coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.).

將該後烘烤著色塗膜的膜厚、及該後烘烤著色塗膜的吸收光譜的最長波長側的極大吸收波長或吸收光譜的最長波長側的肩峰的波長示於表AD21中。 The film thickness of the post-baked painted film, and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the post-baked painted film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD21.

實施例S-3 Example S-3

按照以下比例將各成分混合,獲得著色組成物S-3。 The ingredients are mixed in the following proportions to obtain the coloring composition S-3.

著色劑(A):實施例E-3中獲得的包含式(Ia2-SA)所表示的化合物的混合物 2.24份;樹脂(B):樹脂B1溶液 33.6份;溶劑(E):丙二醇單甲醚乙酸酯 0.581份;溶劑(E):N-甲基吡咯啶酮 63.6份;調平劑(F):東麗矽酮(Toray Silicone)SH8400(東麗道康寧(Toray Dow Corning)(股)製造) 0.00490份;於2英吋見方的玻璃基板(益格(eagle)XG;康寧(Corning)製造)上,利用旋塗法塗佈著色組成物S-3,之後,在100℃下預烘烤3分鐘,形成預烘烤著色塗膜。 Coloring agent (A): 2.24 parts of the mixture containing the compound represented by formula (Ia2-SA) obtained in Example E-3; Resin (B): 33.6 parts of Resin B1 solution; Solvent (E): 0.581 parts of propylene glycol monomethyl ether acetate; Solvent (E): 63.6 parts of N-methylpyrrolidone; Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning Co., Ltd.) 0.00490 parts; on a 2-inch square glass substrate (Eagle XG; manufactured by Corning), the coloring composition S-3 was applied by spin coating, and then pre-baked at 100°C for 3 minutes to form a pre-baked coloring film.

使用DektakXT(布魯克(BRUKER)製造)測定所獲得的預烘烤著色塗膜的膜厚。 The film thickness of the obtained pre-baked pigmented coating film was measured using DektakXT (manufactured by BRUKER).

使用測色機:LVmicroZ(蘭木達比森(lambda-vision)股份有限公司製造)測定該預烘烤著色塗膜的光譜。 The spectrum of the pre-baked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.).

將該預烘烤著色塗膜的膜厚、及該預烘烤著色塗膜的吸收光譜的最長波長側的極大吸收波長或吸收光譜的最長波長側的肩峰的波長示於表AD21中。 The film thickness of the pre-baked paint film, and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked paint film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD21.

對該預烘烤著色塗膜於230℃下進行30分鐘後烘烤,藉此獲得後烘烤著色塗膜。 The pre-baked colored coating film was post-baked at 230°C for 30 minutes to obtain a post-baked colored coating film.

Figure 109104792-A0305-02-0413-308
Figure 109104792-A0305-02-0413-308

根據所述結果得知,由包含本發明的化合物的著色組成物形成的著色塗膜的吸收光譜的最長波長側的極大吸收波長或吸收光譜的最長波長側的肩峰的波長與由包含C.I.顏料黃138的著色組成物形成的著色塗膜的吸收光譜的最長波長側的極大吸收波長相比,為更長的波長。 According to the results, the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the colored coating formed by the coloring composition containing the compound of the present invention or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum is longer than the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the colored coating formed by the coloring composition containing C.I. Pigment Yellow 138.

[產業上的可利用性] [Industrial availability]

本發明的著色組成物及化合物與包含C.I.顏料黃138的著色組成物相比,可於顏色更濃的彩色濾光片的形成中使用,因此可適宜用於彩色濾光片或液晶顯示裝置等顯示裝置。 The coloring composition and compound of the present invention can be used in the formation of a color filter with a darker color than a coloring composition containing C.I. Pigment Yellow 138, and therefore can be suitably used in a color filter or a display device such as a liquid crystal display device.

Claims (6)

一種著色組成物,包含:下述式(I)所表示的化合物以及溶劑,
Figure 109104792-A0305-02-0415-309
[式(I)中,R1~R5分別獨立地表示氫原子、鹵素原子、氰基、硝基、-SO3M、-CO2M、MM、碳數1~40的一價鏈狀或環狀烴基、構成所述一價鏈狀或環狀烴基的氫原子被取代為鹵素原子、氰基、硝基、-SO3M、-CO2M或MM的基、或者碳數1~40的一價雜環基,構成所述一價雜環基的氫原子亦可取代為鹵素原子、氰基、硝基、-SO3M、-CO2M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的一價鏈狀或環 狀烴基、構成所述一價鏈狀或環狀烴基的氫原子被取代為鹵素原子、氰基、硝基、-SO3M、-CO2M或MM的基、或者碳數1~40的一價雜環基,構成所述一價雜環基的氫原子亦可取代為鹵素原子、氰基、硝基、-SO3M、-CO2M或MM;Q1及Q2分別獨立地表示式(QQ1)~式(QQ3)或式(QQ5)所表示的基;
Figure 109104792-A0305-02-0416-310
式中,RQ1~RQ16及RQ25~RQ30分別獨立地表示氫原子、鹵素原子、硝基、-CO2M、碳數1~12的一價鏈狀或環狀烴基、甲氧基羰基、乙氧基羰基、乙醯基胺基、丙醯基胺基或羥基,※表示鍵結鍵;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]。
A coloring composition comprising: a compound represented by the following formula (I) and a solvent,
Figure 109104792-A0305-02-0415-309
[In formula (I), R1 to R5 each independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, -SO3M , -CO2M , MM, a monovalent chain or cyclic hydrocarbon group having 1 to 40 carbon atoms, a group in which a hydrogen atom constituting the monovalent chain or cyclic hydrocarbon group is substituted with a halogen atom, a cyano group, a nitro group, -SO3M , -CO2M or MM, or a monovalent heterocyclic group having 1 to 40 carbon atoms, wherein a hydrogen atom constituting the monovalent heterocyclic group may be substituted with a halogen atom, a cyano group, a nitro group, -SO3M , -CO2M or MM; R1 and R2 , R2 and R3 , and R3 and R4 are independently selected from the group consisting of: 4 may be bonded to each other to form a ring; M represents a hydrogen atom, an alkali metal atom, a metal atom which may have a ligand, or N(Z 1 )(Z 2 )(Z 3 )(Z 4 ); MM represents an alkali metal atom, a metal atom which 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, a monovalent chain or cyclic hydrocarbon group having 1 to 40 carbon atoms, a hydrogen atom constituting the monovalent chain or cyclic hydrocarbon group substituted with a halogen atom, a cyano group, a nitro group, -SO 3 M, -CO 2 M or MM, or a monovalent heterocyclic group having 1 to 40 carbon atoms, wherein the hydrogen atom constituting the monovalent heterocyclic group may 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 group represented by formula (QQ1) to formula (QQ3) or formula (QQ5);
Figure 109104792-A0305-02-0416-310
In the formula, R Q1 ~R Q16 and R Q25 ~R Q30 independently represent a hydrogen atom, a halogen atom, a nitro group, -CO 2 M, a monovalent chain or cyclic hydrocarbon group having 1 to 12 carbon atoms, a methoxycarbonyl group, an ethoxycarbonyl group, an acetylamino group, a propionylamino group or a hydroxyl group, and ※ represents a bond; when there are plural Z 1 ~Z 4 , M and MM, they may be the same or different from each other].
如請求項1所述的著色組成物,其包含樹脂。 The coloring composition as described in claim 1 comprises a resin. 如請求項1或請求項2所述的著色組成物,其包含聚合性化合物以及聚合起始劑。 The coloring composition as described in claim 1 or claim 2 comprises a polymerizable compound and a polymerization initiator. 一種彩色濾光片,其是由如請求項1或請求項2所述的著色組成物形成。 A color filter, which is formed by the coloring composition as described in claim 1 or claim 2. 一種顯示裝置,包含如請求項4所述的彩色濾光片。 A display device comprising a color filter as described in claim 4. 一種化合物,其由式(I)表示,
Figure 109104792-A0305-02-0417-311
[式(I)中,R1~R5分別獨立地表示氫原子、鹵素原子、氰基、硝基、-SO3M、-CO2M、MM、碳數1~40的一價鏈狀或環狀烴基、構成所述一價鏈狀或環狀烴基的氫原子被取代為鹵素原子、氰基、硝基、-SO3M、-CO2M或MM的基、或者碳數1~40的一價雜環基,構成所述一價雜環基的氫原子亦可取代為鹵素原子、氰基、硝基、-SO3M、-CO2M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的一價鏈狀或環狀烴基、構成所述一價鏈狀或環狀烴基的氫原子被取代為鹵素原子、氰基、硝基、-SO3M、-CO2M或MM的基、或者碳數1~40的一價雜環基,構成所述一價雜環基的氫原子亦可取代為鹵素原子、氰基、硝基、-SO3M、-CO2M或MM;Q1及Q2分別獨立地表示式(QQ1)~式(QQ3)或式(QQ5)所表示的基;
Figure 109104792-A0305-02-0418-312
式中,RQ1~RQ16及RQ25~RQ30分別獨立地表示氫原子、鹵素原子、硝基、-CO2M、碳數1~12的一價鏈狀或環狀烴基、甲氧基羰基、 乙氧基羰基、乙醯基胺基、丙醯基胺基或羥基,※表示鍵結鍵;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]。
A compound represented by formula (I):
Figure 109104792-A0305-02-0417-311
[In formula (I), R1 to R5 each independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, -SO3M , -CO2M , MM, a monovalent chain or cyclic hydrocarbon group having 1 to 40 carbon atoms, a group in which a hydrogen atom constituting the monovalent chain or cyclic hydrocarbon group is substituted with a halogen atom, a cyano group, a nitro group, -SO3M , -CO2M or MM, or a monovalent heterocyclic group having 1 to 40 carbon atoms, wherein a hydrogen atom constituting the monovalent heterocyclic group may be substituted with a halogen atom, a cyano group, a nitro group, -SO3M , -CO2M or MM; R1 and R2 , R2 and R3 , and R3 and R4 are independently selected from the group consisting of: 4 may be bonded to each other to form a ring; M represents a hydrogen atom, an alkali metal atom, a metal atom which may have a ligand, or N(Z 1 )(Z 2 )(Z 3 )(Z 4 ); MM represents an alkali metal atom, a metal atom which 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, a monovalent chain or cyclic hydrocarbon group having 1 to 40 carbon atoms, a hydrogen atom constituting the monovalent chain or cyclic hydrocarbon group substituted with a halogen atom, a cyano group, a nitro group, -SO 3 M, -CO 2 M or MM, or a monovalent heterocyclic group having 1 to 40 carbon atoms, wherein the hydrogen atom constituting the monovalent heterocyclic group may 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 group represented by formula (QQ1) to formula (QQ3) or formula (QQ5);
Figure 109104792-A0305-02-0418-312
In the formula, R Q1 ~R Q16 and R Q25 ~R Q30 independently represent a hydrogen atom, a halogen atom, a nitro group, -CO 2 M, a monovalent chain or cyclic hydrocarbon group having 1 to 12 carbon atoms, a methoxycarbonyl group, an ethoxycarbonyl group, an acetylamino group, a propionylamino group or a hydroxyl group, and ※ represents a bond; when there are plural Z 1 ~Z 4 , M and MM, they may be the same or different from each other].
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* Cited by examiner, † Cited by third party
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TWI480602B (en) 2011-10-12 2015-04-11 Toyo Ink Sc Holdings Co Ltd Coloring composition for color filter, and color filter

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