TWI746916B

TWI746916B - Colored resin composition, filter and display device

Info

Publication number: TWI746916B
Application number: TW107146394A
Authority: TW
Inventors: 髙石悠; 中山智博
Original assignee: 南韓商東友精細化工有限公司
Priority date: 2017-12-27
Filing date: 2018-12-21
Publication date: 2021-11-21
Also published as: TW201927916A; CN109976094A; CN109976094B; KR20190079541A; KR102456389B1; JP7053448B2; JP2019119856A

Abstract

為解決由以往已知的著色樹脂組合物所形成的濾光片的耐化學性及對比度無法充分得到滿足的技術問題，本發明係關於一種包含著色劑、樹脂、聚合性化合物及聚合引發劑的著色樹脂組合物，其中著色劑含有由式（1）所示之化合物。本發明亦關於一種由該著色樹脂組合物形成的濾光片以及顯示裝置。In order to solve the technical problem that the chemical resistance and contrast of the filter formed by the previously known coloring resin composition cannot be sufficiently satisfied, the present invention relates to a colorant, a resin, a polymerizable compound, and a polymerization initiator. The colored resin composition, wherein the colorant contains a compound represented by formula (1). The present invention also relates to a filter and a display device formed from the colored resin composition.

Description

著色樹脂組合物、濾光片以及顯示裝置Colored resin composition, filter and display device

本發明係關於一種著色樹脂組合物、濾光片以及顯示裝置。The invention relates to a coloring resin composition, a filter and a display device.

用於液晶顯示裝置、電致發光顯示裝置以及電漿顯示器等顯示裝置，與CCD、CMOS感測器等固態成像元件的濾光片係由著色樹脂組合物製造。作為這樣的著色樹脂組合物，已知的是作為著色劑含有由下式所示化合物的組合物（專利文獻1）。

The filters used in display devices such as liquid crystal display devices, electroluminescence display devices, and plasma displays, and solid-state imaging elements such as CCD and CMOS sensors are made of colored resin compositions. As such a colored resin composition, a composition containing a compound represented by the following formula as a coloring agent is known (Patent Document 1).

先前技術文獻專利文獻專利文獻1：日本專利特開第2014-005451號。Prior art literature Patent literature Patent Document 1: Japanese Patent Laid-Open No. 2014-005451.

發明要解決的技術問題The technical problem to be solved by the invention

由以往已知的上述著色樹脂組合物形成的濾光片有時耐化學性以及對比度無法充分得到滿足。解決技術問題的手段 The optical filter formed from the aforementioned colored resin composition known in the past may not be sufficiently satisfactory in chemical resistance and contrast. Means to solve technical problems

[1] 一種著色樹脂組合物，其含有著色劑、樹脂、聚合性化合物以及聚合引發劑，該著色劑含有由式（1）所示的化合物。

[在式（1）中， R^101a 至R^101d 以及R^102a 至R^102d 分別獨立地表示可具有取代基的烷基、或者可具有取代基的芳基。 X¹ 與X² 分別獨立地表示氫原子、可具有取代基的烷基、可具有取代基的芳基、可具有取代基的芳烷基、或者由式（X1）至（X4）所示的基團。

R²⁰¹ 與R⁴⁰¹ 分別獨立地表示可具有取代基的烷基、可具有取代基的芳基、可具有取代基的烷氧基或者可具有取代基的芳氧基。 R³⁰¹ 、R³⁰² 與R⁵⁰¹ 至R⁵⁰³ 分別獨立地表示可具有取代基的烷基、或者可具有取代基的芳基。在式（X1）至（X4）中的*表示與氧原子的鍵結部位。構成由X¹ 、X² 、R²⁰¹ 、R⁴⁰¹ 所示的芳基、芳烷基、及芳氧基的芳香族烴環可配位於金屬原子。][1] A coloring resin composition containing a coloring agent, a resin, a polymerizable compound, and a polymerization initiator, and the coloring agent contains a compound represented by formula (1).

[In formula (1), R ^101a to R ^101d and R ^102a to R ^102d each independently represent an optionally substituted alkyl group or an optionally substituted aryl group. X ¹ and X ² each independently represent a hydrogen atom, an optionally substituted alkyl group, an optionally substituted aryl group, an optionally substituted aralkyl group, or the formula (X1) to (X4) Group.

R ²⁰¹ and R ⁴⁰¹ each independently represent an optionally substituted alkyl group, an optionally substituted aryl group, an optionally substituted alkoxy group, or an optionally substituted aryloxy group. R ³⁰¹ , R ³⁰² and R ⁵⁰¹ to R ⁵⁰³ each independently represent an alkyl group which may have a substituent or an aryl group which may have a substituent. * In formulas (X1) to (X4) represents a bonding site with an oxygen atom. The aromatic hydrocarbon ring constituting the aryl group, aralkyl group, and aryloxy group represented by X ¹ , X ² , R ²⁰¹ , and R ^{401 may be coordinated to a metal atom.} ]

[2] 一種濾光片，其係由[1]記載的著色樹脂組合物形成。[2] A filter formed of the colored resin composition described in [1].

[3] 一種顯示裝置，其包含[2]記載的濾光片。發明的效果 [3] A display device including the filter described in [2]. The effect of the invention

本發明的著色樹脂組合物可形成耐化學性優異的濾光片。The colored resin composition of the present invention can form a filter having excellent chemical resistance.

此外，本發明的著色樹脂組合物可形成對比度優異的濾光片。In addition, the colored resin composition of the present invention can form a filter having excellent contrast.

本發明的著色樹脂組合物包含著色劑（以下，有時稱為著色劑（A））、樹脂（以下，有時稱為樹脂（B））、聚合性化合物（以下，有時稱為聚合性化合物（C））、以及聚合引發劑（以下，有時稱為聚合引發劑（D））。The colored resin composition of the present invention includes a colorant (hereinafter, sometimes referred to as colorant (A)), resin (hereinafter, sometimes referred to as resin (B)), and a polymerizable compound (hereinafter, sometimes referred to as polymerizable Compound (C)) and a polymerization initiator (hereinafter, may be referred to as polymerization initiator (D)).

於本發明的著色樹脂組合物中，著色劑包含由式（1）所示的化合物（以下，有時稱為化合物（1））。In the colored resin composition of the present invention, the colorant contains a compound represented by formula (1) (hereinafter, may be referred to as compound (1)).

較佳地，本發明的著色樹脂組合物進一步包含溶劑（以下，有時稱為溶劑（E））。Preferably, the colored resin composition of the present invention further contains a solvent (hereinafter, sometimes referred to as solvent (E)).

本發明的著色樹脂組合物可含有調平劑。The colored resin composition of the present invention may contain a leveling agent.

在本說明書中，除非另有說明，作為各組分而例舉的化合物可單獨使用或組合複數種使用。In this specification, unless otherwise specified, the compounds exemplified as each component may be used alone or in combination of plural kinds.

＜著色劑（A）＞＜Colorant (A)＞

包含於著色劑（A）中的由式（1）所示的化合物為四氮雜卟啉（tetraaza porphyrin）化合物，係中心原子為矽原子、至少一個氧原子（較佳為二個氧原子）直接鍵結於矽原子的化合物。

（在式（1）中，R^101a 至R^101d 以及R^102a 至R^102d 分別獨立地表示可具有取代基的烷基、或者可具有取代基的芳基。 X¹ 與X² 分別獨立地表示氫原子、可具有取代基的烷基、可具有取代基的芳基、可具有取代基的芳烷基、或者由式（X1）至（X4）所示的基團。

R²⁰¹ 與R⁴⁰¹ 分別獨立地表示可具有取代基的烷基、可具有取代基的芳基、可具有取代基烷氧基或者可具有取代基的芳氧基。 R³⁰¹ 、R³⁰² 與R⁵⁰¹ 至R⁵⁰³ 分別獨立地表示可具有取代基的烷基、或者可具有取代基的芳基。在式（X1）至（X4）中的*表示與氧原子的鍵結部位。構成由X¹ 、X² 、R²⁰¹ 、R⁴⁰¹ 所示的芳基、芳烷基、及芳氧基的芳香族烴環可配位於金屬原子。）The compound represented by the formula (1) contained in the coloring agent (A) is a tetraaza porphyrin (tetraaza porphyrin) compound, the central atom of which is a silicon atom and at least one oxygen atom (preferably two oxygen atoms) Compounds directly bonded to silicon atoms.

(In formula (1), R ^101a to R ^101d and R ^102a to R ^102d each independently represent an optionally substituted alkyl group or an optionally substituted aryl group. X ¹ and X ² each independently represent hydrogen Atom, an alkyl group that may have a substituent, an aryl group that may have a substituent, an aralkyl group that may have a substituent, or a group represented by formulas (X1) to (X4).

R ²⁰¹ and R ⁴⁰¹ each independently represent an optionally substituted alkyl group, an optionally substituted aryl group, an optionally substituted alkoxy group, or an optionally substituted aryloxy group. R ³⁰¹ , R ³⁰² and R ⁵⁰¹ to R ⁵⁰³ each independently represent an alkyl group which may have a substituent or an aryl group which may have a substituent. * In formulas (X1) to (X4) represents a bonding site with an oxygen atom. The aromatic hydrocarbon ring constituting the aryl group, aralkyl group, and aryloxy group represented by X ¹ , X ² , R ²⁰¹ , and R ^{401 may be coordinated to a metal atom.} )

在本說明書中，「烷基」包含直鏈狀、支鏈狀以及環狀的基團。此外，「烷氧基」也同樣地包含直鏈狀、支鏈狀以及環狀的基團。In the present specification, "alkyl" includes linear, branched, and cyclic groups. In addition, "alkoxy" also includes linear, branched, and cyclic groups in the same manner.

此外，在本說明書中，「芳基」表示僅由非取代的芳香族烴環形成的基團。In addition, in this specification, the "aryl group" means a group formed only of an unsubstituted aromatic hydrocarbon ring.

在上述式（1）中，R^101a 至R^101d 以及R^102a 至R^102d 為鍵結於四氮雜卟啉骨架的基團。In the above formula (1), R ^101a to R ^101d and R ^102a to R ^102d are groups bonded to the porphyrazine skeleton.

R^101a 至R^101d 的四個基團可相同也可不同，較佳為相同，此外，R^102a 至R^102d 的四個基團可相同也可不同，較佳為相同。The four groups of R ^101a to R ^101d may be the same or different, and are preferably the same. In addition, ^{the four groups of R 102a} to R ^102d may be the same or different, and are preferably the same.

R^101a 與R^102a 、R^101b 與R^102b 、R^101c 與R^102c 、R^101d 與R^102d 的組合可相同也可不同。The combinations of R ^101a and R ^102a , R ^101b and R ^102b , R ^101c and R ^102c , and R ^101d and R ^102d may be the same or different.

R^101a 與R^102a 的組合、R^101b 與R^102b 的組合、R^101c 與R^102c 的組合、R^101d 與R^102d 的組合較佳為相同。The combination of R ^101a and R ^102a , the combination of R ^101b and R ^102b , the combination of R ^101c and R ^102c , and the combination of R ^101d and R ^102d are preferably the same.

再者，在R^101a 與R^102a 的組合、R^101b 與R^102b 的組合、R^101c 與R^102c 的組合、R^101d 與R^102d 的組合為相同的情況下，各組合中的二個基團的位置關係是任意的，化合物（1）存在有四種不同的異構體。Furthermore, when ^{the combination of R 101a} and R ^102a , the combination of R ^101b and R ^102b , the combination of R ^101c and R ^102c , and the combination of R ^101d and R ^102d are the same, the two groups in each combination The positional relationship is arbitrary, and compound (1) has four different isomers.

上述式（1）旨在包含全部四種異構體。此外，四氮雜卟啉化合物可僅包含這些異構體中的一種，也可作為混合物而包含複數種。The above formula (1) is intended to include all four isomers. In addition, the porphyrazine compound may contain only one of these isomers, or may contain a plurality of them as a mixture.

R^101a 至R^101d 以及R^102a 至R^102d 分別獨立地表示可具有取代基的烷基或者可具有取代基的芳基。R ^101a to R ^101d and R ^102a to R ^102d each independently represent an optionally substituted alkyl group or an optionally substituted aryl group.

作為式（1）的R^101a 至R^101d 及R^102a 至R^102d 的可具有取代基的烷基，可列舉直鏈狀、支鏈狀或環狀的烷基。 ^{Examples of the optionally substituted alkyl group of R 101a} to R ^101d and R ^102a to R ^102d of the formula (1) include linear, branched, or cyclic alkyl groups.

作為直鏈狀、支鏈狀或環狀的烷基，可列舉：甲基、乙基、正丙基、正丁基、正戊基、正己基、正庚基、正辛基、正壬基、正癸基、正十一烷基、正十二烷基、正十三烷基、正十四烷基、正十五烷基等直鏈狀烷基；異丙基、異丁基、二級丁基、三級丁基、2-甲基丁基、1-甲基丁基、新戊基、1,2-二甲基丙基、1,1-二甲基丙基、4-甲基戊基、3-甲基戊基、2-甲基戊基、1-甲基戊基、3,3-二甲基丁基、2,3-二甲基丁基、1,3-二甲基丁基、2,2-二甲基丁基、1,2-二甲基丁基、1,1-二甲基丁基、3-乙基丁基、2-乙基丁基、1-乙基丁基、1,1,2-三甲基丙基、1-乙基-2-甲基丙基、2-甲基己基、3-甲基己基、4-甲基己基、5-甲基己基、1-乙基戊基、2,4-二甲基戊基、2-乙基己基、2,5-二甲基己基、2,5,5-三甲基戊基、2,4-二甲基己基、2,2,4-三甲基戊基、1,1-二甲基己基、3,5,5-三甲基己基、4-乙基辛基、4-乙基-4,5-二甲基己基、1,3,5,7-四甲基辛基、4-丁基辛基、6,6-二乙基辛基、6-甲基-4-丁基辛基、3,5-二甲基十七烷基、2,6-二甲基十七烷基、2,4-二甲基十七烷基、2,2,5,5-四甲基己基等支鏈狀烷基；環戊基、環己基、1-環戊基-2,2-二甲基丙基、1-環己基-2,2-二甲基丙基等環狀的烷基（環烷基）。Examples of linear, branched, or cyclic alkyl groups include methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, and n-nonyl. , N-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl and other linear alkyl groups; isopropyl, isobutyl, two Butyl, tertiary, 2-methylbutyl, 1-methylbutyl, neopentyl, 1,2-dimethylpropyl, 1,1-dimethylpropyl, 4-methyl 2-methylpentyl, 3-methylpentyl, 2-methylpentyl, 1-methylpentyl, 3,3-dimethylbutyl, 2,3-dimethylbutyl, 1,3-di Methylbutyl, 2,2-dimethylbutyl, 1,2-dimethylbutyl, 1,1-dimethylbutyl, 3-ethylbutyl, 2-ethylbutyl, 1 -Ethylbutyl, 1,1,2-trimethylpropyl, 1-ethyl-2-methylpropyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5- Methylhexyl, 1-ethylpentyl, 2,4-dimethylpentyl, 2-ethylhexyl, 2,5-dimethylhexyl, 2,5,5-trimethylpentyl, 2, 4-dimethylhexyl, 2,2,4-trimethylpentyl, 1,1-dimethylhexyl, 3,5,5-trimethylhexyl, 4-ethyloctyl, 4-ethyl -4,5-Dimethylhexyl, 1,3,5,7-tetramethyloctyl, 4-butyloctyl, 6,6-diethyloctyl, 6-methyl-4-butyl Octyl, 3,5-dimethylheptadecyl, 2,6-dimethylheptadecyl, 2,4-dimethylheptadecyl, 2,2,5,5-tetramethyl Branched chain alkyl such as hexyl; Cyclic alkyl such as cyclopentyl, cyclohexyl, 1-cyclopentyl-2,2-dimethylpropyl, 1-cyclohexyl-2,2-dimethylpropyl, etc. Group (cycloalkyl).

烷基的碳原子數較佳為1至20，更佳為1至15，進一步佳為1至10，進一步更佳為1至5。The number of carbon atoms of the alkyl group is preferably from 1 to 20, more preferably from 1 to 15, further preferably from 1 to 10, and still more preferably from 1 to 5.

這其中，較佳為碳原子數1至10的直鏈狀或支鏈狀的烷基，更佳為碳原子數1至5的直鏈狀或支鏈狀的烷基，進一步佳為三級丁基。Among them, a linear or branched alkyl group having 1 to 10 carbon atoms is preferable, a linear or branched alkyl group having 1 to 5 carbon atoms is more preferable, and a tertiary chain is more preferable. Butyl.

作為具有取代基的烷基，可列舉烷基的部分氫原子或全部氫原子被鹵素取代的基團，例如可列舉氯甲基、二氯甲基、氟甲基、三氟甲基、五氟乙基、九氟丁基、全氟環丁基、全氟環戊基等。Examples of the substituted alkyl group include groups in which part or all of the hydrogen atoms of the alkyl group are replaced by halogens, such as chloromethyl, dichloromethyl, fluoromethyl, trifluoromethyl, and pentafluoro. Ethyl, nonafluorobutyl, perfluorocyclobutyl, perfluorocyclopentyl, etc.

作為式（1）的R^101a 至R^101d 及R^102a 至R^102d 的可具有取代基的芳基，可列舉苯基、硝基苯基、氰基苯基、羥基苯基、羧基苯基、甲基苯基、二甲基苯基、三甲基苯基、氟苯基、氯苯基、溴苯基、甲氧基苯基、乙氧基苯基、三氟甲基苯基、N,N-二甲基胺基苯基、萘基、硝基萘基、氰基萘基、羥基萘基、甲基萘基、氟萘基、氯萘基、溴萘基、三氟甲基萘基等。 ^{As R 101a} to R ^101d and R ^102a to R ^102d of the formula (1), the aryl groups that may have substituents include phenyl, nitrophenyl, cyanophenyl, hydroxyphenyl, carboxyphenyl, methyl Phenyl, dimethylphenyl, trimethylphenyl, fluorophenyl, chlorophenyl, bromophenyl, methoxyphenyl, ethoxyphenyl, trifluoromethylphenyl, N,N -Dimethylaminophenyl, naphthyl, nitronaphthyl, cyanonaphthyl, hydroxynaphthyl, methylnaphthyl, fluoronaphthyl, chloronaphthyl, bromonaphthyl, trifluoromethylnaphthyl, etc. .

芳基的碳原子數例如為6至20，較佳為6至18，更佳為6至15，進一步佳為6至10。The number of carbon atoms of the aryl group is, for example, 6-20, preferably 6-18, more preferably 6-15, and still more preferably 6-10.

此外，在式（1）中，較佳係R^102a 至R^102d 分別獨立地為由式（R1）所示的基團。

（在式（R1）中，R^601a 至R^601e 分別獨立地表示氫原子、鹵素原子、可具有取代基的烷基、可具有取代基的烷氧基、可具有取代基的芳基、可具有取代基的芳氧基，*表示與四氮雜卟啉骨架的鍵結部位。）In addition, in formula (1), it is preferable that R ^102a to R ^102d are each independently a group represented by formula (R1).

(In formula (R1), R ^601a to R ^601e each independently represent a hydrogen atom, a halogen atom, an optionally substituted alkyl group, an optionally substituted alkoxy group, an optionally substituted aryl group, and an optionally substituted aryl group. The aryloxy group of the substituent, * indicates the bonding site with the porphyrazine skeleton.)

作為式（R1）的R^601a 至R^601e 的可具有取代基的烷基，可列舉在R^101a 至R^101d 以及R^102a 至R^102d 的例子中舉出的可具有取代基的烷基。 ^{As the alkyl group which may have a substituent of R 601a} to R ^601e of formula (R1), the alkyl group which may have a substituent mentioned in the example of R ^101a to R ^101d and R ^102a to R ^102d can be mentioned.

作為式（R1）的R^601a 至R^601e 的可具有取代基的芳基，可列舉在R^101a 至R^101d 以及R^102a 至R^102d 的例子中舉出的可具有取代基的芳基。 ^{As the aryl group which may have a substituent of R 601a} to R ^601e of formula (R1), the aryl group which may have a substituent mentioned in the example of R ^101a to R ^101d and R ^102a to R ^102d can be mentioned.

具體地，可列舉苯基、硝基苯基、氰基苯基、羥基苯基、羧基苯基、甲基苯基、二甲基苯基、三甲基苯基、氟苯基、氯苯基、溴苯基、甲氧基苯基、乙氧基苯基、三氟甲基苯基、N,N-二甲基胺基苯基、萘基、硝基萘基、氰基萘基、羥基萘基、甲基萘基、氟萘基、氯萘基、溴萘基、三氟甲基萘基等。Specifically, phenyl, nitrophenyl, cyanophenyl, hydroxyphenyl, carboxyphenyl, methylphenyl, dimethylphenyl, trimethylphenyl, fluorophenyl, and chlorophenyl can be cited. , Bromophenyl, methoxyphenyl, ethoxyphenyl, trifluoromethylphenyl, N,N-dimethylaminophenyl, naphthyl, nitronaphthyl, cyanonaphthyl, hydroxyl Naphthyl, methylnaphthyl, fluoronaphthyl, chloronaphthyl, bromonaphthyl, trifluoromethylnaphthyl, etc.

作為式（R1）的R^601a 至R^601e 的可具有取代基的烷氧基，可列舉甲氧基、乙氧基、正丙氧基、異丙氧基、正丁氧基、異丁氧基、二級丁氧基、三級丁氧基、正戊氧基、異戊氧基、新戊氧基、正己氧基、正十二烷氧基；環丙氧基、環丁氧基、環戊氧基、環己氧基。 ^{Examples of the alkoxy group that may have substituents of R 601a} to R ^601e of the formula (R1) include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, and isobutoxy , Two-butoxy, three-butoxy, n-pentyloxy, isopentyloxy, neopentyloxy, n-hexyloxy, n-dodecyloxy; cyclopropoxy, cyclobutoxy, ring Pentyloxy, cyclohexyloxy.

作為烷氧基的部分氫原子或全部氫原子被鹵素取代的基團，可列舉氟甲氧基、二氟甲氧基、三氟甲氧基、1,1,2,2,2-五氟乙氧基、1,1,2,2-四氟乙氧基、1,1,2-三氟乙氧基、1,2,2-三氟乙氧基、2,2,2-三氟乙氧基、2,2-二氟乙氧基、1,2-二氟乙氧基、1,1-二氟乙氧基、2-氟乙氧基、1-氟乙氧基、2,2,3,3-四氟-1-丙氧基、2,2,3,3,3-五氟-1-丙氧基、2,2,3,3,4,4,4-七氟-1-丁氧基、2,2,3,4,4,4-六氟-1-丁氧基、2,2,3,3,4,4,5,5-八氟-1-戊氧基、3,3,4,4,5,5,6,6,6-九氟-1-己氧基、4,4,5,5,6,6,7,7,7-九氟-1-庚氧基、2,2,3,3,4,4,5,5,6,6,7,7-十二氟-1-庚氧基、7,7,8,8,8-五氟-1-辛氧基、3,3,4,4,5,5,6,6,7,7,8,8,8-十三氟-1-辛氧基、2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9-十六氟-1-壬氧基、4,4,5,5,6,6,7,7,8,8,9,9,9-十三氟-1-壬氧基、7,7,8,8,9,9,10,10,10-九氟-1-癸氧基、3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-十七氟-1-癸氧基、4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-十五氟-1-癸氧基、7,7,8,8,9,9,10,10,11,11,12,12,12-十三氟-1-十二烷氧基、3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,12-二十一氟-1-十二烷氧基、7,7,8,8,9,9,10,10,11,11,12,12,13,13,14,14,14-十七氟-1-十四烷氧基、1H,1H,2,5-雙（三氟甲基）-3,6-二氧十一氟-1-壬氧基、6-（全氟-1-甲基乙基）-1-己氧基、2-（全氟-1-甲基丁基）-1-乙氧基、2-（全氟-3-甲基丁基）乙氧基、2-（全氟-7-甲基辛基）乙氧基、2H-六氟-2-丙氧基、2,2-雙（三氟甲基）-1-丙氧基等。Examples of groups in which part or all of the hydrogen atoms of the alkoxy group are substituted by halogen include fluoromethoxy, difluoromethoxy, trifluoromethoxy, 1,1,2,2,2-pentafluoro Ethoxy, 1,1,2,2-tetrafluoroethoxy, 1,1,2-trifluoroethoxy, 1,2,2-trifluoroethoxy, 2,2,2-trifluoro Ethoxy, 2,2-difluoroethoxy, 1,2-difluoroethoxy, 1,1-difluoroethoxy, 2-fluoroethoxy, 1-fluoroethoxy, 2, 2,3,3-Tetrafluoro-1-propoxy, 2,2,3,3,3-pentafluoro-1-propoxy, 2,2,3,3,4,4,4-heptafluoro -1-butoxy, 2,2,3,4,4,4-hexafluoro-1-butoxy, 2,2,3,3,4,4,5,5-octafluoro-1-pentyl Oxy, 3,3,4,4,5,5,6,6,6-nonafluoro-1-hexyloxy, 4,4,5,5,6,6,7,7,7-nonafluoro -1-heptyloxy, 2,2,3,3,4,4,5,5,6,6,7,7-dodecafluoro-1-heptyloxy, 7,7,8,8,8 -Pentafluoro-1-octyloxy, 3,3,4,4,5,5,6,6,7,7,8,8,8-Tridecafluoro-1-octyloxy, 2,2, 3,3,4,4,5,5,6,6,7,7,8,8,9,9-hexadecafluoro-1-nonyloxy, 4,4,5,5,6,6, 7,7,8,8,9,9,9-Tridecafluoro-1-nonyloxy, 7,7,8,8,9,9,10,10,10-nonafluoro-1-decyloxy , 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-1-decyloxy, 4,4,5 ,5,6,6,7,7,8,8,9,9,10,10,10-pentafluoro-1-decyloxy, 7,7,8,8,9,9,10,10 ,11,11,12,12,12-Tridecafluoro-1-dodecyloxy, 3,3,4,4,5,5,6,6,7,7,8,8,9,9 ,10,10,11,11,12,12,12-twenty-one fluoro-1-dodecyloxy, 7,7,8,8,9,9,10,10,11,11,12, 12,13,13,14,14,14-Heptadecafluoro-1-tetradecyloxy, 1H,1H,2,5-bis(trifluoromethyl)-3,6-dioxundecafluoro- 1-Nonyloxy, 6-(perfluoro-1-methylethyl)-1-hexyloxy, 2-(perfluoro-1-methylbutyl)-1-ethoxy, 2-(all Fluoro-3-methylbutyl)ethoxy, 2-(perfluoro-7-methyloctyl)ethoxy, 2H-hexafluoro-2-propoxy, 2,2-bis(trifluoromethyl) Group)-1-propoxy and so on.

作為式（R1）的R^601a 至R^601e 的可具有取代基的芳氧基，例如可列舉碳原子數為6至20的芳氧基。 ^{As the aryloxy group which may have a substituent of R 601a} to R ^601e of the formula (R1), for example, an aryloxy group having 6 to 20 carbon atoms can be cited.

具體地，可列舉苯氧基、1-萘氧基、2-萘氧基、2-甲基苯氧基、4-甲基苯氧基、4-三級丁基苯氧基、2-甲氧基苯氧基、4-異丙基苯氧基等。Specifically, phenoxy, 1-naphthyloxy, 2-naphthyloxy, 2-methylphenoxy, 4-methylphenoxy, 4-tertiary butylphenoxy, 2-methyl Oxyphenoxy, 4-isopropylphenoxy, etc.

在可具有取代基的芳氧基中的取代基沒有特別限定，例如，可列舉碳原子數1至8的直鏈狀或支鏈狀或環狀的烷基、碳原子數1至8的直鏈狀或支鏈狀或環狀的烷氧基、胺基、單-或雙-烷基胺基（烷基的碳原子數為1至8）、鹵素原子、氰基、羥基、硝基等。The substituent in the optionally substituted aryloxy group is not particularly limited. For example, a straight-chain or branched-chain or cyclic alkyl group having 1 to 8 carbon atoms, and a straight-chain or branched or cyclic alkyl group having 1 to 8 carbon atoms can be mentioned. Chain or branched or cyclic alkoxy group, amino group, mono- or bis-alkylamino group (the number of carbon atoms of the alkyl group is 1 to 8), halogen atom, cyano group, hydroxyl group, nitro group, etc. .

作為式（R1）所示的基團的具體例，可列舉苯基、甲基苯基、二甲基苯基、三甲基苯基、氟苯基、氯苯基、溴苯基、甲氧基苯基、乙氧基苯基、三氟甲基苯基等。Specific examples of the group represented by the formula (R1) include phenyl, methylphenyl, dimethylphenyl, trimethylphenyl, fluorophenyl, chlorophenyl, bromophenyl, methoxy Phenyl group, ethoxy phenyl group, trifluoromethyl phenyl group, etc.

此外，較佳地，式（R1）的R^601a 至R^601e 中的至少一個為氫原子以外的基團。In addition, preferably, ^{at least one of R 601a} to R ^601e in formula (R1) is a group other than a hydrogen atom.

此外，較佳地，作為由式（R1）所示的基團，R^601a 、R^601c 及R^601e 中的至少一個分別獨立地為氟原子、氯原子、溴原子、甲基或三氟甲基。In addition, preferably, as the group represented by the formula (R1) ^{, at least one of R 601a} , R ^601c and R ^601e is each independently a fluorine atom, a chlorine atom, a bromine atom, a methyl group, or a trifluoromethyl group. .

作為具體例，可列舉：2-氟苯基、3-氟苯基、4-氟苯基、2,3-二氟苯基、2,4-二氟苯基、2,5-二氟苯基、2,6-二氟苯基、3,4-二氟苯基、3,5-二氟苯基、2,4,6-三氟苯基、2,3,5,6-四氟苯基、2,3,4,5,6-五氟苯基等鍵結有氟原子的苯基；2-氯苯基、3-氯苯基、4-氯苯基、2,3-二氯苯基、2,4-二氯苯基、2,5-二氯苯基、2,6-二氯苯基、3,4-二氯苯基、3,5-二氯苯基、2,4,6-三氯苯基、2,3,5,6-四氯苯基、2,3,4,5,6-五氯苯基等鍵結有氯原子的苯基；2-溴苯基、3-溴苯基、4-溴苯基、2,3-二溴苯基、2,4-二溴苯基、2,5-二溴苯基、2,6-二溴苯基、3,4-二溴苯基、3,5-二溴苯基、2,4,6-三溴苯基、2,3,5,6-四溴苯基、2,3,4,5,6-五溴苯基等鍵結有溴原子的苯基；2-甲基苯基、3-甲基苯基、4-甲基苯基、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、2,4,6-三甲基苯基、2,3,5,6-四甲基苯基、2,3,4,5,6-五甲基苯基等鍵結有烷基的苯基；2-三氟甲基苯基、3-三氟甲基苯基、4-三氟甲基苯基、2,3-二三氟甲基苯基、2,4-二三氟甲基苯基、2,5-二三氟甲基苯基、2,6-二三氟甲基苯基、3,4-二三氟甲基苯基、3,5-二三氟甲基苯基、2,4,6-三三氟甲基苯基、2,3,5,6-四三氟甲基苯基、2,3,4,5,6-五三氟甲基苯基等鍵結有氟化烷基的苯基等。Specific examples include: 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2,3-difluorophenyl, 2,4-difluorophenyl, 2,5-difluorobenzene Group, 2,6-difluorophenyl, 3,4-difluorophenyl, 3,5-difluorophenyl, 2,4,6-trifluorophenyl, 2,3,5,6-tetrafluoro Phenyl, 2,3,4,5,6-pentafluorophenyl and other phenyl groups bonded with fluorine atoms; 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2,3-di Chlorophenyl, 2,4-Dichlorophenyl, 2,5-Dichlorophenyl, 2,6-Dichlorophenyl, 3,4-Dichlorophenyl, 3,5-Dichlorophenyl, 2 ,4,6-trichlorophenyl, 2,3,5,6-tetrachlorophenyl, 2,3,4,5,6-pentachlorophenyl and other phenyl groups bonded with chlorine atoms; 2-bromo Phenyl, 3-bromophenyl, 4-bromophenyl, 2,3-dibromophenyl, 2,4-dibromophenyl, 2,5-dibromophenyl, 2,6-dibromophenyl , 3,4-dibromophenyl, 3,5-dibromophenyl, 2,4,6-tribromophenyl, 2,3,5,6-tetrabromophenyl, 2,3,4,5 ,6-Pentabromophenyl and other phenyl groups bonded with bromine atoms; 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2,3-dimethylphenyl, 2, 4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 3,4-dimethylphenyl, 3,5-dimethylphenyl, 2, 4,6-trimethylphenyl, 2,3,5,6-tetramethylphenyl, 2,3,4,5,6-pentamethylphenyl and other phenyl groups bonded with alkyl groups; 2 -Trifluoromethylphenyl, 3-trifluoromethylphenyl, 4-trifluoromethylphenyl, 2,3-ditrifluoromethylphenyl, 2,4-ditrifluoromethylphenyl, 2,5-ditrifluoromethylphenyl, 2,6-ditrifluoromethylphenyl, 3,4-ditrifluoromethylphenyl, 3,5-ditrifluoromethylphenyl, 2, 4,6-tritrifluoromethylphenyl, 2,3,5,6-tetratrifluoromethylphenyl, 2,3,4,5,6-pentatrifluoromethylphenyl, etc. are bonded with fluorine The phenyl group of the alkyl group and so on.

這些之中，較佳為：2-氟苯基、4-氟苯基、2,4-二氟苯基、2,6-二氟苯基等鍵結有氟原子的苯基；2-氯苯基、4-氯苯基、2,4-二氯苯基、2,6-二氯苯基等鍵結有氯原子的苯基；2-溴苯基、4-溴苯基、2,4-二溴苯基、2,6-二溴苯基等鍵結有溴原子的苯基；2-甲基苯基、4-甲基苯基、2,4-二甲基苯基、2,6-二甲基苯基等鍵結有烷基的苯基；2-三氟甲基苯基、4-三氟甲基苯基、2,4-二三氟甲基苯基、2,6-二三氟甲基苯基等鍵結有氟化烷基的苯基。Among these, preferred are: 2-fluorophenyl, 4-fluorophenyl, 2,4-difluorophenyl, 2,6-difluorophenyl, and other phenyl groups to which fluorine atoms are bonded; 2-chloro Phenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 2,6-dichlorophenyl and other phenyl groups bonded with chlorine atoms; 2-bromophenyl, 4-bromophenyl, 2, 4-dibromophenyl, 2,6-dibromophenyl and other phenyl groups bonded with bromine atoms; 2-methylphenyl, 4-methylphenyl, 2,4-dimethylphenyl, 2 ,6-Dimethylphenyl and other phenyl groups bonded with alkyl groups; 2-trifluoromethylphenyl, 4-trifluoromethylphenyl, 2,4-ditrifluoromethylphenyl, 2, A phenyl group to which a fluorinated alkyl group is bonded, such as 6-ditrifluoromethylphenyl group.

此外，作為由上述式（R1）所示的基團以外的可列舉的可具有取代基的芳基，可列舉萘基、硝基萘基、氰基萘基、羥基萘基、甲基萘基、氟萘基、氯萘基、溴萘基、三氟甲基萘基等。In addition, examples of aryl groups that may have substituents other than the group represented by the above formula (R1) include naphthyl, nitronaphthyl, cyanonaphthyl, hydroxynaphthyl, and methylnaphthyl. , Fluoronaphthyl, chloronaphthyl, bromonaphthyl, trifluoromethylnaphthyl, etc.

在鍵結於四氮雜卟啉骨架的基團中，較佳係R^101a 至R^101d 分別獨立地為可具有取代基的直鏈狀或支鏈狀的烷基，較佳為碳原子數1至10的直鏈狀或支鏈狀的烷基，更佳為碳原子數1至5的直鏈狀或支鏈狀的烷基。特別地，較佳係R^101a 至R^101d 均為三級丁基。Among the groups bonded to the porphyrazine skeleton, it is preferable that R ^101a to R ^101d are each independently a linear or branched alkyl group which may have a substituent, and preferably has 1 carbon atom. The linear or branched alkyl group of up to 10 is more preferably a linear or branched alkyl group having 1 to 5 carbon atoms. In particular, it is preferable that R ^101a to R ^101d are all tertiary butyl groups.

在鍵結於四氮雜卟啉骨架的基團中，較佳係R^102a 至R^102d 分別獨立地為由上述式（R1）所示的基團。此外，在R^102a 至R^102d 為由上述式（R1）所示的基團的情況下，較佳係式（R1）的R^601a 至R^601e 中的至少一個為氫原子以外的基團。較佳係R^601a 、R^601c 及R^601e 中的至少一個分別獨立地為氟原子、氯原子、溴原子、甲基或三氟甲基，更佳為鍵結有氟原子的苯基，特別地，較佳係R^102a 至R^102d 均為2-氟苯基。Among the groups bonded to the porphyrazine skeleton, it is preferable that R ^102a to R ^102d are each independently a group represented by the above formula (R1). In addition, when R ^102a to R ^102d are groups represented by the above formula (R1), it is preferable ^{that at least one of R 601a} to R ^601e in the formula (R1) is a group other than a hydrogen atom. Preferably, ^{at least one of R 601a} , R ^601c and R ^601e is each independently a fluorine atom, a chlorine atom, a bromine atom, a methyl group or a trifluoromethyl group, more preferably a phenyl group to which a fluorine atom is bonded, especially Preferably, R ^102a to R ^102d are all 2-fluorophenyl groups.

在由上述式（1）所示的四氮雜卟啉化合物中，具有中心原子為Si，作為軸向配位體在Si上鍵結有二個O（氧原子），各自的O上鍵結有X¹ 或X² 的結構。In the porphyrazine compound represented by the above formula (1), the central atom is Si, and two O (oxygen atoms) are bonded to Si as an axial ligand, and each O is bonded There are X ¹ or X ² structures.

以下，對作為軸向配位體的結構的一部分的X¹ 與X² 的較佳結構進行說明。 ^{Hereinafter, preferred structures of X 1} and X ² as part of the structure of the axial ligand will be described.

X¹ 與X² 可為相同的基團，也可為不同的基團。X ¹ and X ² may be the same group or different groups.

X¹ 與X² 分別獨立地表示氫原子、可具有取代基的烷基、可具有取代基的芳基、可具有取代基的芳烷基、或者由下式（X1）至（X4）所示的基團。在式（X1）至（X4）中的*表示與氧原子的鍵結部位。

X ¹ and X ² each independently represent a hydrogen atom, an optionally substituted alkyl group, an optionally substituted aryl group, an optionally substituted aralkyl group, or are represented by the following formulas (X1) to (X4)的组。 The group. * In formulas (X1) to (X4) represents a bonding site with an oxygen atom.

R²⁰¹ 與R⁴⁰¹ 分別獨立地表示可具有取代基的烷基、可具有取代基的芳基、可具有取代基烷氧基或者可具有取代基的芳氧基。R ²⁰¹ and R ⁴⁰¹ each independently represent an optionally substituted alkyl group, an optionally substituted aryl group, an optionally substituted alkoxy group, or an optionally substituted aryloxy group.

R³⁰¹ 、R³⁰² 與R⁵⁰¹ 至R⁵⁰³ 分別獨立地表示可具有取代基的烷基、或者可具有取代基的芳基。R ³⁰¹ , R ³⁰² and R ⁵⁰¹ to R ⁵⁰³ each independently represent an alkyl group which may have a substituent or an aryl group which may have a substituent.

作為X¹ 或X² 的可具有取代基的烷基、可具有取代基的芳基，可列舉在R^101a 至R^101d 以及R^102a 至R^102d 的例子中舉出的可具有取代基的烷基、可具有取代基的芳基。Examples of the alkyl group which may have a substituent and the aryl group which may have a substituent of X ¹ or X ² ^{include the alkyl group which may have a substituent mentioned in the examples of R 101a} to R ^101d and R ^102a to R ^102d . , Aryl groups that may have substituents.

作為X¹ 或X² 的可具有取代基的芳烷基，可列舉在作為上述芳基而說明的基團上鍵結有亞甲基、伸乙基、伸丙基等碳原子數1至5的烷二基的基團等。Examples of the aralkyl group that may have a substituent for X ¹ or X ² include the groups described as the above aryl group with a methylene group, an ethylene group, a propylene group, and the like, which have 1 to 5 carbon atoms. The alkanediyl group and so on.

式（X1）中的R²⁰¹ 表示可具有取代基的烷基、可具有取代基的芳基、可具有取代基的烷氧基、可具有取代基的芳氧基。表示R²⁰¹ 的烷基的碳原子數較佳為1至20，更佳為5至20，進一步佳為5至15。表示R²⁰¹ 的芳基的碳原子數例如為6至20，較佳為6至18，更佳為6至15，進一步佳為6至10。 ^{R 201} in the formula (X1) represents an optionally substituted alkyl group, an optionally substituted aryl group, an optionally substituted alkoxy group, and an optionally substituted aryloxy group. The number of carbon atoms of the alkyl group representing R ²⁰¹ is preferably from 1 to 20, more preferably from 5 to 20, and even more preferably from 5 to 15. The number of carbon atoms of the aryl group representing R ^{201 is} , for example, 6-20, preferably 6-18, more preferably 6-15, and still more preferably 6-10.

作為可具有取代基的烷基、以及可具有取代基的芳基，可列舉在R^101a 至R^101d 以及R^102a 至R^102d 的例子中舉出的可具有取代基的烷基、以及可具有取代基的芳基。As the alkyl group which may have a substituent and the aryl group which may have a substituent, the alkyl group which may have a substituent mentioned in the example of R ^101a to R ^101d and R ^102a to R ^102d , and the alkyl group which may have a substituent are mentioned. Aryl group.

作為可具有取代基的烷氧基、以及可具有取代基的芳氧基，可列舉作為式（R1）的R^601a 至R^601e 舉出的可具有取代基的烷氧基、以及可具有取代基的芳氧基。As the alkoxy group which may have a substituent and the aryloxy group which may have a substituent, the alkoxy group which may have a substituent mentioned as R ^601a to R ^{601e of} formula (R1), and the alkoxy group which may have a substituent, and the aryloxy group which may have a substituent are mentioned的aryloxy.

作為式（X1）中的R²⁰¹ ，較佳為可被取代的烷基、可被取代的芳基，更佳為直鏈狀或支鏈狀的烷基、可被取代的苯基、可被取代的環戊二烯基陰離子，進一步佳為1-乙基戊基、苯基、3-硝基苯基、4-羧基苯基、3-羧基苯基、4-羥基苯基、二茂鐵等。 ^{R 201} in the formula (X1) is preferably an optionally substituted alkyl group, an optionally substituted aryl group, more preferably a linear or branched alkyl group, an optionally substituted phenyl group, and an optionally substituted aryl group. The substituted cyclopentadienyl anion is further preferably 1-ethylpentyl, phenyl, 3-nitrophenyl, 4-carboxyphenyl, 3-carboxyphenyl, 4-hydroxyphenyl, ferrocene Wait.

式（X2）中的R³⁰¹ 及R³⁰² 分別獨立地表示可具有取代基的烷基、或者可具有取代基的芳基。 ^{R 301} and R ³⁰² in formula (X2) each independently represent an optionally substituted alkyl group or an optionally substituted aryl group.

作為可具有取代基的烷基以及可具有取代基的芳基，可列舉在R^101a 至R^101d 及R^102a 至R^102d 的例子中舉出的可具有取代基的烷基、以及可具有取代基的芳基。As the alkyl group which may have a substituent and the aryl group which may have a substituent, the alkyl group which may have a substituent mentioned in the example of R ^101a to R ^101d and R ^102a to R ^102d , and the alkyl group which may have a substituent are mentioned.的aryl.

式（X3）中的R⁴⁰¹ 表示可具有取代基的烷基、可具有取代基的芳基、可具有取代基的烷氧基、或者可具有取代基的芳氧基。 ^{R 401} in the formula (X3) represents an optionally substituted alkyl group, an optionally substituted aryl group, an optionally substituted alkoxy group, or an optionally substituted aryloxy group.

作為可具有取代基的烷基以及可具有取代基的芳基，可列舉在R^101a 至R^101d 以及R^102a 至R^102d 的例子中舉出的可具有取代基的烷基、以及可具有取代基的芳基。As the alkyl group which may have a substituent and the aryl group which may have a substituent, the alkyl group which may have a substituent mentioned in the example of R ^101a to R ^101d and R ^102a to R ^102d , and the alkyl group which may have a substituent are mentioned的aryl.

作為可具有取代基的烷氧基以及可具有取代基的芳氧基，可列舉作為式（R1）的R^601a 至R^601e 舉出的可具有取代基的烷氧基、以及可具有取代基的芳氧基。As the alkoxy group which may have a substituent and the aryloxy group which may have a substituent, the alkoxy group which may have a substituent mentioned as R ^601a to R ^{601e of} formula (R1), and the alkoxy group which may have a substituent are mentioned. Aryloxy.

式（X4）中的R⁵⁰¹ 至R⁵⁰³ 分別獨立地表示可具有取代基的烷基、或者可具有取代基的芳基。 ^{R 501} to R ⁵⁰³ in formula (X4) each independently represent an alkyl group which may have a substituent or an aryl group which may have a substituent.

其中，較佳係式（X4）中的R⁵⁰¹ 至R⁵⁰³ 分別獨立地為可具有取代基的烷基，更佳為碳原子數1至5的烷基，進一步佳為甲基、乙基。Wherein, in (X4) R is preferably based formula ⁵⁰¹ to R ⁵⁰³ each independently represent an optionally substituted alkyl group, more preferably an alkyl group having 1 to 5 carbon atoms, more excellent is methyl, ethyl.

在X¹ 與X² 中的可具有取代基的芳基較佳為由下述式（2）所示的基團。

The aryl group which may have a substituent in X ¹ and X ² is preferably a group represented by the following formula (2).

式（2）中的R⁷⁰¹ 表示CO₂ R^701a 、可具有取代基的烷氧基、可具有取代基的芳氧基、鹵素原子、硝基、氰基、羥基、可具有取代基（例如鹵素原子）的烷基、或者含有氮原子的雜環基團，n表示0至5的整數，R^701a 表示氫原子、可具有取代基的烷基、或者可具有取代基的芳基，*表示與氧原子的鍵結部位。在n為2以上的整數的情況下，複數個R⁷⁰¹ 各自可相同也可不同。 ^{R 701} in formula (2) represents CO ₂ R ^701a , optionally substituted alkoxy, optionally substituted aryloxy, halogen atom, nitro, cyano, hydroxyl, optionally substituted (for example, halogen Atom) alkyl group or a heterocyclic group containing a nitrogen atom, n represents an integer from 0 to 5, R ^701a represents a hydrogen atom, an optionally substituted alkyl group, or an optionally substituted aryl group, and * represents and The bonding site of the oxygen atom. When n is an integer of 2 or more, each of a plurality of R ⁷⁰¹ may be the same or different.

此外，在四氮雜卟啉化合物中，在式（1）中，X¹ 與X² 中的其中一者可為由式（2）所示的基團，另一者為其他基團。In addition, in the porphyrazine compound, in the formula (1), one of X ¹ and X ² may be a group represented by the formula (2), and the other may be another group.

式（2）中的n為0至5的整數。在n為0的情況下，式（2）表示苯基。N in formula (2) is an integer from 0 to 5. When n is 0, formula (2) represents a phenyl group.

在n為2以上的整數的情況下，複數個R⁷⁰¹ 各自可相同也可不同。在n為1的情況下，較佳係R⁷⁰¹ 的位置為相對於與氧原子的結合部位*為p-位。When n is an integer of 2 or more, each of a plurality of R ⁷⁰¹ may be the same or different. When n is 1, it is preferable ^{that the position of R 701} is the p-position relative to the bonding site* with the oxygen atom.

在R⁷⁰¹ 為可具有取代基的烷氧基或可具有取代基的芳氧基的情況下，作為可具有取代基的烷氧基以及可具有取代基的芳氧基，可列舉作為式（R1）的R^601a 至R^601e 舉出的可具有取代基的烷氧基、以及可具有取代基的芳氧基。When R ⁷⁰¹ is an alkoxy group which may have a substituent or an aryloxy group which may have a substituent, as the alkoxy group which may have a substituent and the aryloxy group which may have a substituent, the formula (R1 ) R ^601a to R ^601e exemplify an alkoxy group which may have a substituent, and an aryloxy group which may have a substituent.

在R⁷⁰¹ 為可具有取代基的烷基的情況下，作為可具有取代基的烷基，可列舉在R^101a 至R^101d 以及R^102a 至R^102d 的例子中舉出的可具有取代基的烷基。When R ⁷⁰¹ is an optionally substituted alkyl group, examples of the optionally substituted alkyl group include the optionally substituted alkyl groups exemplified in the examples of R ^101a to R ^101d and R ^102a to R ^102d . base.

含有氮原子的雜環基較佳為哌嗪基、哌啶基、吡咯啶基、咪唑啶基、吡唑啶基等，其中更佳為哌嗪基。The heterocyclic group containing a nitrogen atom is preferably piperazinyl, piperidinyl, pyrrolidinyl, imidazolidinyl, pyrazolidinyl, etc., and more preferably piperazinyl.

在R⁷⁰¹ 為CO₂ R^701a 的情況下，如果R^701a 為氫原子則CO₂ R^701a 表示羧基，如果R^701a 為可具有取代基的烷基或者可具有取代基芳基則CO₂ R^701a 表示醯氧基羰基。When R ⁷⁰¹ is CO ₂ R ^701a , if R ^701a is a hydrogen atom, CO ₂ R ^701a represents a carboxyl group, and if R ^701a is an optionally substituted alkyl group or an optionally substituted aryl group, CO ₂ R ^701a represents Aceoxycarbonyl.

在R^701a 為可具有取代基的烷基或可具有取代基的芳基的情況下，作為可具有取代基的烷基及可具有取代基的芳基，可列舉在R^101a 至R^101d 以及R^102a 至R^102d 的例子中舉出的可具有取代基的烷基、以及可具有取代基的芳基。When R ^701a is an optionally substituted alkyl group or an optionally substituted aryl group, examples of the optionally substituted alkyl group and the optionally substituted aryl group include R ^101a to R ^101d and R The alkyl group which may have a substituent and the aryl group which may have a substituent mentioned in the example of ^102a to R ^102d.

在這些基團中，作為由式（2）所示的基團，更佳為4-羧基苯基、苯基、3-羥基苯基、3,5-二羥基苯基、3,5-二氟苯基、4-哌嗪基苯基、3,5-二甲基-4-羥基苯基、3,5,6-三甲基-4-羥基苯基、4-三級丁基苯基、3-硝基苯基、3-羧基苯基、4-氰基苯基、4-三氟甲基苯基，特別佳為4-羧基苯基、3,5-二氟苯基、3,5,6-三甲基-4-羥基苯基、4-三級丁基苯基、3-羧基苯基、4-氰基苯基、4-三氟甲基苯基。Among these groups, the group represented by formula (2) is more preferably 4-carboxyphenyl, phenyl, 3-hydroxyphenyl, 3,5-dihydroxyphenyl, 3,5-dihydroxyphenyl Fluorophenyl, 4-piperazinylphenyl, 3,5-dimethyl-4-hydroxyphenyl, 3,5,6-trimethyl-4-hydroxyphenyl, 4-tertiary butylphenyl , 3-nitrophenyl, 3-carboxyphenyl, 4-cyanophenyl, 4-trifluoromethylphenyl, particularly preferably 4-carboxyphenyl, 3,5-difluorophenyl, 3, 5,6-Trimethyl-4-hydroxyphenyl, 4-tertiarybutylphenyl, 3-carboxyphenyl, 4-cyanophenyl, 4-trifluoromethylphenyl.

構成由X¹ 、X² 、R²⁰¹ 、R⁴⁰¹ 所示的芳基、芳烷基、及芳氧基的芳香族烴環可配位於金屬原子。The aromatic hydrocarbon ring constituting the aryl group, aralkyl group, and aryloxy group represented by X ¹ , X ² , R ²⁰¹ , and R ^{401 may be coordinated to a metal atom.}

芳香族烴環例如為苯環、萘環、環戊二烯基陰離子環等，較佳為環戊二烯基陰離子環。The aromatic hydrocarbon ring is, for example, a benzene ring, a naphthalene ring, a cyclopentadienyl anion ring, etc., preferably a cyclopentadienyl anion ring.

金屬原子可為Fe、Cu、Cr、Co等，較佳為Fe。The metal atom may be Fe, Cu, Cr, Co, etc., preferably Fe.

可配位於金屬原子表示可與芳香族烴環一起形成夾層型的金屬錯合物。Coordination to a metal atom means that it can form a sandwich-type metal complex with an aromatic hydrocarbon ring.

在式（1）中，較佳地，X¹ 與X² 的至少任一者為氫原子、可具有取代基的芳基、可具有取代基的芳烷基、由式（X1）所示的基團（較佳係R²⁰¹ 為可具有取代基的烷基、可具有取代基的芳基）、由式（X4）所示的基團（較佳係R⁵⁰¹ 至R⁵⁰³ 為可具有取代基的烷基），更佳地，X¹ 與X² 二者分別獨立地為氫原子、可具有取代基的芳基、可具有取代基的芳烷基、由式（X1）所示的基團（較佳係R²⁰¹ 為可具有取代基的烷基、可具有取代基的芳基）、或者由式（X4）所示的基團（較佳係R⁵⁰¹ 至R⁵⁰³ 為可具有取代基的烷基）。In the formula (1), preferably, ^{at least any one of X 1} and X ² is a hydrogen atom, an aryl group that may have a substituent, an aralkyl group that may have a substituent, and the one represented by the formula (X1) Group (preferably R ²⁰¹ is an optionally substituted alkyl group or an optionally substituted aryl group), a group represented by formula (X4) (preferably R ⁵⁰¹ to R ⁵⁰³ are optionally substituted More preferably, X ¹ and X ² are each independently a hydrogen atom, an aryl group that may have a substituent, an aralkyl group that may have a substituent, and a group represented by formula (X1) (Preferably R ²⁰¹ is an optionally substituted alkyl group or an optionally substituted aryl group), or a group represented by formula (X4) (preferably R ⁵⁰¹ to R ⁵⁰³ are optionally substituted alkyl).

此外，在式（1）中，較佳地， X¹ 與X² 的可具有取代基的芳基為至少任一者為由式（2）所示的基團，更佳地，二者分別獨立地為由式（2）所示的基團。In addition, in formula (1), preferably, ^{at least one of the aryl groups that may have substituents for X 1} and X ² is a group represented by formula (2), and more preferably, the two are separately It is independently a group represented by formula (2).

在式（1）中，進一步佳地，X¹ 與X² 二者均為氫原子、非取代的芳基、具有羧基的芳基、具有羥基的芳基、具有鹵素原子的芳基、具有含氮原子的雜環的芳基、具有烷基的芳基、具有硝基的芳基、具有氰基的芳基、具有烷基與羥基的芳基、具有CF₃ -或CF₃ CF₂ -或CF₃ CF₂ CF₂ -的芳基、與芳香族烴環及金屬原子共同形成夾層型金屬錯合物的芳烷基、R²⁰¹ 為直鏈狀或支鏈狀的烷基的由式（X1）所示的基團、R²⁰¹ 為具有羧基或硝基的芳基的由式（X1）所示的基團、R²⁰¹ 為非取代的芳基的由式（X1）所示的基團、R²⁰¹ 為與芳香族烴環及金屬原子共同形成金屬錯合物的芳基的由式（X1）所示的基團、R⁵⁰¹ 至R⁵⁰³ 為直鏈狀或支鏈狀的烷基的由式（X4）所示的基團；尤其佳為4-羧基苯基羰基、三甲基矽基、4-羧基苯基、1-乙基戊基羰基、苯基、苯基羰基、3-硝基苯基羰基、3-羧基苯基羰基、3-羥基苯基、3,5-二羥基苯基、3,5-二氟苯基、4-哌嗪基苯基、3,5-二甲基-4-羥基苯基、3,5,6-三甲基-4-羥基苯基、二茂鐵甲基、二茂鐵羰基、4-三級丁基苯基、3-硝基苯基、3-羧基苯基、4-氰基苯基、4-三氟甲基苯基；特別佳為4-羧基苯基羰基、三甲基矽基、4-羧基苯基、3,5-二氟苯基、3,5,6-三甲基-4-羥基苯基、4-三級丁基苯基、3-羧基苯基、4-氰基苯基、4-三氟甲基苯基或者苯基。In formula (1), it is further preferred that both X ¹ and X ² are hydrogen atoms, unsubstituted aryl groups, aryl groups having carboxyl groups, aryl groups having hydroxyl groups, aryl groups having halogen atoms, and having A heterocyclic aryl group having a nitrogen atom, an aryl group having an alkyl group, an aryl group having a nitro group, an aryl group having a cyano group, an aryl group having an alkyl group and a hydroxyl group, CF ₃ -or CF ₃ CF ₂ -or CF ₃ CF _₂ CF ₂ - aryl group, with an aromatic hydrocarbon ring and a metal atom forming an aromatic group together sandwich-type metal complex compound, R ²⁰¹ is an alkyl group linear or branched by the formula (X1 ), the group ^{represented by formula (X1) where R 201} is an aryl group having a carboxyl or nitro group, the group represented by formula (X1) where R ^{201 is an} unsubstituted aryl group, R ²⁰¹ is a group represented by formula (X1) that forms an aryl group of a metal complex together with an aromatic hydrocarbon ring and a metal atom, and R ⁵⁰¹ to R ⁵⁰³ are linear or branched alkyl groups. The group represented by formula (X4); especially preferred are 4-carboxyphenylcarbonyl, trimethylsilyl, 4-carboxyphenyl, 1-ethylpentylcarbonyl, phenyl, phenylcarbonyl, 3-nitro Phenylcarbonyl, 3-carboxyphenylcarbonyl, 3-hydroxyphenyl, 3,5-dihydroxyphenyl, 3,5-difluorophenyl, 4-piperazinylphenyl, 3,5-dimethyl 4-hydroxyphenyl, 3,5,6-trimethyl-4-hydroxyphenyl, ferrocene methyl, ferrocene carbonyl, 4-tertiary butyl phenyl, 3-nitrophenyl , 3-carboxyphenyl, 4-cyanophenyl, 4-trifluoromethylphenyl; particularly preferred are 4-carboxyphenylcarbonyl, trimethylsilyl, 4-carboxyphenyl, 3,5-di Fluorophenyl, 3,5,6-trimethyl-4-hydroxyphenyl, 4-tertiarybutylphenyl, 3-carboxyphenyl, 4-cyanophenyl, 4-trifluoromethylphenyl Or phenyl.

如果X¹ 與X² 為上述基團，則所形成的濾光片不僅具有優異的耐化學性，更顯示出高的對比度。If X ¹ and X ² are the above-mentioned groups, the formed filter not only has excellent chemical resistance, but also exhibits high contrast.

作為呈現出高對比的X¹ 與X² ，較佳為可具有取代基的芳基、R²⁰¹ 為與芳香族烴環及金屬原子共同形成夾層型金屬錯合物的芳基的由式（X1）所示的基團，更佳為苯基、4-羧基苯基、3-羧基苯基、4-氰基苯基、4-三氟甲基苯基、二茂鐵羰基。 ^{As X 1} and X ² exhibiting a high contrast, an aryl group that may have a substituent is preferred, and R ²⁰¹ is an aryl group that forms a sandwich-type metal complex with an aromatic hydrocarbon ring and a metal atom by the formula (X1 The groups shown in) are more preferably phenyl, 4-carboxyphenyl, 3-carboxyphenyl, 4-cyanophenyl, 4-trifluoromethylphenyl, and ferrocene carbonyl.

由式（1）所示的化合物通常為吸收在590奈米附近顯示橙色的光的化合物，其吸收最大波長（λmax）較佳為570至620奈米。The compound represented by the formula (1) is generally a compound that absorbs light showing orange in the vicinity of 590 nm, and its absorption maximum wavelength (λmax) is preferably 570 to 620 nm.

可藉由改變鍵結於由式（1）所示化合物的四氮雜卟啉骨架的取代基來改變由式（1）所示化合物的吸收最大波長。此外，吸收最大波長的較佳的上限值為620奈米，更佳的上限值為615奈米。此外，吸收最大波長的較佳的下限值為570奈米，更佳的下限值為575奈米。吸收最大波長可經由分光光度計而進行測量。The maximum wavelength of absorption of the compound represented by the formula (1) can be changed by changing the substituents bonded to the porphyrazine skeleton of the compound represented by the formula (1). In addition, the preferable upper limit value of the absorption maximum wavelength is 620 nm, and the more preferable upper limit value is 615 nm. In addition, the preferable lower limit of the absorption maximum wavelength is 570 nanometers, and the more preferable lower limit is 575 nanometers. The maximum absorption wavelength can be measured by a spectrophotometer.

由式（1）所示化合物具有將鄰近波谷部分包含的整體特別窄的吸收光譜，作為將鄰近波谷部分包含的整體特別窄的吸收光譜的指標，在吸收光譜中從吸收最大波長的長波長側的基線的上升波長到吸收最大波長為止的波長寬度為40奈米以下，較佳地，在吸收最大波長中的半值寬度為20奈米以下。The compound represented by formula (1) has a particularly narrow absorption spectrum as a whole that includes adjacent troughs, as an indicator of a particularly narrow absorption spectrum that includes adjacent troughs. In the absorption spectrum, from the long wavelength side of the absorption maximum wavelength The wavelength width from the rising wavelength of the baseline to the maximum absorption wavelength is 40 nanometers or less, and preferably, the half-value width in the absorption maximum wavelength is 20 nanometers or less.

將吸收最大波長中的吸光度設為1時，將基線的上升波長確定為從長波長側判斷吸光度為0.01以上的波長。When the absorbance in the absorption maximum wavelength is set to 1, the rising wavelength of the baseline is determined to be the wavelength at which the absorbance is judged to be 0.01 or more from the long-wavelength side.

然後，求出從上升波長到吸收最大波長為止的距離（波長寬度）。Then, the distance (wavelength width) from the rising wavelength to the maximum absorption wavelength is obtained.

在本說明書中，半值寬度是指半值全寬，其表示在吸收光譜中由在吸收最大波長中的吸光係數值的1/2值處所劃平行於橫軸的直線與該峰所形成的二個交點間的距離（奈米）。In this specification, the half-value width refers to the full width at half-value, which means the peak formed by a straight line parallel to the horizontal axis drawn at 1/2 of the value of the absorption coefficient in the absorption maximum wavelength in the absorption spectrum. The distance (in nanometers) between two intersections.

此外，較佳地，關於由式（1）所示的化合物，在式（1）中的X¹ 與X² 的至少一者為由式（2）所示的基團。In addition, preferably, regarding the compound represented by formula (1), ^{at least one of X 1} and X ² in formula (1) is a group represented by formula (2).

如果X¹ 及X² 的至少一者為由式（2）所示的基團，則由於能夠抑制來自由式（1）所示化合物的螢光發光，可防止對色調產生影響的多餘光的產生。If ^{at least one of X 1} and X ² is a group represented by the formula (2), the fluorescent light emission from the compound represented by the formula (1) can be suppressed, thereby preventing excessive light that affects the color tone. produce.

螢光強度可藉由使用螢光分光光度計將吸收最大波長作為激發波長來測定螢光光譜而進行評價，螢光強度弱是較佳的。The fluorescence intensity can be evaluated by measuring the fluorescence spectrum using a fluorescence spectrophotometer with the absorption maximum wavelength as the excitation wavelength, and it is preferable that the fluorescence intensity is weak.

由式（1）所示的化合物係藉由以下步驟得到。The compound represented by formula (1) is obtained by the following steps.

首先，從由下述式（4）所示的1,2-二氰基乙烯化合物的順式體得到由下述式（5）所示的二亞胺基異吡咯衍生物。First, the diiminoisopyrrole derivative represented by the following formula (5) is obtained from the cis isomer of the 1,2-dicyanoethylene compound represented by the following formula (4).

得到由式（4）所示的1,2-二氰基乙烯化合物的順式體的方法可使用日本專利申請特開平11-043619號中記載的方法，得到式（5）所示的二亞胺基異吡咯衍生物的方法可使用日本專利申請特開平02-000665號中記載的方法。

（在式（4）與式（5）中，R¹⁰¹ 及R¹⁰² 分別獨立地表示可具有取代基的烷基、或可具有取代基的芳基。具體地，可列舉在R^101a 至R^101d 及R^102a 至R^102d 的例子中舉出的可具有取代基的烷基、可具有取代基的芳基。）The method for obtaining the cis isomer of the 1,2-dicyanoethylene compound represented by the formula (4) can use the method described in Japanese Patent Application Laid-Open No. 11-043619 to obtain the dicyanide represented by the formula (5) As the method of the aminoisopyrrole derivative, the method described in Japanese Patent Application Laid-Open No. 02-000665 can be used.

(In formula (4) and formula (5), R ¹⁰¹ and R ¹⁰² each independently represent an optionally substituted alkyl group or an optionally substituted aryl group. Specifically, R ^101a to R ^101d And the alkyl group which may have a substituent and the aryl group which may have a substituent mentioned in the examples of ^{R 102a} to R ^102d.)

接著，藉由將式（5）所示的二亞胺基異吡咯衍生物與Si源（例如SiCl₄ ）混合並加熱使其發生環化反應，經由水解得到中心原子為Si、Si的軸向配位體為OH基的化合物（式（1）中的X¹ 與X² 均為H的化合物）。Next, by mixing the diiminoisopyrrole derivative represented by the formula (5) with a Si source (such as SiCl ₄ ) and heating it to cause a cyclization reaction, the axial center atom of Si and Si is obtained through hydrolysis. Compounds in which the ligand is an OH group (compounds in which both X ¹ and X ² in formula (1) are H).

對於上述得到的化合物，藉由添加具有欲取代軸向配位體之結構的化合物並進行回流等方法，可將X¹ 與X² 從氫原子取代為其他的取代基。For the compound obtained above, by adding a compound having a structure to be substituted for the axial ligand and performing a method such as refluxing, X ¹ and X ² can be substituted from a hydrogen atom to other substituents.

例如，藉由添加羧酸或酚類使在羧基或酚性羥基與Si的軸向配位體OH基之間發生脫水聚合反應，可將X¹ 與X² 從氫原子取代為其他的取代基。For example, by adding a carboxylic acid or phenol to cause a dehydration polymerization reaction between the carboxyl group or phenolic hydroxyl group and the OH group of the axial ligand of Si, X ¹ and X ² can be substituted from hydrogen atoms to other substituents .

此外，藉由添加矽基化劑，也可將X¹ 與X² 從氫原子取代為其他的取代基。In addition, by adding a silylating agent, X ¹ and X ² can also be substituted from hydrogen atoms to other substituents.

作為用於上述取代的羧酸、酚類，可列舉脂肪族羧酸、芳香族羧酸、酚類、羥基羧酸等。Examples of the carboxylic acids and phenols used for the above substitution include aliphatic carboxylic acids, aromatic carboxylic acids, phenols, and hydroxycarboxylic acids.

具體地，可列舉苯甲酸、羥基苯甲酸、硝基苯甲酸、對苯二甲酸、間苯二甲酸、苯酚、乙基己酸等。Specifically, benzoic acid, hydroxybenzoic acid, nitrobenzoic acid, terephthalic acid, isophthalic acid, phenol, ethylhexanoic acid, etc. can be mentioned.

作為矽基化劑，可列舉N,O-雙（三甲基矽基）乙醯胺、三甲基氯矽烷等。Examples of the silylating agent include N,O-bis(trimethylsilyl)acetamide, trimethylchlorosilane, and the like.

相對於著色劑（A）的總量，由式（1）所示的化合物的含有率較佳為0.1質量%以上50質量%以下，更佳為0.5質量%以上50質量%以下，進一步佳為1質量%以上50質量%以下。Relative to the total amount of the colorant (A), the content of the compound represented by formula (1) is preferably 0.1% by mass or more and 50% by mass or less, more preferably 0.5% by mass or more and 50% by mass or less, and still more preferably 1% by mass or more and 50% by mass or less.

相對於固體成分總量，由式（1）所示的化合物的含有率較佳為0.2質量%以上20質量%以下，更佳為0.5質量%以上15質量%以下，進一步佳為1質量%以上12質量%以下。Relative to the total solid content, the content of the compound represented by formula (1) is preferably 0.2% by mass or more and 20% by mass or less, more preferably 0.5% by mass or more and 15% by mass or less, and still more preferably 1% by mass or more 12% by mass or less.

相對於固體成分總量，著色劑（A）的含有率較佳為5質量%以上60質量%以下，更佳為8質量%以上55質量%以下，進一步佳為10質量%以上50質量%以下。Relative to the total solid content, the content of the colorant (A) is preferably 5% by mass or more and 60% by mass or less, more preferably 8% by mass or more and 55% by mass or less, and still more preferably 10% by mass or more and 50% by mass or less .

這裡，在本說明書中的「固體成分總量」是指從著色樹脂組合物總量中除去溶劑含有量之後的量。固體成分總量以及相對於其的各成分的含有量，例如，可藉由液相層析法或氣相層析法等習知的分析手段而測定。Here, the "total solid content" in this specification means the amount after removing the solvent content from the total amount of the colored resin composition. The total solid content and the content of each component relative to it can be measured, for example, by conventional analysis means such as liquid chromatography or gas chromatography.

作為著色劑（A），本發明的著色樹脂組合物可含有由式（1）所示的化合物以及化合物（1）以外的著色劑（以下，有時稱為著色劑（A1））。著色劑（A1）可含有一或二種以上的著色劑。As the coloring agent (A), the coloring resin composition of the present invention may contain the compound represented by the formula (1) and a coloring agent other than the compound (1) (hereinafter, may be referred to as a coloring agent (A1)). The coloring agent (A1) may contain one or two or more coloring agents.

著色劑（A1）可為染料也可為顏料。作為染料，可列舉色彩索引（Color Index）（英國染料與色料師學會（The Society of Dyers and Colourists）出版）以及染料筆記（色染社）中記載的習知的染料。此外，根據化學結構，可列舉偶氮染料、蒽醌染料、三苯基甲烷染料、二苯并哌喃（xanthene）染料、花青染料、萘醌染料、醌亞胺染料、次甲基染料、偶氮次甲基染料、方酸菁（squarylium）染料、吖啶染料、苯乙烯基染料、香豆素染料、喹啉染料、硝基染料以及酞菁染料等。這些之中，較佳為有機溶劑可溶性染料。這些染料可以二種以上併用。The colorant (A1) may be a dye or a pigment. Examples of dyes include conventional dyes described in the Color Index (published by The Society of Dyers and Colourists) and Dye Notes (Color Dyers Society). In addition, according to the chemical structure, azo dyes, anthraquinone dyes, triphenylmethane dyes, xanthene dyes, cyanine dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, Azomethine dyes, squarylium dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline dyes, nitro dyes and phthalocyanine dyes, etc. Among these, organic solvent-soluble dyes are preferred. These dyes can be used in combination of two or more kinds.

具體地，可列舉以下的色彩索引（C.I.）編號的染料。 C.I.溶劑黃14、15、23、24、25、38、62、63、68、79、81、82、83、89、94、98、99、162； C.I.酸性黃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.活性黃2、76、116； C.I.直接黃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.分散黃51、54、76； C.I.溶劑橙2、7、11、15、26、41、54、56、99； C.I.酸性橙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.活性橙16； C.I.直接橙26、34、39、41、46、50、52、56、57、61、64、65、68、70、96、97、106、107； C.I.溶劑紅24、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.酸性紅73、80、91、92、97、138、151、211、274、289； C.I.酸性紫34、102； C.I.分散紫26、27； C.I.溶劑紫11、13、14、26、31、36、37、38、45、47、48、51、59、60； C.I.溶劑藍14、18、35、36、45、58、59、59:1、63、68、69、78、79、83、94、97、98、100、101、102、104、105、111、112、122、128、132、136、139； C.I.酸性藍25、27、40、45、78、80、112； C.I.直接藍40； C.I.分散藍1、14、56、60； C.I.溶劑綠1、3、5、28、29、32、33； C.I.酸性綠3、5、9、25、27、28、41； C.I.鹼性綠1； C.I.還原綠1等。Specifically, the dyes with the following color index (C.I.) numbers can be cited. C.I. Solvent Yellow 14, 15, 23, 24, 25, 38, 62, 63, 68, 79, 81, 82, 83, 89, 94, 98, 99, 162; CI 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. Reactive Yellow 2, 76, 116; CI Direct Yellow 2, 4, 28, 33, 34, 35, 38, 39, 43, 44, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102 , 108, 109, 129, 132, 136, 138, 141; C.I. Disperse Yellow 51, 54, 76; C.I. Solvent Orange 2, 7, 11, 15, 26, 41, 54, 56, 99; C.I. Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 149, 162, 169, 173; C.I. Reactive Orange 16; C.I. Direct Orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107; CI Solvent Red 24, 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. Acid Red 73, 80, 91, 92, 97, 138, 151, 211, 274, 289; C.I. Acid Violet 34, 102; C.I. Disperse Violet 26, 27; C.I. Solvent Violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60; CI Solvent Blue 14, 18, 35, 36, 45, 58, 59, 59: 1, 63, 68, 69, 78, 79, 83, 94, 97, 98, 100, 101, 102, 104, 105, 111 , 112, 122, 128, 132, 136, 139; C.I. Acid Blue 25, 27, 40, 45, 78, 80, 112; C.I. Direct Blue 40; C.I. Disperse Blue 1, 14, 56, 60; C.I. Solvent Green 1, 3, 5, 28, 29, 32, 33; C.I. Acid Green 3, 5, 9, 25, 27, 28, 41; C.I. Basic Green 1; C.I. Vat Green 1 and so on.

作為顏料，可使用習知的顏料，例如，可列舉在色彩索引（英國染料與色料師學會出版）中被分類為顏料的顏料。可以二種以上組合使用。As the pigment, conventional pigments can be used, for example, pigments classified as pigments in the Color Index (published by the British Society of Dyestuffs and Colorists). Two or more types can be used in combination.

具體地，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等黃色顔料； C.I.顏料橙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9、97、105、122、123、144、149、166、168、176、177、179、180、192、202、208、209、215、216、224、242、254、255、264、265、266、268、269、273、溴化二酮吡咯并吡咯等紅色顏料； C.I.顏料藍15、15:3、15:4、15:6、60等藍色顏料； C.I.顏料紫1、19、23、29、32、36、38等紫色顏料； C.I.顏料綠7、36、58、59等綠色顏料。Specifically, CI Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 129, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 185, 194, 214 and other yellow pigments; C.I. Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73 and other orange pigments; CI Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 179, 180, 192, 202, 208, 209, 215, 216, 224, 242, 254, 255, 264 , 265, 266, 268, 269, 273, brominated diketopyrrolopyrrole and other red pigments; C.I. Pigment Blue 15, 15:3, 15:4, 15:6, 60 and other blue pigments; C.I. Purple pigments such as pigment violet 1, 19, 23, 29, 32, 36, 38; C.I. Pigment Green 7, 36, 58, 59 and other green pigments.

作為著色劑（A1），較佳為紅色顏料、黃色顏料，更佳為C.I.顏料紅177、179、202、208、242、254、269，C.I.顏料黃138、139、150、185，溴化二酮吡咯并吡咯。As the colorant (A1), red pigments and yellow pigments are preferred, and CI Pigment Red 177, 179, 202, 208, 242, 254, 269 are more preferred, CI Pigment Yellow 138, 139, 150, 185, two bromide Ketopyrrolopyrrole.

根據需要，可對著色劑（A1）實施松香處理、使用導入有酸性或鹼性基的著色劑衍生物的表面處理、經由高分子化合物等對顏料等表面的接枝處理、基於硫酸微粒化法等的微粒化處理、用於除去雜質的經由有機溶劑或水等的清洗處理、基於離子性雜質的離子交換法等的去除處理等。較佳地，顏料等的粒徑係各自基本均勻。藉由含有分散劑而進行分散處理，使著色劑（A1）在分散液中成為均勻分散的狀態。If necessary, the colorant (A1) can be treated with rosin, surface treatment using a colorant derivative with acidic or basic groups introduced, grafting treatment to the surface of pigments via polymer compounds, etc., based on sulfuric acid micronization method Micronization treatment such as, for removing impurities, cleaning treatment through organic solvents or water, etc., removal treatment by ion exchange methods such as ionic impurities, etc. Preferably, the particle diameters of the pigments and the like are each substantially uniform. By containing the dispersing agent and performing the dispersion treatment, the colorant (A1) is uniformly dispersed in the dispersion liquid.

作為分散劑，可列舉表面活性劑，可為陽離子類、陰離子類、非離子類以及兩性表面活性劑。具體地，可列舉聚酯類、多胺類以及丙烯酸類等表面活性劑等。作為其他的分散劑，也可使用後述的樹脂（B）。這些分散劑可單獨使用或者二種以上組合使用。作為分散劑，按照商品名稱表示，可列舉KP（信越化學工業股份有限公司製造）、FLOWLEN（共榮社化學股份有限公司製造）、SOLSPERSE（註冊商標）（捷利康股份有限公司製造）、EFKA（註冊商標）（巴斯夫（BASF）公司製造）、AJISPER（註冊商標）（味之素精細化學股份有限公司製造）以及Disperbyk（註冊商標）（畢克化學（BYK-Chemie）公司製造）、BYK（註冊商標）（畢克化學公司製造）等。As the dispersant, surfactants can be cited, and cationic, anionic, nonionic, and amphoteric surfactants can be used. Specifically, surfactants such as polyesters, polyamines, and acrylics can be cited. As another dispersant, the resin (B) described later can also be used. These dispersants can be used alone or in combination of two or more kinds. As a dispersant, according to the product name, KP (manufactured by Shin-Etsu Chemical Co., Ltd.), FLOWLEN (manufactured by Kyoeisha Chemical Co., Ltd.), SOLSPERSE (registered trademark) (manufactured by Zelikon Co., Ltd.), EFKA (manufactured by Shin-Etsu Chemical Co., Ltd.), Registered trademark) (manufactured by BASF), AJISPER (registered trademark) (manufactured by Ajinomoto Fine Chemicals Co., Ltd.), Disperbyk (registered trademark) (manufactured by BYK-Chemie), BYK (registered Trademark) (manufactured by BYK Chemical Company), etc.

在使用分散劑的情況下，相對於著色劑（A1）100質量份，分散劑的使用量較佳為100質量份以下，更佳為5質量份以上且50質量份以下。如果分散劑的使用量在上述範圍內，有能夠得到更均勻的分散狀態的含有著色劑（A1）的液體的傾向。In the case of using a dispersant, the amount of the dispersant used is preferably 100 parts by mass or less, and more preferably 5 parts by mass or more and 50 parts by mass or less relative to 100 parts by mass of the colorant (A1). If the amount of the dispersant used is within the above range, there is a tendency that a colorant (A1)-containing liquid in a more uniform dispersion state can be obtained.

在著色劑樹脂組合物中，在固體成分總量中，著色劑（A1）的含有量通常為0質量%以上50質量%以下，較佳為0質量%以上40質量%以下，更佳為0質量%以上30質量%以下。In the colorant resin composition, the content of the colorant (A1) in the total solid content is usually 0% by mass to 50% by mass, preferably 0% by mass to 40% by mass, and more preferably 0 The mass% is above 30 mass%.

＜樹脂（B）＞＜Resin (B)＞

樹脂（B）沒有特別限定，但較佳為鹼可溶性樹脂，更佳為具有源自從不飽和羧酸與不飽和羧酸酐構成的組中所選的至少一種單體（a）（以下，有時稱為「（a）」）的結構單元的樹脂。較佳地，樹脂（B）進一步具有從源自具有碳原子數2至4的環狀醚結構與烯屬不飽和鍵的單體（b）（以下有時稱為「（b）」）的結構單元、源自可與（a）共聚合的單體（c）（但，與（a）及（b）不同）（以下稱為「（c）」）的結構單元、以及在側鏈上具有烯屬不飽和鍵的結構單元構成的組中所選的至少一種結構單元。The resin (B) is not particularly limited, but it is preferably an alkali-soluble resin, and more preferably has at least one monomer (a) derived from the group consisting of unsaturated carboxylic acid and unsaturated carboxylic anhydride (hereinafter, there are When called "(a)") the resin of the structural unit. Preferably, the resin (B) further has a monomer (b) (hereinafter sometimes referred to as "(b)") derived from a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond Structural units, structural units derived from monomers (c) copolymerizable with (a) (but different from (a) and (b)) (hereinafter referred to as "(c)"), and on the side chain At least one structural unit selected from the group consisting of structural units having ethylenically unsaturated bonds.

作為（a），具體地，例如，可列舉丙烯酸、甲基丙烯酸、馬來酸酐、伊康酸酐、3,4,5,6-四氫鄰苯二甲酸酐、琥珀酸單［2-（甲基）丙烯醯氧基乙基］酯，較佳為丙烯酸、甲基丙烯酸、馬來酸酐。As (a), specifically, for example, acrylic acid, methacrylic acid, maleic anhydride, itaconic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, succinic acid mono[2-(form) Yl) acryloxyethyl] ester, preferably acrylic acid, methacrylic acid, maleic anhydride.

此外，在本說明書中，「（甲基）丙烯酸」表示由丙烯酸以及甲基丙烯酸構成的組中所選的至少一種。「（甲基）丙烯醯基」以及「（甲基）丙烯酸酯」等的表述也具有同樣的意思。In addition, in this specification, "(meth)acrylic acid" means at least one selected from the group consisting of acrylic acid and methacrylic acid. Expressions such as "(meth)acryloyl" and "(meth)acrylate" also have the same meaning.

較佳地，（b）為具有碳原子數2至4的環狀醚結構（例如，由環氧乙烷環、氧呾環與四氫呋喃環構成的組中所選的至少一種）及（甲基）丙烯醯氧基的單體。Preferably, (b) is a cyclic ether structure having 2 to 4 carbon atoms (for example, at least one selected from the group consisting of an oxirane ring, an oxygen ring and a tetrahydrofuran ring) and (methyl ) A monomer of propylene oxy group.

作為（b），例如，可列舉（甲基）丙烯酸縮水甘油酯、乙烯基苄基縮水甘油醚、3,4-環氧三環[5.2.1.0^2,6 ]（甲基）丙烯酸癸酯、3-乙基-3-（甲基）丙烯醯氧基甲基氧呾、（甲基）丙烯酸四氫糠酯等，較佳為（甲基）丙烯酸縮水甘油酯、3,4-環氧三環[5.2.1.0^2,6 ]（甲基）丙烯酸癸酯、3-乙基-3-（甲基）丙烯醯氧基甲基氧呾。As (b), for example, glycidyl (meth)acrylate, vinyl benzyl glycidyl ether, 3,4-epoxy tricyclo[5.2.1.0 ^2,6 ] decyl (meth)acrylate, 3-Ethyl-3-(meth)acryloyloxymethyloxy, tetrahydrofurfuryl (meth)acrylate, etc., preferably glycidyl (meth)acrylate, 3,4-epoxy three Cyclo[5.2.1.0 ^2,6 ](meth)decyl acrylate, 3-ethyl-3-(meth)propenoxymethyloxy group.

作為（c），例如，可列舉（甲基）丙烯酸甲酯、（甲基）丙烯酸丁酯、（甲基）丙烯酸環己酯、（甲基）丙烯酸-2-甲基環己酯、三環[5.2.1.0^2,6 ]癸烷-8-基（甲基）丙烯酸、苄酯（甲基）丙烯酸酯、（甲基）丙烯酸-2-羥基乙酯、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、苯乙烯、乙烯基甲苯等，較佳為苯乙烯、乙烯基甲苯、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、（甲基）丙烯酸-2-羥基乙酯等。As (c), for example, methyl (meth)acrylate, butyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclic [5.2.1.0 ^2,6 ] Decane-8-yl (meth)acrylic acid, benzyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, N-phenylmaleimide , N-cyclohexyl maleimide, N-benzyl maleimide, styrene, vinyl toluene, etc., preferably styrene, vinyl toluene, N-phenyl maleimide, N -Cyclohexylmaleimide, N-benzylmaleimide, 2-hydroxyethyl (meth)acrylate, etc.

具有在側鏈具有烯屬不飽和鍵的結構單元的樹脂可藉由使（a）及（c）的共聚物與（b）加成聚合，或者使（b）及（c）的共聚物與（a）加成聚合而製備。該樹脂也可為使（b）及（c）的共聚物與（a）加成聚合，然後再進一步與羧酸酐反應的樹脂。A resin having a structural unit with an ethylenically unsaturated bond in the side chain can be made by addition polymerization of the copolymer of (a) and (c) and (b), or the copolymer of (b) and (c) with (A) Prepared by addition polymerization. The resin may be a resin obtained by addition polymerization of the copolymer of (b) and (c) and (a), and then further reacting with carboxylic anhydride.

樹脂（B）的聚苯乙烯換算的重量平均分子量較佳為3,000至100,000，更佳為5,000至50,000，進一步佳為5,000至30,000。The weight average molecular weight in terms of polystyrene of the resin (B) is preferably 3,000 to 100,000, more preferably 5,000 to 50,000, and still more preferably 5,000 to 30,000.

樹脂（B）的分子量分布［重量平均分子量（Mw）／數量平均分子量（Mn）］較佳為1.1至6，更佳為1.2至4。The molecular weight distribution [weight average molecular weight (Mw)/number average molecular weight (Mn)] of the resin (B) is preferably 1.1 to 6, and more preferably 1.2 to 4.

樹脂（B）的酸值，按固體成分換算，較佳為50至170 mg-KOH/g（毫克-KOH／公克），更佳為60至150 mg-KOH/g，進一步佳為70至135 mg-KOH/g。這裡，酸值是指作為中和1公克樹脂（B）所需要的氫氧化鉀的量（毫克）而測定的值。例如可經由使用氫氧化鉀水溶液進行滴定而求得。The acid value of the resin (B), in terms of solid content, is preferably 50 to 170 mg-KOH/g (mg-KOH/gram), more preferably 60 to 150 mg-KOH/g, further preferably 70 to 135 mg-KOH/g. Here, the acid value refers to a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 gram of resin (B). For example, it can be obtained by titration using an aqueous potassium hydroxide solution.

樹脂（B）的含有率，相對於固體成分總量，較佳為10至70質量%，更佳為15至65質量%，進一步佳為20至60質量%。The content of the resin (B) relative to the total solid content is preferably 10 to 70% by mass, more preferably 15 to 65% by mass, and still more preferably 20 to 60% by mass.

＜聚合性化合物（C）＞＜Polymerizable compound (C)＞

聚合性化合物（C）為藉由從聚合引發劑（D）產生的活性自由基及／或酸而能夠聚合的化合物，例如，可列舉具有聚合性的烯屬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 a living radical and/or acid generated from the polymerization initiator (D). For example, a compound having a polymerizable ethylenic unsaturated bond, etc., are preferred. It is a (meth)acrylate compound.

其中，較佳地，聚合物性化合物（C）為具有三個以上烯屬不飽和鍵的聚合性化合物。作為這樣的聚合性化合物，例如，可列舉三羥甲基丙烷三（甲基）丙烯酸酯、新戊四醇三（甲基）丙烯酸酯、新戊四醇四（甲基）丙烯酸酯、二新戊四醇五（甲基）丙烯酸酯、二新戊四醇六（甲基）丙烯酸酯等。Among them, preferably, the polymerizable compound (C) is a polymerizable compound having three or more ethylenically unsaturated bonds. As such polymerizable compounds, for example, trimethylolpropane tri(meth)acrylate, neopentaerythritol tri(meth)acrylate, neopentaerythritol tetra(meth)acrylate, dixin Pentaerythritol penta(meth)acrylate, dineopentaerythritol hexa(meth)acrylate, etc.

聚合性化合物（C）的重量平均分子量較佳為150以上2,900以下，更佳為250以上1,500以下。The weight average molecular weight of the polymerizable compound (C) is preferably from 150 to 2,900, and more preferably from 250 to 1,500.

聚合性化合物（C）的含有率，相對於固體成分總量，較佳為3至60質量%，更佳為5至50質量%，進一步佳為11至40質量%。The content of the polymerizable compound (C) relative to the total solid content is preferably 3 to 60% by mass, more preferably 5 to 50% by mass, and still more preferably 11 to 40% by mass.

＜聚合引發劑（D）＞＜Polymerization initiator (D)＞

聚合引發劑（D）只要是藉由光或熱的作用產生活性自由基、酸等而能夠引發聚合的化合物就沒有特別限定，可使用習知的聚合引發劑。作為產生活性自由基的聚合引發劑，例如，可列舉N-苯甲醯氧基-1-（4-苯基氫硫基苯基）丁烷-1-酮-2-亞胺、N-苯甲醯氧基-1-（4-苯基氫硫基苯基）辛烷-1-酮-2-亞胺、N-苯甲醯氧基-1-（4-苯基氫硫基苯基）-3-環戊基丙烷-1-酮-2-亞胺、2-甲基-2-嗎福林基-1-（4-甲基氫硫基苯基）丙烷-1-酮、2-二甲基胺基-1-（4-嗎福林基苯基）-2-苄基丁烷-1-酮、1-羥基環己烷苯基酮、2,4-雙（三氯甲基）-6-向日葵基-1,3,5-三嗪、2,4,6-三甲基苯甲醯基二苯基氧化膦、2,2'-雙（2-氯苯基）-4,4',5,5'-四苯基聯咪唑等。The polymerization initiator (D) is not particularly limited as long as it is a compound capable of initiating polymerization by generating active radicals, acids, etc. by the action of light or heat, and conventional polymerization initiators can be used. As a polymerization initiator that generates living radicals, for example, N-benzyloxy-1-(4-phenylhydrothiophenyl)butan-1-one-2-imine, N-benzene Formyloxy-1-(4-phenylsulfanylphenyl)octane-1-one-2-imine, N-benzyloxy-1-(4-phenylsulfanylphenyl) )-3-cyclopentylpropan-1-one-2-imine, 2-methyl-2-morpholinyl-1-(4-methylsulfanylphenyl)propane-1-one, 2 -Dimethylamino-1-(4-morpholinylphenyl)-2-benzylbutan-1-one, 1-hydroxycyclohexane phenyl ketone, 2,4-bis(trichloromethyl) Group)-6-sunflower-1,3,5-triazine, 2,4,6-trimethylbenzyldiphenylphosphine oxide, 2,2'-bis(2-chlorophenyl)- 4,4',5,5'-tetraphenylbiimidazole, etc.

較佳地，聚合引發劑為含有由三嗪化合物、醯基氧化膦化合物、烷基苯基酮化合物、O-醯基肟化合物及聯咪唑化合物構成的組中所選的至少一種的聚合引發劑，更佳為含有O-醯基肟化合物的聚合引發劑。Preferably, the polymerization initiator is a polymerization initiator containing at least one selected from the group consisting of a triazine compound, an acyl phosphine oxide compound, an alkyl phenyl ketone compound, an O-acyl oxime compound, and a biimidazole compound , More preferably a polymerization initiator containing an O-oxime compound.

相對於樹脂（B）及聚合性化合物（C）的總量100質量份，聚合引發劑（D）的含有量較佳為0.1至30質量份、更佳為1至20質量份。如果聚合引發劑（D）的含有量在上述範圍內，由於具有高靈敏化且曝光時間縮短的傾向，濾光片的生產性可提高。The content of the polymerization initiator (D) is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass relative to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). If the content of the polymerization initiator (D) is within the above-mentioned range, the productivity of the filter can be improved due to the tendency of high sensitivity and shortening of the exposure time.

相對於聚合引發劑（D）的總量，O-醯基肟化合物的含有率較佳為50質量%以上，更佳為80質量%以上，進一步佳為90質量%以上、特別佳為95質量%以上。如果O-醯基肟化合物的含有率在上述範圍內，存在有即使在形成著色圖案時的靈敏度、顯影性、著色劑含有率高的情況下也能製作高亮度的濾光片的傾向。Relative to the total amount of the polymerization initiator (D), the content of the O-acetoxime compound is preferably 50% by mass or more, more preferably 80% by mass or more, still more preferably 90% by mass or more, particularly preferably 95% by mass %above. If the content of the O-acetoxime compound is within the above range, there is a tendency that a high-brightness filter can be produced even when the sensitivity, developability, and colorant content when forming a colored pattern are high.

本發明的著色樹脂組合物也可含有聚合引發助劑。The colored resin composition of the present invention may also contain a polymerization initiation assistant.

＜聚合引發助劑（D1）＞＜Polymerization initiator (D1)＞

聚合引發助劑（D1）是為了促進藉由聚合引發劑引發聚合的聚合性化合物的聚合而使用的化合物，或者為增感劑。在含有聚合引發助劑（D1）的情況下，通常與聚合引發劑（D）組合使用。The polymerization initiation adjuvant (D1) is a compound used to promote polymerization of a polymerizable compound whose polymerization is initiated by a polymerization initiator, or a sensitizer. When the polymerization initiator (D1) is contained, it is usually used in combination with the polymerization initiator (D).

作為聚合引發助劑（D1），可列舉4,4'-雙（二甲基胺基）二苯甲酮（通稱為米其勒酮）、4,4'-雙（二乙基胺基）二苯甲酮、9,10-二甲氧基蒽、2,4-二乙基硫氧雜蒽酮、N-苯基甘胺酸等。As the polymerization initiation aid (D1), 4,4'-bis(dimethylamino)benzophenone (commonly referred to as Michele ketone), 4,4'-bis(diethylamino) Benzophenone, 9,10-dimethoxyanthracene, 2,4-diethylthioxanthone, N-phenylglycine, etc.

在使用這些聚合引發助劑（D1）的情況下，其含有量相對於樹脂（B）及聚合性化合物（C）的總量100質量份，較佳為0.1至30質量份、更佳為1至20質量份。如果聚合引發助劑（D1）的量在該範圍內，可以進一步地以高靈敏度形成著色圖案，有濾光片的生產性提高的傾向。In the case of using these polymerization initiation aids (D1), the content thereof is preferably 0.1 to 30 parts by mass, more preferably 1 with respect to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C) To 20 parts by mass. If the amount of the polymerization initiation aid (D1) is within this range, a colored pattern can be further formed with high sensitivity, and the productivity of the filter tends to be improved.

較佳地，本發明的著色樹脂組合物含有溶劑。Preferably, the colored resin composition of the present invention contains a solvent.

＜溶劑（E）＞＜Solvent (E)＞

溶劑（E）沒有特別限定，可使用本領域常用的溶劑。例如，可列舉酯溶劑（分子內含有-COO-但不含-O-的溶劑）、醚溶劑（分子內含有-O-但不含-COO-的溶劑）、醚酯溶劑（分子內含有-COO-與-O-的溶劑）、酮溶劑（分子內含有-CO-但不含-COO-的溶劑）、醇溶劑（分子內含有OH但不含-O-、-CO-與-COO-的溶劑）、芳香烴溶劑、醯胺溶劑、二甲基亞碸等。The solvent (E) is not particularly limited, and solvents commonly used in this field can be used. For example, ester solvents (solvents containing -COO- but not -O- in the molecule), ether solvents (solvents containing -O- but not -COO- in the molecule), ether ester solvents (solvents that contain-in the molecule) COO- and -O- solvents), ketone solvents (solvents containing -CO- but not -COO- in the molecule), alcohol solvents (containing OH in the molecule but not -O-, -CO- and -COO- Solvents), aromatic hydrocarbon solvents, amide solvents, dimethyl sulfide, etc.

作為溶劑，可列舉乳酸乙酯、乳酸丁酯、2-羥基異丁酸甲酯、乙酸正丁酯、丁酸乙酯、丁酸丁酯、丙酮酸乙酯、乙醯乙酸乙酯、環己醇乙酸酯以及γ-丁內酯等酯溶劑（分子內含有-COO-但不含-O-的溶劑）；乙二醇單丁醚、二乙二醇單甲醚、丙二醇單甲醚、3-甲氧基-1-丁醇、二乙二醇二甲醚、二乙二醇甲基乙基醚等醚溶劑（分子內含有-O-但不含-COO-的溶劑）；3-甲氧基丙酸甲酯、3-乙氧基丙酸乙酯、3-甲氧基丁基乙酸酯、丙二醇單甲醚乙酸酯、乙二醇單***乙酸酯、二乙二醇單***乙酸酯等醚酯溶劑（分子內含有-COO-與-O-的溶劑）；4-羥基-4-甲基-2-戊酮、庚酮、4-甲基-2-戊酮、環己酮等酮溶劑（分子內含有-CO-但不含-COO-的溶劑）；丁醇、環己醇、丙二醇等醇溶劑（分子內含有OH但不含-O-、-CO-與-COO-的溶劑）等。可列舉甲苯、二甲苯等芳香烴溶劑。可列舉N,N-二甲基甲醯胺、N,N-二甲基乙醯胺以及N-甲基吡咯啶酮等醯胺溶劑。Examples of solvents include ethyl lactate, butyl lactate, methyl 2-hydroxyisobutyrate, n-butyl acetate, ethyl butyrate, butyl butyrate, ethyl pyruvate, ethyl acetate, and cyclohexane. Alcohol acetate and γ-butyrolactone and other ester solvents (solvents containing -COO- but not -O- in the molecule); ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether, Ether solvents such as 3-methoxy-1-butanol, diethylene glycol dimethyl ether, and diethylene glycol methyl ethyl ether (solvents containing -O- but not -COO- in the molecule); 3- Methyl methoxypropionate, ethyl 3-ethoxypropionate, 3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol Ether ester solvents such as monoethyl ether acetate (solvents containing -COO- and -O- in the molecule); 4-hydroxy-4-methyl-2-pentanone, heptanone, 4-methyl-2-pentanone Ketone solvents such as, cyclohexanone (solvents containing -CO- but not -COO- in the molecule); alcohol solvents such as butanol, cyclohexanol, propylene glycol (containing OH but not -O-, -CO- in the molecule) And -COO- solvent) and so on. Examples include aromatic hydrocarbon solvents such as toluene and xylene. Examples of amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.

作為溶劑，更佳為丙二醇單甲醚乙酸酯、丙二醇單甲醚、乳酸乙酯、環己酮及3-乙氧基丙酸乙酯。As the solvent, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate, cyclohexanone, and ethyl 3-ethoxypropionate are more preferred.

溶劑較佳為含有丙二醇單甲醚乙酸酯的混合溶劑。作為與丙二醇單甲醚乙酸酯組合的溶劑，較佳為乳酸乙酯、丙二醇單甲基醚、3-乙氧基丙酸乙酯、二乙二醇單甲基醚、二乙二醇單乙基醚、二丙二醇甲基醚乙酸酯、3-甲氧基丁基乙酸酯、3-甲氧基-1-丁醇及4-羥基-4-甲基-2-戊酮；更佳為丙二醇單甲基醚、二丙二醇甲基醚乙酸酯、乳酸乙酯、3-甲氧基丁基乙酸酯、3-甲氧基-1-丁醇及3-乙氧基丙酸乙酯；進一步佳為乳酸乙酯、4-羥基-4-甲基-2-戊酮及丙二醇單甲基醚。The solvent is preferably a mixed solvent containing propylene glycol monomethyl ether acetate. As a solvent combined with propylene glycol monomethyl ether acetate, ethyl lactate, propylene glycol monomethyl ether, ethyl 3-ethoxypropionate, diethylene glycol monomethyl ether, and diethylene glycol monomethyl ether are preferred. Ethyl ether, dipropylene glycol methyl ether acetate, 3-methoxybutyl acetate, 3-methoxy-1-butanol and 4-hydroxy-4-methyl-2-pentanone; more Preferably, propylene glycol monomethyl ether, dipropylene glycol methyl ether acetate, ethyl lactate, 3-methoxybutyl acetate, 3-methoxy-1-butanol and 3-ethoxypropionic acid Ethyl; more preferably ethyl lactate, 4-hydroxy-4-methyl-2-pentanone and propylene glycol monomethyl ether.

相對於溶劑總量，所述與丙二醇單甲醚乙酸酯混合的溶劑的含有率較佳為1質量%以上50質量%以下，更佳為3質量%以上40質量%以下，進一步佳為5質量%以上30質量%以下。The content of the solvent mixed with propylene glycol monomethyl ether acetate is preferably 1% by mass or more and 50% by mass or less, more preferably 3% by mass or more and 40% by mass or less, and still more preferably 5 The mass% is above 30 mass%.

當含有溶劑（E）的情況下，相對於本發明著色樹脂組合物的總量，溶劑（E）的含有率較佳為20至80質量%，更佳為25至75質量%。換言之，著色樹脂組合物的固體成分總量較佳為5至30質量%，更佳為8至25質量%。當溶劑（E）的含有率在上述範圍內時，在塗覆過程中的平整度變得良好，且在形成濾光片時顏色濃度不會不足從而有顯示特性變得良好的趨勢。When the solvent (E) is contained, relative to the total amount of the colored resin composition of the present invention, the content of the solvent (E) is preferably 20 to 80% by mass, more preferably 25 to 75% by mass. In other words, the total solid content of the colored resin composition is preferably 5 to 30% by mass, more preferably 8 to 25% by mass. When the content rate of the solvent (E) is within the above range, the flatness during the coating process becomes good, and the color density is not insufficient when the filter is formed, and there is a tendency for the display characteristics to become good.

＜其他成分＞＜Other ingredients＞

本發明的著色樹脂組合物可根據需要包含調平劑、填料、其他聚合物化合物、黏合促進劑、抗氧化劑、光穩定劑、鏈轉移劑等在本領域習知的添加劑。The coloring resin composition of the present invention may contain leveling agents, fillers, other polymer compounds, adhesion promoters, antioxidants, light stabilizers, chain transfer agents and other additives known in the art as needed.

＜著色樹脂組合物的製造方法＞<Method for manufacturing colored resin composition>

本發明中的著色樹脂組合物是藉由將著色劑（A）、樹脂（B）、聚合性化合物（C）、聚合引發劑（D）、根據需要的溶劑（E）及其他組分混合而製作的。The coloring resin composition of the present invention is obtained by mixing the colorant (A), the resin (B), the polymerizable compound (C), the polymerization initiator (D), the solvent (E) and other components as needed. maded.

＜濾光片的製造方法＞＜Manufacturing method of optical filter＞

作為由本發明的著色樹脂組合物製備著色圖案的方法，可列舉光刻法、噴墨法、印刷法等。特別地，光刻法是較佳的。在光刻法中，可藉由在曝光時不使用光遮罩及／或不顯影來形成作為上述著色樹脂組合物層的固化產物的著色塗膜。由此形成的著色圖案或著色塗膜即是本發明的濾光片。As a method of preparing a colored pattern from the colored resin composition of the present invention, a photolithography method, an inkjet method, a printing method, and the like can be cited. In particular, photolithography is preferable. In the photolithography method, a colored coating film as a cured product of the colored resin composition layer can be formed by not using a light mask and/or not developing during exposure. The colored pattern or colored coating film thus formed is the filter of the present invention.

著色樹脂組合物可製備耐化學性與對比度優異的濾光片。濾光片可作為用於顯示裝置（例如，液晶顯示裝置、有機EL裝置、電子紙等）及固態成像元件的濾光片而有用。The colored resin composition can prepare a filter with excellent chemical resistance and contrast. The filter can be useful as a filter for display devices (for example, liquid crystal display devices, organic EL devices, electronic paper, etc.) and solid-state imaging elements.

實施例Example

下面將經由列舉實施例的方式對本發明進行更具體的說明，但本發明並不旨在透過以下實施例而受到限制，當然有可能在符合前後文宗旨的範圍內適當加以修改或變化而實施，且所有這些修改或變化都包括在本發明的技術範圍內。Hereinafter, the present invention will be described in more detail by way of enumerating examples, but the present invention is not intended to be limited by the following examples. Of course, it may be implemented with appropriate modifications or changes within the scope that conforms to the purpose of the context. And all these modifications or changes are included in the technical scope of the present invention.

[合成例1][Synthesis Example 1]

（二亞胺基異吡咯衍生物的合成）(Synthesis of diimino isopyrrole derivatives)

藉由日本專利第3961078號公報中描述的合成方法獲得由式（x）表示的化合物。另外，從由式（x）表示的化合物，以與日本專利申請特開平02-000665號公報中描述的合成方法相同的方式獲得由式（y）表示的化合物。

The compound represented by formula (x) is obtained by the synthesis method described in Japanese Patent No. 3961078. In addition, from the compound represented by the formula (x), the compound represented by the formula (y) is obtained in the same manner as the synthesis method described in Japanese Patent Application Laid-Open No. 02-000665.

[合成例2][Synthesis Example 2]

在裝有冷凝管、溫度計與攪拌器的反應器中，投入喹啉（20毫升）、SiCl₄ （2.38公克），在120℃下加入2.45公克的由式（Y）表示的化合物，在150℃下反應3小時。將反應溶液在80℃下倒入稀鹽酸中，濾出沉澱物並用甲醇洗滌，得到0.8公克的由式（a-1）表示的化合物。

In a reactor equipped with a condenser, a thermometer and a stirrer, put quinoline (20 ml) and SiCl ₄ (2.38 g), add 2.45 g of the compound represented by formula (Y) at 120°C, and at 150°C React for 3 hours. The reaction solution was poured into dilute hydrochloric acid at 80°C, and the precipitate was filtered and washed with methanol to obtain 0.8 g of the compound represented by the formula (a-1).

[合成例3][Synthesis Example 3]

在裝有冷凝管、溫度計與攪拌器的25毫升反應器中，投入由式（a-1）表示的化合物（2.0公克）、二甲基乙醯胺（10毫升）、對苯二甲酸（1.5公克），回流2小時。冷卻後濃縮反應溶液，並經由矽膠管柱層析法純化，得到0.6公克的由式（a-2）表示的化合物。

In a 25 ml reactor equipped with a condenser, thermometer and stirrer, put the compound represented by formula (a-1) (2.0 g), dimethylacetamide (10 ml), and terephthalic acid (1.5 G), reflux for 2 hours. After cooling, the reaction solution was concentrated and purified by silica gel column chromatography to obtain 0.6 g of the compound represented by formula (a-2).

[合成例4][Synthesis Example 4]

在裝有冷凝管、溫度計與攪拌器的反應器中，投入由式（a-1）表示的化合物（1公克）、吡啶（3毫升）、N,O-雙（三甲基矽基）乙醯胺（1公克），在90℃下攪拌1小時。將反應溶液倒入水中，濾出沉澱的固體並過濾，並經由矽膠管柱層析法純化，得到0.5公克的由式（a-3）表示的化合物。

In a reactor equipped with a condenser, a thermometer and a stirrer, put the compound represented by the formula (a-1) (1 g), pyridine (3 ml), and N,O-bis(trimethylsilyl) ethyl Amide (1 g), stir at 90°C for 1 hour. The reaction solution was poured into water, the precipitated solid was filtered and filtered, and purified by silica gel column chromatography to obtain 0.5 g of the compound represented by formula (a-3).

[合成例5][Synthesis Example 5]

在裝有冷凝管、溫度計與攪拌器的25毫升反應器中，投入由式（a-1）表示的化合物（2.0公克）、均三甲苯（10毫升）、4-羥基苯甲酸（1.5公克），並回流2小時。冷卻後，濃縮反應溶液，用矽膠管柱層析法純化，得到1.2公克的由式（a-4）表示的化合物。

In a 25 ml reactor equipped with a condenser, thermometer and stirrer, put the compound represented by formula (a-1) (2.0 g), mesitylene (10 ml), and 4-hydroxybenzoic acid (1.5 g) , And reflux for 2 hours. After cooling, the reaction solution was concentrated and purified by silica gel column chromatography to obtain 1.2 g of the compound represented by formula (a-4).

[合成例6][Synthesis Example 6]

除了將合成例5中的4-羥基苯甲酸替換為2-乙基己酸之外，使用與合成例5中相同的方法，得到1.6公克的由式（a-5）表示的化合物。

Except for replacing 4-hydroxybenzoic acid in Synthesis Example 5 with 2-ethylhexanoic acid, the same method as in Synthesis Example 5 was used to obtain 1.6 g of the compound represented by formula (a-5).

[合成例7][Synthesis Example 7]

除了將合成例5中的4-羥基苯甲酸替換為苯酚之外，使用與合成例5中相同的方法，得到1.0公克的由式（a-6）表示的化合物。

Except for replacing 4-hydroxybenzoic acid in Synthesis Example 5 with phenol, the same method as in Synthesis Example 5 was used to obtain 1.0 g of the compound represented by formula (a-6).

[合成例8][Synthesis Example 8]

在裝有冷凝管、溫度計與攪拌器的25毫升反應器中，投入由式（a-1）表示的化合物（2.0公克）、均三甲苯（10毫升）、苯甲酸（1.5公克），並回流2小時。冷卻後，濃縮反應溶液，用矽膠管柱層析法純化，得到1.2公克的由式（a-7）表示的化合物。

Put the compound represented by formula (a-1) (2.0 g), mesitylene (10 ml), and benzoic acid (1.5 g) into a 25 ml reactor equipped with a condenser, thermometer and stirrer, and reflux 2 hours. After cooling, the reaction solution was concentrated and purified by silica gel column chromatography to obtain 1.2 g of the compound represented by formula (a-7).

[合成例9][Synthesis Example 9]

除了將合成例8中的苯甲酸替換為3-硝基苯甲酸（1.5公克）之外，使用與合成例8中相同的方法，得到1.4公克的由式（a-8）表示的化合物。

Except for replacing the benzoic acid in Synthesis Example 8 with 3-nitrobenzoic acid (1.5 g), the same method as in Synthesis Example 8 was used to obtain 1.4 g of the compound represented by the formula (a-8).

[合成例10][Synthesis Example 10]

除了將合成例8中的苯甲酸替換為間苯二甲酸、均三甲苯替換為二甲基乙醯胺之外，使用與合成例8中相同的方法，得到0.5公克的由式（a-9）表示的化合物。

Except for replacing benzoic acid with isophthalic acid and mesitylene with dimethylacetamide in Synthesis Example 8, the same method as in Synthesis Example 8 was used to obtain 0.5 g of the formula (a-9 ) Represents the compound.

[合成例11][Synthesis Example 11]

從由式（x）表示的化合物，藉由日本專利第3961078號公報中描述的合成方法獲得由式（b-1）表示的化合物。

From the compound represented by the formula (x), the compound represented by the formula (b-1) is obtained by the synthesis method described in Japanese Patent No. 3961078.

[合成例12][Synthesis Example 12]

在裝有回流冷凝器、滴液漏斗與攪拌器的燒瓶中，適量通入氮氣而置換成為氮氣氣氛，加入乳酸乙酯141份、丙二醇單甲醚乙酸酯178份，邊攪拌邊加熱至85℃。然後，在5小時內滴加以下的混合溶液：丙烯酸38份、3,4-環氧三環[5.2.1.0^2,6 ]癸-8-基丙烯酸酯與3,4-環氧三環[5.2.1.0^2,6 ]癸-9-基丙烯酸酯的混合物（含有率為1:1）25份、環己基馬來醯亞胺137份、甲基丙烯酸-2-羥乙酯50份、丙二醇單甲醚乙酸酯338份。另一方面，在6小時內滴加藉由將5份2,2-偶氮雙異丁腈溶解在88份丙二醇單甲醚乙酸酯中而得的混合溶液。滴加完成後，在相同溫度下保持4小時，然後冷卻至室溫，得到B型黏度（23℃）為23毫帕．秒（mPa·s）、固體成分為25.6%的共聚物（樹脂（B-1））溶液。所生成的共聚物的重量平均分子量Mw為8000、固體成分酸值為111 mg-KOH/g、分散度為2.1。樹脂（B-1）具有以下結構單元。

In a flask equipped with a reflux condenser, a dropping funnel and a stirrer, an appropriate amount of nitrogen was introduced to replace it with a nitrogen atmosphere. 141 parts of ethyl lactate and 178 parts of propylene glycol monomethyl ether acetate were added, and heated to 85 while stirring. ℃. Then, the following mixed solution was added dropwise within 5 hours: 38 parts of acrylic acid, 3,4-epoxy tricyclic [5.2.1.0 ^2,6 ] dec-8-yl acrylate and 3,4-epoxy tricyclic [ 5.2.1.0 ^2,6 ] 25 parts of mixture of dec-9-yl acrylate (content ratio 1:1), 137 parts of cyclohexyl maleimide, 50 parts of 2-hydroxyethyl methacrylate, propylene glycol 338 parts of monomethyl ether acetate. On the other hand, a mixed solution obtained by dissolving 5 parts of 2,2-azobisisobutyronitrile in 88 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After the addition is complete, keep it at the same temperature for 4 hours, and then cool to room temperature to obtain a type B viscosity (23°C) of 23 mPa. Second (mPa·s), 25.6% solid content copolymer (resin (B-1)) solution. The weight average molecular weight Mw of the produced copolymer was 8000, the solid content acid value was 111 mg-KOH/g, and the dispersion degree was 2.1. The resin (B-1) has the following structural units.

樹脂的聚苯乙烯換算的重量平均分子量（Mw）與數量平均分子量（Mn）係藉由GPC法在以下條件下測量。裝置：HLC-8120 GPC（東曹股份有限公司製造）管柱：TSK-GELG 2000 HXL 管柱溫度：40℃ 溶劑：THF 流速：1.0毫升／分鐘（mL/min）測試液的固體成分濃度：0.001至0.01質量% 注入量：50微升（μL）檢測器：RI 校準標準材料：TSK STANDARD POLYSTYRENE F-40、F-4、F-288、A-2500、A-500（東曹股份有限公司製造）The weight average molecular weight (Mw) and number average molecular weight (Mn) of the resin in terms of polystyrene are measured by the GPC method under the following conditions. Device: HLC-8120 GPC (manufactured by Tosoh Corporation) Column: TSK-GELG 2000 HXL Column temperature: 40℃ Solvent: THF Flow rate: 1.0 ml/min (mL/min) Solid content concentration of the test liquid: 0.001 to 0.01% by mass Injection volume: 50 microliters (μL) Detector: RI Calibration standard materials: TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Co., Ltd.)

以上述得到的聚苯乙烯換算的重量平均分子量與數量平均分子量之比（Mw/Mn）作為分散度。The ratio (Mw/Mn) of the weight average molecular weight in terms of polystyrene obtained above and the number average molecular weight (Mw/Mn) was used as the degree of dispersion.

[合成例13][Synthesis Example 13]

在裝有冷凝管、溫度計、攪拌器的25毫升反應器中加入由式（a-1）所示的化合物（0.20公克）、二乙二醇二甲醚（5.5公克）、間苯二酚（0.23公克），在150℃下攪拌2小時。冷卻後，將反應溶液滴加到20%的氯化鈉水溶液30公克中，濾取沉澱的固體並用水洗滌。將固體用水分散並洗滌後，在40℃的真空烘箱中乾燥，得到0.23公克的由式（a-10）所示的化合物。

Add the compound represented by formula (a-1) (0.20 g), diethylene glycol dimethyl ether (5.5 g), and resorcinol ( 0.23 g), stir at 150°C for 2 hours. After cooling, the reaction solution was added dropwise to 30 g of a 20% sodium chloride aqueous solution, and the precipitated solid was filtered and washed with water. After the solid was dispersed and washed with water, it was dried in a vacuum oven at 40°C to obtain 0.23 g of the compound represented by formula (a-10).

[合成例14][Synthesis Example 14]

除了將合成例13中的間苯二酚替換為間苯三酚之外，使用與合成例13中相同的方法，得到0.24公克的由式（a-11）表示的化合物。

Except for replacing the resorcinol in Synthesis Example 13 with phloroglucinol, the same method as in Synthesis Example 13 was used to obtain 0.24 g of the compound represented by the formula (a-11).

[合成例15][Synthesis Example 15]

除了將合成例13中的間苯二酚替換為3,5-二氟苯酚之外，使用與合成例13中相同的方法，得到0.20公克的由式（a-12）表示的化合物。

Except for replacing resorcinol in Synthesis Example 13 with 3,5-difluorophenol, the same method as in Synthesis Example 13 was used to obtain 0.20 g of the compound represented by formula (a-12).

[合成例16][Synthesis Example 16]

除了將合成例13中的間苯二酚替換為1-（4-羥基苯基）哌嗪之外，使用與合成例13中相同的方法，得到0.23公克的由式（a-13）表示的化合物。

Except that the resorcinol in Synthesis Example 13 was replaced with 1-(4-hydroxyphenyl)piperazine, the same method as in Synthesis Example 13 was used to obtain 0.23 g of the formula (a-13) Compound.

[合成例17][Synthesis Example 17]

除了將合成例13中的間苯二酚替換為2,6-二甲基氫醌之外，使用與合成例13中相同的方法，得到0.20公克的由式（a-14）表示的化合物。

Except that the resorcinol in Synthesis Example 13 was replaced with 2,6-dimethylhydroquinone, the same method as in Synthesis Example 13 was used to obtain 0.20 g of the compound represented by formula (a-14).

[合成例18][Synthesis Example 18]

除了將合成例13中的間苯二酚替換為三甲基氫醌之外，使用與合成例13中相同的方法，得到0.21公克的由式（a-15）表示的化合物。

Except that the resorcinol in Synthesis Example 13 was replaced with trimethylhydroquinone, the same method as in Synthesis Example 13 was used to obtain 0.21 g of the compound represented by formula (a-15).

[合成例19][Synthesis Example 19]

除了將合成例13中的間苯二酚替換為羥甲基二茂鐵之外，使用與合成例13中相同的方法，得到0.20公克的由式（a-16）表示的化合物。

Except that the resorcinol in Synthesis Example 13 was replaced with hydroxymethylferrocene, the same method as in Synthesis Example 13 was used to obtain 0.20 g of the compound represented by formula (a-16).

[合成例20][Synthesis Example 20]

除了將合成例13中的間苯二酚替換為二茂鐵羧酸之外，使用與合成例13中相同的方法，得到0.29公克的由式（a-17）表示的化合物。

Except for replacing the resorcinol in Synthesis Example 13 with ferrocene carboxylic acid, the same method as in Synthesis Example 13 was used to obtain 0.29 g of the compound represented by formula (a-17).

[合成例21][Synthesis Example 21]

在裝有冷凝管、溫度計、攪拌器的50毫升的反應器中，投入由式（a-1）所示的化合物（9.0公克）、甲苯（20毫升）、4-三級丁基苯酚（8.1公克），在100℃下攪拌3小時。然後用矽膠管柱純化，得到6.3公克的由式（a-18）表示的化合物。

In a 50 ml reactor equipped with a condenser, a thermometer, and a stirrer, put the compound represented by formula (a-1) (9.0 g), toluene (20 ml), and 4-tertiary butylphenol (8.1 G), stir at 100°C for 3 hours. It was then purified with a silica gel column to obtain 6.3 g of the compound represented by formula (a-18).

[合成例22][Synthesis Example 22]

在裝有冷凝管、溫度計、攪拌器的50毫升的反應器中，投入由式（a-1）所示的化合物（1.5公克）、甲苯（20毫升）、3-硝基苯酚（2.8公克），在100℃下攪拌0.5小時。然後用矽膠管柱純化，得到1.0公克的由式（a-19）表示的化合物。

In a 50 ml reactor equipped with a condenser, a thermometer, and a stirrer, put the compound represented by formula (a-1) (1.5 g), toluene (20 ml), and 3-nitrophenol (2.8 g) , Stir at 100°C for 0.5 hours. Then, it was purified with a silica gel column to obtain 1.0 g of the compound represented by formula (a-19).

[合成例23][Synthesis Example 23]

在裝有冷凝管、溫度計、攪拌器的25毫升的反應器中，投入由式（a-1）所示的化合物（1.9公克）、甲苯（10毫升）、3-羥基苯甲酸（3.3公克），在回流下攪拌0.5小時。然後釋放至水／乙酸乙酯中，過濾沉澱物並取出後，溶於N,N-二甲基甲醯胺，並加入黏土、矽膠進行處理，得到1.5公克的由式（a-20）表示的化合物。

In a 25 ml reactor equipped with a condenser, a thermometer, and a stirrer, put the compound represented by formula (a-1) (1.9 g), toluene (10 ml), and 3-hydroxybenzoic acid (3.3 g) , Stir under reflux for 0.5 hours. Then release into water/ethyl acetate, filter the precipitate and take it out, dissolve it in N,N-dimethylformamide, add clay and silica gel for treatment, and obtain 1.5 g of which is represented by formula (a-20) compound of.

[合成例24][Synthesis Example 24]

在裝有冷凝管、溫度計、攪拌器的50毫升的反應器中，投入由式（a-1）所示的化合物（1.5公克）、甲苯（15毫升）、4-氰基苯酚（3.0公克），在100℃下攪拌20分鐘，然後冷卻至室溫後，經由過濾除去不溶物，使用矽膠管柱進行純化，得到0.7公克的由式（a-21）表示的化合物。

In a 50 ml reactor equipped with a condenser, a thermometer, and a stirrer, put the compound represented by formula (a-1) (1.5 g), toluene (15 ml), and 4-cyanophenol (3.0 g) After stirring at 100°C for 20 minutes, and then cooling to room temperature, the insoluble matter was removed by filtration and purified using a silica gel column to obtain 0.7 g of the compound represented by formula (a-21).

[合成例25][Synthesis Example 25]

在裝有冷凝管、溫度計、攪拌器的50毫升的反應器中，投入由式（a-1）所示的化合物（1.5公克）、甲苯（15毫升）、4-三氟甲基苯酚（3.0公克），在100℃下攪拌20分鐘，然後冷卻至室溫後，經由過濾除去不溶物，使用矽膠管柱進行純化，得到1.6公克的由式（a-22）表示的化合物。

In a 50 ml reactor equipped with a condenser, a thermometer, and a stirrer, put the compound represented by formula (a-1) (1.5 g), toluene (15 ml), and 4-trifluoromethylphenol (3.0 G), stirred at 100°C for 20 minutes, and then cooled to room temperature, filtered to remove insolubles, and purified using a silica gel column to obtain 1.6 g of the compound represented by formula (a-22).

[合成例26][Synthesis Example 26]

利用日本專利申請特開平2016-27075號中描述的合成方法，得到式（c-1）表示的化合物。

Using the synthesis method described in Japanese Patent Application Laid-Open No. 2016-27075, the compound represented by formula (c-1) is obtained.

＜著色樹脂組合物的製備＞<Preparation of colored resin composition>

[實施例1][Example 1]

藉由混合以下組分，獲得著色樹脂組合物。化合物（1）：由式（a-1）所示化合物 3份樹脂（B）：樹脂（B-1）（按固體成分換算） 65份聚合性化合物（C）：二新戊四醇六丙烯酸酯（KAYARAD（註冊商標）DPHA，日本化藥股份有限公司製造） 35份聚合引發劑（D）：N-苯甲醯氧基-1-（4-苯基氫硫基苯基）辛-1-酮-2-亞胺（IRGACURE（註冊商標）OXE01，巴斯夫公司製造，O-醯基肟化合物） 7份溶劑（E）：丙二醇單甲醚乙酸酯 501份乳酸乙酯 38份調平劑（H）：聚醚改性矽油（Toray Silicone SH8400，由東麗道康寧股份有限公司製造） 0.10份By mixing the following components, a colored resin composition is obtained. Compound (1): 3 parts of compound represented by formula (a-1) Resin (B): Resin (B-1) (calculated as solid content) 65 parts Polymerizable compound (C): 35 parts of dineopentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA, manufactured by Nippon Kayaku Co., Ltd.) Polymerization initiator (D): N-benzyloxy-1-(4-phenylhydrothiophenyl)oct-1-one-2-imine (IRGACURE (registered trademark) OXE01, manufactured by BASF, O-acetoxime compound) 7 servings Solvent (E): 501 parts of propylene glycol monomethyl ether acetate 38 parts of ethyl lactate Leveling agent (H): 0.10 parts of polyether modified silicone oil (Toray Silicone SH8400, manufactured by Toray Dow Corning Co., Ltd.)

[實施例2][Example 2]

除了使用由式（a-2）所示的化合物來替換由式（a-1）所示的化合物外，採用與實施例1相同的方法，獲得著色樹脂組合物。Except for using the compound represented by formula (a-2) instead of the compound represented by formula (a-1), the same method as in Example 1 was used to obtain a colored resin composition.

[實施例3][Example 3]

除了使用由式（a-3）所示的化合物來替換由式（a-1）所示的化合物外，採用與實施例1相同的方法，獲得著色樹脂組合物。Except for using the compound represented by formula (a-3) instead of the compound represented by formula (a-1), the same method as in Example 1 was used to obtain a colored resin composition.

[實施例4][Example 4]

除了使用由式（a-4）所示的化合物來替換由式（a-1）所示的化合物外，採用與實施例1相同的方法，獲得著色樹脂組合物。Except that the compound represented by formula (a-4) was used instead of the compound represented by formula (a-1), the same method as in Example 1 was used to obtain a colored resin composition.

[實施例5][Example 5]

除了使用由式（a-5）所示的化合物來替換由式（a-1）所示的化合物外，採用與實施例1相同的方法，獲得著色樹脂組合物。Except for using the compound represented by formula (a-5) instead of the compound represented by formula (a-1), the same method as in Example 1 was used to obtain a colored resin composition.

[實施例6][Example 6]

除了使用由式（a-6）所示的化合物來替換由式（a-1）所示的化合物外，採用與實施例1相同的方法，獲得著色樹脂組合物。Except for using the compound represented by formula (a-6) instead of the compound represented by formula (a-1), the same method as in Example 1 was used to obtain a colored resin composition.

[實施例7][Example 7]

除了使用由式（a-7）所示的化合物來替換由式（a-1）所示的化合物外，採用與實施例1相同的方法，獲得著色樹脂組合物。Except for using the compound represented by formula (a-7) instead of the compound represented by formula (a-1), the same method as in Example 1 was used to obtain a colored resin composition.

[實施例8][Example 8]

除了使用由式（a-8）所示的化合物來替換由式（a-1）所示的化合物外，採用與實施例1相同的方法，獲得著色樹脂組合物。Except for using the compound represented by formula (a-8) instead of the compound represented by formula (a-1), the same method as in Example 1 was used to obtain a colored resin composition.

[實施例9][Example 9]

除了使用由式（a-9）所示的化合物來替換由式（a-1）所示的化合物外，採用與實施例1相同的方法，獲得著色樹脂組合物。Except for using the compound represented by the formula (a-9) instead of the compound represented by the formula (a-1), the same method as in Example 1 was used to obtain a colored resin composition.

[分散液1的製備][Preparation of Dispersion 1]

將C. I.顏料紅254（顏料）14份、丙烯酸類顏料分散劑4.9份、樹脂（B-1）（按固體成分換算）4.2份、丙二醇單甲醚乙酸酯74份及乳酸乙酯2.5份混合，利用珠磨機將顏料徹底分散以製備分散液1。Mix 14 parts of CI Pigment Red 254 (pigment), 4.9 parts of acrylic pigment dispersant, 4.2 parts of resin (B-1) (calculated as solid content), 74 parts of propylene glycol monomethyl ether acetate and 2.5 parts of ethyl lactate. , Use a bead mill to thoroughly disperse the pigment to prepare Dispersion 1.

[實施例10][Example 10]

藉由將以下組分混合，獲得著色樹脂組合物。化合物（1）：由式（a-1）表示的化合物 5份著色劑（A1）：分散液1 422份樹脂（B）：樹脂（B-1）（按固體成分換算） 40份聚合性化合物（C）：二新戊四醇六丙烯酸酯（KAYARAD（註冊商標）DPHA，日本化藥股份有限公司製造） 35份聚合引發劑（D）：N-苯甲醯氧基-1-（4-苯基氫硫基苯基）辛-1-酮-2-亞胺（IRGACURE（註冊商標）OXE01；巴斯夫公司；O-醯基肟化合物） 7.0份溶劑（E）：丙二醇單甲醚乙酸酯 553份乳酸乙酯 22份調平劑（H）：聚醚改性矽油（Toray Silicone SH8400，東麗道康寧股份有限公司製造） 0.10份By mixing the following components, a colored resin composition is obtained. Compound (1): 5 parts of compound represented by formula (a-1) Coloring agent (A1): 1,422 parts of dispersion Resin (B): Resin (B-1) (calculated as solid content) 40 parts Polymerizable compound (C): 35 parts of dineopentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA, manufactured by Nippon Kayaku Co., Ltd.) Polymerization initiator (D): N-benzyloxy-1-(4-phenylhydrothiophenyl)oct-1-one-2-imine (IRGACURE (registered trademark) OXE01; BASF; O -Oxime compound) 7.0 servings Solvent (E): 553 parts of propylene glycol monomethyl ether acetate 22 parts of ethyl lactate Leveling agent (H): 0.10 parts of polyether modified silicone oil (Toray Silicone SH8400, manufactured by Toray Dow Corning Co., Ltd.)

[實施例11][Example 11]

除了使用由式（a-3）所示的化合物來替換由式（a-1）所示的化合物外，採用與實施例10相同的方法，獲得著色樹脂組合物。Except for using the compound represented by formula (a-3) instead of the compound represented by formula (a-1), the same method as in Example 10 was used to obtain a colored resin composition.

[比較例1][Comparative Example 1]

除了使用由式（b-1）所示的化合物來替換由式（a-1）所示的化合物外，採用與實施例1相同的方法，獲得著色樹脂組合物。Except for using the compound represented by the formula (b-1) instead of the compound represented by the formula (a-1), the same method as in Example 1 was used to obtain a colored resin composition.

＜濾光片（著色塗膜）的製備1＞<Preparation of filter (coloring coating) 1>

在5公分見方的玻璃基板（Eagle 2000，康寧公司製造）上，使用旋塗法塗布著色樹脂組合物，然後在100℃下預烘烤3分鐘而形成著色樹脂組合物層。冷卻後，使用曝光機（TME-150RSK，拓普康股份有限公司製造），在大氣氣氛下，利用60毫焦耳／平方公分（mJ/cm² ）的曝光量（365奈米基準）來進行光照射。然後在烘箱中於230℃下進行20分鐘的後烘烤，獲得濾光片。On a 5 cm square glass substrate (Eagle 2000, manufactured by Corning Corporation), the colored resin composition was applied using a spin coating method, and then pre-baked at 100° C. for 3 minutes to form a colored resin composition layer. After cooling, use an exposure machine (TME-150RSK, manufactured by Topcon Co., Ltd.), in an atmospheric atmosphere, with ^{an exposure dose of 60 millijoules/cm² (mJ/cm 2} ) (365nm standard) Irradiate. Then, post-baking was performed in an oven at 230°C for 20 minutes to obtain a filter.

[實施例12][Example 12]

除了使用由式（a-10）所示的化合物來替換由式（a-1）所示的化合物外，採用與實施例1相同的方法，獲得著色樹脂組合物。Except for using the compound represented by formula (a-10) instead of the compound represented by formula (a-1), the same method as in Example 1 was used to obtain a colored resin composition.

[實施例13][Example 13]

除了使用由式（a-11）所示的化合物來替換由式（a-1）所示的化合物外，採用與實施例1相同的方法，獲得著色樹脂組合物。Except for using the compound represented by formula (a-11) instead of the compound represented by formula (a-1), the same method as in Example 1 was used to obtain a colored resin composition.

[實施例14][Example 14]

除了使用由式（a-12）所示的化合物來替換由式（a-1）所示的化合物外，採用與實施例1相同的方法，獲得著色樹脂組合物。Except that the compound represented by formula (a-12) was used instead of the compound represented by formula (a-1), the same method as in Example 1 was used to obtain a colored resin composition.

[實施例15][Example 15]

除了使用由式（a-13）所示的化合物來替換由式（a-1）所示的化合物外，採用與實施例1相同的方法，獲得著色樹脂組合物。Except for using the compound represented by formula (a-13) instead of the compound represented by formula (a-1), the same method as in Example 1 was used to obtain a colored resin composition.

[實施例16][Example 16]

除了使用由式（a-14）所示的化合物來替換由式（a-1）所示的化合物外，採用與實施例1相同的方法，獲得著色樹脂組合物。Except for using the compound represented by the formula (a-14) instead of the compound represented by the formula (a-1), the same method as in Example 1 was used to obtain a colored resin composition.

[實施例17][Example 17]

除了使用由式（a-15）所示的化合物來替換由式（a-1）所示的化合物外，採用與實施例1相同的方法，獲得著色樹脂組合物。Except for using the compound represented by the formula (a-15) instead of the compound represented by the formula (a-1), the same method as in Example 1 was used to obtain a colored resin composition.

[實施例18][Example 18]

除了使用由式（a-16）所示的化合物來替換由式（a-1）所示的化合物外，採用與實施例1相同的方法，獲得著色樹脂組合物。Except for using the compound represented by the formula (a-16) instead of the compound represented by the formula (a-1), the same method as in Example 1 was used to obtain a colored resin composition.

[實施例19][Example 19]

除了使用由式（a-17）所示的化合物來替換由式（a-1）所示的化合物外，採用與實施例1相同的方法，獲得著色樹脂組合物。Except that the compound represented by formula (a-17) was used instead of the compound represented by formula (a-1), the same method as in Example 1 was used to obtain a colored resin composition.

[實施例20][Example 20]

除了使用由式（a-18）所示的化合物來替換由式（a-1）所示的化合物外，採用與實施例1相同的方法，獲得著色樹脂組合物。Except for using the compound represented by the formula (a-18) instead of the compound represented by the formula (a-1), the same method as in Example 1 was used to obtain a colored resin composition.

[實施例21][Example 21]

除了使用由式（a-19）所示的化合物來替換由式（a-1）所示的化合物外，採用與實施例1相同的方法，獲得著色樹脂組合物。Except that the compound represented by formula (a-19) was used instead of the compound represented by formula (a-1), the same method as in Example 1 was used to obtain a colored resin composition.

[實施例22][Example 22]

除了使用由式（a-20）所示的化合物來替換由式（a-1）所示的化合物外，採用與實施例1相同的方法，獲得著色樹脂組合物。Except for using the compound represented by formula (a-20) instead of the compound represented by formula (a-1), the same method as in Example 1 was used to obtain a colored resin composition.

[實施例23][Example 23]

除了使用由式（a-21）所示的化合物來替換由式（a-1）所示的化合物外，採用與實施例1相同的方法，獲得著色樹脂組合物。Except that the compound represented by formula (a-21) was used instead of the compound represented by formula (a-1), the same method as in Example 1 was used to obtain a colored resin composition.

[實施例24][Example 24]

除了使用由式（a-22）所示的化合物來替換由式（a-1）所示的化合物外，採用與實施例1相同的方法，獲得著色樹脂組合物。Except that the compound represented by formula (a-22) was used instead of the compound represented by formula (a-1), the same method as in Example 1 was used to obtain a colored resin composition.

[實施例25][Example 25]

藉由將以下組分混合，獲得著色樹脂組合物。化合物（1）：由式（a-1）所示的化合物 5份著色劑（A1）：由式（c-1）所示的化合物 24份樹脂（B）：樹脂（B-1）（按固體成分換算） 40份聚合性化合物（C）：二新戊四醇六丙烯酸酯（KAYARAD（註冊商標）DPHA，日本化藥股份有限公司製造） 35份聚合引發劑（D）：N-苯甲醯氧基-1-（4-苯基氫硫基苯基）辛-1-酮-2-亞胺（IRGACURE（註冊商標）OXE01；巴斯夫公司；O-醯基肟化合物） 7.0份溶劑（E）：丙二醇單甲醚乙酸酯 553份乳酸乙酯 22份調平劑（H）：聚醚改性矽油（Toray Silicone SH8400，東麗道康寧股份有限公司製造） 0.10份By mixing the following components, a colored resin composition is obtained. Compound (1): 5 parts of compound represented by formula (a-1) Coloring agent (A1): 24 parts of compound represented by formula (c-1) Resin (B): Resin (B-1) (calculated as solid content) 40 parts Polymerizable compound (C): 35 parts of dineopentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA, manufactured by Nippon Kayaku Co., Ltd.) Polymerization initiator (D): N-benzyloxy-1-(4-phenylhydrothiophenyl)oct-1-one-2-imine (IRGACURE (registered trademark) OXE01; BASF; O -Oxime compound) 7.0 servings Solvent (E): 553 parts of propylene glycol monomethyl ether acetate 22 parts of ethyl lactate Leveling agent (H): 0.10 parts of polyether modified silicone oil (Toray Silicone SH8400, manufactured by Toray Dow Corning Co., Ltd.)

[實施例26][Example 26]

除了使用由式（a-3）所示的化合物來替換由式（a-1）所示的化合物外，採用與實施例25相同的方法，獲得著色樹脂組合物。Except for using the compound represented by the formula (a-3) instead of the compound represented by the formula (a-1), the same method as in Example 25 was used to obtain a colored resin composition.

[實施例27][Example 27]

除了使用由式（a-5）所示的化合物來替換由式（a-1）所示的化合物外，採用與實施例25相同的方法，獲得著色樹脂組合物。Except for using the compound represented by formula (a-5) instead of the compound represented by formula (a-1), the same method as in Example 25 was used to obtain a colored resin composition.

[實施例28][Example 28]

除了使用由式（a-7）所示的化合物來替換由式（a-1）所示的化合物外，採用與實施例25相同的方法，獲得著色樹脂組合物。Except for using the compound represented by the formula (a-7) instead of the compound represented by the formula (a-1), the same method as in Example 25 was used to obtain a colored resin composition.

[實施例29][Example 29]

除了使用由式（a-16）所示的化合物來替換由式（a-1）所示的化合物外，採用與實施例25相同的方法，獲得著色樹脂組合物。Except that the compound represented by formula (a-16) was used instead of the compound represented by formula (a-1), the same method as in Example 25 was used to obtain a colored resin composition.

[實施例30][Example 30]

除了使用由式（a-17）所示的化合物來替換由式（a-1）所示的化合物外，採用與實施例25相同的方法，獲得著色樹脂組合物。Except for using the compound represented by formula (a-17) instead of the compound represented by formula (a-1), the same method as in Example 25 was used to obtain a colored resin composition.

[比較例2][Comparative Example 2]

除了使用由式（b-1）所示的化合物來替換由式（a-1）所示的化合物外，採用與實施例25相同的方法，獲得著色樹脂組合物。Except that the compound represented by formula (b-1) was used instead of the compound represented by formula (a-1), the same method as in Example 25 was used to obtain a colored resin composition.

＜耐化學性試驗＞＜Chemical resistance test＞

將藉由濾光片的製備1的方法所得的濾光片浸入調節至40℃的N-甲基吡咯碇酮中30分鐘。對於浸入前及浸入後的濾光片，在波長400至780奈米處使用色度計（OSP-SP-200，奧林巴斯股份有限公司製造）來測定分光光譜，在最大吸收波長λmax處計算吸光度變化率（浸入前的吸光度／浸入後的吸光度）。吸光度變化率越低，表示耐化學性越好。結果顯示於下表1與表2中。The filter obtained by the method of preparation 1 of the filter was immersed in N-methylpyrrolidone adjusted to 40°C for 30 minutes. For the filter before and after immersion, use a colorimeter (OSP-SP-200, manufactured by Olympus Co., Ltd.) at a wavelength of 400 to 780 nm to measure the spectroscopic spectrum, at the maximum absorption wavelength λmax Calculate the absorbance change rate (absorbance before immersion/absorbance after immersion). The lower the absorbance change rate, the better the chemical resistance. The results are shown in Table 1 and Table 2 below.

表1

Table 1

表2

Table 2

＜濾光片（著色塗膜）的製備2 ＞＜Preparation of optical filter (colored coating film) 2 ＞

在5公分見方的玻璃基板（Eagle 2000，康寧公司製造）上，使用旋塗法塗布著色樹脂組合物，然後使用真空乾燥器（VCD Micro-Tec股份有限公司製造），使最終壓力達到66帕（Pa）而減壓乾燥，形成著色樹脂組合物層。冷卻後，使用曝光機（TME-150RSK，拓普康股份有限公司製造），在大氣氣氛下，利用60毫焦耳／平方公分的曝光量（365奈米基準）來進行光照射。然後在烘箱中於100℃下進行3分鐘的後烘烤，獲得濾光片。On a 5 cm square glass substrate (Eagle 2000, manufactured by Corning Incorporated), spin coating was used to coat the colored resin composition, and then a vacuum dryer (manufactured by VCD Micro-Tec Co., Ltd.) was used to achieve a final pressure of 66 Pa ( Pa) and dried under reduced pressure to form a colored resin composition layer. After cooling, an exposure machine (TME-150RSK, manufactured by Topcon Co., Ltd.) was used to irradiate light with an exposure amount of 60 millijoules/cm² (365 nm standard) in an atmospheric atmosphere. Then, post-baking was performed in an oven at 100° C. for 3 minutes to obtain a filter.

＜對比度測量＞＜Contrast measurement＞

對於藉由濾光片的製備2的方法所得的濾光片，使用對比度計（CT-1，壺阪電機股份有限公司製造，色彩色差計BM-5A，拓普康股份有限公司製造，光源，F-10，偏振膜，壺阪電機股份有限公司製造），將空白值設為30000而測量對比度。結果顯示在表3與4中。濾光片的對比度存在有依賴於螢光強度的傾向，且隨著螢光強度越低，對比度變得更高。For the filter obtained by the method of preparation 2 of the filter, a contrast meter (CT-1, manufactured by Kosaka Electric Co., Ltd., color and color difference meter BM-5A, manufactured by Topcon Co., Ltd., light source, F -10, polarizing film, manufactured by Kosaka Electric Co., Ltd.), set the blank value to 30000 and measure the contrast. The results are shown in Tables 3 and 4. The contrast of the filter tends to depend on the intensity of fluorescence, and as the intensity of fluorescence decreases, the contrast becomes higher.

表3

table 3

表4

Table 4

無none

Claims

一種著色樹脂組合物，其含有著色劑、樹脂、聚合性化合物以及聚合引發劑，其中該著色劑含有由式(1)所示之化合物，

在式(1)中，R^101a至R^101d分別獨立地表示三級丁基，R^102a至R^102d分別獨立地表示由式(R1)所示的基團，

R^601a至R^601e分別獨立地表示氫原子、鹵素原子、可具有取代基的烷基、可具有取代基的烷氧基、可具有取代基的芳基、可具有取代基的芳氧基，且R^601a、R^601c及R^601e中的至少一個為氟原子，於式(R1)中的*表示與四氮雜卟啉骨架的鍵結部位，X¹與X²分別獨立地表示氫原子、可具有取代基的烷基、可具有取代基的芳基、可具有取代基的芳烷基、或者由式(X1)至(X4)所示的基團，

R²⁰¹與R⁴⁰¹分別獨立地表示可具有取代基的烷基、可具有取代基的芳基、可具有取代基烷氧基或者可具有取代基的芳氧基，R³⁰¹、R³⁰²與R⁵⁰¹至R⁵⁰³分別獨立地表示可具有取代基的烷基、或者可具有取代基的芳基，在式(X1)至(X4)中的*表示與氧原子的鍵結部位，構成由X¹、X²、R²⁰¹、R⁴⁰¹所示的芳基、芳烷基、及芳氧基的芳香族烴環可配位於金屬原子。 A coloring resin composition containing a coloring agent, a resin, a polymerizable compound, and a polymerization initiator, wherein the coloring agent contains a compound represented by formula (1),

In formula (1), R ^101a to R ^101d each independently represent a tertiary butyl group, and R ^102a to R ^102d each independently represent a group represented by formula (R1),

R ^601a to R ^601e each independently represent a hydrogen atom, a halogen atom, an optionally substituted alkyl group, an optionally substituted alkoxy group, an optionally substituted aryl group, an optionally substituted aryloxy group, and At least one of R ^601a , R ^601c, and R ^601e is a fluorine atom. In formula (R1), * represents the bonding site with the porphyrazine skeleton, and X ¹ and X ² each independently represent a hydrogen atom, A substituted alkyl group, a substituted aryl group, a substituted aralkyl group, or a group represented by formulas (X1) to (X4),

R ²⁰¹ and R ⁴⁰¹ each independently represent an optionally substituted alkyl group, an optionally substituted aryl group, an optionally substituted alkoxy group or an optionally substituted aryloxy group, R ³⁰¹ , R ³⁰² and R ⁵⁰¹ To R ⁵⁰³ each independently represent an alkyl group that may have a substituent or an aryl group that may have a substituent, and * in formulas (X1) to (X4) represents a bonding site with an oxygen atom, and the composition is composed of X ¹ , The aromatic hydrocarbon ring of the aryl group, aralkyl group, and aryloxy group represented by X ² , R ²⁰¹ , and R ^{401 may be coordinated to a metal atom.}

一種濾光片，其係由根據請求項1所述的著色樹脂組合物形成。 A filter which is formed of the colored resin composition according to claim 1.

一種顯示裝置，其包含根據請求項2所述的濾光片。A display device comprising the optical filter according to claim 2.