TWI716505B

TWI716505B - Compound, coloring composition, color filter and display device

Info

Publication number: TWI716505B
Application number: TW105139714A
Authority: TW
Inventors: 嘉村亮平; 栂井學; 朴昭妍
Original assignee: 南韓商東友精細化工有限公司
Priority date: 2015-12-15
Filing date: 2016-12-01
Publication date: 2021-01-21
Also published as: KR102185986B1; KR20170071435A; TW201731968A; CN106883195B; JP6920048B2; CN106883195A; JP2017110187A

Abstract

本發明的課題在於提供耐溶劑性優異的濾色器、包含其的顯示裝置、可提供它們的化合物、以及著色組合物。本發明的化合物由式(A-I)表示。 The subject of the present invention is to provide a color filter having excellent solvent resistance, a display device including the color filter, a compound capable of providing them, and a coloring composition. The compound of the present invention is represented by formula (A-I).

Description

化合物、著色組合物、濾色器和顯示裝置 Compound, coloring composition, color filter and display device

發明領域 Invention field

本發明涉及化合物及包含其的著色組合物。 The present invention relates to compounds and coloring compositions containing them.

發明背景 Background of the invention

在液晶顯示裝置、電致發光顯示裝置和等離子體顯示器等顯示裝置中使用的濾色器的製造中使用了著色組合物。作為這樣的著色組合物，已知有包含由下述式表示的化合物等的著色組合物。 The coloring composition is used in the production of color filters used in display devices such as liquid crystal display devices, electroluminescence display devices, and plasma displays. As such a coloring composition, a coloring composition containing a compound represented by the following formula and the like is known.

[現有技術文獻] [Prior Art Literature] [專利文獻] [Patent Literature]

專利文獻1：WO2012/053211號 Patent Document 1: WO2012/053211

專利文獻2：日本特開2015-38201號公報 Patent Document 2: Japanese Patent Application Publication No. 2015-38201

發明概要 Summary of the invention

就以往已知的上述化合物而言，吸光度、電壓保持率並不能充分滿足需要，另外由包含該化合物的著色組合物形成的濾色器有時不能充分滿足耐溶劑性。 In the conventionally known compounds, the absorbance and voltage holding ratio are not sufficiently satisfactory, and a color filter formed from a coloring composition containing the compound may not sufficiently satisfy solvent resistance.

本發明包含以下發明。 The present invention includes the following inventions.

[1]由式(A-I)表示的化合物。 [1] A compound represented by formula (A-I).

[式(A-I)中，R⁴¹~R⁴⁴各自獨立地表示氫原子、碳數1~20的飽和烴基、可具有取代基的碳數6~20的芳香族烴基或可具有取代基的碳數7~30的芳烷基，該芳香族烴基和該芳烷基可具有的取代基可以是-SO₃ ^-或-SO₂-N^--SO₂-R^f，該碳數1~20的飽和烴基中，該飽和烴基中所含的氫原子可以被取代或未取代的胺基或鹵素原子取代，該飽和烴基的碳數為2~20的情況下，該飽和烴基中所含的亞甲基可被替換為氧原子或-CO-。不過，在該碳數2~20的飽和烴基中，鄰接的亞甲基不會同時被替換為氧原子，末端的亞甲基不會被替換為氧原子或-CO-。R⁴¹與R⁴²可結合並與它們結合的氮原子一起形成環，R⁴³與R⁴⁴可結合並與它們結合的氮原子一起形成環。 [In formula (AI), R ⁴¹ to R ⁴⁴ each independently represent a hydrogen atom, a saturated hydrocarbon group with 1 to 20 carbons, an optionally substituted aromatic hydrocarbon group with 6 to 20 carbons, or a substituted carbon number The aralkyl group of 7-30, the aromatic hydrocarbon group and the substituent that the aralkyl group may have may be -SO ₃ ^- or -SO ₂ -N ^-- SO ₂ -R ^f , the saturated carbon number of 1-20 In the hydrocarbon group, the hydrogen atom contained in the saturated hydrocarbon group may be substituted by a substituted or unsubstituted amine group or halogen atom. When the saturated hydrocarbon group has 2 to 20 carbon atoms, the methylene group contained in the saturated hydrocarbon group Can be replaced by oxygen atom or -CO-. However, in this saturated hydrocarbon group with 2 to 20 carbon atoms, the adjacent methylene groups are not simultaneously replaced with oxygen atoms, and the terminal methylene groups are not replaced with oxygen atoms or -CO-. R ⁴¹ and R ⁴² may be combined with the nitrogen atom to which they are combined to form a ring, and R ⁴³ and R ⁴⁴ may be combined with the nitrogen atom to which they are combined to form a ring.

R⁴⁷~R⁵⁴各自獨立地表示氫原子、鹵素原子、硝基、羥基、-SO₃ ^-、-SO₂-N^--SO₂-R^f、或碳數1~8的烷基，構成該烷基的亞甲基可以被替換為氧原子或-CO-，R⁴⁸與R⁵²可相互結合而形成-NH-、-S-、或-SO₂-。不過，該烷基中，鄰接的亞甲基不會同時被替換為氧原子，末端的亞甲基不會被替換為氧原子或-CO-。 R ⁴⁷ ~ R ⁵⁴ each independently represent a hydrogen atom, a halogen atom, a nitro group, a hydroxyl _{^{_{group, -SO 3 -, -SO 2 -N}}} - -SO 2 -R f, or an alkyl group having 1 to 8 carbon atoms constituting the The methylene group of the alkyl group can be replaced with an oxygen atom or -CO-, and R ⁴⁸ and R ⁵² can be combined with each other to form -NH-, -S-, or -SO ₂ -. However, in this alkyl group, adjacent methylene groups are not simultaneously replaced with oxygen atoms, and terminal methylene groups are not replaced with oxygen atoms or -CO-.

環T¹表示碳數3~10的芳香族雜環，該芳香族雜環可具有碳數1~20的飽和烴基、取代或未取代的胺基或可具有取代基的碳數6~20的芳香族烴基。該芳香族烴基可具有的取代基可以為-SO₃ ^-或-SO₂-N^--SO₂-R^f。 Ring T ¹ represents an aromatic heterocyclic ring having 3 to 10 carbon atoms. The aromatic heterocyclic ring may have a saturated hydrocarbon group having 1 to 20 carbon atoms, a substituted or unsubstituted amine group, or a substituted or unsubstituted amine group having 6 to 20 carbon atoms. Aromatic hydrocarbon group. The substituent that the aromatic hydrocarbon group may have may be -SO ₃ ^- or -SO ₂ -N ^-- SO ₂ -R ^f .

M^r+表示氫離子、r價的金屬離子或者取代或未取代的銨離子。 M ^r+ represents hydrogen ion, r-valent metal ion, or substituted or unsubstituted ammonium ion.

k表示由式(A-I)表示的化合物具有的-SO₃ ^-的個數和-SO₂-N^--SO₂-R^f的個數之和。 k represents the sum of the number of -SO ₃ ^-and the number of -SO ₂ -N ^-- SO ₂ -R ^f that the compound represented by formula (AI) has.

r表示1以上的整數。 r represents an integer of 1 or more.

R^f表示碳數1~12的氟烷基。 R ^f represents a fluoroalkyl group having 1 to 12 carbon atoms.

不過，由式(A-I)表示的化合物具有至少1個-SO₂-N^--SO₂-R^f。] However, the compound represented by the formula (AI) has at least one -SO ₂ -N ^-- SO ₂ -R ^f . ]

[2][1]所述的化合物，其中，M^r+為金屬離子。 [2] The compound according to [1], wherein Mr ⁺ is a metal ion.

[3][1]或[2]所述的化合物，其中，由上述T¹所示的芳香族雜環是由下述式(A-t1)表示的環。 [3] The compound according to [1] or [2], wherein the aromatic heterocyclic ring represented by the above T ^{1 is} a ring represented by the following formula (A-t1).

[式(A-t1)中，環T²表示碳數3~10的芳香族雜環。 [In formula (A-t1), ring T ² represents an aromatic heterocyclic ring having 3 to 10 carbon atoms.

R⁴⁵和R⁴⁶各自獨立地表示氫原子、可具有取代基的碳數1~20的飽和烴基、可具有取代基的碳數6~20的芳香族烴基或可具有取代基的碳數7~30的芳烷基，該飽和烴基的碳數為2~20的情況下，該飽和烴基中所含的亞甲基可被替換為氧原子或-CO-。不過，該碳數2~20的飽和烴基中，鄰接的亞甲基不會同時被替換為氧原子，末端的亞甲基不會被替換為氧原子或-CO-。R⁴⁵與R⁴⁶可結合並與它們結合的氮原子一起形成環。 R ⁴⁵ and R ⁴⁶ each independently represent a hydrogen atom, an optionally substituted saturated hydrocarbon group having 1 to 20 carbon atoms, an optionally substituted aromatic hydrocarbon group having 6 to 20 carbon atoms, or an optionally substituted carbon number 7 to In an aralkyl group of 30, when the saturated hydrocarbon group has 2 to 20 carbon atoms, the methylene group contained in the saturated hydrocarbon group may be replaced with an oxygen atom or -CO-. However, in this saturated hydrocarbon group with 2 to 20 carbon atoms, adjacent methylene groups are not simultaneously replaced with oxygen atoms, and the terminal methylene groups are not replaced with oxygen atoms or -CO-. R ⁴⁵ and R ⁴⁶ may be combined to form a ring together with the nitrogen atom to which they are bonded.

R⁵⁵表示碳數1~20的飽和烴基、或可具有取代基的碳數6~20的芳香族烴基。 R ⁵⁵ represents a saturated hydrocarbon group having 1 to 20 carbons, or an optionally substituted aromatic hydrocarbon group having 6 to 20 carbons.

k1表示0或1。 k1 represents 0 or 1.

*表示與碳陽離子的鍵合端。] * Indicates the bonding end with the carbocation. ]

[4]著色組合物，其包含[1]~[3]中的任一項所述的化合物。 [4] A coloring composition containing the compound described in any one of [1] to [3].

[5]由[4]所述的著色組合物形成的濾色器。 [5] A color filter formed from the coloring composition described in [4].

[6]顯示裝置，其包含[5]所述的濾色器。 [6] A display device including the color filter described in [5].

本發明的化合物的吸光度、電壓保持率優異，採用包含該化合物的著色組合物，能夠形成耐溶劑性優異的濾色器。 The compound of the present invention has excellent absorbance and voltage retention, and a coloring composition containing the compound can form a color filter having excellent solvent resistance.

具體實施方式 Detailed ways

本發明的化合物由式(A-I)表示。以下也將由式(A-I)表示的化合物稱為化合物(A-I)。本發明的化合物中也包含其互變異構體、它們的鹽。 The compound of the present invention is represented by formula (A-I). Hereinafter, the compound represented by formula (A-I) is also referred to as compound (A-I). The compounds of the present invention are also Including its tautomers and their salts.

[式(A-I)中，R⁴¹~R⁴⁴各自獨立地表示氫原子、碳數1~20的飽和烴基、可具有取代基的碳數6~20的芳香族烴基或可具有取代基的碳數7~30的芳烷基，該芳香族烴基和該芳烷基可具有的取代基可以是-SO₃ ^-或-SO₂-N^--SO₂-R^f，該碳數1~20的飽和烴基中，該飽和烴基中所含的氫原子可以被取代或未取代的胺基或鹵素原子取代，該飽和烴基的碳數為2~20的情況下，該飽和烴基中所含的亞甲基可被替換為氧原子或-CO-。不過，該碳數2~20的飽和烴基中，鄰接的亞甲基不會同時被替換為氧原子，末端的亞甲基不會被替換為氧原子或-CO-。R⁴¹與R⁴²可結合並與它們結合的氮原子一起形成環，R⁴³與R⁴⁴可結合並與它們結合的氮原子一起形成環。 [In formula (AI), R ⁴¹ to R ⁴⁴ each independently represent a hydrogen atom, a saturated hydrocarbon group with 1 to 20 carbons, an optionally substituted aromatic hydrocarbon group with 6 to 20 carbons, or a substituted carbon number The aralkyl group of 7-30, the aromatic hydrocarbon group and the substituent that the aralkyl group may have may be -SO ₃ ^- or -SO ₂ -N ^-- SO ₂ -R ^f , the saturated carbon number of 1-20 In the hydrocarbon group, the hydrogen atom contained in the saturated hydrocarbon group may be substituted by a substituted or unsubstituted amine group or halogen atom. When the saturated hydrocarbon group has 2 to 20 carbon atoms, the methylene group contained in the saturated hydrocarbon group Can be replaced by oxygen atom or -CO-. However, in this saturated hydrocarbon group with 2 to 20 carbon atoms, adjacent methylene groups are not simultaneously replaced with oxygen atoms, and the terminal methylene groups are not replaced with oxygen atoms or -CO-. R ⁴¹ and R ⁴² may be combined with the nitrogen atom to which they are combined to form a ring, and R ⁴³ and R ⁴⁴ may be combined with the nitrogen atom to which they are combined to form a ring.

環T¹表示碳數3~10的芳香族雜環，該芳香族雜環可具有碳數1~20的飽和烴基或可具有取代基的碳數6~20的芳香族烴基。該芳香族烴基可具有的取代基可以為-SO₃ ^-或-SO₂-N^--SO₂-R^f。 The ring T ¹ represents an aromatic heterocyclic ring having 3 to 10 carbon atoms, and the aromatic heterocyclic ring may have a saturated hydrocarbon group having 1 to 20 carbon atoms or an optionally substituted aromatic hydrocarbon group having 6 to 20 carbon atoms. The substituent that the aromatic hydrocarbon group may have may be -SO ₃ ^- or -SO ₂ -N ^-- SO ₂ -R ^f .

r表示1以上的整數。 r represents an integer of 1 or more.

由環T¹表示的芳香族雜環可以是單環也可以是稠合環。由環T¹表示的芳香族雜環的碳數為3~10，優選為3~8。另外，芳香族雜環優選為5~10元環，更優選為5~9元環。作為單環的芳香族雜環，例如可列舉出吡咯環、噁唑環、吡唑環、咪唑環、噻唑環等含氮原子的5元環；呋喃環、噻吩環等不含氮原子的5元環；吡啶環、嘧啶環、噠嗪環、吡嗪環等含氮原子的6元環等，作為稠合環的芳香族雜環，可列舉出吲哚環、苯并咪唑環、苯并噻唑環、喹啉環等含氮原子的稠合環；苯并呋喃環等不含氮原子的稠合環等。 The aromatic heterocyclic ring represented by ring T ¹ may be a monocyclic ring or a condensed ring. T by the ring carbon atoms of the aromatic heterocyclic ring ^represented 3 to 10, preferably 3 to 8. In addition, the aromatic heterocyclic ring is preferably a 5- to 10-membered ring, and more preferably a 5- to 9-membered ring. Examples of monocyclic aromatic heterocycles include 5-membered rings containing nitrogen atoms such as pyrrole ring, oxazole ring, pyrazole ring, imidazole ring, and thiazole ring; and 5 membered rings containing no nitrogen atom such as furan ring and thiophene ring. 6-membered ring containing nitrogen atoms such as pyridine ring, pyrimidine ring, pyridazine ring, pyrazine ring, etc. As the aromatic heterocyclic ring of the condensed ring, indole ring, benzimidazole ring, benzo Condensed rings containing nitrogen atoms such as thiazole rings and quinoline rings; condensed rings containing no nitrogen atoms such as benzofuran rings.

作為環T¹的芳香族雜環可具有的取代基，可列舉出鹵素原子、氰基、可具有取代基的碳數1~20的飽和烴基(優選地碳數1~20的烷基)、取代或未取代的胺基或可具有取代基的碳數6~20的芳香族烴基等，優選地，可列舉出碳數1~20的飽和烴基(優選地碳數1~20的烷基)、取代或未取代的胺基或可具有取代基的碳數6~20的芳香族烴基。 Examples of substituents that the aromatic heterocyclic ring of ring T ¹ may have include halogen atoms, cyano groups, and optionally substituted saturated hydrocarbon groups having 1 to 20 carbons (preferably alkyl groups having 1 to 20 carbons), A substituted or unsubstituted amine group or an aromatic hydrocarbon group having 6 to 20 carbons which may have a substituent, etc. Preferably, a saturated hydrocarbon group having 1 to 20 carbons (preferably an alkyl group having 1 to 20 carbons) is mentioned , A substituted or unsubstituted amine group or an optionally substituted aromatic hydrocarbon group with 6 to 20 carbons.

其中，作為環T¹的芳香族雜環，優選含氮原子的芳香族雜環，更優選含氮原子的5元環的芳香族雜環。 Among them, as the aromatic heterocyclic ring of ring T ¹ , a nitrogen atom-containing aromatic heterocyclic ring is preferable, and a nitrogen atom-containing 5-membered aromatic heterocyclic ring is more preferable.

另外，環T¹更優選為由式(A-t1)表示的環。 In addition, the ring T ^{1 is} more preferably a ring represented by formula (A-t1).

k1表示0或1。 k1 represents 0 or 1.

作為環T²的芳香族雜環，可列舉出與環T1中例示的芳香族雜環同樣的環。 Examples of the aromatic heterocyclic ring of the ring T ² include the same rings as the aromatic heterocyclic ring exemplified in the ring T ¹ .

進而，環T¹特別優選由式(A-t1-1)表示的環。 Furthermore, the ring T ^{1 is} particularly preferably a ring represented by formula (A-t1-1).

[式(A-t1-1)中，R⁵⁶表示氫原子、碳數1~20的飽和烴基、或可具有取代基的碳數6~20的芳香族烴基。 [In formula (A-t1-1), R ⁵⁶ represents a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbons, or an optionally substituted aromatic hydrocarbon group having 6 to 20 carbons.

X2表示氧原子、-N(R⁵⁷)-或硫原子。 X2 represents an oxygen atom, -N(R ⁵⁷ )- or a sulfur atom.

R⁵⁷表示氫原子或碳數1~10的烷基。 R ⁵⁷ represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms.

R⁴⁵和R⁴⁶與上述同義。 R ⁴⁵ and R ⁴⁶ have the same meaning as above.

另外，環T¹也優選為由式(A-t2)表示的環。 In addition, the ring T ^{1 is} also preferably a ring represented by formula (A-t2).

[式(A-t2)中，環T³表示具有氮原子的碳數3~10的芳香族雜環。 [In formula (A-t2), ring T ³ represents an aromatic heterocyclic ring having 3 to 10 carbon atoms and having a nitrogen atom.

R⁵⁸表示碳數1~20的飽和烴基、可具有取代基的碳數6~20的芳香族烴基、-SO₃ ^-、或-SO₂-N^--SO₂-R^f。 R ⁵⁸ represents a saturated hydrocarbon group having a carbon number of 1 to 20 carbon atoms may have a substituent, an aromatic hydrocarbon group having 6 to 20, -SO ₃ ^-, or _{^{_{^{-SO 2 -N - -SO 2 -R f}}}} .

R⁵⁹表示氫原子、可具有取代基的碳數1~20的飽和烴基、可具有取代基的碳數6~20的芳香族烴基或可具有取代基的碳數7~30的芳烷基。 R ⁵⁹ represents a hydrogen atom, an optionally substituted saturated hydrocarbon group having 1 to 20 carbons, an optionally substituted aromatic hydrocarbon group having 6 to 20 carbons, or an optionally substituted aralkyl group having 7 to 30 carbons.

k2表示0或1。 k2 represents 0 or 1.

環T¹也更優選為由式(A-t2-1)表示的環。 The ring T ^{1 is} also more preferably a ring represented by formula (A-t2-1).

[式(A-t2-1)中，R⁶⁰表示氫原子、碳數1~20的飽和烴基、或可具有取代基的碳數6~20的芳香族烴基。 [In the formula (A-t2-1), R ⁶⁰ represents a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbons, or an optionally substituted aromatic hydrocarbon group having 6 to 20 carbons.

R⁶¹表示氫原子、-SO₃ ^-、或-SO₂-N^--SO₂-R^f。 R ⁶¹ represents a hydrogen atom, -SO ₃ ^-, or _{^{_{^{-SO 2 -N - -SO 2 -R f}}}} .

R⁵⁹與上述同義。 R ⁵⁹ is synonymous with the above.

由R⁴¹~R⁴⁶、R⁵⁵、R⁵⁶和R⁵⁸~R⁶⁰表示的碳數1~20的飽和烴基可以是直鏈狀、分支鏈狀和環狀的任一個。作為直鏈狀或分支鏈狀的飽和烴基，可列舉出甲基、乙基、丙基、丁基、戊基、己基、庚基、辛基、壬基、癸基、十二烷基、十六烷基、二十烷基等直鏈狀烷基；異丙基、異丁基、異戊基、新戊基、2-乙基己基等分支鏈狀烷基等。該飽和烴基的碳數優選為1~10，更優選為1~8，進一步優選為1~6。 The saturated hydrocarbon group having 1 to 20 carbon atoms represented by R ⁴¹ to R ⁴⁶ , R ⁵⁵ , R ⁵⁶ and R ⁵⁸ to R ⁶⁰ may be any of linear, branched and cyclic. Examples of linear or branched saturated hydrocarbon groups include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, and decyl groups. Straight-chain alkyl such as hexaalkyl and eicosyl; branched alkyl such as isopropyl, isobutyl, isopentyl, neopentyl, 2-ethylhexyl, etc. The carbon number of the saturated hydrocarbon group is preferably 1-10, more preferably 1-8, and still more preferably 1-6.

由R⁴¹~R⁴⁶、R⁵⁵、R⁵⁶和R⁵⁸~R⁶⁰表示的環狀的飽和烴基可以為單環，也可為多環。作為該環狀的飽和烴基，可列舉出環丙基、環丁基、環戊基、環己基、金剛烷基等脂環式飽和烴基。該環狀的飽和烴基的碳數優選為3~10，更優選為6~10。 The cyclic saturated hydrocarbon group represented by R ⁴¹ to R ⁴⁶ , R ⁵⁵ , R ⁵⁶ and R ⁵⁸ to R ⁶⁰ may be monocyclic or polycyclic. Examples of the cyclic saturated hydrocarbon group include alicyclic saturated hydrocarbon groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and adamantyl. The carbon number of the cyclic saturated hydrocarbon group is preferably 3-10, and more preferably 6-10.

作為由R⁴¹~R⁴⁶、R⁵⁵、R⁵⁶和R⁵⁸~R⁶⁰表示的飽和烴基的具體例，可列舉出由下述式表示的基團。下述式中，*表示鍵合端。 Specific examples of saturated hydrocarbon groups represented by R ⁴¹ to R ⁴⁶ , R ⁵⁵ , R ⁵⁶ and R ⁵⁸ to R ⁶⁰ include groups represented by the following formulas. In the following formula, * represents a bonding end.

由R⁴¹~R⁴⁶、R⁵⁵、R⁵⁶和R⁵⁸~R⁶⁰表示的飽和烴基可以被取代或未取代的胺基或鹵素原子取代。作為取代胺基，例如可列舉出二甲基胺基、二乙基胺基等烷基胺基。另外，作為鹵素原子，可列舉出氟、氯、溴、碘。另外，鹵素原子為氟原子的情況下，由R⁴¹~R⁴⁶、R⁵⁵、R⁵⁶和R⁵⁸~R⁶⁰表示的被鹵素原子(氟原子)取代的飽和烴基優選為三氟甲基、五氟乙基、七氟丙基等全氟烷基。 The saturated hydrocarbon groups represented by R ⁴¹ to R ⁴⁶ , R ⁵⁵ , R ⁵⁶ and R ⁵⁸ to R ⁶⁰ may be substituted with substituted or unsubstituted amine groups or halogen atoms. Examples of substituted amino groups include alkylamino groups such as dimethylamino and diethylamino. In addition, examples of the halogen atom include fluorine, chlorine, bromine, and iodine. In addition, when the halogen atom is a fluorine atom, the saturated hydrocarbon group represented by R ⁴¹ to R ⁴⁶ , R ⁵⁵ , R ⁵⁶ and R ⁵⁸ to R ⁶⁰ substituted with a halogen atom (fluorine atom) is preferably a trifluoromethyl, five Perfluoroalkyl groups such as fluoroethyl and heptafluoropropyl.

作為具有取代基的碳數1~20的飽和烴基，例如可列舉出由下述式表示的基團。下述式中，*表示與氮原子等的鍵合端。 As a saturated hydrocarbon group having 1 to 20 carbon atoms having a substituent, for example, a group represented by the following formula can be cited. In the following formula, * means that with nitrogen atom etc. Bonded end.

作為由R⁴⁷~R⁵⁴表示的碳數1~8的烷基，可列舉出作為由R⁴¹表示的飽和烴基例示的直鏈狀或分支鏈狀的飽和烴基中的碳數1~8的基團。 Examples of the alkyl group having 1 to 8 carbon atoms represented by R ⁴⁷ to R ⁵⁴ include groups having 1 to 8 carbon atoms in the linear or branched saturated hydrocarbon groups exemplified by the saturated hydrocarbon group represented by R ⁴¹ group.

另外，作為由R⁵⁷表示的碳數1~10的烷基，可列舉出作為由R⁴¹表示的飽和烴基例示的直鏈狀或分支鏈狀的飽和烴基中的碳數1~10的基團。 In addition, examples of the alkyl group having 1 to 10 carbon atoms represented by R ⁵⁷ include groups having 1 to 10 carbon atoms in the linear or branched saturated hydrocarbon group exemplified as the saturated hydrocarbon group represented by R ⁴¹ .

由R⁴¹~R⁴⁶表示的飽和烴基的碳數為2~20的情況下，該飽和烴基中所含的亞甲基可以被替換為氧原子或-CO-。不過，該碳數2~20的飽和烴基中，鄰接的亞甲基不會同時地被替換為氧原子，末端的亞甲基不會被替換為氧原子或-CO-。這種情況下，作為飽和烴基，優選直鏈狀或分支鏈狀的飽和烴基(即直鏈狀或分支鏈狀烷基)，更優選直鏈狀的飽和烴基(即直鏈狀烷基)。亞甲基可被替換為氧原子或-CO-的飽和烴基的優選的碳數為2~10，更優選為2~8。另外亞甲基被替換為氧原子或-CO-時，末端與氧原子或-CO-之間、或者氧原子或-CO-與氧原子或-CO-之間的碳數為1以上，優選為1~5，更優選為2~3，進一步優選為2。在飽和烴基的亞甲基被替換為氧原子或-CO-的基團中，例如包含烷氧基烷基；或(烷氧基烷氧基)烷基、(烷氧基烷氧基烷氧基)烷基、(烷氧基烷氧基烷氧基烷氧基)烷基、(烷氧基烷氧基烷氧基烷氧基烷氧基)烷基、(烷氧基烷氧基烷氧基烷氧基烷氧基烷氧基)烷基等多烷氧基烷基等，烷氧基單元的重複數例如為1~6，優選為1~4，更優選為1~2。在更優選的具體例中，可列舉出由下述式表示的基團。下述式中，*表示與氮原子的鍵合端。 When the saturated hydrocarbon group represented by R ⁴¹ to R ⁴⁶ has 2 to 20 carbon atoms, the methylene group contained in the saturated hydrocarbon group may be replaced with an oxygen atom or -CO-. However, in this saturated hydrocarbon group with 2 to 20 carbon atoms, adjacent methylene groups are not simultaneously replaced with oxygen atoms, and the terminal methylene groups are not replaced with oxygen atoms or -CO-. In this case, the saturated hydrocarbon group is preferably a linear or branched saturated hydrocarbon group (that is, a linear or branched alkyl group), and a linear saturated hydrocarbon group (that is, a linear alkyl group) is more preferable. The preferable carbon number of the saturated hydrocarbon group in which a methylene group can be substituted with an oxygen atom or -CO- is 2-10, More preferably, it is 2-8. When the methylene group is replaced with an oxygen atom or -CO-, the number of carbons between the terminal and the oxygen atom or -CO-, or between the oxygen atom or -CO- and the oxygen atom or -CO- is 1 or more, preferably It is 1 to 5, more preferably 2 to 3, and even more preferably 2. In the group in which the methylene group of the saturated hydrocarbon group is replaced with an oxygen atom or -CO-, for example, an alkoxyalkyl group; or (alkoxyalkoxy)alkyl group, (alkoxyalkoxyalkoxy group) Group) alkyl, (alkoxy alkoxy alkoxy alkoxy) alkyl, (alkoxy alkoxy alkoxy alkoxy alkoxy) alkyl, (alkoxy alkoxy alkoxy) The number of repetitions of the alkoxy unit is, for example, 1 to 6, preferably 1 to 4, and more preferably 1 to 2, such as polyalkoxyalkyl groups such as oxyalkoxyalkoxyalkyloxy) alkyl. In a more preferable specific example, a group represented by the following formula can be mentioned. In the following formula, * represents the bonding terminal to the nitrogen atom.

另外，由R⁴¹~R⁴⁶、R⁵⁵、R⁵⁶和R⁵⁸~R⁶⁰表示的可具有取代基的芳香族烴基的碳數優選為6~20，更優選為6~15，進一步優選為6~12。作為該芳香族烴基，可列舉出苯基、甲苯基、二甲苯基、萘基、蒽基、菲基、聯苯基、三聯苯基等，優選為苯基、萘基、甲苯基、二甲苯基，特別優選為苯基。另外，該芳香族烴基可具有1或2個以上的取代基。作為該取代基，可列舉出氟原子、氯原子、碘原子、溴原子等鹵素原子；氯甲基、三氟甲基等碳數1~6的鹵代烷基；甲氧基、乙氧基等碳數1~6的烷氧基；羥基；胺磺醯基；甲基磺醯基等碳數1~6的烷基磺醯基；甲氧基羰基、乙氧基羰基等碳數1~6的烷氧基羰基；-SO₃ ^-；-SO₂-N^--SO₂-R^f等，可以為-SO₃ ^-或-SO₂-N^--SO₂-R^f。不過，-SO₃ ^-或-SO₂-N^--SO₂-R^f優選與芳香族烴基的芳香族烴環直接結合，即，將與芳香族烴環結合的氫原子取代。 In addition, the number of carbon atoms of the optionally substituted aromatic hydrocarbon group represented by R ⁴¹ to R ⁴⁶ , R ⁵⁵ , R ⁵⁶ and R ⁵⁸ to R ⁶⁰ is preferably 6 to 20, more preferably 6 to 15, and still more preferably 6. ~12. Examples of the aromatic hydrocarbon group include phenyl, tolyl, xylyl, naphthyl, anthracenyl, phenanthryl, biphenyl, terphenyl, etc., preferably phenyl, naphthyl, tolyl, and xylene The group is particularly preferably a phenyl group. In addition, the aromatic hydrocarbon group may have 1 or 2 or more substituents. Examples of the substituent include halogen atoms such as fluorine atom, chlorine atom, iodine atom, and bromine atom; halogenated alkyl groups having 1 to 6 carbon atoms such as chloromethyl and trifluoromethyl; and carbon atoms such as methoxy and ethoxy. Alkoxy with 1~6; hydroxyl; sulfamsulfonyl; alkylsulfonyl with 1 to 6 carbons such as methylsulfonyl; methoxycarbonyl, ethoxycarbonyl and other carbon 1 to 6 alkoxycarbonyl _{^{_{group; -SO 3 -; -SO 2 -N}}} - -SO 2 -R f , etc., may be -SO ₃ ^- or _{^{_{^{-SO 2 -N - -SO 2 -R f}}}} . However, -SO ₃ ^- or -SO ₂ -N ^-- SO ₂ -R ^f is preferably directly bonded to the aromatic hydrocarbon ring of the aromatic hydrocarbon group, that is, the hydrogen atom bonded to the aromatic hydrocarbon ring is substituted.

作為可具有取代基的芳香族烴基的具體例，例如可列舉出由下述式表示的基團。下述式中，*表示與氮原子的鍵合端。 As a specific example of the aromatic hydrocarbon group which may have a substituent, the group represented by the following formula is mentioned, for example. In the following formula, * represents the bonding terminal to the nitrogen atom.

作為由R⁴¹~R⁴⁶、R⁵⁹表示的可具有取代基的芳烷基，可列舉出在作為上述芳香族烴基說明的基團上結合了亞甲基、亞乙基、亞丙基等碳數1~10(優選地碳數1~5)的亞烷基的基團等。該芳烷基的碳數優選為7~30，更優選為7~20，進一步優選為碳數7~17。 Examples of the optionally substituted aralkyl groups represented by R ⁴¹ to R ⁴⁶ and R ⁵⁹ include the groups described as the above aromatic hydrocarbon groups bonded with carbons such as methylene, ethylene, and propylene. The number of 1 to 10 (preferably carbon number of 1 to 5) alkylene group and the like. The carbon number of the aralkyl group is preferably 7-30, more preferably 7-20, and even more preferably 7-17.

作為R⁴¹和R⁴²結合並與它們結合的氮原子一起形成的環、R⁴³和R⁴⁴結合並與它們結合的氮原子一起形成的環、以及R⁴⁵和R⁴⁶結合並與它們結合的氮原子一起形成的環，可列舉出吡咯烷環、嗎啉環、哌啶環、哌嗪環等含氮非芳香族4~7元環，優選地，可列舉出吡咯烷環、哌啶環等只具有1個氮原子作為雜原子的4~7元環。 As the ring formed by combining R ⁴¹ and R ⁴² with the nitrogen atom to which they are bonded, the ring formed by combining R ⁴³ and R ⁴⁴ with the nitrogen atom to which they are bonded, and the nitrogen bonded to and bonded to R ⁴⁵ and R ⁴⁶ The ring formed by the atoms includes a pyrrolidine ring, a morpholine ring, a piperidine ring, a piperazine ring and other nitrogen-containing non-aromatic 4-7 membered rings. Preferably, a pyrrolidine ring, a piperidine ring, etc. A 4- to 7-membered ring with only one nitrogen atom as a heteroatom.

作為R⁵⁸，優選碳數1~20的飽和烴基、或可具有取代基的碳數6~20的芳香族烴基。 As R ⁵⁸ , a saturated hydrocarbon group having 1 to 20 carbon atoms or an optionally substituted aromatic hydrocarbon group having 6 to 20 carbon atoms is preferable.

其中，作為R⁴¹~R⁴⁴、R⁵⁵、R⁵⁶、R⁵⁸~R⁶⁰，優選碳數1~20的飽和烴基或可具有取代基的芳香族烴基，各自獨立地，更優選為碳數1~8的飽和烴基或由下述式表示的芳香族烴基。R⁵⁵、R⁵⁶、R⁵⁸~R⁶⁰進一步優選為由下述式表示的芳香族烴基。下述式中，*表示與氮原子的鍵合端。 Among them, as R ⁴¹ to R ⁴⁴ , R ⁵⁵ , R ⁵⁶ , R ⁵⁸ to R ⁶⁰ , a saturated hydrocarbon group having 1 to 20 carbons or an aromatic hydrocarbon group that may have a substituent is preferable, and each independently, more preferably a carbon number of 1 ~8 saturated hydrocarbon group or aromatic hydrocarbon group represented by the following formula. R ⁵⁵ , R ⁵⁶ , and R ⁵⁸ to R ^{60 are} more preferably aromatic hydrocarbon groups represented by the following formula. In the following formula, * represents the bonding terminal to the nitrogen atom.

R⁴⁵~R⁴⁶優選各自獨立地為碳數1~20的飽和烴基、構成碳數2~20的烷基的亞甲基被替換為氧原子或-CO-的基團、或可具有取代基的芳香族烴基，或者R⁴⁵與R⁴⁶結合並與它們結合的氮原子一起形成環。R⁴⁵~R⁴⁶更優選各自獨立地為碳數1~8的飽和烴基、烷氧基烷基、或由下述式表示的芳香族烴基，或者R⁴⁵與R⁴⁶結合而形成只具有1個氮原子作為雜原子的4~7元環，進一步優選各自獨立地為碳數1~8的飽和烴基、烷氧基烷基、或由下述式表示的芳香族烴基。下述式中，*表示與氮原子的鍵合端。 R ⁴⁵ to R ^{46 are} preferably each independently a saturated hydrocarbon group having 1 to 20 carbons, a group in which the methylene group constituting an alkyl group having 2 to 20 carbons is replaced with an oxygen atom or -CO-, or may have a substituent Or R ⁴⁵ and R ⁴⁶ combine to form a ring with the nitrogen atom to which they are combined. More preferably, R ⁴⁵ to R ⁴⁶ are each independently a saturated hydrocarbon group having 1 to 8 carbons, an alkoxyalkyl group, or an aromatic hydrocarbon group represented by the following formula, or R ⁴⁵ and R ^{46 are} combined to form only one A 4- to 7-membered ring in which a nitrogen atom is a hetero atom is more preferably a saturated hydrocarbon group having 1 to 8 carbon atoms, an alkoxyalkyl group, or an aromatic hydrocarbon group represented by the following formula. In the following formula, * represents the bonding terminal to the nitrogen atom.

另外，作為由R⁴⁷~R⁵⁴表示的碳數1~8的烷基，可列舉出作為由R⁴¹表示的飽和烴基例示的直鏈狀或分支鏈狀的飽和烴基中的碳數1~8的基團。另外，作為由R⁴⁷~R⁵⁴表示的構成碳數2~8的烷基的亞甲基被替換為氧原子或-CO-的基團(不過，該烷基中，鄰接的亞甲基不會同時被替換為氧原子，末端的亞甲基不會被替換為氧原子或-CO-)，可列舉出從由上述R⁴¹~R⁴⁶表示的構成碳數2~20的烷基的亞甲基被替換為氧原子或-CO-的基團中選擇的碳數8以下的基團。作為由R⁴⁷~R⁵⁴表示的碳數1~8的烷基，更優選地，可列舉出由下述式表示的基團。下述式中，*表示與碳原子的鍵合端。 In addition, examples of the alkyl group having 1 to 8 carbon atoms represented by R ⁴⁷ to R ⁵⁴ include linear or branched saturated hydrocarbon groups exemplified by the saturated hydrocarbon group represented by R ⁴¹ having carbon numbers of 1 to 8 The group. In addition, the methylene group that constitutes the alkyl group having 2 to 8 carbon atoms represented by R ⁴⁷ to R ⁵⁴ is replaced with an oxygen atom or -CO- group (however, in the alkyl group, the adjacent methylene group is not Will be replaced with an oxygen atom at the same time, and the methylene group at the terminal will not be replaced with an oxygen atom or -CO-). Examples include the alkylene groups represented by R ⁴¹ to R ⁴⁶ that constitute an alkyl group with 2 to 20 carbon atoms. The methyl group is replaced with a group with 8 or less carbon atoms selected from the group of oxygen atom or -CO-. As the C1-C8 alkyl group represented by R ⁴⁷ to R ⁵⁴ , more preferably, a group represented by the following formula can be cited. In the following formula, * represents a bonding terminal to a carbon atom.

R⁴⁷~R⁵⁴，從合成的容易性的方面出發，優選各自獨立地為氫原子、鹵素原子或碳數1~8的烷基，更優選各自獨立地為氫原子、甲基、氟原子或氯原子。 R ⁴⁷ to R ⁵⁴ are each independently a hydrogen atom, a halogen atom, or an alkyl group having 1 to 8 carbon atoms, more preferably each independently a hydrogen atom, a methyl group, a fluorine atom, or Chlorine atom.

另外，作為R⁵⁷，優選氫原子或碳數1~5的烷基。 In addition, as R ⁵⁷ , a hydrogen atom or an alkyl group having 1 to 5 carbon atoms is preferable.

作為R⁶¹，優選氫原子。 As R ⁶¹ , a hydrogen atom is preferable.

作為由M^r+表示的r價的金屬離子，可列舉出鋰離子、鈉離子、鉀離子等鹼金屬離子；鈹離子、鎂離子、鈣離子、鍶離子、鋇離子等鹼土類金屬離子；鈦離子、鋯離子、鉻離子、錳離子、鐵離子、鈷離子、鎳離子、銅離子等過渡金屬離子；鋅離子、鎘離子、鋁離子、銦離子、錫離子、鉛離子、鉍離子等典型金屬離子等。r為1以上，優選為2以上，優選為5以下，更優選為4以下，進一步優選為3以下。另外，作為由M^r+表示的取代或未取代的銨離子，可列舉出四烷基銨離子等季銨離子。 Examples of metal ions with r valence represented by Mr ⁺ include alkali metal ions such as lithium ion, sodium ion, and potassium ion; alkaline earth metal ions such as beryllium ion, magnesium ion, calcium ion, strontium ion, and barium ion; and titanium ion , Zirconium ion, chromium ion, manganese ion, iron ion, cobalt ion, nickel ion, copper ion and other transition metal ions; zinc ion, cadmium ion, aluminum ion, indium ion, tin ion, lead ion, bismuth ion and other typical metal ions Wait. r is 1 or more, preferably 2 or more, preferably 5 or less, more preferably 4 or less, and still more preferably 3 or less. In addition, examples of the substituted or unsubstituted ammonium ion represented by Mr ⁺ include quaternary ammonium ions such as tetraalkylammonium ions.

作為M^r+，從電壓保持率的觀點出發，優選r價的金屬離子，更優選鹼土類金屬離子、典型金屬離子等，進一步優選鎂離子、鋇離子、鋅離子。作為M^r+，從吸光度的方面出發，優選氫離子或鹼金屬離子，更優選氫離子。 As Mr ⁺ , from the viewpoint of voltage retention, r-valent metal ions are preferable, alkaline earth metal ions, typical metal ions, etc. are more preferable, and magnesium ions, barium ions, and zinc ions are still more preferable. As Mr ⁺ , from the viewpoint of absorbance, a hydrogen ion or an alkali metal ion is preferable, and a hydrogen ion is more preferable.

式(A-I)中，M^r+的個數成為比由式(A-I)表示的化合物具有的-SO₃ ^-的個數和-SO₂-N^--SO₂-R^f的個數之和(k)少1個的數。因此，化合物(A-I)成為價數為0、即電中性的化合物。具有-SO₃ ^-的情況下，-SO₃ ^-的個數優選為6以下，更優選為3以下，可以為1以上。另外，-SO₃ ^-的個數也優選為0。 In the formula (AI), the number of Mr ⁺ is more than the sum of the number of -SO ₃ ^-and the number of -SO ₂ -N ^-- SO ₂ -R ^f that the compound represented by the formula (AI) has (k ) One less number. Therefore, the compound (AI) has a valence of 0, that is, an electrically neutral compound. The case, -SO ₃ ^{^- -} the number of -SO ₃ having preferably 6 or less, more preferably 3 or less, may be 1 or more. In addition, the number of -SO ₃ ^- is also preferably zero.

作為由R^f表示的碳數1~12的氟烷基，可列舉出一氟甲基、二氟甲基、三氟甲基(全氟甲基)、一氟乙基、二氟乙基、三氟乙基、四氟乙基、五氟乙基(全氟乙基)、一氟丙基、二氟丙基、三氟丙基、四氟丙基、五氟丙基、六氟丙基、七氟丙基(全氟丙基)、一氟丁基、二氟丁基、三氟丁基、四氟丁基、五氟丁基、六氟丁基、七氟丁基、八氟丁基、九氟丁基(全氟丁基)等。其中，作為由R^f表示的氫原子的全部或一部分被氟原子取代的烷基(氟烷基)，優選全氟烷基。另外，由R^f表示的氫原子的全部或一部分被氟原子取代的烷基(氟烷基)的碳數優選為1~10，更優選為1~5，進一步優選為1~3。 Examples of the fluoroalkyl group having 1 to 12 carbon atoms represented by R ^f include monofluoromethyl, difluoromethyl, trifluoromethyl (perfluoromethyl), monofluoroethyl, difluoroethyl, Trifluoroethyl, tetrafluoroethyl, pentafluoroethyl (perfluoroethyl), monofluoropropyl, difluoropropyl, trifluoropropyl, tetrafluoropropyl, pentafluoropropyl, hexafluoropropyl , Heptafluoropropyl (perfluoropropyl), monofluorobutyl, difluorobutyl, trifluorobutyl, tetrafluorobutyl, pentafluorobutyl, hexafluorobutyl, heptafluorobutyl, octafluorobutyl Base, nonafluorobutyl (perfluorobutyl), etc. Among them, as the alkyl group (fluoroalkyl group) in which all or part of the hydrogen atoms represented by R ^f are substituted with fluorine atoms, a perfluoroalkyl group is preferable. In addition, the carbon number of the alkyl group (fluoroalkyl group) in which all or part of the hydrogen atoms represented by R ^f are substituted with fluorine atoms is preferably 1-10, more preferably 1-5, and still more preferably 1-3.

化合物(A-I)具有至少1個-SO₂-N^--SO₂-R^f。-SO₂-N^--SO₂-R^f的個數為1以上，優選為1~7，更優選為1~4，進一步優選為1或2，特別優選為2。 The compound (AI) has at least one -SO ₂ -N ^-- SO ₂ -R ^f . The number of -SO ₂ -N ^-- SO ₂ -R ^f is 1 or more, preferably 1 to 7, more preferably 1 to 4, still more preferably 1 or 2, and particularly preferably 2.

另外，化合物(A-I)也優選具有-SO₂-N^--SO₂-R^f且不具有-SO₃ ^-，也優選具有-SO₂-N^--SO₂-R^f和-SO₃ ^-。具有 -SO₂-N^--SO₂-R^f和-SO₃ ^-的情況下，在化合物(A-I)中含有至少1個-SO₂-N^--SO₂-R^f，-SO₂-N^--SO₂-R^f和-SO₃ ^-的合計的個數優選為2~7，更優選為2~4，進一步優選為2。 Further, the compound (AI) also preferably have -SO _₂ -N ^- -SO ₂ -R ^f does not have -SO ₃ ^-, also preferably having -SO _₂ -N ^- -SO ₂ -R ^f, and -SO ₃ ^-. In the case of having -SO ₂ -N ^-- SO ₂ -R ^f and -SO ₃ ^- , the compound (AI) contains at least one -SO ₂ -N ^-- SO ₂ -R ^f , -SO ₂ -N ^- -SO ₂ -R ^f, and -SO ₃ ^- the total number of preferably 2 to 7, more preferably 2 to 4, more preferably 2.

該-SO₂-N^--SO₂-R^f或-SO₃ ^-優選被作為上述R⁴⁷~R⁵⁴的任一個而含有，或者與由R⁴¹~R⁴⁴表示的可具有取代基的碳數6~20的芳香族烴基、由R⁴¹~R⁴⁴表示的可具有取代基的碳數7~30的芳烷基、和將由T¹表示的芳香族雜環的氫原子取代的碳數6~20的芳香族烴基的任一個結合，更優選地，與由R⁴¹~R⁴⁴表示的可具有取代基的碳數6~20的芳香族烴基、由R⁴¹~R⁴⁴表示的可具有取代基的碳數7~30的芳烷基結合，進一步優選地，與由R⁴¹~R⁴⁴表示的可具有取代基的碳數6~20的芳香族烴基、由R⁴¹~R⁴⁴表示的可具有取代基的碳數7~30的芳烷基中的芳香族烴環(苯環)的從與氮原子的結合位置來看的對位結合。 The -SO ₂ -N ^-- SO ₂ -R ^f or -SO ₃ ^- is preferably contained as any of the above-mentioned R ⁴⁷ to R ⁵⁴ , or is combined with the number of carbon atoms represented by R ⁴¹ to R ⁴⁴ that may have a substituent 6-20 aromatic hydrocarbon groups, optionally substituted aralkyl groups with 7-30 carbons represented by R ⁴¹ to R ⁴⁴ , and 6 to carbon atoms substituted with hydrogen atoms of the aromatic heterocyclic ring represented by T ¹ the aromatic hydrocarbon according to any one of the binding 20, and more preferably, R ⁴¹ ~ by the aromatic hydrocarbon group having 6 to 20 carbon atoms may have a substituent group represented by R ^44, R ⁴¹ ~ R ⁴⁴ may have a substituent represented by the group In combination with an aralkyl group having 7 to 30 carbon atoms, it is more preferable to combine with an aromatic hydrocarbon group having 6 to 20 carbon atoms represented by R ⁴¹ to R ⁴⁴ that may have substituents, and those represented by R ⁴¹ to R ⁴⁴ may have The aromatic hydrocarbon ring (benzene ring) in the aralkyl group having 7 to 30 carbon atoms of the substituent is bonded at the para position viewed from the bonding position with the nitrogen atom.

不過，在芳香族烴基或芳烷基上結合有-SO₂-N^--SO₂-R^f或-SO₃ ^-的情況下，-SO₂-N^--SO₂-R^f或-SO₃ ^-優選與芳香族烴基或芳烷基的芳香族烴環直接結合。即-SO₂-N^--SO₂-R^f或-SO₃ ^-優選取代了與芳香族烴環結合的氫原子。 However, when -SO ₂ -N ^-- SO ₂ -R ^f or -SO ₃ ^- is bonded to the aromatic hydrocarbon group or aralkyl group, -SO ₂ -N ^-- SO ₂ -R ^f or -SO ₃ ^-It is preferably directly bonded to the aromatic hydrocarbon ring of the aromatic hydrocarbon group or aralkyl group. That is, -SO ₂ -N ^-- SO ₂ -R ^f or -SO ₃ ^- preferably replaces the hydrogen atom bonded to the aromatic hydrocarbon ring.

-SO₂-N^--SO₂-R^f和-SO₃ ^-可結合於同一芳香族烴環，但優選結合於不同的芳香族烴環。 -SO ₂ -N ^-- SO ₂ -R ^f and -SO ₃ ^- may be bonded to the same aromatic hydrocarbon ring, but are preferably bonded to different aromatic hydrocarbon rings.

再有，化合物(A-I)優選不具有烯屬不飽和鍵。 Furthermore, the compound (A-I) preferably does not have an ethylenically unsaturated bond.

作為化合物(A-I)，也優選將具有 -SO₂-N^--SO₂-R^f且不具有-SO₃ ^-的化合物和具有-SO₂-N^--SO₂-R^f和-SO₃ ^-的化合物並用。這種情況下，具有-SO₂-N^--SO₂-R^f且不具有-SO₃ ^-的化合物與具有-SO₂-N^--SO₂-R^f和-SO₃ ^-的化合物的摩爾比(具有-SO₂-N^--SO₂-R^f且不具有-SO₃ ^-的化合物/具有-SO₂-N^--SO₂-R^f和-SO₃ ^-的化合物)優選為0.01以上，更優選為0.05以上，進一步優選為0.1以上，可以為50以下，更優選為10以下，進一步優選為5以下，特別優選地，可為1以下。 As the compound (AI), also preferably having -SO _₂ -N ^- -SO ₂ -R ^f does not have -SO ₃ ^- and a compound having -SO _₂ -N ^- -SO ₂ -R ^f, and -SO ₃ ^- The compound used together. In this case, having a -SO _₂ -N ^- -SO ₂ -R ^f does not have -SO ₃ ^- and a compound having -SO ₂ -N ^- mol of compound ^- -SO ₂ -R ^f -SO ₃ and ratio (having a -SO _₂ -N ^- -SO ₂ -R ^f does not have -SO ₃ ^- compound / having -SO _₂ -N ^- -SO ₂ -R ^f, and -SO ₃ ^- compound) is preferably 0.01 or more , More preferably 0.05 or more, still more preferably 0.1 or more, may be 50 or less, more preferably 10 or less, still more preferably 5 or less, particularly preferably, 1 or less.

化合物(A-I)優選為由下述式(A-I1)表示的化合物。 The compound (A-I) is preferably a compound represented by the following formula (A-I1).

[式(A-I1)中，R⁸¹~R⁹⁰各自獨立地表示氫原子、碳數1~20的飽和烴基、鹵素原子、-SO₃ ^-或-SO₂-N^--SO₂-R^f。 [In formula (A-I1), R ⁸¹ to R ⁹⁰ each independently represent a hydrogen atom, a saturated hydrocarbon group with 1 to 20 carbon atoms, a halogen atom, -SO ₃ ^- or -SO ₂ -N ^-- SO ₂ -R ^f .

k1表示由式(A-I1)表示的化合物具有的-SO₃ ^-的個數和-SO₂-N^--SO₂-R^f的個數之和。 k1 represents the sum of the number of -SO ₃ ^-and the number of -SO ₂ -N ^-- SO ₂ -R ^f that the compound represented by the formula (A-I1) has.

R⁴¹、R⁴³、R⁴⁷~R⁵⁴、T¹、M^r+、r、R^f與上述同義。 R ⁴¹ , R ⁴³ , R ⁴⁷ to R ⁵⁴ , T ¹ , Mr ⁺ , r, R ^f have the same meaning as above.

不過，由式(A-I1)表示的化合物具有至少1個 -SO₂-N^--SO₂-R^f。] However, the compound represented by the formula (A-I1) has at least one -SO ₂ -N ^-- SO ₂ -R ^f . ]

作為由R⁸¹~R⁹⁰表示的碳數1~20的飽和烴基，可列舉出與作為由R⁴¹表示的飽和烴基例示的基團同樣的基團。作為R⁸¹~R⁹⁰，優選氫原子、碳數1~8的飽和烴基、-SO₃ ^-或-SO₂-N^--SO₂-R^f，更優選氫原子、-SO₃ ^-或-SO₂-N^--SO₂-R^f，進一步優選氫原子或-SO₂-N^--SO₂-R^f。 Examples of the saturated hydrocarbon group having 1 to 20 carbon atoms represented by R ⁸¹ to R ⁹⁰ include the same groups as those exemplified as the saturated hydrocarbon group represented by R ⁴¹ . As R ⁸¹ to R ⁹⁰ , a hydrogen atom, a saturated hydrocarbon group having 1 to 8 carbon atoms, -SO ₃ ^- or -SO ₂ -N ^-- SO ₂ -R ^f are preferable, and a hydrogen atom, -SO ₃ ^- or -SO is more preferable ₂ -N ^-- SO ₂ -R ^f , more preferably a hydrogen atom or -SO ₂ -N ^-- SO ₂ -R ^f .

另外，-SO₂-N^--SO₂-R^f或-SO₃ ^-優選(e)被作為上述R⁴⁷~R⁵⁴的任一個而含有，或者(f)被作為R⁸¹~R⁹⁰的任一個而含有，或者(g)與將由T¹表示的芳香族雜環的氫原子取代的碳數6~20的芳香族烴基結合，或者作為這些(e)~(g)的組合存在，更優選作為(f)、(g)或這些(f)~(g)的組合存在，進一步優選作為(f)存在。另外，R⁸¹~R⁹⁰中，優選為選自R⁸⁶和R⁸⁹中的1個以上。 In addition, -SO ₂ -N ^-- SO ₂ -R ^f or -SO ₃ ^- preferably (e) is contained as any of the above-mentioned R ⁴⁷ to R ⁵⁴ , or (f) is contained as any of R ⁸¹ to R ⁹⁰ It is contained in one, or (g) is combined with an aromatic hydrocarbon group having 6 to 20 carbons substituted by a hydrogen atom of an aromatic heterocyclic ring represented by T ¹ , or exists as a combination of these (e) to (g), more preferably It exists as (f), (g), or a combination of these (f)-(g), More preferably, it exists as (f). In addition, among R ⁸¹ to R ⁹⁰ , one or more selected from R ⁸⁶ and R ⁸⁹ is preferred.

化合物(A-I1)中所含的-SO₂-N^--SO₂-R^f的數優選為1~7，更優選為1~4，進一步優選為1或2。另外化合物(A-I1)具有-SO₂-N^--SO₂-R^f和-SO₃ ^-的情況下，在化合物(A-I1)中包含至少1個-SO₂-N^--SO₂-R^f，-SO₂-N^--SO₂-R^f和-SO₃ ^-的合計的個數(k1)優選為2~7，更優選為2~4，進一步優選為2。 The number of -SO ₂ -N ^-- SO ₂ -R ^f contained in the compound (A-I1) is preferably 1-7, more preferably 1-4, and still more preferably 1 or 2. In addition, when the compound (A-I1) has -SO ₂ -N ^-- SO ₂ -R ^f and -SO ₃ ^- , the compound (A-I1) contains at least one -SO ₂ -N ^-- SO ₂ The total number (k1) of -R ^f , -SO ₂ -N ^-- SO ₂ -R ^f and -SO ₃ ^- is preferably 2-7, more preferably 2-4, and still more preferably 2.

作為化合物(A-I1)，也優選將具有-SO₂-N^--SO₂-R^f且不具有-SO₃ ^-的化合物和具有-SO₂-N^--SO₂-R^f和-SO₃ ^-的化合物並用。這種情況下，具有-SO₂-N^--SO₂-R^f且不具有-SO₃ ^-的化合物與具有-SO₂-N^--SO₂-R^f和-SO₃ ^-的化合物的摩爾比(具有 -SO₂-N^--SO₂-R^f且不具有-SO₃ ^-的化合物/具有-SO₂-N^--SO₂-R^f和-SO₃ ^-的化合物)優選為0.01以上，更優選為0.05以上，進一步優選為0.1以上，可以為50以下，更優選為10以下，進一步優選為5以下，特別優選地，可以為1以下。 As the compound (A-I1), a compound having -SO ₂ -N ^-- SO ₂ -R ^{f but} not -SO ₃ ^-and a compound having -SO ₂ -N ^-- SO ₂ -R ^f and -SO _{Combination of 3} ^- compounds. In this case, having a -SO _₂ -N ^- -SO ₂ -R ^f does not have -SO ₃ ^- and a compound having -SO ₂ -N ^- mol of compound ^- -SO ₂ -R ^f -SO ₃ and ratio (having a -SO _₂ -N ^- -SO ₂ -R ^f does not have -SO ₃ ^- compound / having -SO _₂ -N ^- -SO ₂ -R ^f, and -SO ₃ ^- compound) is preferably 0.01 or more , More preferably 0.05 or more, still more preferably 0.1 or more, may be 50 or less, more preferably 10 or less, still more preferably 5 or less, and particularly preferably, may be 1 or less.

作為化合物(A-I)，如下述表1~12中所示那樣，可列舉出由式(A-I-I)表示的化合物(A-I-1)~化合物(A-I-632)等。表中，*表示鍵合端。 As the compound (A-I), as shown in the following Tables 1 to 12, the compound (A-I-1) to the compound (A-I-632) represented by the formula (A-I-I) and the like can be cited. In the table, * indicates the bonding end.

不過，由式(A-I-I)表示的化合物具有2個-SO₂-N^--SO₂-CF₃，或者具有1個-SO₂-N^--SO₂-CF₃和1個-SO₃ ^-，該-SO₂-N^--SO₂-CF₃或-SO₃ ^-被作為R^h的任一個而含有，或者與由Ph1~Ph12表示的芳香族烴基的芳香族烴環(苯環)結合，優選地，結合於R⁴¹~R⁴⁴中的Ph1~Ph12所示的芳香族烴基的芳香族烴環(苯環)的從鍵合端來看的對位。 However, the compound represented by formula (AII) having two -SO _₂ -N ^- -SO ₂ -CF _3, or having an -SO _₂ -N ^- -SO ₂ -CF ₃ and a -SO ₃ ^-, The -SO ₂ -N ^-- SO ₂ -CF ₃ or -SO ₃ ^- is contained as any of R ^h , or is bonded to the aromatic hydrocarbon ring (benzene ring) of the aromatic hydrocarbon group represented by Ph1 to Ph12, Preferably, the para position of the aromatic hydrocarbon ring (benzene ring) bonded to the aromatic hydrocarbon group represented by Ph1 to Ph12 in R ⁴¹ to R ⁴⁴ from the bonding end.

表1~12中，Me表示甲基，Et表示乙基，iPr表示異丙基，Bt表示正丁基，EOE表示乙氧基乙基，14Bt表示丁烷-1,4-二基，Ph1~Ph12意味著由下述式表示的基團。式中，*表示鍵合端。 In Tables 1-12, Me means methyl, Et means ethyl, iPr means isopropyl, Bt means n-butyl, EOE means ethoxyethyl, 14Bt means butane-1,4-diyl, Ph1~ Ph12 means a group represented by the following formula. In the formula, * represents the bonding end.

另外，作為化合物(A-I)，如下述表13中所示那樣，也可列舉出由式(A-I-II)表示的化合物(A-I-634)~化合物(A-I-657)等。表中，*表示鍵合端。 In addition, as the compound (A-I), as shown in Table 13 below, compounds (A-I-634) to (A-I-657) represented by formula (A-I-II) and the like can also be cited. In the table, * indicates the bonding end.

不過，由式(A-I-II)表示的化合物平均具有1個-SO₂-N^--SO₂-CF₃和-SO₂-NH-SO₂-CF₃，該-SO₂-N^--SO₂-CF₃和-SO₂-NH-SO₂-CF₃被作為R^h的任一個而含有，或者與由Ph1、Ph13、Ph14的任一個表示的芳香族烴基的芳香族烴環(苯環)結合。 However, the compound represented by the formula (AI-II) has on average one -SO ₂ -N ^-- SO ₂ -CF ₃ and -SO ₂ -NH-SO ₂ -CF ₃ , the -SO ₂ -N ^-- SO ₂ -CF ₃ and -SO ₂ -NH-SO ₂ -CF ₃ are contained as any of R ^h , or an aromatic hydrocarbon ring (benzene ring) with an aromatic hydrocarbon group represented by any of Ph1, Ph13, and Ph14 ) Combine.

表13中，Me表示甲基，Et表示乙基，iPr表示異丙基，Bt表示正丁基，EOE表示乙氧基乙基，Hex表示正己基，Ph1、Ph13、Ph14意味著由下述式表示的基團。 In Table 13, Me represents methyl, Et represents ethyl, iPr represents isopropyl, Bt represents n-butyl, EOE represents ethoxyethyl, Hex represents n-hexyl, Ph1, Ph13, Ph14 are represented by the following formula Represents the group.

式中，*表示鍵合端。 In the formula, * represents the bonding end.

化合物(A-I)也能夠將由下述式(A-III)表示的化合物(以下也稱為化合物(A-III))混合而使用。 The compound (A-I) can also be used by mixing a compound represented by the following formula (A-III) (hereinafter also referred to as a compound (A-III)).

[式(A-III)中，R^21a~R^24a各自獨立地表示氫原子、碳數1~20的飽和烴基、可具有取代基的碳數6~20的芳香族烴基或可具有取代基的碳數7~30的芳烷基，該芳香族烴基和該芳烷基可具有的取代基可以為-SO₃ ^-，在該碳數1~20的飽和烴基中，該飽和烴基中所含的氫原子可以被取代或未取代的胺基或鹵素原子取代，該碳數1~20的飽和烴基為碳數2~20的烷基的情況下，該烷基中所含的亞甲基可以被替換為氧原子或-CO-。不過，該碳數2~20的烷基中，鄰接的亞甲基不會同時被替換為氧原子，末端的亞甲基不會被替換為氧原子或-CO-。R^21a與R^22a可結合並與它們結合的氮原子一起形成環，R^23a與R^24a可以結合並與它們結合的氮原子一起形成環。 [In formula (A-III), R ^21a to R ^24a each independently represent a hydrogen atom, a saturated hydrocarbon group with 1 to 20 carbons, an optionally substituted aromatic hydrocarbon group with 6 to 20 carbons, or an optionally substituted carbon atoms, an aralkyl group having 7 to 30, the aromatic hydrocarbon group and the aralkyl group may have a substituent group may be ₃ is -SO ^-, in which a saturated hydrocarbon group having 1 to 20 carbon atoms, a saturated hydrocarbon group contained in the The hydrogen atom may be substituted by a substituted or unsubstituted amine group or a halogen atom. When the saturated hydrocarbon group having 1 to 20 carbon atoms is an alkyl group having 2 to 20 carbon atoms, the methylene group contained in the alkyl group may be Replace with oxygen atom or -CO-. However, in this C2-C20 alkyl group, adjacent methylene groups are not simultaneously replaced with oxygen atoms, and terminal methylene groups are not replaced with oxygen atoms or -CO-. R ^21a and R ^22a may be combined with the nitrogen atom to which they are combined to form a ring, and R ^23a and R ^24a may be combined with the nitrogen atom to which they are combined to form a ring.

R^27a~R^34a各自獨立地表示氫原子、鹵素原子、硝基、羥基、-SO₃ ^-或碳數1~8的烷基，構成該烷基的亞甲基可以被替換為氧原子或-CO-。R^28a與R^32a可相互結合而形成-NH-、-S-、或-SO₂-。 R ^27a to R ^34a each independently represent a hydrogen atom, a halogen atom, a nitro group, a hydroxyl group, -SO ₃ ^- or an alkyl group having 1 to 8 carbons, and the methylene group constituting the alkyl group may be replaced with an oxygen atom or- CO-. R ^28a and R ^32a may combine with each other to form -NH-, -S-, or -SO ₂ -.

環T¹⁰表示碳數3~10的芳香族雜環，該芳香族雜環可具有碳數1~20的飽和烴基或可具有取代基的碳數6~20的芳香族烴基。該芳香族烴基可具有的取代基可以為-SO₃ ^-。 The ring T ¹⁰ represents an aromatic heterocyclic ring having 3 to 10 carbon atoms, and the aromatic heterocyclic ring may have a saturated hydrocarbon group having 1 to 20 carbon atoms or an optionally substituted aromatic hydrocarbon group having 6 to 20 carbon atoms. The aromatic hydrocarbon group may have a substituent group may be -SO ₃ ^-.

M^r+和r與上述同義。 M ^r+ and r have the same meaning as above.

k2表示由式(A-III)表示的化合物具有的-SO₃ ^-的個數。 k2 represents the number of -SO ₃ ^- possessed by the compound represented by formula (A-III).

不過，由式(A-III)表示的化合物具有至少1個-SO₃ ^-。] However, the compound represented by the formula (A-III) having at least one -SO ₃ ^-. ]

由R^21a~R^24a表示的飽和烴基、芳香族烴基、芳烷基各自可列舉出與由R⁴¹~R⁴⁴表示的飽和烴基、芳香族烴基、芳烷基同樣的基團。 The saturated hydrocarbon groups, aromatic hydrocarbon groups, and aralkyl groups represented by R ^21a to R ^24a each include the same groups as the saturated hydrocarbon groups, aromatic hydrocarbon groups, and aralkyl groups represented by R ⁴¹ to R ⁴⁴ .

另外，作為由R^27a~R^34a表示的烷基，可列舉出與由R⁴⁷~R⁵⁴表示的烷基同樣的基團。 In addition, as the alkyl group represented by R ^27a to R ^34a , the same groups as the alkyl group represented by R ⁴⁷ to R ^{54 can be} cited.

進而，化合物(A-III)優選具有1個以上的-SO₃ ^-，具體地，-SO₃ ^-更優選(a’)被作為R^27a~R^34a的任一個而含有，或者(b’)與由上述R^21a~R^24a表示的可具有取代基的碳數6~20的芳香族烴基結合，或者(c’)與由R^21a~R^24a表示的可具有取代基的碳數7~30的芳烷基結合，或者(d’)與將由T³表示的芳香族雜環的氫原子取代的碳數6~20的芳香族烴基的任一個結合，或者為這些(a’) ~(d’)的組合，更優選為(b’)、(c’)、(d’)或這些(b’)~(d’)的組合。-SO₃ ^-的數優選為0~6，更優選為1~6，進一步優選為1~3。 Further, (A-III) is preferably a compound having one or more -SO ₃ ^-, in particular, -SO ₃ ^- and more preferably (a ') according to any R ^27a ~ R ^34a is a contained, or is used as (b') Combine with the above-mentioned R ^21a to R ^24a and optionally substituted aromatic hydrocarbon groups having 6 to 20 carbon atoms, or (c') and R ^21a to R ^24a and optionally substituted carbon numbers 7 to 30 Or (d') and any one of the aromatic hydrocarbon groups having 6 to 20 carbon atoms substituted by the hydrogen atom of the aromatic heterocyclic ring represented by T ³ , or these (a') ~(d The combination of') is more preferably (b'), (c'), (d') or a combination of these (b') to (d'). The number of -SO ₃ ^- is preferably 0-6, more preferably 1-6, and still more preferably 1-3.

-SO₃ ^-可結合於同一芳香族烴環，但優選結合於不同的芳香族烴環。 -SO ₃ ^- may be bonded to the same aromatic hydrocarbon ring, but is preferably bonded to different aromatic hydrocarbon rings.

將化合物(A-I)和化合物(A-III)混合的情況下，化合物(A-III)的含量，相對於化合物(A-I)100摩爾，優選1摩爾以上，更優選為20摩爾以上，進一步優選為40摩爾以上，優選為90摩爾以下，更優選為80摩爾以下，進一步優選為70摩爾以下。 In the case of mixing compound (AI) and compound (A-III), the content of compound (A-III) relative to 100 mol of compound (AI) is preferably 1 mol or more, more preferably 20 mol or more, and still more preferably 40 mol or more, preferably 90 mol or less, more preferably 80 mol or less, and even more preferably 70 mol or less.

化合物(A-I)例如能夠通過將由式(A-IV)表示的化合物(以下有時稱為化合物(A-IV))磺化而製成化合物(A-III)，與由下述式(A-II)表示的化合物反應而製造。化合物(A-I)根據需要可與包含r價的金屬離子M^r+的鹵化物(優選地氯化物)、醋酸鹽、磷酸鹽、硫酸鹽、矽酸鹽、氰化物等反應。化合物(A-IV)優選為鹽酸鹽、磷酸鹽、高氯酸鹽、BF₄鹽、PF₆鹽等。 Compound (AI), for example, can be made into compound (A-III) by sulfonating a compound represented by formula (A-IV) (hereinafter sometimes referred to as compound (A-IV)), and can be made into compound (A-III) by the following formula (A-IV) II) The compound shown is produced by reacting. The compound (AI) can react with halide (preferably chloride), acetate, phosphate, sulfate, silicate, cyanide, etc., containing the r-valent metal ion Mr ⁺ as required. Compound (A-IV) is preferably hydrochloride, phosphate, perchlorate, BF ₄ salt, PF ₆ salt, or the like.

[式(A-IV)中，R^1a~R^4a各自獨立地表示可被取代或未取代的胺基或鹵素原子取代的碳數1~20的飽和烴基、碳數2~20的烷基且構成該烷基的亞甲基被替換為氧原子或-CO-的基團、可具有取代基的碳數6~20的芳香族烴基、可具有取代基的碳數7~30的芳烷基或氫原子。R^1a與R^2a可結合並與它們結合的氮原子一起形成環，R^3a與R^4a可結合並與它們結合的氮原子一起形成環。 [In formula (A-IV), R ^1a to R ^4a each independently represent a saturated hydrocarbon group with 1 to 20 carbons, an alkyl group with 2 to 20 carbons, which may be substituted by a substituted or unsubstituted amine group or a halogen atom, and The methylene group constituting the alkyl group is substituted with an oxygen atom or -CO-, an aromatic hydrocarbon group having 6 to 20 carbons which may have a substituent, and an aralkyl group having 7 to 30 carbons which may have a substituent Or a hydrogen atom. R ^1a and R ^2a may be combined with the nitrogen atom to which they are combined to form a ring, and R ^3a and R ^4a may be combined with the nitrogen atom to which they are combined to form a ring.

R^7a~R^14a各自獨立地表示氫原子、鹵素原子、硝基、羥基或碳數1~8的烷基，構成該烷基的亞甲基可被替換為氧原子或-CO-。R^8a與R^12a可相互結合而形成-NH-、-S-、或-SO₂-。 R ^7a to R ^14a each independently represent a hydrogen atom, a halogen atom, a nitro group, a hydroxyl group, or an alkyl group having 1 to 8 carbon atoms, and the methylene group constituting the alkyl group may be replaced with an oxygen atom or -CO-. R ^8a and R ^12a may be combined with each other to form -NH-, -S-, or -SO ₂ -.

環T¹¹表示碳數3~10的芳香族雜環，該芳香族雜環可具有碳數1~20的飽和烴基或可具有取代基的碳數6~20的芳香族烴基。 The ring T ¹¹ represents an aromatic heterocyclic ring having 3 to 10 carbon atoms, and the aromatic heterocyclic ring may have a saturated hydrocarbon group having 1 to 20 carbon atoms or an optionally substituted aromatic hydrocarbon group having 6 to 20 carbon atoms.

M¹表示Cl^-、磷酸離子、高氯酸離子、BF₄ ^-、PF₆ ^-。] M ¹ represents Cl ^-, phosphate ion, perchlorate _{^{_{^{ion, BF 4 -, PF 6 -}}}} . ]

[式(A-III)中，R^21a~R^24a、R^27a~R^34a、環T¹⁰、M^r+、r、k2與上述同義。 [In formula (A-III), R ^21a to R ^24a , R ^27a to R ^34a , ring T ¹⁰ , Mr ⁺ , r, and k2 have the same meaning as above.

[式(A-II)中，R^f與上述同義。] [In formula (A-II), R ^f has the same meaning as above. ]

[式(A-I)中，R⁴¹~R⁴⁴、R⁴⁷~R⁵⁴、環T¹、k、M^r+和r與上述同義。] [In formula (AI), R ⁴¹ to R ⁴⁴ , R ⁴⁷ to R ⁵⁴ , ring T ¹ , k, Mr ⁺ and r have the same meaning as above. ]

作為磺化的方法，可列舉出公知的各種方法，例如Journal of Organic Chemistry，(1994)，第59卷，# 11，第3232-3236頁中記載的方法。 As the method of sulfonation, various known methods can be cited, for example, the method described in Journal of Organic Chemistry, (1994), Vol. 59, #11, pp. 3232-3236.

本發明的化合物(A-I)能夠應用於纖維製品，例如通過在纖維材料中混煉、浸漬、附著等而能夠使纖維材料著色。 The compound (A-I) of the present invention can be applied to fiber products, for example, the fiber material can be colored by kneading, impregnating, adhering, etc. in the fiber material.

本發明的著色組合物包含著色劑(A)，著色劑(A)包含化合物(A-I)。本發明的著色組合物優選還包含溶劑(E)，更優選還包含樹脂(B)、聚合性化合物(C)、聚合引發劑(D)。可還包含聚合引發助劑(D1)、流平劑(F)。 The coloring composition of the present invention contains a colorant (A), and the colorant (A) contains a compound (A-I). The coloring composition of the present invention preferably further contains a solvent (E), and more preferably further contains a resin (B), a polymerizable compound (C), and a polymerization initiator (D). The polymerization initiator (D1) and the leveling agent (F) may be further included.

以下有時將包含樹脂(B)、聚合性化合物(C)和聚合引發劑(D)的著色組合物稱為著色固化性樹脂組合物。 Hereinafter, the colored composition containing the resin (B), the polymerizable compound (C), and the polymerization initiator (D) may be referred to as a colored curable resin composition.

本說明書中，作為各成分例示的化合物，只要無特別說明，則能夠單獨地使用或將多種組合使用。 In this specification, the compound exemplified as each component can be used singly or in combination of multiple types unless otherwise specified.

溶劑(E) Solvent (E)

對溶劑(E)並無特別限定，能夠使用該領域中通常使用的溶劑。例如，可列舉酯溶劑(在分子內包含-COO-、不含-O-的溶劑)、醚溶劑(在分子內包含-O-、不含-COO-的溶劑)、醚酯溶劑(在分子內包含-COO-和-O-的溶劑)、酮溶劑(在分子內包含-CO-、不含-COO-的溶劑)、醇溶劑(在分子內包含OH、不含-O-、-CO-和-COO-的溶劑)、芳香族烴溶劑、醯胺溶劑、二甲基亞碸等。 The solvent (E) is not particularly limited, and solvents generally used in this field can be used. For example, ester solvents (solvents containing -COO- and no -O- in the molecule), ether solvents (solvents that contain -O- and no -COO- in the molecule), ether ester solvents (Solvents containing -COO- and -O-), ketone solvents (solvents containing -CO- and no -COO- in the molecule), alcohol-soluble Agents (solvents containing OH in the molecule and not containing -O-, -CO- and -COO-), aromatic hydrocarbon solvents, amide solvents, dimethyl sulfide, etc.

作為酯溶劑，可列舉乳酸甲酯、乳酸乙酯、乳酸丁酯、2-羥基異丁酸甲酯、醋酸乙酯、醋酸正丁酯、醋酸異丁酯、甲酸戊酯、醋酸異戊酯、丙酸丁酯、丁酸異丙酯、丁酸乙酯、丁酸丁酯、丙酮酸甲酯、丙酮酸乙酯、丙酮酸丙酯、乙醯乙酸甲酯、乙醯乙酸乙酯、環己醇乙酸酯、γ-丁內酯等。 As the ester solvent, methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutyrate, ethyl acetate, n-butyl acetate, isobutyl acetate, pentyl formate, isoamyl acetate, Butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetyl acetate, ethyl acetyl acetate, cyclohexane Alcohol acetate, γ-butyrolactone, etc.

作為醚溶劑，可列舉乙二醇單甲基醚、乙二醇單乙基醚、乙二醇單丙基醚、乙二醇單丁基醚、二甘醇單甲基醚、二甘醇單乙基醚、二甘醇單丁基醚、丙二醇單甲基醚、丙二醇單乙基醚、丙二醇單丙基醚、丙二醇單丁基醚、3-甲氧基-1-丁醇、3-甲氧基-3-甲基丁醇、四氫呋喃、四氫吡喃、1,4-二噁烷、二甘醇二甲基醚、二甘醇二乙基醚、二甘醇甲基乙基醚、二甘醇二丙基醚、二甘醇二丁基醚、茴香醚、苯***和甲基茴香醚等。 As the ether solvent, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol mono Ethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methyl Oxyoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, Diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenethyl ether and methyl anisole, etc.

作為醚酯溶劑，可列舉甲氧基醋酸甲酯、甲氧基醋酸乙酯、甲氧基醋酸丁酯、乙氧基醋酸甲酯、乙氧基醋酸乙酯、3-甲氧基丙酸甲酯、3-甲氧基丙酸乙酯、3-乙氧基丙酸甲酯、3-乙氧基丙酸乙酯、2-甲氧基丙酸甲酯、2-甲氧基丙酸乙酯、2-甲氧基丙酸丙酯、2-乙氧基丙酸甲酯、2-乙氧基丙酸乙酯、2-甲氧基-2-甲基丙酸甲酯、2-乙氧基-2-甲基丙酸乙酯、3-甲氧基丁基乙酸酯、3-甲基-3-甲氧基丁基乙酸酯、丙二醇單甲基醚乙酸酯、丙二醇單乙基醚乙酸酯、丙二醇單丙基醚乙酸酯、乙二醇單甲基醚乙酸酯、乙二醇單乙基醚乙酸酯、二甘醇單乙基醚乙酸酯、二甘醇單丁基醚乙酸酯和二丙二醇甲基醚乙酸酯等。 Examples of ether ester solvents include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, and methyl 3-methoxypropionate. Ester, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate Ester, 2-methoxypropyl propionate, 2-ethoxy methyl propionate, 2-ethoxy ethyl propionate, 2-methoxy-2-methyl propionate, 2-ethyl Ethyl oxy-2-methylpropionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol mono B Base ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate Alcohol monobutyl ether acetate and dipropylene glycol methyl ether acetate, etc.

作為酮溶劑，可列舉4-羥基-4-甲基-2-戊酮、丙酮、2-丁酮、2-庚酮、3-庚酮、4-庚酮、4-甲基-2-戊酮、環戊酮、環己酮和異佛爾酮等。 Examples of the ketone solvent include 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone Ketones, cyclopentanone, cyclohexanone and isophorone, etc.

作為醇溶劑，可列舉甲醇、乙醇、丙醇、丁醇、己醇、環己醇、乙二醇、丙二醇和甘油等。 Examples of alcohol solvents include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerin.

作為芳香族烴溶劑，可列舉苯、甲苯、二甲苯和1,3,5-三甲基苯等。 As an aromatic hydrocarbon solvent, benzene, toluene, xylene, 1,3,5-trimethylbenzene, etc. are mentioned.

作為醯胺溶劑，可列舉N,N-二甲基甲醯胺、N,N-二甲基乙醯胺和N-甲基吡咯烷酮等。 Examples of the amide solvent include N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, and the like.

這些溶劑可單獨使用，也可將2種以上並用。 These solvents may be used alone or in combination of two or more kinds.

其中，優選乙二醇單甲基醚、乙二醇單丁基醚、丙二醇單甲基醚、二甘醇單甲基醚、二甘醇單乙基醚、丙二醇單甲基醚乙酸酯、二丙二醇甲基醚乙酸酯、3-甲氧基-1-丁醇、3-甲氧基丁基乙酸酯、3-乙氧基丙酸乙酯、乳酸乙酯、N-甲基吡咯烷酮、4-羥基-4-甲基-2-戊酮、N,N-二甲基甲醯胺等，更優選乙二醇單丁基醚、丙二醇單甲基醚、丙二醇單甲基醚乙酸酯、二丙二醇甲基醚乙酸酯、3-甲氧基-1-丁醇、3-甲氧基丁基乙酸酯、3-乙氧基丙酸乙酯、乳酸乙酯、N-甲基吡咯烷酮。 Among them, ethylene glycol monomethyl ether, ethylene glycol monobutyl ether, propylene glycol monomethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, propylene glycol monomethyl ether acetate, Dipropylene glycol methyl ether acetate, 3-methoxy-1-butanol, 3-methoxybutyl acetate, ethyl 3-ethoxypropionate, ethyl lactate, N-methylpyrrolidone , 4-hydroxy-4-methyl-2-pentanone, N,N-dimethylformamide, etc., more preferably ethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetic acid Ester, dipropylene glycol methyl ether acetate, 3-methoxy-1-butanol, 3-methoxybutyl acetate, ethyl 3-ethoxypropionate, ethyl lactate, N-methyl Pyrrolidone.

包含溶劑(E)的情況下，溶劑(E)的含有率，相對於著色組合物的總量，優選為70~95質量%，更優選為75~92質量%。換言之，著色組合物的固體成分的總量優選為5~30質量%，更優選為8~25質量%。如果溶劑(E)的含有率在上述的範圍，則塗布時的平坦性變得良好，另外形成了濾色器時色濃度不會不足，因此具有顯示特性變得良好的傾向。 When the solvent (E) is included, the content of the solvent (E) is preferably 70 to 95% by mass relative to the total amount of the coloring composition, and more Preferably it is 75-92 mass %. In other words, the total solid content of the coloring composition is preferably 5 to 30% by mass, and more preferably 8 to 25% by mass. If the content of the solvent (E) is in the above-mentioned range, the flatness during application becomes good, and the color density is not insufficient when the color filter is formed, so there is a tendency for the display characteristics to become good.

本說明書中“固體成分的總量”是指從著色組合物中將溶劑(E)除去了的成分的合計量。固體成分的總量及相對於其的各成分的含量例如能夠採用液相色譜或氣相色譜等公知的分析手段測定。 In this specification, the "total amount of solid content" refers to the total amount of the components from the coloring composition from which the solvent (E) has been removed. The total amount of solid content and the content of each component relative to it can be measured by a known analysis means such as liquid chromatography or gas chromatography.

著色劑(A) Colorant (A)

著色劑(A)可單獨地使用以本發明的化合物(A-I)作為有效成分的染料，但為了調色，即，為了調整分光特性，可還包含其他的染料(A1)、顏料(P)、或它們的混合物。 The colorant (A) may be a dye containing the compound (AI) of the present invention as an active ingredient alone, but for the purpose of toning, that is, to adjust the spectral characteristics, it may further contain other dyes (A1), pigments (P), Or a mixture of them.

作為染料(A1)，可列舉油溶性染料、酸性染料、鹼性染料、直接染料、媒染染料、酸性染料的胺鹽、酸性染料的磺醯胺衍生物等染料，可列舉例如在色指數(The Society of Dyers and Colourists出版)中分類為染料的化合物、染色筆記(色染社)中記載的公知的染料。此外，根據化學結構，可列舉偶氮染料、菁染料、三苯基甲烷染料、呫噸染料、酞菁染料、萘醌染料、醌亞胺染料、次甲基染料、偶氮甲鹼染料、方酸染料、吖啶染料、苯乙烯基染料、香豆素染料、喹啉染料和硝基染料等。這些中，優選使用有機溶劑可溶性染料。 Examples of the dye (A1) include dyes such as oil-soluble dyes, acid dyes, basic dyes, direct dyes, mordant dyes, amine salts of acid dyes, and sulfonamide derivatives of acid dyes. Examples include A compound classified as a dye in Society of Dyers and Colourists, and a known dye described in the dyeing note (Sei Dyesha). In addition, according to the chemical structure, azo dyes, cyanine dyes, triphenylmethane dyes, xanthene dyes, phthalocyanine dyes, naphthoquinone dyes, quinonimine dyes, methine dyes, azomethine dyes, square Acid dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline dyes and nitro dyes. Among these, organic solvent-soluble dyes are preferably used.

作為染料(A1)，具體地，可列舉出C.I.溶劑黃4(以下省略C.I.溶劑黃的記載，只記載序號。)、14、15、23、24、25、38、62、63、68、79、81、82、83、89、94、98、99、162；C.I.溶劑紅24、45、49、90、91、118、119、122、124、125、127、130、132、145、160、218；C.I.溶劑橙2、7、11、15、26、41、54、56、99；C.I.溶劑藍4、5、37、67、70、90；C.I.溶劑綠1、4、5、7、34、35等C.I.溶劑染料、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、91、92、97、98、99、111、112、113、114、116、119、123、128、134、135、138、139、140、144、150、151、155、157、160、161、163、168、169、172、177、178、179、184、190、193、196、197、199、202、203、204、205、207、211、212、214、220、221、228、230、232、235、238、240、242、243、251、274、289；C.I.酸性紅1、4、8、14、17、18、26、27、29、31、34、35、37、42、44、50、51、52、57、66、73、87、88、91、92、94、97、103、111、114、129、133、134、138、143、145、150、151、158、176、182、183、195、198、206、211、215、216、217、227、228、249、252、257、258、260、261、266、268、270、274、277、280、281、289、308、312、315、316、339、341、345、346、 349、382、383、388、394、401、412、417、418、422、426；C.I.酸性橙6、7、8、10、12、26、50、51、52、56、62、63、64、74、75、94、95、107、108、169、173；C.I.酸性紫6B、7、9、17、19、30、102、120；C.I.酸性藍1、7、9、15、18、22、29、42、59、60、62、70、72、74、82、83、86、87、90、92、93、100、102、103、104、113、117、120、126、130、131、142、147、151、154、158、161、166、167、168、170、171、184、187、192、199、210、229、234、236、242、243、256、259、267、285、296、315、335；C.I.酸性綠1、3、5、9、16、50、58、63、65、80、104、105、106、109等C.I.酸性染料、C.I.直接黃2、33、34、35、38、39、43、47、50、54、58、68、69、70、71、86、93、94、95、98、102、108、109、129、136、138、141；C.I.直接紅79、82、83、84、91、92、96、97、98、99、105、106、107、172、173、176、177、179、181、182、184、204、207、211、213、218、220、221、222、232、233、234、241、243、246、250；C.I.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.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.直接橙26、34、39、41、46、50、52、56、57、61、64、65、68、70、96、97、106、107；C.I.直接紫47、52、54、59、60、65、66、79、80、81、82、84、89、90、93、95、96、103、104；C.I.直接藍1、2、6、8、15、22、25、41、57、71、76、78、80、81、84、85、86、90、93、94、95、97、98、99、100、101、106、107、108、109、113、114、115、117、119、120、137、149、150、153、155、156、158、159、160、161、162、163、164、165、166、167、168、170、171、172、173、188、189、190、192、193、194、195、196、198、199、200、201、202、203、207、209、210、212、213、214、222、225、226、228、229、236、237、238、242、243、244、245、246、247、248、249、250、251、252、256、257、259、260、268、274、275、293；C.I.直接綠25、27、31、32、34、37、63、65、66、67、68、69、72、77、79、82等C.I.直接染料、C.I.分散黃51、54、76等C.I.分散染料、C.I.鹼性紅1、10；C.I.鹼性藍1、3、5、7、9、19、24、25、26、28、29、40、41、54、58、59、64、65、66、67、68； C.I.鹼性綠1等C.I.鹼性染料、C.I.活性黃2、76、116；C.I.活性橙16；C.I.活性紅36等C.I.活性染料、C.I.媒染黃5、8、10、16、20、26、30、31、33、42、43、45、56、61、62、65；C.I.媒染紅1、2、4、9、12、14、17、18、19、22、23、24、25、26、27、30、32、33、36、37、38、39、41、43、45、46、48、53、56、63、71、74、85、86、88、90、94、95；C.I.媒染橙3、4、5、8、12、13、14、20、21、23、24、28、29、32、34、35、36、37、42、43、47、48；C.I.媒染紫1、2、4、5、7、14、22、24、30、31、32、37、40、41、44、45、47、48、53、58；C.I.媒染藍1、2、3、7、9、12、13、15、16、19、20、21、22、26、30、31、39、40、41、43、44、49、53、61、74、77、83、84；C.I.媒染綠1、3、4、5、10、15、26、29、33、34、35、41、43、53等C.I.媒染染料、C.I.還原綠1等C.I.還原染料等。其中優選紫色染料。 Specific examples of the dye (A1) include CI Solvent Yellow 4 (hereinafter the description of CI Solvent Yellow is omitted, and only the serial number is given.), 14, 15, 23, 24, 25, 38, 62, 63, 68, 79 , 81, 82, 83, 89, 94, 98, 99, 162; CI Solvent Red 24, 45, 49, 90, 91, 118, 119, 122, 124, 125, 127, 130, 132, 145, 160, 218; CI solvent orange 2, 7, 11, 15, 26, 41, 54, 56, 99; CI solvent blue 4, 5, 37, 67, 70, 90; CI solvent green 1, 4, 5, 7, 34 , 35 and other CI solvent dyes, CI acid yellow 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 91, 92, 97, 98, 99, 111, 112, 113, 114, 116, 119, 123, 128, 134, 135, 138, 139, 140, 144, 150, 151, 155, 157, 160, 161, 163,168,169,172,177,178,179,184,190,193,196,197,199,202,203,204,205,207,211,212,214,220,221,228,230, 232, 235, 238, 240, 242, 243, 251, 274, 289; CI Acid Red 1, 4, 8, 14, 17, 18, 26, 27, 29, 31, 34, 35, 37, 42, 44 , 50, 51, 52, 57, 66, 73, 87, 88, 91, 92, 94, 97, 103, 111, 114, 129, 133, 134, 138, 143, 145, 150, 151, 158, 176 ,182,183,195,198,206,211,215,216,217,227,228,249,252,257,258,260,261,266,268,270,274,277,280,281,289 , 308, 312, 315, 316, 339, 341, 345, 346, 349, 382, 383, 388, 394, 401, 412, 417, 418, 422, 426; CI Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64 , 74, 75, 94, 95, 107, 108, 169, 173; CI Acid Violet 6B, 7, 9, 17, 19, 30, 102, 120; CI Acid Blue 1, 7, 9, 15, 18, 22 , 29, 42, 59, 60, 62, 70, 72, 74, 82, 83, 86, 87, 90, 92, 93, 100, 102, 103, 104, 113, 117, 120, 126, 130, 131 ,142,147,151,154,158,161,166,167,168,170,171,184,187,192,199,210,229,234,236,242,243,256,259,267,285 , 296, 315, 335; CI acid green 1, 3, 5, 9, 16, 50, 58, 63, 65, 80, 104, 105, 106, 109 and other CI acid dyes, CI direct yellow 2, 33, 34 , 35, 38, 39, 43, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 136, 138, 141; CI Direct Red 79, 82, 83, 84, 91, 92, 96, 97, 98, 99, 105, 106, 107, 172, 173, 176, 177, 179, 181, 182, 184, 204, 207, 211, 213,218,220,221,222,232,233,234,241,243,246,250; CI 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; CI direct yellow 2, 4, 28, 33, 34, 35, 38, 39, 43, 44, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 132, 136, 138, 141; CI Direct Orange 26 , 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107; CI direct purple 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104; CI direct blue 1, 2, 6, 8, 15, 22, 25, 41, 57, 71, 76 , 78, 80, 81, 84, 85, 86, 90, 93, 94, 95, 97, 98, 99, 100, 101, 106, 107, 108, 109, 113, 114, 115, 117, 119, 120 ,137,149,150,153,155,156,158,159,160,161,162,163,164,165,166,167,168,170,171,172,173,188,189,190,192 , 193, 194, 195, 196, 198, 199, 200, 201, 202, 203, 207, 209, 210, 212, 213, 214, 222, 225, 226, 228, 229, 236, 237, 238, 242 , 243, 244, 245, 246, 247, 248, 249, 250, 251, 252, 256, 257, 259, 260, 268, 274, 275, 293; CI direct green 25, 27, 31, 32, 34, CI direct dyes such as 37, 63, 65, 66, 67, 68, 69, 72, 77, 79, 82, CI disperse dyes such as CI Disperse Yellow 51, 54, 76, CI Basic Red 1, 10; CI Basic Blue 1, 3, 5, 7, 9, 19, 24, 25, 26, 28, 29, 40, 41, 54, 58, 59, 64, 65, 66, 67, 68; CI basic dyes such as CI Basic Green 1, CI Reactive Yellow 2, 76, 116; CI Reactive Orange 16; CI Reactive Dyes such as CI Reactive Red 36, CI Mordant Yellow 5, 8, 10, 16, 20, 26, 30 , 31, 33, 42, 43, 45, 56, 61, 62, 65; CI Mordant Red 1, 2, 4, 9, 12, 14, 17, 18, 19, 22, 23, 24, 25, 26, 27, 30, 32, 33, 36, 37, 38, 39, 41, 43, 45, 46, 48, 53, 56, 63, 71, 74, 85, 86, 88, 90, 94, 95; CI mordant Orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48; CI Mordant Violet 1, 2, 4, 5, 7, 14, 22, 24, 30, 31, 32, 37, 40, 41, 44, 45, 47, 48, 53, 58; CI Mordant Blue 1, 2, 3, 7, 9 , 12, 13, 15, 16, 19, 20, 21, 22, 26, 30, 31, 39, 40, 41, 43, 44, 49, 53, 61, 74, 77, 83, 84; CI mordant green 1, 3, 4, 5, 10, 15, 26, 29, 33, 34, 35, 41, 43, 53 and other CI mordant dyes, CI vat green 1 and other CI vat dyes, etc. Among them, purple dyes are preferred.

作為顏料(P)，並無特別限定，能夠使用公知的顏料，例如可列舉出色指數(The Society of Dyers and Colourists出版)中分類為顏料的顏料。 The pigment (P) is not particularly limited, and known pigments can be used. For example, pigments classified as pigments in the Excellent Index (published by The Society of Dyers and Colourists) can be cited.

作為顏料，例如可列舉出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、194、214等黃色顏料；C.I.顏料橙13、31、36、38、40、42、43、51、55、59、61、64、65、71、73等橙色的顏料；C.I.顏料紅9、97、105、122、123、144、149、166、168、176、177、180、192、209、215、216、224、242、254、255、264、265等紅色顏料；C.I.顏料藍15、15：3、15：4、15：6、60等青色顏料；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等綠色顏料；C.I.顏料棕23、25等棕色顏料；C.I.顏料黑1、7等黑色顏料等。 Examples of pigments include CI Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 129, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 194, 214 and other yellow pigments; CI pigment orange 13, 31, 36, 38, 40, 42, 43, 51, Orange pigments such as 55, 59, 61, 64, 65, 71, 73; CI Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 180, 192, 209, 215 , 216, 224, 242, 254, 255, 264, 265 and other red pigments; CI pigment blue 15, 15: 3, 15: 4, 15: 6, 60 and other cyan pigments; CI pigment violet 1, 19, 23, 29 , 32, 36, 38 and other purple pigments; CI Pigment Green 7, 36, 58 and other green pigments; CI Pigment Brown 23, 25 and other brown pigments; CI Pigment Black 1, 7 and other black pigments.

顏料(P)優選為酞菁顏料和二噁嗪顏料，更優選為選自C.I.顏料藍15：6和顏料紫23中的至少一種。通過包含上述的顏料，透射光譜的最適化容易，濾色器的耐光性和耐化學品性變得良好。 The pigment (P) is preferably a phthalocyanine pigment and a dioxazine pigment, and more preferably at least one selected from the group consisting of C.I. Pigment Blue 15:6 and Pigment Violet 23. By including the above-mentioned pigment, the transmission spectrum is easily optimized, and the light resistance and chemical resistance of the color filter become good.

對於顏料，根據需要，可實施松香處理、使用了導入了酸性基團或鹼性基團的顏料衍生物等的表面處理、採用高分子化合物等的對顏料表面的接枝處理、採用硫酸微粒化法等的微粒化處理、或者採用用於將雜質除去的有機溶劑、水等的洗淨處理、離子性雜質的採用離子交換法等的除去處理等。顏料優選粒徑是均一的。 For pigments, if necessary, rosin treatment, surface treatment using pigment derivatives introduced with acidic or basic groups, etc., grafting treatment to the surface of the pigment using polymer compounds, etc., and micronization with sulfuric acid Method, etc., or use to remove impurities Cleaning treatment of organic solvents, water, etc., removal treatment of ionic impurities by ion exchange methods, etc. The pigment preferably has a uniform particle size.

顏料通過含有顏料分散劑而進行分散處理，能夠得到顏料在溶液中均勻地分散的狀態的顏料分散液。顏料可各自單獨地進行分散處理，也可將多種混合進行分散處理。 The pigment contains a pigment dispersant and is subjected to a dispersion treatment to obtain a pigment dispersion in a state where the pigment is uniformly dispersed in the solution. The pigments may be separately subjected to dispersion treatment, or plural kinds may be mixed and subjected to dispersion treatment.

作為上述顏料分散劑，例如可列舉出表面活性劑，可以是陽離子系、陰離子系、非離子系、兩性的任一種的表面活性劑。具體地，可列舉出聚酯系、多胺系、丙烯酸系等的顏料分散劑等。這些顏料分散劑可單獨使用或者將2種以上組合使用。作為顏料分散劑，以商品名表示，可列舉出KP(信越化學工業(株)製造)、

(共榮社化學(株)製造)、

(註冊商標)(

(株)製造)、EFKA(註冊商標)(BASF公司製造)、

(註冊商標)(味之素

(株)製造)、Disperbyk(註冊商標)(

一株式會社製造)等。 As said pigment dispersing agent, surfactant is mentioned, for example, It may be any surfactant of a cationic type, an anionic type, a nonionic type, and amphoteric. Specifically, a polyester-based, polyamine-based, acrylic-based pigment dispersant, etc. can be cited. These pigment dispersants can be used individually or in combination of 2 or more types. As a pigment dispersant, it is represented by a trade name, and includes KP (manufactured by Shin-Etsu Chemical Co., Ltd.),

(Manufactured by Kyoeisha Chemical Co., Ltd.),

(Trademark)(

(Manufactured by Co., Ltd.), EFKA (registered trademark) (manufactured by BASF Corporation),

(Registered trademark) (Ajinomoto

(Manufactured by Co., Ltd.), Disperbyk (registered trademark) (

One Co., Ltd.) and so on.

使用顏料分散劑的情況下，其使用量相對於顏料100質量份，優選為100質量份以下，更優選為5質量份以上且50質量份以下。如果顏料分散劑的使用量在上述的範圍，則具有得到均勻的分散狀態的顏料分散液的傾向。 In the case of using a pigment dispersant, the amount 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 with respect to 100 parts by mass of the pigment. If the amount of the pigment dispersant used is within the above range, there is a tendency to obtain a pigment dispersion in a uniformly dispersed state.

化合物(A-I)的含有率，相對於固體成分的總量，優選為5質量%以上且70質量%以下，更優選為5質量%以上且60質量%以下，進一步優選為5質量%以上且50質量%以下。 The content of the compound (AI) relative to the total solid content is preferably 5% by mass or more and 70% by mass or less, more preferably 5% by mass or more and 60% by mass or less, and still more preferably 5% by mass or more and 50% by mass. Less than mass%.

另外，化合物(A-I)的含有率，相對於著色劑(A)的總量，優選為1質量%以上且100質量%以下，更優選為10質量%以上且100質量%以下。 In addition, the content of the compound (A-I) relative to the total amount of the colorant (A) is preferably 1% by mass or more and 100% by mass or less, and more preferably 10% by mass or more and 100% by mass or less.

另外，將化合物(A-I)與化合物(A-III)混合使用的情況下，化合物(A-I)與化合物(A-III)的合計的含有率，相對於固體成分的總量，優選為10質量%以上且70質量%以下，更優選為15質量%以上且60質量%以下。 In addition, when compound (AI) and compound (A-III) are used in combination, the total content of compound (AI) and compound (A-III) is preferably 10% by mass relative to the total solid content. Above and 70% by mass or less, and more preferably 15% by mass or more and 60% by mass or less.

包含染料(A1)的情況下，其含有率相對於著色劑(A)的總量，優選為0.5質量%以上且90質量%以下，更優選為0.5質量%以上且70質量%以下。包含顏料(P)的情況下，其含有率相對於著色劑(A)的總量，優選為1質量%以上且99質量%以下，更優選為1質量%以上且70質量%以下。 When the dye (A1) is contained, its content relative to the total amount of the colorant (A) is preferably 0.5% by mass or more and 90% by mass or less, and more preferably 0.5% by mass or more and 70% by mass or less. When the pigment (P) is contained, its content relative to the total amount of the colorant (A) is preferably 1% by mass or more and 99% by mass or less, and more preferably 1% by mass or more and 70% by mass or less.

著色劑(A)的含有率，相對於固體成分的總量，優選為5質量%以上且70質量%以下，更優選為5質量%以上且60質量%以下，進一步優選為5質量%以上且50質量%以下。 The content of the coloring agent (A) relative to the total solid content is preferably 5 mass% or more and 70 mass% or less, more preferably 5 mass% or more and 60 mass% or less, and still more preferably 5 mass% or more and 50% by mass or less.

樹脂(B) Resin (B)

樹脂(B)優選為鹼可溶性樹脂(B)。鹼可溶性樹脂(B)(以下有時稱為“樹脂(B)”)是包含來自從不飽和羧酸和不飽和羧酸酐中選擇的至少一種的單體(Ba)的結構單元的共聚物。 The resin (B) is preferably an alkali-soluble resin (B). The alkali-soluble resin (B) (hereinafter sometimes referred to as "resin (B)") is a copolymer containing structural units derived from at least one monomer (Ba) selected from unsaturated carboxylic acids and unsaturated carboxylic anhydrides.

作為這樣的樹脂(B)，可列舉以下的樹脂[K1]~[K6]等。 As such resin (B), the following resin [K1]-[K6] etc. are mentioned.

樹脂[K1]具有來自選自不飽和羧酸和不飽和羧酸酐中的至少一種的單體(a)(以下有時稱為“(a)”)的結構單元和來自具有碳數2~4的環狀醚結構和烯屬不飽和鍵的單體(b)(以下有時稱為“(b)”)的結構單元的共聚物；樹脂[K2]具有來自(a)的結構單元和來自(b)的結構單元、以及來自可與(a)共聚的單體(c)(不過，與(a)和(b)不同。)(以下有時稱為“(c)”)的結構單元的共聚物；樹脂[K3]具有來自(a)的結構單元和來自(c)的結構單元的共聚物；樹脂[K4]具有使(b)與來自(a)的結構單元加成的結構單元和來自(c)的結構單元的樹脂(共聚物)；樹脂[K5]具有使(a)與來自(b)的結構單元加成的結構單元和來自(c)的結構單元的樹脂(共聚物)；樹脂[K6]具有使(a)加成於來自(b)的結構單元、進而使羧酸酐加成的結構單元和來自(c)的結構單元的樹脂(共聚物)。 Resin [K1] has a resin derived from unsaturated carboxylic acid and unsaturated carboxylic anhydride The structural unit of at least one of the monomers (a) (hereinafter sometimes referred to as "(a)") and the monomer (b) derived from a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond (Hereinafter sometimes referred to as "(b)") copolymer of structural units; resin [K2] has structural units derived from (a), structural units derived from (b), and monomers copolymerizable with (a) Body (c) (However, it is different from (a) and (b).) (hereinafter sometimes referred to as "(c)") copolymer of structural units; resin [K3] has structural units derived from (a) and Copolymer of the structural unit derived from (c); resin [K4] has a structural unit added to the structural unit from (a) and a resin (copolymer) derived from the structural unit of (c); resin [ K5] A resin (copolymer) having a structural unit added to (a) and a structural unit derived from (b) and a structural unit derived from (c); resin [K6] has a resin (a) added to the structural unit derived from (b) A resin (copolymer) derived from the structural unit of (c) and the structural unit to which carboxylic anhydride is added further.

作為(a)，具體地，可列舉例如丙烯酸、甲基丙烯酸、巴豆酸、鄰-、間-、對-乙烯基苯甲酸等不飽和單羧酸類；馬來酸、富馬酸、檸康酸、中康酸、衣康酸、3-乙烯基鄰苯二甲酸、4-乙烯基鄰苯二甲酸、3,4,5,6-四氫鄰苯二甲酸、1,2,3,6-四氫鄰苯二甲酸、二甲基四氫鄰苯二甲酸、1,4-環己烯二羧酸等不飽和二羧酸類；甲基-5-降冰片烯-2,3-二羧酸、5-羧基雙環[2.2.1]庚-2-烯、5,6-二羧基雙環[2.2.1]庚-2-烯、5-羧基-5-甲基雙環[2.2.1]庚-2-烯、5-羧基-5-乙基雙環[2.2.1]庚-2-烯、5-羧基-6-甲基雙環[2.2.1]庚-2-烯、5-羧基-6-乙基雙環[2.2.1]庚-2-烯等含有羧基的雙環不飽和化合物類；馬來酸酐、檸康酸酐、衣康酸酐、3-乙烯基鄰苯二甲酸酐、4-乙烯基鄰苯二甲酸酐、3,4,5,6-四氫鄰苯二甲酸酐、1,2,3,6-四氫鄰苯二甲酸酐、二甲基四氫鄰苯二甲酸酐、5,6-二羧基雙環[2.2.1]庚-2-烯酐等不飽和二羧酸酐類；琥珀酸單[2-(甲基)丙烯醯氧基乙基]酯、鄰苯二甲酸單[2-(甲基)丙烯醯氧基乙基]酯等2元以上的多元羧酸的不飽和單[(甲基)丙烯醯氧基烷基]酯類；α-(羥基甲基)丙烯酸這樣的在同一分子中含有羥基和羧基的不飽和丙烯酸酯類等。 Specific examples of (a) include unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, ortho-, meta-, and p-vinyl benzoic acid; maleic acid, fumaric acid, citraconic acid , Mesaconic acid, itaconic acid, 3-vinyl phthalic acid, 4-vinyl phthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6- Unsaturated dicarboxylic acids such as tetrahydrophthalic acid, dimethyltetrahydrophthalic acid and 1,4-cyclohexene dicarboxylic acid; Methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo[2.2.1]hept-2-ene, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene, 5-carboxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-carboxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-carboxy-6-methylbicyclo[ 2.2.1]Hept-2-ene, 5-carboxy-6-ethylbicyclo[2.2.1]hept-2-ene and other bicyclic unsaturated compounds containing carboxyl groups; maleic anhydride, citraconic anhydride, itaconic anhydride , 3-vinyl phthalic anhydride, 4-vinyl phthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride Unsaturated dicarboxylic acid anhydrides such as formic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride; succinic acid mono[2-(methyl) Unsaturated mono[(meth)acryloxy group of polycarboxylic acid with two or more valences, such as acryloxyethyl] ester and phthalic acid mono[2-(meth)acryloxyethyl] ester Alkyl]esters; α-(hydroxymeth)acrylic acid, such as unsaturated acrylates containing hydroxyl and carboxyl groups in the same molecule.

這些中，從共聚反應性的方面、得到的樹脂在鹼水溶液中的溶解性的方面出發，優選丙烯酸、甲基丙烯酸、馬來酸酐等。 Among these, acrylic acid, methacrylic acid, maleic anhydride, etc. are preferable from the viewpoint of copolymerization reactivity and the solubility of the obtained resin in an aqueous alkali solution.

(b)是指例如具有碳數2~4的環狀醚結構(例如，選自環氧乙烷環、氧雜環丁烷環和四氫呋喃環中的至少1種)和烯屬不飽和鍵的聚合性化合物。 (b) refers to, for example, a cyclic ether structure having 2 to 4 carbon atoms (for example, at least one selected from the group consisting of an oxirane ring, an oxetane ring, and a tetrahydrofuran ring) and an ethylenically unsaturated bond Polymeric compound.

(b)優選具有碳數2~4的環狀醚和(甲基)丙烯醯氧基的單體。 (b) A monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth)acryloxy group is preferred.

應予說明，本說明書中，“(甲基)丙烯酸”表示選自丙烯酸和甲基丙烯酸中的至少1種。“(甲基)丙烯醯基”和“(甲基)丙烯酸酯”等的表述也具有同樣的意思。 It should be noted that in this specification, "(meth)acrylic acid" means selected from At least one of acrylic acid and methacrylic acid. Expressions such as "(meth)acryloyl" and "(meth)acrylate" also have the same meaning.

作為(b)，可列舉例如具有環氧乙基和烯屬不飽和鍵的單體(b1)(以下有時稱為“(b1)”)、具有氧雜環丁基和烯屬不飽和鍵的單體(b2)(以下有時稱為“(b2)”)、具有四氫呋喃基和烯屬不飽和鍵的單體(b3)(以下有時稱為“(b3)”)等。 Examples of (b) include monomers (b1) having an oxirane group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b1)"), and an oxetanyl group and an ethylenically unsaturated bond. The monomer (b2) (hereinafter sometimes referred to as "(b2)"), the monomer (b3) having a tetrahydrofuran group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b3)"), etc.

作為(b1)，可列舉例如具有直鏈狀或分支鏈狀的脂肪族不飽和烴被環氧化的結構的單體(b1-1)(以下有時稱為“(b1-1)”)、具有脂環式不飽和烴被環氧化的結構的單體(b1-2)(以下有時稱為“(b1-2)”)。 Examples of (b1) include monomers (b1-1) having a structure in which linear or branched aliphatic unsaturated hydrocarbons are epoxidized (hereinafter sometimes referred to as "(b1-1)"), A monomer (b1-2) having a structure in which an alicyclic unsaturated hydrocarbon is epoxidized (hereinafter may be referred to as "(b1-2)").

作為(b1-1)，可列舉(甲基)丙烯酸縮水甘油酯、(甲基)丙烯酸β-甲基縮水甘油酯、(甲基)丙烯酸β-乙基縮水甘油酯、縮水甘油基乙烯基醚、鄰-乙烯基苄基縮水甘油基醚、間-乙烯基苄基縮水甘油基醚、對-乙烯基苄基縮水甘油基醚、α-甲基-鄰-乙烯基苄基縮水甘油基醚、α-甲基-間-乙烯基苄基縮水甘油基醚、α-甲基-對-乙烯基苄基縮水甘油基醚、2,3-雙(縮水甘油氧基甲基)苯乙烯、2,4-雙(縮水甘油氧基甲基)苯乙烯、2,5-雙(縮水甘油氧基甲基)苯乙烯、2,6-雙(縮水甘油氧基甲基)苯乙烯、2,3,4-三(縮水甘油氧基甲基)苯乙烯、2,3,5-三(縮水甘油氧基甲基)苯乙烯、2,3,6-三(縮水甘油氧基甲基)苯乙烯、3,4,5-三(縮水甘油氧基甲基)苯乙烯、2,4,6-三(縮水甘油氧基甲基)苯乙烯等。 Examples of (b1-1) include glycidyl (meth)acrylate, β-methylglycidyl (meth)acrylate, β-ethylglycidyl (meth)acrylate, and glycidyl vinyl ether , O-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, α-methyl-o-vinylbenzyl glycidyl ether, α-Methyl-m-vinylbenzyl glycidyl ether, α-methyl-p-vinylbenzyl glycidyl ether, 2,3-bis(glycidyloxymethyl)styrene, 2, 4-bis(glycidoxymethyl)styrene, 2,5-bis(glycidoxymethyl)styrene, 2,6-bis(glycidoxymethyl)styrene, 2,3, 4-tris(glycidoxymethyl)styrene, 2,3,5-tris(glycidoxymethyl)styrene, 2,3,6-tris(glycidoxymethyl)styrene, 3,4,5-tris(glycidoxymethyl)styrene, 2,4,6-tris(glycidoxymethyl)styrene, etc.

作為(b1-2)，可列舉乙烯基環己烯一氧化物、1,2-環氧-4-乙烯基環己烷(例如，

(註冊商標)2000；(株)大賽璐製造)、(甲基)丙烯酸3,4-環氧環己基甲酯(例如，

(註冊商標)A400；(株)大賽璐製造)、(甲基)丙烯酸3,4-環氧環己基甲酯(例如，

M100；(株)大賽璐製造)、由式(BI)表示的化合物和由式(BII)表示的化合物等。 As (b1-2), vinylcyclohexene monoxide, 1,2-epoxy-4-vinylcyclohexane (for example,

(Registered trademark) 2000; (manufactured by Daicel), 3,4-epoxycyclohexyl methyl (meth)acrylate (for example,

(Registered trademark) A400; (manufactured by Daicel), 3,4-epoxycyclohexyl methyl (meth)acrylate (for example,

M100; (manufactured by Daicel Co., Ltd.), a compound represented by formula (BI), a compound represented by formula (BII), and the like.

[式(BI)和式(BII)中，R^a和R^b各自獨立地表示氫原子、或者碳數1~4的烷基，該烷基中所含的氫原子可被羥基取代。 [In formula (BI) and formula (BII), R ^a and R ^b each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the hydrogen atom contained in the alkyl group may be substituted by a hydroxyl group.

X^a和X^b表示單鍵、*-R^c-、*-R^c-O-、*-R^c-S-或*-R^c-NH-。 X ^a and X ^b represents a single ^{bond, * - R c -, *} - R c -O -, * - R c -S- or * -R ^c -NH-.

R^c表示碳數1~6的亞烷基。 R ^c represents an alkylene group having 1 to 6 carbon atoms.

*表示與O的鍵合端。] * Indicates the bonding end with O. ]

作為R^a、R^b的碳數1~4的烷基，可列舉出甲基、乙基、正丙基、異丙基、正丁基、仲丁基、叔丁基等。 As R ^a, R ^b is an alkyl group having 1 to 4 carbon atoms include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, t-butyl and the like.

作為R^a、R^b的氫原子被羥基取代的烷基，可列舉羥基甲基、1-羥基乙基、2-羥基乙基、1-羥基丙基、2-羥基丙基、3-羥基丙基、1-羥基-1-甲基乙基、2-羥基-1-甲基乙基、1-羥基丁基、2-羥基丁基、3-羥基丁基、4-羥基丁基等。 Examples of the alkyl groups in which the hydrogen atoms of R ^a and R ^b are substituted with hydroxy groups include hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 1-hydroxypropyl, 2-hydroxypropyl, and 3-hydroxypropyl. Group, 1-hydroxy-1-methylethyl, 2-hydroxy-1-methylethyl, 1-hydroxybutyl, 2-hydroxybutyl, 3-hydroxybutyl, 4-hydroxybutyl, etc.

作為R^a和R^b，優選氫原子、碳數1~4的烷基、或碳數1~4的羥基烷基，更優選為氫原子、或碳數1~4的烷基，具體地，優選地可列舉出氫原子、甲基、乙基、羥基甲基、1-羥基乙基、2-羥基乙基，更優選地可列舉出氫原子、甲基。 As R ^a and R ^b , a hydrogen atom, an alkyl group having 1 to 4 carbons, or a hydroxyalkyl group having 1 to 4 carbons is preferable, and a hydrogen atom or an alkyl group having 1 to 4 carbons is more preferable. Specifically, Preferably, a hydrogen atom, a methyl group, an ethyl group, a hydroxymethyl group, a 1-hydroxyethyl group, and a 2-hydroxyethyl group are mentioned, and more preferably, a hydrogen atom and a methyl group are mentioned.

作為R^c的亞烷基，可列舉出直鏈狀或分支鏈狀的亞烷基，具體地，可列舉出亞甲基、亞乙基、丙烷-1,3-二基、丁烷-1,4-二基、戊烷-1,5-二基、己烷-1,6-二基等直鏈狀亞烷基；丙烷-1,2-二基等分支鏈狀亞烷基。 Examples of the alkylene group of R ^c include linear or branched alkylene groups, and specific examples include methylene, ethylene, propane-1,3-diyl, and butane-1 ,4-diyl, pentane-1,5-diyl, hexane-1,6-diyl and other linear alkylene groups; propane-1,2-diyl and other branched chain alkylene groups.

作為X^a和X^b，優選單鍵、*-R^c-、或*-R^c-O-，更優選為單鍵、或*-R^c-O-，特別優選為單鍵、亞甲基、亞乙基、*-CH₂-O-和*-CH₂CH₂-O-，更優選地可列舉出單鍵、*-CH₂CH2-O-(*表示與O的鍵合端)。 X ^a and X ^{b are} preferably a single bond, *-R ^c -, or *-R ^c -O-, more preferably a single bond, or *-R ^c -O-, and particularly preferably a single bond and methylene , Ethylene, *-CH ₂ -O- and *-CH ₂ CH ₂ -O-, more preferably single bond, *-CH ₂ CH2-O- (* represents the bonding end with O) .

作為由式(BI)表示的化合物，可列舉出由式(BI-1)~式(BI-15)的任一個表示的化合物等。其中，優選由式(BI-1)、式(BI-3)、式(BI-5)、式(BI-7)、式(BI-9)或式(BI-11)~式(BI-15)表示的化合物，更優選由式(BI-1)、式(BI-7)、式(BI-9)或式(BI-15)表示的化合物。 As the compound represented by formula (BI), a compound represented by any one of formula (BI-1) to formula (BI-15), and the like can be cited. Among them, the formula (BI-1), the formula (BI-3), the formula (BI-5), the formula (BI-7), the formula (BI-9) or the formula (BI-11) ~ the formula (BI- The compound represented by 15) is more preferably a compound represented by formula (BI-1), formula (BI-7), formula (BI-9), or formula (BI-15).

作為由式(BII)表示的化合物，可列舉出由式(BII-1)~式(BII-15)的任一個表示的化合物等。其中，優選由式(BII-1)、式(BII-3)、式(BII-5)、式(BII-7)、式(BII-9)或式(BII-11)~式(BII-15)表示的化合物，更優選由式(BII-1)、式(BII-7)、式(BII-9)或式(BII-15)表示的化合物。 As a compound represented by formula (BII), the compound etc. which are represented by any one of formula (BII-1)-formula (BII-15) are mentioned. Among them, the formula (BII-1), formula (BII-3), formula (BII-5), formula (BII-7), formula (BII-9) or formula (BII-11) ~ formula (BII- The compound represented by 15) is more preferably a compound represented by formula (BII-1), formula (BII-7), formula (BII-9), or formula (BII-15).

由式(BI)表示的化合物和由式(BII)表示的化合物可各自單獨使用，也可將由式(BI)表示的化合物與由式(BII)表示的化合物並用。將它們並用的情況下，由式(BI)表示的化合物和由式(BII)表示的化合物的含有比率以摩爾基準計，優選為5：95~95：5，更優選為10：90~90：10，進一步優選為20：80~80：20。 The compound represented by formula (BI) and the compound represented by formula (BII) may each be used alone, or the compound represented by formula (BI) may be used in combination with the compound represented by formula (BII). When these are used in combination, the content ratio of the compound represented by the formula (BI) and the compound represented by the formula (BII) on a molar basis is preferably 5:95 to 95:5, more preferably 10:90 to 90 : 10, more preferably 20:80 to 80:20.

作為(b2)，更優選具有氧雜環丁基和(甲基)丙烯醯氧基的單體。作為(b2)，可列舉3-甲基-3- 甲基丙烯醯氧基甲基氧雜環丁烷、3-甲基-3-丙烯醯氧基甲基氧雜環丁烷、3-乙基-3-甲基丙烯醯氧基甲基氧雜環丁烷、3-乙基-3-丙烯醯氧基甲基氧雜環丁烷、3-甲基-3-甲基丙烯醯氧基乙基氧雜環丁烷、3-甲基-3-丙烯醯氧基乙基氧雜環丁烷、3-乙基-3-甲基丙烯醯氧基乙基氧雜環丁烷、3-乙基-3-丙烯醯氧基乙基氧雜環丁烷等。 As (b2), a monomer having an oxetanyl group and a (meth)acryloxy group is more preferable. As (b2), 3-methyl-3- Methacryloxymethyloxetane, 3-methyl-3-methacryloxymethyloxetane, 3-ethyl-3-methacryloxymethyloxetane Cyclobutane, 3-ethyl-3-propenyloxymethyloxetane, 3-methyl-3-methylpropenyloxyethyloxetane, 3-methyl-3 -Acrylic oxyethyl oxetane, 3-ethyl-3-methacrylic oxyethyl oxetane, 3-ethyl-3-propenoxy ethyl oxetane Butane etc.

作為(b3)，更優選具有四氫呋喃基和(甲基)丙烯醯氧基的單體。作為(b3)，具體地，可列舉丙烯酸四氢糠酯(例如，

V # 150、大阪有機化學工業(株)製造)、甲基丙烯酸四氢糠酯等。 As (b3), a monomer having a tetrahydrofuran group and a (meth)acryloxy group is more preferable. As (b3), specifically, tetrahydrofurfuryl acrylate (for example,

V # 150, Osaka Organic Chemical Industry Co., Ltd.), tetrahydrofurfuryl methacrylate, etc.

作為(b)，在能夠進一步提高得到的濾色器的耐熱性、耐化學品性等的可靠性的方面，優選為(b1)。進而，在著色組合物的保存穩定性優異的方面，更優選(b1-2)。 As (b), (b1) is preferable from the point which can further improve the reliability of the heat resistance, chemical resistance, etc. of the color filter obtained. Furthermore, (b1-2) is more preferable in terms of excellent storage stability of the coloring composition.

作為(c)，可列舉例如(甲基)丙烯酸甲酯、(甲基)丙烯酸乙酯、(甲基)丙烯酸正丁酯、(甲基)丙烯酸仲丁酯、(甲基)丙烯酸叔丁酯、(甲基)丙烯酸2-乙基己酯、(甲基)丙烯酸十二烷基酯、(甲基)丙烯酸月桂酯、(甲基)丙烯酸硬脂酯、(甲基)丙烯酸環戊酯、(甲基)丙烯酸環己酯、(甲基)丙烯酸2-甲基環己酯、(甲基)丙烯酸三環[5.2.1.0^2,6]癸烷-8-基酯(在該技術領域中，作為慣用名，稱為“(甲基)丙烯酸雙環戊酯”。此外，有時稱為“(甲基)丙烯酸三環癸酯”。)、(甲基)丙烯酸三環[5.2.1.0^2,6]癸烯-8-基酯(該技術領域中，作為慣用名，稱為“(甲基)丙烯酸雙環戊烯酯”。)、(甲基)丙烯酸雙環戊氧基乙酯、(甲基)丙烯酸異冰片酯、(甲基)丙烯酸金剛烷酯、(甲基)丙烯酸烯丙酯、(甲基)丙烯酸炔丙酯、(甲基)丙烯酸苯酯、(甲基)丙烯酸萘酯、(甲基)丙烯酸苄酯等(甲基)丙烯酸酯類；(甲基)丙烯酸2-羥基乙酯、(甲基)丙烯酸2-羥基丙酯等含有羥基的(甲基)丙烯酸酯類；馬來酸二乙酯、富馬酸二乙酯、衣康酸二乙酯等二羧酸二酯；雙環[2.2.1]庚-2-烯、5-甲基雙環[2.2.1]庚-2-烯、5-乙基雙環[2.2.1]庚-2-烯、5-羥基雙環[2.2.1]庚-2-烯、5-羥基甲基雙環[2.2.1]庚-2-烯、5-(2’-羥基乙基)雙環[2.2.1]庚-2-烯、5-甲氧基雙環[2.2.1]庚-2-烯、5-乙氧基雙環[2.2.1]庚-2-烯、5,6-二羥基雙環[2.2.1]庚-2-烯、5,6-二(羥基甲基)雙環[2.2.1]庚-2-烯、5,6-二(2’-羥基乙基)雙環[2.2.1]庚-2-烯、5,6-二甲氧基雙環[2.2.1]庚-2-烯、5,6-二乙氧基雙環[2.2.1]庚-2-烯、5-羥基-5-甲基雙環[2.2.1]庚-2-烯、5-羥基-5-乙基雙環[2.2.1]庚-2-烯、5-羥基甲基-5-甲基雙環[2.2.1]庚-2-烯、5-叔-丁氧基羰基雙環[2.2.1]庚-2-烯、5-環己氧基羰基雙環[2.2.1]庚-2-烯、5-苯氧基羰基雙環[2.2.1]庚-2-烯、5,6-雙(叔-丁氧基羰基)雙環[2.2.1]庚-2-烯、5,6-雙(環己氧基羰基)雙環[2.2.1]庚-2-烯等雙環不飽和化合物類；N-苯基馬來醯亞胺、N-環己基馬來醯亞胺、N-苄基馬來醯亞胺、N-琥珀醯亞胺基-3-馬來醯亞胺苯甲酸鹽、N-琥珀醯亞胺基-4-馬來醯亞胺丁酸鹽、N-琥珀醯亞胺基-6-馬來醯亞胺己酸鹽、N-琥珀醯亞胺基-3-馬來醯亞胺丙酸鹽、N-(9-吖啶基)馬來醯亞胺等二羰基亞胺衍生物類；苯乙烯、α-甲基苯乙烯、間-甲基苯乙烯、對-甲基苯乙烯、乙烯基甲苯、對-甲氧基苯乙烯等含有乙烯基的芳香族化合物；丙烯腈、甲基丙烯腈等含有乙烯基的腈；氯乙烯、偏氯乙烯等鹵代烴；丙烯醯胺、甲基丙烯醯胺等含有乙烯基的醯胺；醋酸乙烯酯等酯；1,3-丁二烯、異戊二烯、2,3-二甲基-1,3-丁二烯等二烯等。 Examples of (c) include methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, sec-butyl (meth)acrylate, and tert-butyl (meth)acrylate , 2-ethylhexyl (meth)acrylate, dodecyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, cyclopentyl (meth)acrylate, Cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclo[5.2.1.0 ^2,6 ]decane-8-yl (meth)acrylate (in this technical field As a common name, it is called "dicyclopentyl (meth)acrylate." In addition, it is sometimes called "tricyclodecyl (meth)acrylate".), tricyclo (meth)acrylate [5.2.1.0 ^{2 ,6} ] decene-8-yl ester (in this technical field, as a common name, called "(meth)acrylate dicyclopentenyl ester".), (meth)acrylate dicyclopentyloxyethyl, (meth) Base) isobornyl acrylate, adamantyl (meth)acrylate, allyl (meth)acrylate, propargyl (meth)acrylate, phenyl (meth)acrylate, naphthyl (meth)acrylate, (Meth)acrylates such as benzyl (meth)acrylate; (meth)acrylates containing hydroxyl groups such as 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate; horses Diethyl ester, diethyl fumarate, diethyl itaconate and other dicarboxylic acid diesters; bicyclo[2.2.1]hept-2-ene, 5-methylbicyclo[2.2.1]hept- 2-ene, 5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxybicyclo[2.2.1]hept-2-ene, 5-hydroxymethylbicyclo[2.2.1]hept-2-ene Ene, 5-(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5-methoxybicyclo[2.2.1]hept-2-ene, 5-ethoxybicyclo[2.2. 1]Hept-2-ene, 5,6-dihydroxybicyclo[2.2.1]hept-2-ene, 5,6-bis(hydroxymethyl)bicyclo[2.2.1]hept-2-ene, 5, 6-Bis(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5,6-dimethoxybicyclo[2.2.1]hept-2-ene, 5,6-diethoxy Bicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-ethylbicyclo[2.2.1]hept-2 -Ene, 5-hydroxymethyl-5-methylbicyclo[2.2.1]hept-2-ene, 5-tert-butoxycarbonylbicyclo[2.2.1]hept-2-ene, 5-cyclohexyloxy Carbonyl carbonyl bicyclo[2.2.1]hept-2-ene, 5-phenoxycarbonyl bicyclo[2.2.1]hept-2-ene, 5,6-bis(tert-butoxycarbonyl)bicyclo[2.2.1 ]Hept-2-ene, 5,6-bis(cyclohexoxycarbonyl)bicyclo[2.2.1]hept-2-ene and other bicyclic unsaturated compounds; N-phenylmaleimide, N-ring Hexylmaleimide, N-benzylmaleimide, N-succinimidyl- 3-maleimidin benzoate, N-succinimidyl-4-maleimidin butyrate, N-succinimidyl-6-maleimidin caproate, Dicarbonylimine derivatives such as N-succinimidyl-3-maleimine propionate, N-(9-acridinyl)maleimine; styrene, α-methylbenzene Aromatic compounds containing vinyl groups such as ethylene, m-methylstyrene, p-methylstyrene, vinyl toluene, and p-methoxystyrene; nitriles containing vinyl groups such as acrylonitrile and methacrylonitrile; Halogenated hydrocarbons such as vinyl chloride and vinylidene chloride; vinyl-containing amides such as acrylamide and methacrylamide; esters such as vinyl acetate; 1,3-butadiene, isoprene, 2,3 -Diene such as dimethyl-1,3-butadiene, etc.

這些中，作為(c)，從共聚反應性和耐熱性的方面出發，優選含有乙烯基的芳香族化合物、二羰基亞胺衍生物類、雙環不飽和化合物類。具體地，優選苯乙烯、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、雙環[2.2.1]庚-2-烯等。 Among these, as (c), from the viewpoints of copolymerization reactivity and heat resistance, aromatic compounds containing vinyl groups, dicarbonylimine derivatives, and bicyclic unsaturated compounds are preferred. Specifically, styrene, vinyl toluene, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo[2.2.1]heptane-2 -Ene, etc.

樹脂[K1]中，來自各個單體的結構單元的比率，在構成樹脂[K1]的全部結構單元中，優選為來自(a)的結構單元：2~60摩爾%來自(b)的結構單元：40~98摩爾%，更優選為來自(a)的結構單元：10~50摩爾%來自(b)的結構單元：50~90摩爾%。 In resin [K1], the ratio of the structural units derived from each monomer is preferably the structural unit derived from (a): 2-60 mol% of the structural unit derived from (b) among all the structural units constituting the resin [K1] : 40 to 98 mol%, more preferably structural unit derived from (a): 10 to 50 mol% structural unit derived from (b): 50 to 90 mol%.

如果樹脂[K1]的結構單元的比率在上述的範圍內，存在著色組合物的保存穩定性、形成著色圖案時的顯影性、和得到的濾色器的耐溶劑性優異的傾向。 If the ratio of the structural units of the resin [K1] is within the above-mentioned range, the storage stability of the coloring composition, the developability when forming a colored pattern, and And the color filter obtained tends to be excellent in solvent resistance.

樹脂[K1]能夠例如參考文獻《高分子合成的實驗法》(大津隆行著出版社(株)化學同人第1版第1次印刷1972年3月1日發行)中記載的方法和該文獻中記載的引用文獻來製造。 The resin [K1] can, for example, refer to the method described in the document "Experimental Method of Polymer Synthesis" (Otsu Takayuki Publishing Co., Ltd., Chemical Doujin 1st Edition, First Printing Issued on March 1, 1972) and the document Manufactured by the cited literature.

具體地，可列舉通過將(a)和(b)的規定量、聚合引發劑和溶劑等裝入反應容器中，例如，用氮將氧置換，從而形成脫氧氣氛，邊攪拌邊加熱和保溫的方法。應予說明，對於在此使用的聚合引發劑和溶劑等並無特別限定，能夠使用該領域中通常使用的物質。作為聚合引發劑，可列舉例如偶氮化合物(2,2’-偶氮二異丁腈、2,2’-偶氮二(2,4-二甲基戊腈)等)、有機過氧化物(過氧化苯甲醯等)，作為溶劑，只要將各單體溶解即可，可列舉作為本發明的著色組合物的溶劑(E)列舉的溶劑等。 Specifically, it can be exemplified by filling the predetermined amounts of (a) and (b), polymerization initiator, solvent, etc. in a reaction vessel, for example, replacing oxygen with nitrogen to form a deoxygenating atmosphere, heating and keeping warm while stirring method. In addition, the polymerization initiator, solvent, etc. used here are not particularly limited, and those generally used in this field can be used. Examples of the polymerization initiator include azo compounds (2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), etc.), organic peroxides (Benzyl peroxide etc.) As a solvent, what is necessary is just to dissolve each monomer, and the solvent etc. mentioned as the solvent (E) of the coloring composition of this invention are mentioned.

應予說明，對於得到的共聚物，可原樣地使用反應後的溶液，也可使用濃縮或稀釋的溶液，也可使用採用再沉澱等方法作為固體(粉體)取出的產物。特別地，該聚合時，作為溶劑，通過使用本發明的著色組合物中所含的溶劑，能夠原樣地將反應後的溶液在本發明的著色組合物的製備中使用，因此能夠使本發明的著色組合物的製造工序簡化。 In addition, for the obtained copolymer, the reaction solution may be used as it is, a concentrated or diluted solution may be used, or a product taken out as a solid (powder) by a method such as reprecipitation may be used. In particular, during the polymerization, by using the solvent contained in the coloring composition of the present invention as a solvent, the reacted solution can be used as it is in the preparation of the coloring composition of the present invention, so that the The manufacturing process of the coloring composition is simplified.

樹脂[K2]中，來自各個單體的結構單元的比率，在構成樹脂[K2]的全部結構單元中，優選為來自(a)的結構單元：2~45摩爾% 來自(b)的結構單元：2~95摩爾%來自(c)的結構單元：1~65摩爾%，更優選為來自(a)的結構單元：5~40摩爾%來自(b)的結構單元：5~80摩爾%來自(c)的結構單元：5~60摩爾%。 In the resin [K2], the ratio of the structural unit derived from each monomer, among all the structural units constituting the resin [K2], is preferably the structural unit derived from (a): 2 to 45 mol% Structural unit derived from (b): 2~95 mol% Structural unit derived from (c): 1~65 mol%, more preferably structural unit derived from (a): 5-40 mol% Structural unit derived from (b) : 5 to 80 mol% of the structural unit derived from (c): 5 to 60 mol%.

如果樹脂[K2]的結構單元的比率在上述的範圍內，存在著色組合物的保存穩定性、形成著色圖案時的顯影性、以及得到的濾色器的耐溶劑性、耐熱性和機械強度優異的傾向。 If the ratio of the structural units of the resin [K2] is within the above range, the storage stability of the colored composition, the developability when forming a colored pattern, and the resulting color filter have excellent solvent resistance, heat resistance, and mechanical strength Propensity.

樹脂[K2]能夠例如與作為樹脂[K1]的製造方法記載的方法同樣地製造。 The resin [K2] can be manufactured in the same manner as the method described as the manufacturing method of the resin [K1], for example.

樹脂[K3]中，來自各個單體的結構單元的比率，在構成樹脂[K3]的全部結構單元中，優選為來自(a)的結構單元：2~60摩爾%來自(c)的結構單元：40~98摩爾%，更優選為來自(a)的結構單元：10~50摩爾%來自(c)的結構單元：50~90摩爾%。 In resin [K3], the ratio of the structural units derived from each monomer is preferably the structural unit derived from (a): 2-60 mol% of the structural unit derived from (c) among all the structural units constituting the resin [K3] : 40 to 98 mol%, more preferably a structural unit derived from (a): 10 to 50 mol%, a structural unit derived from (c): 50 to 90 mol%.

樹脂[K3]能夠例如與作為樹脂[K1]的製造方法記載的方法同樣地製造。 The resin [K3] can be manufactured in the same manner as the method described as the manufacturing method of the resin [K1], for example.

樹脂[K4]能夠通過得到(a)與(c)的共聚物，使(b)具有的碳數2~4的環狀醚與(a)具有的羧酸和/或羧酸酐加成而製造。 Resin [K4] can be produced by obtaining a copolymer of (a) and (c) and adding the cyclic ether with 2 to 4 carbon atoms in (b) to the carboxylic acid and/or carboxylic anhydride of (a) .

首先，能夠與作為樹脂[K1]的製造方法記載的方法同樣地製造(a)與(c)的共聚物。這種情形下，來自各個單體的結構單元的比率優選為與樹脂[K3]中列舉的比率相同的比率。 First, the copolymer of (a) and (c) can be produced in the same manner as the method described as the production method of resin [K1]. In this case, the ratio of the structural unit derived from each monomer is preferably the same as the ratio listed in the resin [K3].

接下來，使(b)具有的碳數2~4的環狀醚與上述共聚物中的來自(a)的羧酸和/或羧酸酐的一部分反應。 Next, the cyclic ether having 2 to 4 carbon atoms in (b) is reacted with a part of the carboxylic acid and/or carboxylic anhydride derived from (a) in the above-mentioned copolymer.

接著(a)與(c)的共聚物的製造，將燒瓶內氣氛由氮置換為空氣，將(b)、羧酸或羧酸酐與環狀醚的反應催化劑(例如三(二甲基胺基甲基)苯酚等)和阻聚劑(例如氫醌等)等裝入燒瓶內，例如，在60~130℃下反應1~10小時，從而能夠製造樹脂[K4]。 Following the production of the copolymer of (a) and (c), the atmosphere in the flask is replaced by nitrogen to air, and the reaction catalyst of (b), carboxylic acid or carboxylic anhydride and cyclic ether (for example, tris(dimethylamino) (Methyl)phenol, etc.) and a polymerization inhibitor (for example, hydroquinone, etc.) are put in a flask, and reacted at 60 to 130°C for 1 to 10 hours, for example, to produce resin [K4].

(b)的使用量，相對於(a)100摩爾，優選5~80摩爾，更優選為10~75摩爾。通過將(b)的使用量調整到該範圍，存在著色組合物的保存穩定性、形成圖案時的顯影性、以及得到的圖案的耐溶劑性、耐熱性、機械強度和感度的平衡變得良好的傾向。由於環狀醚的反應性高，未反應的(b)不易殘存，因此作為用於樹脂[K4]的(b)，優選(b1)，更優選(b1-1)。 The amount of (b) used is preferably 5 to 80 moles, and more preferably 10 to 75 moles relative to 100 moles of (a). By adjusting the use amount of (b) to this range, the storage stability of the coloring composition, the developability during pattern formation, and the solvent resistance, heat resistance, mechanical strength, and sensitivity of the resulting pattern become good. Propensity. Since the reactivity of the cyclic ether is high, and the unreacted (b) is unlikely to remain, the (b) used for the resin [K4] is preferably (b1), and more preferably (b1-1).

上述反應催化劑的使用量，相對於(a)、(b)和(c)的合計量100質量份，優選0.001~5質量份。上述阻聚劑的使用量，相對於(a)、(b)和(c)的合計量100質量份，優選0.001~5質量份。 The amount of the reaction catalyst used is preferably 0.001 to 5 parts by mass relative to 100 parts by mass of the total amount of (a), (b) and (c). The amount of the polymerization inhibitor used is preferably 0.001 to 5 parts by mass relative to 100 parts by mass of the total amount of (a), (b) and (c).

對於各試劑的進料方法、反應溫度和反應時間等反應條件，能夠考慮製造設備、聚合產生的放熱量等適當地調整。再有，與聚合條件同樣地，能夠考慮製造設備、聚合產生的放熱量等，適當地調整進料方法、反應溫度。 For the feeding method, reaction temperature and reaction time of each reagent The reaction conditions for the intermittence can be appropriately adjusted in consideration of manufacturing equipment, heat generation from polymerization, and the like. In addition, in the same manner as the polymerization conditions, it is possible to appropriately adjust the feeding method and the reaction temperature in consideration of the production equipment, the amount of heat generated by polymerization, and the like.

製造樹脂[K5]時，作為第一階段，與上述的樹脂[K1]的製造方法同樣地，得到(b)與(c)的共聚物。與上述同樣地，得到的共聚物可原樣地使用反應後的溶液，也可使用濃縮或稀釋的溶液，也可使用採用再沉澱等方法作為固體(粉體)取出的產物。 In the production of resin [K5], as the first stage, the copolymer of (b) and (c) is obtained in the same manner as the method for producing resin [K1] described above. In the same manner as described above, the resulting copolymer may be used as it is, a concentrated or diluted solution, or a product taken out as a solid (powder) by a method such as reprecipitation.

來自(b)和(c)的結構單元的比率，相對於構成上述(b)和(c)的共聚物的全部結構單元的合計摩爾數，優選各自為來自(b)的結構單元：5~95摩爾%來自(c)的結構單元：5~95摩爾%，更優選為來自(b)的結構單元：10~90摩爾%來自(c)的結構單元：10~90摩爾%。 The ratio of the structural units derived from (b) and (c), relative to the total number of moles of all the structural units constituting the copolymer of (b) and (c), is preferably a structural unit derived from (b): 5~ 95 mol% of structural units derived from (c): 5 to 95 mol%, more preferably structural units derived from (b): 10 to 90 mol% structural units derived from (c): 10 to 90 mol%.

進而，作為第二階段，在與樹脂[K4]的製造方法同樣的條件下，通過使(a)具有的羧酸或羧酸酐與(b)和(c)的共聚物具有的來自(b)的環狀醚反應，從而能夠得到樹脂[K5]。 Furthermore, as the second stage, under the same conditions as the production method of resin [K4], the copolymer of (a) having carboxylic acid or carboxylic anhydride and (b) and (c) derived from (b) The cyclic ether reacts to obtain resin [K5].

第二階段中，與上述(b)和(c)的共聚物反應的(a)的使用量，相對於(b)100摩爾，優選5~80摩爾。由於環狀醚的反應性高，未反應的(b)不易殘存，因此作為用於樹脂[K5]的(b)，優選(b1)，更優選(b1-1)。 In the second stage, the amount of (a) used to react with the copolymer of (b) and (c) above is preferably 5 to 80 moles relative to 100 moles of (b). Due to the high reactivity of the cyclic ether, the unreacted (b) is not easy to remain, so it is used as For (b) of resin [K5], (b1) is preferable, and (b1-1) is more preferable.

樹脂[K6]是進一步使羧酸酐與樹脂[K5]反應而成的樹脂。使羧酸酐與由環狀醚與由羧酸或羧酸酐的反應產生的羥基反應。 Resin [K6] is a resin obtained by further reacting carboxylic anhydride and resin [K5]. The carboxylic acid anhydride is reacted with the hydroxyl group produced by the reaction of the cyclic ether with the carboxylic acid or the carboxylic anhydride.

樹脂[K6]是進一步使羧酸酐與樹脂[K5]反應而得到的樹脂，具體地，能夠通過使羧酸酐與通過來自(b)的環狀醚和(a)的羧酸或羧酸酐的反應而產生的羥基反應而製造。 Resin [K6] is a resin obtained by further reacting carboxylic anhydride with resin [K5]. Specifically, it can be obtained by reacting carboxylic anhydride with the cyclic ether derived from (b) and the carboxylic acid or carboxylic anhydride of (a) The generated hydroxyl groups are produced by reaction.

作為羧酸酐，可列舉馬來酸酐、檸康酸酐、衣康酸酐、3-乙烯基鄰苯二甲酸酐、4-乙烯基鄰苯二甲酸酐、3,4,5,6-四氫鄰苯二甲酸酐、1,2,3,6-四氫鄰苯二甲酸酐、二甲基四氫鄰苯二甲酸酐、5,6-二羧基雙環[2.2.1]庚-2-烯酐等。羧酸酐的使用量，相對於(a)的使用量1摩爾，優選0.5~1摩爾。 Examples of carboxylic anhydrides include maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinyl phthalic anhydride, 4-vinyl phthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride Dicarboxylic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride, etc. . The amount of carboxylic anhydride used is preferably 0.5 to 1 mole with respect to 1 mole of the use amount of (a).

作為樹脂(B)，具體地，可列舉(甲基)丙烯酸3,4-環氧環己基甲酯/(甲基)丙烯酸共聚物、(甲基)丙烯酸3,4-環氧三環[5.2.1.0^2.6]癸酯/(甲基)丙烯酸共聚物等樹脂[K1]；(甲基)丙烯酸縮水甘油酯/(甲基)丙烯酸苄酯/(甲基)丙烯酸共聚物、(甲基)丙烯酸縮水甘油酯/苯乙烯/(甲基)丙烯酸共聚物、(甲基)丙烯酸3,4-環氧三環[5.2.1.0^2.6]癸酯/(甲基)丙烯酸/N-環己基馬來醯亞胺共聚物、(甲基)丙烯酸3,4-環氧三環[5.2.1.0^2.6]癸酯/(甲基)丙烯酸/乙烯基甲苯共聚物、3-甲基-3-(甲基)丙烯醯氧基甲基氧雜環丁烷/(甲基)丙烯酸/苯乙烯共聚物等樹脂[K2]；(甲基)丙烯酸苄酯/(甲基)丙烯酸共聚物、苯乙烯/(甲基)丙烯酸共聚物、(甲基)丙烯酸苄酯/(甲基)丙烯酸三環癸酯/(甲基)丙烯酸共聚物等樹脂[K3]；使(甲基)丙烯酸縮水甘油酯與(甲基)丙烯酸苄酯/(甲基)丙烯酸共聚物加成而成的樹脂、使(甲基)丙烯酸縮水甘油酯與(甲基)丙烯酸三環癸酯/苯乙烯/(甲基)丙烯酸共聚物加成而成的樹脂、使(甲基)丙烯酸縮水甘油酯與(甲基)丙烯酸三環癸酯/(甲基)丙烯酸苄酯/(甲基)丙烯酸共聚物加成而成的樹脂等樹脂[K4]；使(甲基)丙烯酸與(甲基)丙烯酸三環癸酯/(甲基)丙烯酸縮水甘油酯的共聚物反應的樹脂、使(甲基)丙烯酸與(甲基)丙烯酸三環癸酯/苯乙烯/(甲基)丙烯酸縮水甘油酯的共聚物反應而成的樹脂等樹脂[K5]；使(甲基)丙烯酸與(甲基)丙烯酸三環癸酯/(甲基)丙烯酸縮水甘油酯的共聚物反應而成的樹脂進一步與四氫鄰苯二甲酸酐反應而成的樹脂等樹脂[K6]等。 As the resin (B), specifically, 3,4-epoxycyclohexylmethyl (meth)acrylate/(meth)acrylic acid copolymer, and 3,4-epoxy tricyclo (meth)acrylate [5.2 .1.0 ^2.6 ] Resins such as decyl ester/(meth)acrylic acid copolymer [K1]; glycidyl (meth)acrylate/benzyl (meth)acrylate/(meth)acrylic acid copolymer, (meth)acrylic acid Glycidyl ester/styrene/(meth)acrylic acid copolymer, (meth)acrylic acid 3,4-epoxy tricyclo[5.2.1.0 ^2.6 ] decyl ester/(meth)acrylic acid/N-cyclohexyl maleate Imine copolymer, (meth)acrylic acid 3,4-epoxy tricyclo[5.2.1.0 ^2.6 ]decyl ester/(meth)acrylic acid/vinyl toluene copolymer, 3-methyl-3-(methyl) Resins such as acryloxymethyl oxetane/(meth)acrylic acid/styrene copolymer [K2]; benzyl (meth)acrylate/(meth)acrylic acid copolymer, styrene/(methyl) )Acrylic acid copolymer, benzyl (meth)acrylate/tricyclodecyl (meth)acrylate/(meth)acrylic acid copolymer and other resins [K3]; make glycidyl (meth)acrylate and (meth)acrylate Resin made by addition of benzyl acrylate/(meth)acrylic acid copolymer, adding glycidyl (meth)acrylate and tricyclodecyl (meth)acrylate/styrene/(meth)acrylic acid copolymer Resins such as resins made by the addition of glycidyl (meth)acrylate and tricyclodecyl (meth)acrylate/benzyl (meth)acrylate/(meth)acrylic acid copolymer [K4 ]; Make (meth)acrylic acid and (meth)acrylic acid tricyclodecyl ester/(meth)acrylic acid glycidyl ester copolymer reaction resin, make (meth)acrylic acid and (meth)acrylic acid tricyclodecyl ester /Styrene/glycidyl (meth)acrylate copolymer resin and other resins [K5]; make (meth)acrylic acid and tricyclodecyl (meth)acrylate/glycidyl (meth)acrylate Resin [K6] etc., such as the resin obtained by reacting the copolymer of ester, and tetrahydrophthalic anhydride.

樹脂(B)優選為選自樹脂[K1]、樹脂[K2]和樹脂[K3]中的一種，更優選為選自樹脂[K2]和樹脂[K3]中的一種。如果為這些樹脂，則著色組合物的顯影性優異。從著色圖案與基板的密合性的觀點出發，更優選樹脂[K2]。 The resin (B) is preferably one selected from the group consisting of resin [K1], resin [K2] and resin [K3], and more preferably one selected from resin [K2] and resin [K3]. If it is these resins, the developability of a coloring composition will be excellent. From the viewpoint of the adhesion between the colored pattern and the substrate, resin [K2] is more preferable.

樹脂(B)的聚苯乙烯換算的重均分子量優選為3000~100000，更優選為5000~50000，進一步優選為5000~30000。如果分子量在上述的範圍內，則存在塗膜硬度提高、殘膜率也高、未曝光部對於顯影液的溶解性良好、著色圖案的解析度提高的傾向。 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. If the molecular weight is within the above range, there is coating The film hardness is improved, the residual film rate is also high, the solubility of the unexposed area in the developer is good, and the resolution of the colored pattern tends to be improved.

樹脂(B)的分散度[重均分子量(Mw)/數均分子量(Mn)]優選為1.1~6，更優選為1.2~4。 The degree of dispersion [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)的固體成分換算的酸值優選為30~170mg-KOH/g，更優選為40~150mg-KOH/g，進一步優選為50~135mg-KOH/g。在此，酸值是作為中和樹脂(B)1g所需的氫氧化鉀的量(mg)測定的值，例如，能夠通過使用氫氧化鉀水溶液進行滴定而求出。 The acid value in terms of solid content of the resin (B) is preferably 30 to 170 mg-KOH/g, more preferably 40 to 150 mg-KOH/g, and still more preferably 50 to 135 mg-KOH/g. Here, the acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of the resin (B), and it can be determined, for example, by titration using an aqueous potassium hydroxide solution.

包含樹脂(B)的情況下，樹脂(B)的含有率，相對於固體成分的總量，優選為7~70質量%，更優選為13~65質量%，進一步優選為17~60質量%。如果樹脂(B)的含有率在上述的範圍內，能夠形成著色圖案，而且存在著色圖案的解析度和殘膜率提高的傾向。 When the resin (B) is included, the content of the resin (B) relative to the total solid content is preferably 7 to 70% by mass, more preferably 13 to 65% by mass, and still more preferably 17 to 60% by mass . If the content of the resin (B) is within the above range, a colored pattern can be formed, and the resolution of the colored pattern and the residual film rate tend to increase.

聚合性化合物(C) Polymeric compound (C)

聚合性化合物(C)是能夠利用由聚合引發劑(D)產生的活性自由基和/或酸進行聚合的化合物，可列舉例如具有聚合性的烯屬不飽和鍵的化合物等，優選為(甲基)丙烯酸酯化合物。 The polymerizable compound (C) is a compound that can be polymerized by living radicals and/or acid generated by the polymerization initiator (D), and examples thereof include compounds having polymerizable ethylenic unsaturated bonds, etc., preferably (former Base) Acrylate compound.

作為具有1個烯屬不飽和鍵的聚合性化合物，可列舉例如壬基苯基卡必醇丙烯酸酯、2-羥基-3-苯氧基丙基丙烯酸酯、2-乙基己基卡必醇丙烯酸酯、丙烯酸2-羥基乙酯、N-乙烯基吡咯烷酮等以及上述的(Ba)、(Bb)和(Bc)。 Examples of the polymerizable compound having one ethylenically unsaturated bond include nonylphenyl carbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, and 2-ethylhexyl carbitol acrylate. Ester, 2-hydroxyethyl acrylate, N-vinylpyrrolidone, etc. and the above-mentioned (Ba), (Bb) and (Bc).

作為具有2個烯屬不飽和鍵的聚合性化合物，可列舉例如1,6-己二醇二(甲基)丙烯酸酯、乙二醇二(甲基)丙烯酸酯、新戊二醇二(甲基)丙烯酸酯、三甘醇二(甲基)丙烯酸酯、雙酚A的雙(丙烯醯氧基乙基)醚、3-甲基戊二醇二(甲基)丙烯酸酯等。 As the polymerizable compound having two ethylenically unsaturated bonds, for example, 1,6-hexanediol di(meth)acrylate, ethylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate Base) acrylate, triethylene glycol di(meth)acrylate, bis(acryloxyethyl) ether of bisphenol A, 3-methylpentanediol di(meth)acrylate, etc.

其中，聚合性化合物(C)優選為具有3個以上的烯屬不飽和鍵的聚合性化合物。作為這樣的聚合性化合物，可列舉例如三羥甲基丙烷三(甲基)丙烯酸酯、季戊四醇三(甲基)丙烯酸酯、季戊四醇四(甲基)丙烯酸酯、二季戊四醇五(甲基)丙烯酸酯、二季戊四醇六(甲基)丙烯酸酯、三季戊四醇八(甲基)丙烯酸酯、三季戊四醇七(甲基)丙烯酸酯、四季戊四醇十(甲基)丙烯酸酯、四季戊四醇九(甲基)丙烯酸酯、三(2-(甲基)丙烯醯氧基乙基)異氰脲酸酯、乙二醇改性季戊四醇四(甲基)丙烯酸酯、乙二醇改性二季戊四醇六(甲基)丙烯酸酯、丙二醇改性季戊四醇四(甲基)丙烯酸酯、丙二醇改性二季戊四醇六(甲基)丙烯酸酯、己內酯改性季戊四醇四(甲基)丙烯酸酯、己內酯改性二季戊四醇六(甲基)丙烯酸酯等，其中，優選二季戊四醇五(甲基)丙烯酸酯和二季戊四醇六(甲基)丙烯酸酯。 Among them, the polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds. Examples of such polymerizable compounds include trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, and dipentaerythritol penta(meth)acrylate. , Dipentaerythritol hexa (meth) acrylate, tripentaerythritol octa (meth) acrylate, tripentaerythritol hepta (meth) acrylate, pentaerythritol deca (meth) acrylate, pentaerythritol nine (meth) acrylate , Tris(2-(meth)acryloyloxyethyl) isocyanurate, ethylene glycol modified pentaerythritol tetra(meth)acrylate, ethylene glycol modified dipentaerythritol hexa(meth)acrylate , Propylene glycol modified pentaerythritol tetra (meth) acrylate, propylene glycol modified dipentaerythritol hexa (meth) acrylate, caprolactone modified pentaerythritol tetra (meth) acrylate, caprolactone modified dipentaerythritol hexa (meth) Among them, dipentaerythritol penta(meth)acrylate and dipentaerythritol hexa(meth)acrylate are preferable.

聚合性化合物(C)的重均分子量優選為150以上2900以下，更優選為250~1500。 The weight average molecular weight of the polymerizable compound (C) is preferably 150 or more and 2900 or less, and more preferably 250 to 1500.

包含聚合性化合物(C)的情況下，聚合性化合物(C)的含有率，相對於固體成分的總量，優選為7 質量%以上且65質量%以下，更優選為10質量%以上且60質量%以下，進一步優選為12質量%以上且55質量%以下。 When the polymerizable compound (C) is contained, the content of the polymerizable compound (C) relative to the total solid content is preferably 7 Mass% or more and 65% by mass or less, more preferably 10% by mass or more and 60% by mass or less, and still more preferably 12% by mass or more and 55% by mass or less.

此外，包含樹脂(B)和聚合性化合物(C)的情況下，樹脂(B)與聚合性化合物(C)的含量比[樹脂(B)：聚合性化合物(C)]以質量基準計，優選為20：80~80：20，更優選為30：70~80：20。 In addition, when the resin (B) and the polymerizable compound (C) are contained, the content ratio of the resin (B) to the polymerizable compound (C) [resin (B): polymerizable compound (C)] is calculated on a mass basis, It is preferably 20:80 to 80:20, more preferably 30:70 to 80:20.

如果聚合性化合物(C)的含量在上述的範圍內，存在著色圖案形成時的殘膜率和濾色器的耐化學品性提高的傾向。 If the content of the polymerizable compound (C) is within the above-mentioned range, the residual film rate during the formation of the colored pattern and the chemical resistance of the color filter tend to increase.

聚合引發劑(D) Polymerization initiator (D)

聚合引發劑(D)只要是能夠利用光、熱的作用而產生活性自由基、酸等，引發聚合的化合物，則並無特別限定，能夠使用公知的聚合引發劑。 The polymerization initiator (D) is not particularly limited as long as it is a compound capable of generating active radicals, acids, etc., to initiate polymerization by the action of light and heat, and a known polymerization initiator can be used.

作為聚合引發劑(D)，可列舉O-醯基肟化合物、烷基苯基酮化合物、聯咪唑化合物、三嗪化合物、和醯基氧化膦化合物等。 Examples of the polymerization initiator (D) include O-acyl oxime compounds, alkyl phenyl ketone compounds, biimidazole compounds, triazine compounds, and acyl phosphine oxide compounds.

上述O-醯基肟化合物是具有由式(d1)表示的部分結構的化合物。以下，*表示鍵合端。 The above-mentioned O-acetoxime compound is a compound having a partial structure represented by formula (d1). Hereinafter, * represents the bonding end.

作為上述O-醯基肟化合物，可列舉例如N-苯甲醯氧基-1-(4-苯基硫烷基苯基)丁烷-1-酮-2-亞胺、N-苯甲醯氧基-1-(4-苯基硫烷基苯基)辛烷-1-酮-2-亞胺、N-苯甲醯氧基-1-(4-苯基硫烷基苯基)-3-環戊基丙烷-1-酮-2-亞胺、N-乙醯氧基-1-[9-乙基-6-(2-甲基苯甲醯基)-9H-咔唑-3-基]乙烷-1-亞胺、N-乙醯氧基-1-[9-乙基-6-{2-甲基-4-(3,3-二甲基-2,4-二氧雜環戊基甲氧基)苯甲醯基}-9H-咔唑-3-基]乙烷-1-亞胺、N-乙醯氧基-1-[9-乙基-6-(2-甲基苯甲醯基)-9H-咔唑-3-基]-3-環戊基丙烷-1-亞胺、N-苯甲醯氧基-1-[9-乙基-6-(2-甲基苯甲醯基)-9H-咔唑-3-基]-3-環戊基丙烷-1-酮-2-亞胺等。可使用Irgacure(註冊商標)OXE01、OXE02(以上為BASF公司製造)、N-1919(ADEKA公司製造)等市售品。其中，O-醯基肟化合物優選選自N-苯甲醯氧基-1-(4-苯基硫烷基苯基)丁烷-1-酮-2-亞胺、N-苯甲醯氧基-1-(4-苯基硫烷基苯基)辛烷-1-酮-2-亞胺和N-苯甲醯氧基-1-(4-苯基硫烷基苯基)-3-環戊基丙烷-1-酮-2-亞胺中的至少1種，更優選N-苯甲醯氧基-1-(4-苯基硫烷基苯基)辛烷-1-酮-2-亞胺。 As the above-mentioned O- oxime compound, for example, N-benzyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzyl oxime Oxy-1-(4-phenylsulfanylphenyl)octane-1-one-2-ylidene Amine, N-benzyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropane-1-one-2-imine, N-acetoxy-1-[ 9-Ethyl-6-(2-methylbenzyl)-9H-carbazol-3-yl]ethane-1-imine, N-acetoxy-1-[9-ethyl- 6-{2-Methyl-4-(3,3-dimethyl-2,4-dioxolylmethoxy)benzyl}-9H-carbazol-3-yl]ethane -1-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzyl)-9H-carbazol-3-yl]-3-cyclopentylpropane -1-imine, N-benzyloxy-1-[9-ethyl-6-(2-methylbenzyl)-9H-carbazol-3-yl]-3-cyclopentyl Propan-1-one-2-imine, etc. Commercially available products such as Irgacure (registered trademark) OXE01, OXE02 (the above are made by BASF), and N-1919 (made by ADEKA) can be used. Among them, the O- oxime compound is preferably selected from N-benzyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzyloxy 1-(4-phenylsulfanylphenyl)octane-1-one-2-imine and N-benzyloxy-1-(4-phenylsulfanylphenyl)-3 -At least one of cyclopentylpropane-1-one-2-imine, more preferably N-benzyloxy-1-(4-phenylsulfanylphenyl)octane-1-one- 2-imine.

上述烷基苯基酮化合物是例如具有由式(d2)表示的部分結構或由式(d3)表示的部分結構的化合物。這些部分結構中，苯環可具有取代基。 The above-mentioned alkyl phenyl ketone compound is, for example, a compound having a partial structure represented by formula (d2) or a partial structure represented by formula (d3). In these partial structures, the benzene ring may have a substituent.

作為具有由式(d2)表示的部分結構的化合物，可列舉例如2-甲基-2-嗎啉代-1-(4-甲基硫烷基苯基) 丙烷-1-酮、2-二甲基胺基-1-(4-嗎啉代苯基)-2-苄基丁烷-1-酮、2-(二甲基胺基)-2-[(4-甲基苯基)甲基]-1-[4-(4-嗎啉基)苯基]丁烷-1-酮等。可使用Irgacure 369、907、379(以上為BASF公司製造)等的市售品。 As a compound having a partial structure represented by formula (d2), for example, 2-methyl-2-morpholino-1-(4-methylsulfanylphenyl) Propan-1-one, 2-dimethylamino-1-(4-morpholinophenyl)-2-benzylbutane-1-one, 2-(dimethylamino)-2-[ (4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]butan-1-one and the like. Commercial products such as Irgacure 369, 907, and 379 (the above are made by BASF Corporation) can be used.

作為具有由式(Dd3)表示的部分結構的化合物，可列舉例如2-羥基-2-甲基-1-苯基丙烷-1-酮、2-羥基-2-甲基-1-[4-(2-羥基乙氧基)苯基]丙烷-1-酮、1-羥基環己基苯基酮、2-羥基-2-甲基-1-(4-異丙烯基苯基)丙烷-1-酮的低聚物、α,α-二乙氧基苯乙酮、苯偶醯二甲基縮酮等。 As a compound having a partial structure represented by the formula (Dd3), for example, 2-hydroxy-2-methyl-1-phenylpropane-1-one, 2-hydroxy-2-methyl-1-[4- (2-Hydroxyethoxy)phenyl)propane-1-one, 1-hydroxycyclohexylphenyl ketone, 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propane-1- Oligomers of ketones, α,α-diethoxyacetophenone, benzyl dimethyl ketal, etc.

在感度的方面，作為烷基苯基酮化合物，優選具有由式(d2)表示的部分結構的化合物。 In terms of sensitivity, the alkyl phenyl ketone compound is preferably a compound having a partial structure represented by formula (d2).

上述聯咪唑化合物例如可列舉出由式(d4)表示的化合物。 Examples of the biimidazole compound include a compound represented by formula (d4).

[式(d4)中，R^d1~R^d6表示可具有取代基的碳數6~10的芳基。] [In formula (d4), R ^d1 to R ^d6 represent optionally substituted aryl groups having 6 to 10 carbon atoms. ]

作為R^d1~R^d6的碳數6~10的芳基，可列舉例如苯基、甲苯基、二甲苯基、乙基苯基和萘基等，優選為苯基。 Examples of the aryl group having 6 to 10 carbon atoms of ^Rd1 to ^Rd6 include phenyl, tolyl, xylyl, ethylphenyl, naphthyl, and the like, and phenyl is preferred.

作為可取代上述R^d1~R^d6的芳基的取代基，可列舉例如鹵素原子、碳數1~4的烷氧基等。作為鹵素原子，可列舉例如氟原子、氯原子、溴原子、碘原子等，優選為氯原子。作為碳數1~4的烷氧基，可列舉例如甲氧基、乙氧基、丙氧基、丁氧基等，優選為甲氧基。 As a substituent which can substitute the aryl group of said R ^d1 -R ^d6 , a halogen atom, a C1-C4 alkoxy group, etc. are mentioned, for example. As a halogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc. are mentioned, for example, Preferably it is a chlorine atom. As a C1-C4 alkoxy group, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, etc. are mentioned, for example, Preferably it is a methoxy group.

作為聯咪唑化合物，可列舉例如2,2’-雙(2-氯苯基)-4,4’,5,5’-四苯基聯咪唑、2,2’-雙(2,3-二氯苯基)-4,4’,5,5’-四苯基聯咪唑(例如，參照日本特開平6-75372號公報、日本特開平6-75373號公報等。)、2,2’-雙(2-氯苯基)-4,4’,5,5’-四苯基聯咪唑、2,2’-雙(2-氯苯基)-4,4’,5,5’-四(烷氧基苯基)聯咪唑、2,2’-雙(2-氯苯基)-4,4’,5,5’-四(二烷氧基苯基)聯咪唑、2,2’-雙(2-氯苯基)-4,4’,5,5’-四(三烷氧基苯基)聯咪唑(例如，參照日本特公昭48-38403號公報、日本特開昭62-174204號公報等。)、4,4’,5,5’-位的苯基被烷氧羰基取代的咪唑化合物(例如，參照日本特開平7-10913號公報等)等。其中，優選由下述式表示的化合物和它們的混合物。 As the biimidazole compound, for example, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-di (Chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole (for example, refer to Japanese Patent Laid-Open No. 6-75372, Japanese Patent Laid-Open No. 6-75373, etc.), 2,2'- Bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra (Alkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(dialkoxyphenyl)biimidazole, 2,2' -Bis(2-chlorophenyl)-4,4',5,5'-tetra(trialkoxyphenyl)biimidazole (for example, refer to Japanese Patent Publication No. 48-38403, Japanese Patent Application Publication No. 62- 174204, etc.), imidazole compounds in which the phenyl group at the 4, 4', 5, 5'-position is substituted with an alkoxycarbonyl group (for example, refer to Japanese Patent Application Laid-Open No. 7-10913 etc.). Among them, the compounds represented by the following formulas and their mixtures are preferred.

作為上述三嗪化合物，可列舉例如2,4-雙(三氯甲基)-6-(4-甲氧基苯基)-1,3,5-三嗪、2,4-雙(三氯甲基)-6-(4-甲氧基萘基)-1,3,5-三嗪、2,4-雙(三氯甲基)-6-胡椒基-1,3,5-三嗪、2,4-雙(三氯甲基)-6-(4-甲氧基苯乙烯基)-1,3,5-三嗪、2,4-雙(三氯甲基)-6-[2-(5-甲基呋喃-2-基)乙烯基]-1,3,5-三嗪、2,4-雙(三氯甲基)-6-[2-(呋喃-2-基)乙烯基]-1,3,5-三嗪、2,4-雙(三氯甲基)-6-[2-(4-二乙基胺基-2-甲基苯基)乙烯基]-1,3,5-三嗪、2,4-雙(三氯甲基)-6-[2-(3,4-二甲氧基苯基)乙烯基]-1,3,5-三嗪等。 As the above-mentioned triazine compound, for example, 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 2,4-bis(trichloromethyl) Methyl)-6-(4-methoxynaphthyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-triazine , 2,4-bis(trichloromethyl)-6-(4-methoxystyryl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[ 2-(5-Methylfuran-2-yl)vinyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl) Vinyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)vinyl]- 1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)vinyl]-1,3,5-triazine Wait.

作為上述醯基氧化膦化合物，可列舉2,4,6-三甲基苯甲醯基二苯基氧化膦等。 As the above-mentioned acylphosphine oxide compound, 2,4,6-trimethylbenzyldiphenylphosphine oxide, etc. are mentioned.

進而，作為聚合引發劑(D)，可列舉苯偶姻、苯偶姻甲基醚、苯偶姻乙基醚、苯偶姻異丙基醚、苯偶姻異丁基醚等苯偶姻化合物；二苯甲酮、鄰-苯甲醯基苯甲酸甲酯、4-苯基二苯甲酮、4-苯甲醯基-4’-甲基二苯基硫醚、3,3’,4,4’-四(叔-丁基過氧羰基)二苯甲酮、2,4,6-三甲基二苯甲酮等二苯甲酮化合物；9,10-菲醌、2-乙基蒽醌、樟腦醌等醌化合物；10-丁基-2-氯吖啶酮、苯偶醯、苯基乙醛酸甲酯、二茂鈦化合物等。 Furthermore, as the polymerization initiator (D), benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether can be cited ; Benzophenone, o-benzyl methyl benzoate, 4-phenyl benzophenone, 4-benzyl-4'-methyl diphenyl sulfide, 3,3',4 ,4'-Tetra(tert-butylperoxycarbonyl)benzophenone, 2,4,6-trimethylbenzophenone and other benzophenone compounds; 9,10-phenanthrenequinone, 2-ethyl Quinone compounds such as anthraquinone and camphorquinone; 10-butyl-2-chloroacridone, benzil, methyl phenylglyoxylate, titanocene compounds, etc.

這些優選與後述的聚合引發助劑(D1)(特別是胺類)組合使用。 These are preferably used in combination with the polymerization initiator (D1) (particularly amines) described later.

作為產生酸的聚合引發劑，例如可列舉出4-羥基苯基二甲基鋶-對-甲苯磺酸鹽、4-羥基苯基二甲基鋶六氟銻酸鹽、4-乙醯氧基苯基二甲基鋶-對-甲苯磺酸鹽、4-乙醯氧基苯基甲基苄基鋶六氟銻酸鹽、三苯基鋶-對-甲苯磺酸鹽、三苯基鋶六氟銻酸鹽、二苯基碘鎓對-甲苯磺酸鹽、二苯基碘鎓六氟銻酸鹽等鎓鹽類、硝基苄基甲苯磺酸酯類、苯偶姻甲苯磺酸酯類等。 As a polymerization initiator that generates acid, for example, 4-hydroxyphenyl dimethyl sulfonium-p-toluenesulfonate, 4-hydroxyphenyl dimethyl sulfonium hexafluoroantimonate, 4-acetoxy Phenyl dimethyl sulfonium-p-toluene sulfonate, 4-acetoxy phenyl methyl benzyl hexafluoroantimonate, triphenyl sulfonium-p-toluene sulfonic acid Onium salts such as triphenyl iodonium hexafluoroantimonate, diphenyl iodonium p-toluenesulfonate, diphenyl iodonium hexafluoroantimonate, etc., nitrobenzyl tosylate, benzene Azoin tosylate and so on.

作為聚合引發劑(D)，優選產生活性自由基的聚合引發劑，具體地，為包含選自烷基苯基酮化合物、三嗪化合物、醯基氧化膦化合物、O-醯基肟化合物和聯咪唑化合物中的至少一種的聚合引發劑，更優選地，是包含O-醯基肟化合物的聚合引發劑。 As the polymerization initiator (D), a polymerization initiator that generates living radicals is preferred, specifically, a polymerization initiator selected from the group consisting of alkyl phenyl ketone compounds, triazine compounds, acyl phosphine oxide compounds, O- acyl oxime compounds, and The polymerization initiator of at least one of the imidazole compounds, more preferably, is a polymerization initiator containing an O-acetoxime compound.

包含聚合引發劑(D)的情況下，聚合引發劑(D)的含量，相對於樹脂(B)和聚合性化合物(C)的合計量100質量份，優選為0.1質量份以上且40質量份以下，更優選為1質量份以上且30質量份以下。 When the polymerization initiator (D) is included, the content of the polymerization initiator (D) is preferably 0.1 parts by mass or more and 40 parts by mass relative to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C) Hereinafter, it is more preferably 1 part by mass or more and 30 parts by mass or less.

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

聚合引發助劑(D1)是用於促進用聚合引發劑引發了聚合的聚合性化合物的聚合的化合物或増感劑。包含聚合引發助劑(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 or a sensitizer for accelerating the polymerization of a polymerizable compound whose polymerization has been initiated by a polymerization initiator. When the polymerization initiator (D1) is included, it is usually used in combination with the polymerization initiator (D).

作為聚合引發助劑(D1)，可列舉胺化合物、烷氧基蒽化合物、噻噸酮化合物和羧酸化合物等。 As the polymerization initiation assistant (D1), amine compounds, alkoxyanthracene compounds, thioxanthone compounds, carboxylic acid compounds, and the like can be cited.

作為上述胺化合物，可列舉三乙醇胺、甲基二乙醇胺、三異丙醇胺等鏈烷醇胺；4-二甲基胺基苯甲酸甲酯、4-二甲基胺基苯甲酸乙酯、4-二甲基胺基苯甲酸異戊酯、苯甲酸2-二甲基胺基乙酯、4-二甲基胺基苯甲酸2-乙基己酯等胺基苯甲酸酯；N,N-二甲基對甲苯胺；4,4’- 雙(二甲基胺基)二苯甲酮(通稱米蚩酮)、4,4’-雙(二乙基胺基)二苯甲酮、4,4’-雙(乙基甲基胺基)二苯甲酮等烷基胺基二苯甲酮等，其中，優選烷基胺基二苯甲酮，優選4,4’-雙(二乙基胺基)二苯甲酮。可使用EAB-F(保土穀化學工業(株)製造)等的市售品。 Examples of the above-mentioned amine compounds include alkanolamines such as triethanolamine, methyldiethanolamine, and triisopropanolamine; methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, 4-dimethylaminobenzoic acid isoamyl ester, benzoic acid 2-dimethylamino ethyl ester, 4-dimethylaminobenzoic acid 2-ethylhexyl ester and other amino benzoic acid esters; N, N-Dimethyl p-toluidine; 4,4'- Bis(dimethylamino)benzophenone (commonly known as Michler's ketone), 4,4'-bis(diethylamino)benzophenone, 4,4'-bis(ethylmethylamino) ) Alkylamino benzophenones such as benzophenone and the like, among them, alkylamino benzophenones are preferred, and 4,4'-bis(diethylamino)benzophenone is preferred. Commercial products such as EAB-F (manufactured by Hodogaya Chemical Co., Ltd.) can be used.

作為上述烷氧基蒽化合物，可列舉9,10-二甲氧基蒽、2-乙基-9,10-二甲氧基蒽、9,10-二乙氧基蒽、2-乙基-9,10-二乙氧基蒽、9,10-二丁氧基蒽、2-乙基-9,10-二丁氧基蒽等。 Examples of the above-mentioned alkoxyanthracene compound include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, and 2-ethyl- 9,10-diethoxyanthracene, 9,10-dibutoxyanthracene, 2-ethyl-9,10-dibutoxyanthracene, etc.

作為上述噻噸酮化合物，可列舉2-異丙基噻噸酮、4-異丙基噻噸酮、2,4-二乙基噻噸酮、2,4-二氯噻噸酮、1-氯-4-丙氧基噻噸酮等。 Examples of the thioxanthone compound include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, 1- Chloro-4-propoxythioxanthone and so on.

作為上述羧酸化合物，可列舉苯基硫烷基醋酸、甲基苯基硫烷基醋酸、乙基苯基硫烷基醋酸、甲基乙基苯基硫烷基醋酸、二甲基苯基硫烷基醋酸、甲氧基苯基硫烷基醋酸、二甲氧基苯基硫烷基醋酸、氯苯基硫烷基醋酸、二氯苯基硫烷基醋酸、N-苯基甘胺酸、苯氧基醋酸、萘硫基醋酸、N-萘基甘胺酸、萘氧基醋酸等。 Examples of the above-mentioned carboxylic acid compounds include phenylsulfanyl acetic acid, methylphenylsulfanyl acetic acid, ethylphenylsulfanyl acetic acid, methylethylphenylsulfanyl acetic acid, and dimethylphenylsulfide. Alkyl acetic acid, methoxyphenylsulfanyl acetic acid, dimethoxyphenylsulfanyl acetic acid, chlorophenylsulfanyl acetic acid, dichlorophenylsulfanyl acetic acid, N-phenylglycine, Phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, naphthyloxyacetic acid, etc.

使用這些聚合引發助劑(D1)的情形下，其含量相對於樹脂(B)和聚合性化合物(C)的合計量100質量份，優選為0.1~30質量份，更優選為1~20質量份。如果聚合引發助劑(D1)的量在該範圍內，則能夠進一步以高感度形成著色圖案，濾色器的生產率傾向於提高。 When using these polymerization initiation aids (D1), the content is preferably 0.1 to 30 parts by mass, and more preferably 1 to 20 parts by mass relative to 100 parts by mass of the total amount of the resin (B) and polymerizable compound (C) Copies. If the amount of the polymerization initiation aid (D1) is within this range, a colored pattern can be formed with higher sensitivity, and the productivity of the color filter tends to increase.

流平劑(F) Leveling agent (F)

作為流平劑(F)，可列舉有機矽系表面活性劑、氟系表面活性劑和具有氟原子的有機矽系表面活性劑等。這些可在側鏈具有聚合性基團。 As the leveling agent (F), organosilicon surfactants, fluorine surfactants, organosilicon surfactants having fluorine atoms, and the like can be cited. These may have a polymerizable group in the side chain.

作為有機矽系表面活性劑，可列舉在分子內具有矽氧烷鍵的表面活性劑等。具體地，可列舉

DC3PA、SH7PA、DC11PA、SH21PA、SH28PA、SH29PA、SH30PA、SH8400(東麗-道康寧(株)製造)、KP321、KP322、KP323、KP324、KP326、KP340、KP341(信越化學工業(株)製造)、TSF400、TSF401、TSF410、TSF4300、TSF4440、TSF4445、TSF4446、TSF4452和TSF4460(

‧

‧

‧

合同會社製造)等。 Examples of the organosilicon-based surfactant include surfactants having siloxane bonds in the molecule, and the like. Specifically, one can cite

DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH30PA, SH8400 (manufactured by Toray-Dow Corning Co., Ltd.), KP321, KP322, KP323, KP324, KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400 , TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452 and TSF4460(

‧

Contract company manufacturing) etc.

作為上述的氟系表面活性劑，可列舉在分子內具有氟碳鏈的表面活性劑等。具體地，可列舉

(註冊商標)FC430、FC431(住友3M(株)製造)、

(註冊商標)F142D、F171、F172、F173、F177、F183、F554、R30、RS-718-K(DIC(株)製造)、

(註冊商標)EF301、EF303、EF351、EF352(三菱

電子化成(株)製造)、

(註冊商標)S381、S382、SC101、SC105(旭硝子(株)製造)和E5844((株)

研究所製造)等。 Examples of the above-mentioned fluorine-based surfactants include surfactants having a fluorocarbon chain in the molecule, and the like. Specifically, one can cite

(Registered trademark) FC430, FC431 (manufactured by Sumitomo 3M Co., Ltd.),

(Registered trademark) F142D, F171, F172, F173, F177, F183, F554, R30, RS-718-K (manufactured by DIC Corporation),

(Registered trademark) EF301, EF303, EF351, EF352 (Mitsubishi

Electronic Chemicals Co., Ltd.),

(Registered trademark) S381, S382, SC101, SC105 (manufactured by Asahi Glass Co., Ltd.), and E5844 (co., Ltd.)

Research Institute) etc.

作為上述的具有氟原子的有機矽系表面活性劑，可列舉在分子內具有矽氧烷鍵和氟碳鏈的表面活性劑等。具體地，可列舉

(註冊商標)R08、BL20、F475、F477和F443(DIC(株)製造)等。 Examples of the aforementioned organosilicon surfactants having fluorine atoms include surfactants having siloxane bonds and fluorocarbon chains in the molecule. Specifically, one can cite

(Registered trademark) R08, BL20, F475, F477, F443 (manufactured by DIC Co., Ltd.), etc.

含有流平劑(F)的情況下，其含有率，相對於著色組合物的總量，優選為0.001質量%以上0.5質量%以下，更優選為0.002質量%以上0.4質量%以下，進一步優選為0.005質量%以上0.3質量%以下。如果流平劑(F)的含有率在上述的範圍內，則能夠使濾色器的平坦性變得良好。 When the leveling agent (F) is contained, its content relative to the total amount of the coloring composition is preferably 0.001% by mass to 0.5% by mass, more preferably 0.002% by mass to 0.4% by mass, and still more preferably 0.005 mass% or more and 0.3 mass% or less. If the content of the leveling agent (F) is within the above-mentioned range, the flatness of the color filter can be improved.

其他成分 Other ingredients

著色組合物，根據需要，可包含填充劑、其他的高分子化合物、密合促進劑、抗氧化劑、光穩定劑、鏈轉移劑等該技術領域中公知的添加劑。 The coloring composition may contain additives known in the technical field such as fillers, other polymer compounds, adhesion promoters, antioxidants, light stabilizers, chain transfer agents, and the like as necessary.

著色組合物的製造方法 Manufacturing method of coloring composition

進而，包含樹脂(B)、聚合性化合物(C)、聚合引發劑(D)、溶劑(E)的情形的著色組合物，例如能夠通過將化合物(A-I)、樹脂(B)、聚合性化合物(C)、和聚合引發劑(D)、溶劑(E)、根據需要使用的、化合物(A-I)以外的著色劑(A)、流平劑(F)、聚合引發助劑(D1)和其他成分混合而製備。 Furthermore, the coloring composition in the case of containing resin (B), polymerizable compound (C), polymerization initiator (D), and solvent (E), for example, can be obtained by combining compound (AI), resin (B), polymerizable compound (C), polymerization initiator (D), solvent (E), coloring agent (A) other than compound (AI), leveling agent (F), polymerization initiator (D1) and others if necessary The ingredients are mixed and prepared.

包含顏料(P)的情形下，顏料優選預先與溶劑(E)的一部分或全部混合，使用珠磨機等使其分散直至顏料的平均粒烴成為0.2μm以下左右。此時，根據需要可配合上述顏料分散劑、樹脂(B)的一部分或全部。通過在這樣得到的顏料分散液中混合剩餘的成分以成為規定的濃度，能夠製備目標的著色組合物。 When the pigment (P) is included, the pigment is preferably mixed with a part or all of the solvent (E) in advance and dispersed using a bead mill or the like until the average particle size of the pigment becomes about 0.2 μm or less. At this time, a part or all of the above-mentioned pigment dispersant and resin (B) can be blended as needed. By mixing the remaining components in the pigment dispersion liquid obtained in this way to a predetermined concentration, The target coloring composition can be prepared.

本發明中，可將上述化合物(A-I)與溶劑混合而製成著色分散液。製備了著色分散液後，進而與樹脂(B)、聚合性化合物(C)、聚合引發劑(D)等混合而構成著色組合物，則能夠進一步提高製成濾色器時的耐熱性。 In the present invention, the above-mentioned compound (A-I) can be mixed with a solvent to prepare a colored dispersion. After the colored dispersion liquid is prepared, it is further mixed with the resin (B), the polymerizable compound (C), the polymerization initiator (D), etc. to form a coloring composition, and the heat resistance when used as a color filter can be further improved.

作為溶劑，只要是可作為著色組合物的溶劑(E)使用的溶劑，則能夠使用任何溶劑。為了分散化合物(A-I)，特別優選的溶劑(E1)例如為醚酯溶劑，更優選地，可列舉出將亞烷基二醇或聚亞烷基二醇的一個羥基醚化、將剩餘的羥基酯化的溶劑，例如丙二醇單甲基醚乙酸酯、丙二醇單乙基醚乙酸酯、丙二醇單丙基醚乙酸酯、乙二醇單甲基醚乙酸酯、乙二醇單乙基醚乙酸酯、二甘醇單乙基醚乙酸酯、二甘醇單丁基醚乙酸酯、二丙二醇甲基醚乙酸酯等。這些可單獨使用或包含多種。 As the solvent, any solvent can be used as long as it can be used as the solvent (E) of the coloring composition. In order to disperse the compound (AI), a particularly preferred solvent (E1) is, for example, an ether ester solvent. More preferably, it may be exemplified by etherification of one hydroxyl group of an alkylene glycol or polyalkylene glycol, and etherification of the remaining hydroxyl group. Esterification solvents, such as propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl Ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, dipropylene glycol methyl ether acetate, etc. These may be used alone or in plural.

溶劑(E1)的量，相對於化合物(A-I)1質量份，例如為4~1000質量份，優選為6~200質量份，更優選為9~100質量份。 The amount of the solvent (E1) is, for example, 4 to 1000 parts by mass, preferably 6 to 200 parts by mass, and more preferably 9 to 100 parts by mass relative to 1 part by mass of the compound (A-I).

製備著色分散液時，優選使用分散劑。作為分散劑，例如能夠使用陽離子系、陰離子系、非離子系、兩性、聚酯系、多胺系、丙烯酸系等公知的顏料分散劑。這些顏料分散劑可單獨使用，也可將2種以上組合使用。作為顏料分散劑，用商品名表示，可列舉出KP(信越化學工業(株)製造)、

(共榮社化學(株)製造)、

(

(株)製造)、EFKA(BASF公司製造)、

(味之素

(株)製造)、Disperbyk、BYK(

公司製造)等。 When preparing a colored dispersion, it is preferable to use a dispersant. As the dispersant, for example, known pigment dispersants such as cationic, anionic, nonionic, amphoteric, polyester, polyamine, acrylic, etc. can be used. These pigment dispersants may be used alone or in combination of two or more kinds. As a pigment dispersant, it is represented by a trade name, and includes KP (manufactured by Shin-Etsu Chemical Co., Ltd.),

(Manufactured by Kyoeisha Chemical Co., Ltd.),

(

(Manufactured by Co., Ltd.), EFKA (manufactured by BASF Corporation),

(Ajinomoto

(Manufactured by Co., Ltd.), Disperbyk, BYK (

Company manufacturing) etc.

分散劑的量，相對於化合物(A-I)100質量份，例如為1~1000質量份，優選為3~100質量份，更優選為5~90質量份，特別優選為10~80質量份。 The amount of the dispersant is, for example, 1 to 1000 parts by mass, preferably 3 to 100 parts by mass, more preferably 5 to 90 parts by mass, and particularly preferably 10 to 80 parts by mass relative to 100 parts by mass of compound (A-I).

另外，在著色組合物中包含染料(A1)的情況下，根據需要可預先包含染料(A1)的一部分或全部、優選地全部。著色分散液中的染料(A1)的量，相對於化合物(A-I)100質量份，例如，為0.1~20質量份，優選為0.5~15質量份，更優選為1~10質量份。 In addition, when the dye (A1) is contained in the coloring composition, a part or all, preferably all of the dye (A1) may be contained in advance as necessary. The amount of the dye (A1) in the coloring dispersion liquid is, for example, 0.1 to 20 parts by mass, preferably 0.5 to 15 parts by mass, and more preferably 1 to 10 parts by mass relative to 100 parts by mass of the compound (A-I).

上述著色分散液，根據需要，可預先包含著色組合物中使用的樹脂(B)的一部分或全部、優選地一部分。通過預先包含樹脂(B)，能夠進一步改善製成著色組合物時的分散性。著色分散液中的樹脂(B)的固體成分換算量，相對於化合物(A-I)100質量份，例如，為1~300質量份，優選為10~100質量份，更優選為20~70質量份。 The above-mentioned colored dispersion liquid may contain a part or all of the resin (B) used in the colored composition in advance, preferably a part, if necessary. By including the resin (B) in advance, it is possible to further improve the dispersibility when it is made into a colored composition. The solid content conversion amount of the resin (B) in the colored dispersion liquid is, for example, 1 to 300 parts by mass, preferably 10 to 100 parts by mass, and more preferably 20 to 70 parts by mass relative to 100 parts by mass of the compound (AI) .

製備分散液時，優選在適宜地加入了必要的成分後，使用分散裝置進行微細分散。作為分散裝置，能夠使用珠磨機裝置。作為使用的珠粒，一般為氧化鋯珠粒等硬質珠粒，其粒徑例如選自0.05mm以上且20mm以下的範圍，優選為0.1~10mm，更優選為0.1~0.5mm。 When preparing a dispersion, it is preferable to finely disperse it using a dispersing device after adding necessary components as appropriate. As the dispersion device, a bead mill device can be used. The beads used are generally hard beads such as zirconia beads, and the particle size is selected from the range of 0.05 mm or more and 20 mm or less, for example, preferably 0.1 to 10 mm, and more preferably 0.1 to 0.5 mm.

另外，優選將化合物(A-I)預先溶解於溶劑(E)的一部分或全部而製備溶液。更優選用孔徑0.01~1μm左右的過濾器將該溶液過濾。 In addition, it is preferable to dissolve the compound (A-I) in the solvent (E) in advance Part or all of the solution is prepared. It is more preferable to filter the solution with a filter having a pore diameter of about 0.01 to 1 μm.

優選用孔徑0.01~10μm左右的過濾器將混合後的著色組合物過濾。 It is preferable to filter the mixed coloring composition with a filter having a pore diameter of about 0.01 to 10 μm.

濾色器的製造方法 Manufacturing method of color filter

作為由本發明的著色組合物製造著色圖案的方法，可列舉光刻法、噴墨法、印刷法等。其中，優選光刻法。光刻法是將上述著色組合物塗布於基板，乾燥而形成著色組合物層，經由光掩模將該著色組合物層曝光而顯影的方法。光刻法中，通過在曝光時不使用光掩模和/或不顯影，從而能夠形成作為上述著色組合物層的固化物的著色塗膜。能夠使這樣形成的著色圖案、著色塗膜作為濾色器。 As a method of producing a colored pattern from the coloring composition of the present invention, a photolithography method, an inkjet method, a printing method, etc. may be mentioned. Among them, photolithography is preferred. The photolithography method is a method of applying the coloring composition described above to a substrate, drying to form a coloring composition layer, and exposing the coloring composition layer through a photomask to develop it. In the photolithography method, by not using a photomask and/or not developing during exposure, it is possible to form a colored coating film that is a cured product of the colored composition layer. The colored pattern and colored coating film formed in this way can be used as a color filter.

對製作的濾色器的膜厚並無特別限定，能夠根據目的、用途等適當調整，例如，為0.1~30μm，優選為0.1~20μm，更優選為0.5~6μm。 The film thickness of the produced color filter is not particularly limited, and can be appropriately adjusted according to the purpose, use, etc., and is, for example, 0.1 to 30 μm, preferably 0.1 to 20 μm, and more preferably 0.5 to 6 μm.

作為基板，可使用石英玻璃、硼矽酸玻璃、鋁矽酸鹽玻璃、對表面進行了二氧化矽塗布的鈉鈣玻璃等的玻璃板、聚碳酸酯、聚甲基丙烯酸甲酯、聚對苯二甲酸乙二醇酯等的樹脂板、矽、在上述基板上形成了鋁、銀、銀/銅/鈀合金薄膜等的產物。在這些基板上可形成另外的濾色器層、樹脂層、電晶體、電路等。 As the substrate, glass plates such as quartz glass, borosilicate glass, aluminosilicate glass, soda lime glass coated with silica, polycarbonate, polymethyl methacrylate, and poly-p-phenylene can be used. Resin plates such as ethylene dicarboxylate, silicon, aluminum, silver, silver/copper/palladium alloy thin films, etc. are formed on the above-mentioned substrates. Additional color filter layers, resin layers, transistors, circuits, etc. can be formed on these substrates.

採用光刻法的各色像素的形成能夠在公知或慣用的裝置、條件下進行。例如，能夠如下所述製作。 The formation of pixels of each color by photolithography can be performed under known or customary equipment and conditions. For example, it can be produced as follows.

首先，將著色組合物塗布在基板上，通過加熱乾燥(預烘焙)和/或減壓乾燥，從而將溶劑等揮發成分除去而乾燥，得到平滑的著色組合物層。 First, the coloring composition is coated on the substrate and dried by heating (pre- Bake) and/or drying under reduced pressure to remove volatile components such as the solvent and dry to obtain a smooth coloring composition layer.

作為塗布方法，可列舉旋塗法、狹縫塗布法、狹縫和旋轉塗布法等。 As the coating method, a spin coating method, a slit coating method, a slit and spin coating method, etc. can be cited.

進行加熱乾燥時的溫度優選30~120℃，更優選50~110℃。此外，作為加熱時間，優選為10秒~60分鐘，更優選為30秒~30分鐘。 The temperature at the time of heat drying is preferably 30 to 120°C, and more preferably 50 to 110°C. In addition, the heating time is preferably 10 seconds to 60 minutes, and more preferably 30 seconds to 30 minutes.

進行減壓乾燥的情形下，優選在50~150Pa的壓力下、20~25℃的溫度範圍下進行。 In the case of drying under reduced pressure, it is preferably performed under a pressure of 50 to 150 Pa and a temperature range of 20 to 25°C.

對著色組合物層的膜厚並無特別限定，可根據目標的濾色器的膜厚適當選擇。 The film thickness of the coloring composition layer is not particularly limited, and can be appropriately selected according to the film thickness of the target color filter.

接下來，對於著色組合物層，經由用於形成目標的著色圖案的光掩模而曝光。對該光掩模上的圖案並無特別限定，可使用與目標的用途相符的圖案。 Next, the coloring composition layer is exposed through a photomask for forming a target coloring pattern. The pattern on the photomask is not particularly limited, and a pattern suitable for the intended use can be used.

作為用於曝光的光源，優選產生250~450nm的波長的光的光源。例如，可使用將不到350nm的光用將該波長範圍截斷的濾波器截斷，或者使用將436nm附近、408nm附近、365nm附近的光用將這些波長範圍取出的帶通濾波器選擇性地取出。具體地，作為光源，可列舉水銀燈、發光二極體、金屬鹵化物燈、鹵素燈等。 As a light source used for exposure, a light source that generates light with a wavelength of 250 to 450 nm is preferable. For example, it is possible to use a filter that cuts light below 350 nm with a wavelength range that cuts off, or use a band pass filter that cuts light in the vicinity of 436 nm, 408 nm, and 365 nm to extract these wavelength ranges. Specifically, as the light source, a mercury lamp, a light emitting diode, a metal halide lamp, a halogen lamp, etc. can be cited.

由於能夠對曝光面全體均勻地照射平行光線，進行光掩模和形成了著色組合物層的基板的正確的對位，因此優選使用掩模對準器和步進器等曝光裝置。 Since parallel light rays can be uniformly irradiated to the entire exposure surface and the photomask and the substrate on which the coloring composition layer is formed can be accurately aligned, it is preferable to use exposure devices such as a mask aligner and a stepper.

通過使曝光後的著色組合物層與顯影液接觸而顯影，從而在基板上形成著色圖案。通過顯影，著色組合物層的未曝光部在顯影液中溶解而被除去。作為顯影液，優選例如氫氧化鉀、碳酸氫鈉、碳酸鈉、氫氧化四甲基銨等鹼性化合物的水溶液。這些鹼性化合物的水溶液中的濃度優選為0.01~10質量%，更優選為0.03~5質量%。進而，顯影液可包含表面活性劑。 By contacting the exposed coloring composition layer with the developer Touch and develop to form a colored pattern on the substrate. By development, the unexposed part of the coloring composition layer is dissolved and removed in the developer. As the developer, for example, aqueous solutions of alkaline compounds such as potassium hydroxide, sodium hydrogen carbonate, sodium carbonate, and tetramethylammonium hydroxide are preferred. The concentration in the aqueous solution of these basic compounds is preferably 0.01 to 10% by mass, and more preferably 0.03 to 5% by mass. Furthermore, the developer may contain a surfactant.

顯影方法可以是旋覆浸沒法、浸漬法和噴霧法等的任一種。進而，在顯影時可使基板傾斜任意的角度。 The development method may be any of the rotary immersion method, dipping method, and spray method. Furthermore, the substrate can be inclined at an arbitrary angle during development.

顯影後優選進行水洗。 It is preferable to wash with water after development.

進而，優選對得到的著色圖案進行後烘焙。後烘焙溫度優選150~250℃，更優選160~235℃。後烘焙時間優選1~120分鐘，更優選10~60分鐘。 Furthermore, it is preferable to post-bak the obtained colored pattern. The post-baking temperature is preferably 150 to 250°C, more preferably 160 to 235°C. The post-baking time is preferably 1 to 120 minutes, more preferably 10 to 60 minutes.

本發明的化合物的吸光度高，並且採用使用了其的著色組合物，能夠製造耐溶劑性優異的濾色器。該濾色器可用作用於顯示裝置(例如，液晶顯示裝置、有機EL裝置、電子紙等)和固體攝像元件的濾色器。 The compound of the present invention has a high absorbance, and a coloring composition using the compound can be used to produce a color filter having excellent solvent resistance. This color filter can be used as a color 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

以下通過實施例對本發明更詳細地說明，但本發明並不受這些實施例限定。例中，表示含量乃至使用量的%和份，只要無特別說明，則為質量基準。 Hereinafter, the present invention will be described in more detail through examples, but the present invention is not limited by these examples. In the examples, it means the content and the used amount in% and parts. Unless otherwise specified, it is a quality standard.

另外，只要無特別說明，則反應在氮氣氣氛下進行。以下中，化合物的結構通過質量分析(LC；Agilent製1200型、MASS；Agilent製LC/MSD型)確認。 In addition, unless otherwise specified, the reaction proceeds under a nitrogen atmosphere. In the following, the structure of the compound was confirmed by mass analysis (LC; Agilent 1200 type, MASS; Agilent LC/MSD type).

實施例1 Example 1

在具有冷卻管和攪拌裝置的燒瓶中投入了硫氰酸鉀10.0份、乙腈55.0份後，在室溫下攪拌了30分鐘。歷時10分鐘滴入2-氟苯甲醯氯(東京化成工業(株)製造)13.6份，在室溫下攪拌了2小時。滴入N-乙基-鄰-甲苯胺(東京化成工業(株)製造)11.6份，在室溫下攪拌了30分鐘。使氯醋酸鈉30.0份溶解於離子交換水40.8份中，滴入了該溶液後，滴入30%氫氧化鈉水溶液22.9份。滴入結束後，在室溫下攪拌了20小時。加入了離子交換水204.0份後，在室溫下攪拌1小時，濾取析出的固體。將得到的固體用乙腈41.0份清洗後，用離子交換水200.0份清洗，得到了由式(B-I-1)表示的化合物的濕餅。在具有冷卻管和攪拌裝置的燒瓶中投入離子交換水68.0份、甲苯68.0份、醋酸15.8份，在室溫下攪拌了30分鐘。加入全部量的得到的由式(B-I-1)表示的化合物的濕餅，在室溫下攪拌了2小時。加入30%氫氧化鈉水溶液35.4份，通過分液精製得到了有機層。使用離子交換水68.0份對得到的有機層進行了分液精製後，使用35%鹽酸水溶液進行分液精製。在得到的有機層中加入硫酸鎂，攪拌了1小時後，將固體過濾分離。將溶劑蒸餾，得到了18.5份的由式(B-I-2)表示的化合物。收率為69%。 After putting 10.0 parts of potassium thiocyanate and 55.0 parts of acetonitrile in a flask equipped with a cooling tube and a stirring device, the mixture was stirred at room temperature for 30 minutes. 13.6 parts of 2-fluorobenzyl chloride (manufactured by Tokyo Chemical Industry Co., Ltd.) was dripped over 10 minutes, and it stirred at room temperature for 2 hours. 11.6 parts of N-ethyl-o-toluidine (manufactured by Tokyo Chemical Industry Co., Ltd.) was dropped, and the mixture was stirred at room temperature for 30 minutes. 30.0 parts of sodium chloroacetate was dissolved in 40.8 parts of ion-exchange water, and after this solution was dropped, 22.9 parts of a 30% sodium hydroxide aqueous solution was dropped. After the dripping, it was stirred at room temperature for 20 hours. After adding 204.0 parts of ion exchange water, the mixture was stirred at room temperature for 1 hour, and the precipitated solid was collected by filtration. The obtained solid was washed with 41.0 parts of acetonitrile and then washed with 200.0 parts of ion-exchange water to obtain a wet cake of the compound represented by formula (B-I-1). 68.0 parts of ion-exchanged water, 68.0 parts of toluene, and 15.8 parts of acetic acid were put into a flask equipped with a cooling tube and a stirring device, and stirred at room temperature for 30 minutes. The entire amount of the obtained wet cake of the compound represented by formula (B-I-1) was added, and stirred at room temperature for 2 hours. 35.4 parts of 30% sodium hydroxide aqueous solution was added, and the organic layer was obtained by liquid separation and purification. After liquid separation and purification of the obtained organic layer using 68.0 parts of ion-exchange water, 35% hydrochloric acid aqueous solution was used for liquid separation and purification. Magnesium sulfate was added to the obtained organic layer, and after stirring for 1 hour, the solid was separated by filtration. The solvent was distilled to obtain 18.5 parts of the compound represented by formula (B-I-2). The yield was 69%.

在具有冷卻管和攪拌裝置的燒瓶中投入N-甲基苯胺(東京化成工業(株)製造)15.3份和N,N-二甲基甲醯胺60份後，對混合溶液進行了冰冷。在冰冷下歷時30分鐘一點點地加入了60%氫化鈉(東京化成工業(株)製造)5.7份後，邊升溫到室溫邊攪拌了1小時。將4,4’-二氟二苯甲酮(東京化成工業(株)製造)10.4份一點點地加入反應液中，在室溫下攪拌了24小時。將反應液一點點地加入冰水200份中後，在室溫下靜置15小時，通過傾析將水除去，則作為殘渣得到了黏稠固體。在該黏稠固體中加入了甲醇60份後，在室溫下攪拌了15小時。將析出的固體過濾分離後，用柱色譜精製。將精製的淡黃色固體在減壓下60℃下乾燥，得到了9.8份的由式(BP-1)表示的化合物。收率為53%。 After putting 15.3 parts of N-methylaniline (manufactured by Tokyo Chemical Industry Co., Ltd.) and 60 parts of N,N-dimethylformamide into a flask equipped with a cooling tube and a stirring device, the mixed solution was ice-cooled. After 5.7 parts of 60% sodium hydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was added little by little over 30 minutes under ice cooling, the mixture was stirred for 1 hour while raising the temperature to room temperature. 10.4 parts of 4,4'-difluorobenzophenone (manufactured by Tokyo Chemical Industry Co., Ltd.) was added little by little, and stirred at room temperature for 24 hours. The reaction liquid was added little by little to 200 parts of ice water, and the mixture was allowed to stand at room temperature for 15 hours, and the water was removed by decantation to obtain a viscous solid as a residue. After adding 60 parts of methanol to this viscous solid, it was stirred at room temperature for 15 hours. After the precipitated solid was separated by filtration, it was purified by column chromatography. The purified pale yellow solid was dried at 60°C under reduced pressure to obtain 9.8 parts of the compound represented by the formula (BP-1). The yield was 53%.

在具有冷卻管和攪拌裝置的燒瓶中投入了由式(B-I-2)表示的化合物8.2份、由式(BP-1)表示的化合物10.0份和甲苯20.0份後，接下來，加入***12.2 份，在95~100℃下攪拌了3小時。接下來，將反應混合物冷卻到室溫後，用異丙醇170.0份稀釋。接下來，將稀釋的反應溶液注入飽和食鹽水300.0份中後，加入甲苯100份，攪拌了30分鐘。接著，停止攪拌，靜置30分鐘，結果分離為有機層與水層。通過分液操作將水層廢棄後，將有機層用飽和食鹽水300份清洗。在有機層中加入適當量的芒硝，攪拌了30分鐘後，過濾，得到了乾燥的有機層。用蒸發器將得到的有機層的溶劑餾除，得到了青紫色固體。進而對青紫色固體在減壓下60℃下進行乾燥，得到了18.4份的由式(A-IV-1)表示的化合物。收率為100%。 After putting 8.2 parts of the compound represented by the formula (BI-2), 10.0 parts of the compound represented by the formula (BP-1), and 20.0 parts of toluene into a flask with a cooling tube and a stirring device, then, oxychlorination was added Phosphorus 12.2 It was stirred at 95-100°C for 3 hours. Next, after cooling the reaction mixture to room temperature, it was diluted with 170.0 parts of isopropanol. Next, after pouring the diluted reaction solution into 300.0 parts of saturated brine, 100 parts of toluene was added, and the mixture was stirred for 30 minutes. Then, the stirring was stopped, and the mixture was allowed to stand for 30 minutes. As a result, it was separated into an organic layer and an aqueous layer. After the water layer was discarded by the liquid separation operation, the organic layer was washed with 300 parts of saturated brine. An appropriate amount of Glauber's salt was added to the organic layer, and after stirring for 30 minutes, it was filtered to obtain a dry organic layer. The solvent of the obtained organic layer was distilled off with an evaporator to obtain a purple solid. Furthermore, the blue-violet solid was dried at 60°C under reduced pressure to obtain 18.4 parts of the compound represented by the formula (A-IV-1). The yield was 100%.

由式(A-IV-1)表示的化合物的鑒定(質量分析)離子化模式=ESI+：m/z=687.3[M-Cl]⁺準確質量：722.3 Identification (mass analysis) of the compound represented by formula (A-IV-1) Ionization mode=ESI+: m/z=687.3[M-Cl] ⁺ exact mass: 722.3

在具有冷卻管和攪拌裝置的燒瓶中投入由式(A-IV-1)表示的化合物12.4份、氯仿45.5份，攪拌。接下來，投入氯磺酸(東京化成工業(株)製造)10份，在25~30℃下攪拌了18小時。冷卻到室溫後，投入N,N-二甲基甲醯胺210份，將反應液一點點地滴入甲苯2610份中。攪拌了1小時後，將過濾而得到的固體用甲苯870份清洗後，在減壓下60℃下乾燥，得到了12.9份的由式(A-III-1)表示的化合物。收率為89%。 12.4 parts of the compound represented by formula (A-IV-1) and 45.5 parts of chloroform were put into a flask equipped with a cooling tube and a stirring device, and stirred. Next, 10 parts of chlorosulfonic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) was added and stirred at 25 to 30°C for 18 hours. After cooling to room temperature, add 210 parts of N,N-dimethylformamide, and drop 2610 parts of toluene into the reaction solution. in. After stirring for 1 hour, the solid obtained by filtration was washed with 870 parts of toluene, and then dried at 60° C. under reduced pressure to obtain 12.9 parts of the compound represented by the formula (A-III-1). The yield was 89%.

由式(A-III-1)表示的化合物的鑒定(質量分析)離子化模式=ESI+：m/z=845.3[M]⁺準確質量：846.2 Identification (mass analysis) of the compound represented by formula (A-III-1) Ionization mode=ESI+: m/z=845.3[M] ⁺ exact mass: 846.2

在具有冷卻管和攪拌裝置的燒瓶中加入由式(A-III-1)表示的化合物69.8份、氯仿418份，攪拌。滴入***369.7份，在60℃下攪拌了4小時。放冷到室溫後，將反應溶液注入到冷水5000份中後，攪拌了30分鐘。停止攪拌，靜置了30分鐘，結果分離為有機層與水層。將得到的有機層使用冷水4000份進行2次分液清洗。使三氟甲磺醯胺14.7份、三乙胺10份溶解於氯仿100份後，加入有機層中，在室溫下反應了12小時。將反應溶液注入離子交換水5000份中後，攪拌了30分鐘。停止攪拌，靜置了30分鐘，結果分離為有機層和水層。將得到的有機層使用離子交換水4000份進行2次分液清洗。在有機層中加入硫酸鎂200份，攪拌了1小時後，用蒸發器將得到的有機層的溶劑餾除，得到了青紫色固體。進而，將青紫色固體在減壓下60℃下乾燥，得到了44.2份的由式(A-III-1)、式(A-II-1)、式(A-II-2)表示的化合物的32：41：16混合物(摩爾基準)。將該混合物稱為色料(A-II-3)。 69.8 parts of the compound represented by formula (A-III-1) and 418 parts of chloroform were added to a flask equipped with a cooling tube and a stirring device, and stirred. 369.7 parts of phosphorus oxychloride were dropped, and the mixture was stirred at 60°C for 4 hours. After allowing to cool to room temperature, the reaction solution was poured into 5000 parts of cold water and stirred for 30 minutes. The stirring was stopped, and the mixture was allowed to stand for 30 minutes. As a result, it was separated into an organic layer and an aqueous layer. The obtained organic layer was separated and washed twice with 4000 parts of cold water. After dissolving 14.7 parts of trifluoromethanesulfonamide and 10 parts of triethylamine in 100 parts of chloroform, they were added to the organic layer and reacted at room temperature for 12 hours. After pouring the reaction solution into 5000 parts of ion-exchange water, it was stirred for 30 minutes. The stirring was stopped, and the mixture was allowed to stand for 30 minutes. As a result, it separated into an organic layer and an aqueous layer. The obtained organic layer was separated and washed twice with 4000 parts of ion exchange water. 200 parts of magnesium sulfate was added to the organic layer, and after stirring for 1 hour, the organic layer The solvent was distilled off to obtain a blue-purple solid. Furthermore, the blue-purple solid was dried at 60°C under reduced pressure to obtain 44.2 parts of compounds represented by formula (A-III-1), formula (A-II-1), and formula (A-II-2) 32:41:16 mixture (on a molar basis). This mixture is called a colorant (A-II-3).

由式(A-II-1)表示的化合物的鑒定(質量分析)離子化模式=ESI+：m/z=978.5[M]⁺準確質量：977.2 Identification (mass analysis) of the compound represented by formula (A-II-1) Ionization mode=ESI+: m/z=978.5[M] ⁺ exact mass: 977.2

由式(A-II-2)表示的化合物的鑒定(質量分析)離子化模式=ESI+：m/z=1109.5[M]⁺準確質量：1108.1 Identification (mass analysis) of the compound represented by formula (A-II-2) Ionization mode=ESI+: m/z=1109.5[M] ⁺ exact mass: 1108.1

實施例2 Example 2

在具有冷卻管和攪拌裝置的燒瓶中投入由(A-IV-1) 表示的化合物2.0份、二氯甲烷5.7份，在25~30℃下滴入氯磺酸1.6份，在同溫度下攪拌了3小時。接下來，滴入DMF 3.3份、離子交換水0.3份的混合物以致不超過25℃，製成溶液。將該溶液注入甲苯32.7份中，將液體部分分離，再次將殘渣用甲苯16.3份清洗。用蒸發器對剩餘的殘渣進行減壓濃縮，通過將該濃縮物注入離子交換水31.2份中，從而使結晶析出，過濾。將該粗過濾物用20%氯化鈉水溶液13.0份懸浮，過濾，將濾取的固體用20%氯化鈉水溶液13.0份清洗，在35℃下減壓乾燥。接下來，將該乾燥物溶解於甲醇6.2份，將不溶物過濾後，用蒸發器減壓濃縮，在35℃下進行減壓乾燥，從而作為青色固體得到了由式(A-III-1)表示的化合物1.9份。收率為97.9%。 Put into the flask with cooling pipe and stirring device (A-IV-1) 2.0 parts of the indicated compound, 5.7 parts of dichloromethane, 1.6 parts of chlorosulfonic acid were dropped at 25-30°C, and the mixture was stirred at the same temperature for 3 hours. Next, a mixture of 3.3 parts of DMF and 0.3 parts of ion-exchange water was dropped so as not to exceed 25°C to prepare a solution. This solution was poured into 32.7 parts of toluene, the liquid part was separated, and the residue was washed again with 16.3 parts of toluene. The remaining residue was concentrated under reduced pressure with an evaporator, and the concentrate was poured into 31.2 parts of ion-exchanged water to precipitate crystals and filtered. This crude filter was suspended with 13.0 parts of 20% sodium chloride aqueous solution, filtered, and the filtered solid was washed with 13.0 parts of 20% sodium chloride aqueous solution, and dried under reduced pressure at 35°C. Next, the dried product was dissolved in 6.2 parts of methanol, the insoluble matter was filtered, concentrated under reduced pressure with an evaporator, and dried under reduced pressure at 35°C to obtain the formula (A-III-1) as a cyan solid 1.9 parts of the indicated compound. The yield was 97.9%.

以下的反應在氮氣氛下進行。在具有冷卻管和攪拌裝置的燒瓶中投入上述得到的由式(A-III-1)表示的化合物2.0份和乙腈10.0份，在70~80℃下滴入*** 1.0份。在同溫度下攪拌2小時。接下來，冷卻到5℃，在該反應液中投入了三氟甲磺醯胺1.0份。接著，在5~15℃下滴入三乙胺2.3份，在15~30℃下攪拌了2小時。在該反應液中注入甲乙酮10.0份、20%氯化鈉水溶液10.0份，用蒸發器進行了減壓濃縮。在該濃縮殘渣中注入二氯甲烷15.0份、離子交換水10.0份，使有機層與水層分離，用蒸發器對有機層進行減壓濃縮，在35℃下進行減壓乾燥，從而作為青色固體得到了由式(A-II-2)表示的化合物3.1份。收率為107.7%。 The following reactions were carried out in a nitrogen atmosphere. Put 2.0 parts of the compound represented by the formula (A-III-1) and 10.0 parts of acetonitrile obtained above into a flask equipped with a cooling tube and a stirring device, and drop phosphorus oxychloride at 70~80℃ 1.0 copies. Stir at the same temperature for 2 hours. Next, it cooled to 5 degreeC, and 1.0 part of trifluoromethanesulfonamide was put into this reaction liquid. Next, 2.3 parts of triethylamine was dripped at 5-15 degreeC, and it stirred at 15-30 degreeC for 2 hours. 10.0 parts of methyl ethyl ketone and 10.0 parts of 20% sodium chloride aqueous solution were poured into this reaction liquid, and it concentrated under reduced pressure with an evaporator. 15.0 parts of dichloromethane and 10.0 parts of ion-exchanged water were poured into the concentrated residue to separate the organic layer from the water layer. The organic layer was concentrated under reduced pressure with an evaporator and dried under reduced pressure at 35°C to obtain a blue solid 3.1 parts of the compound represented by formula (A-II-2) were obtained. The yield was 107.7%.

實施例3 Example 3

在具有冷卻管和攪拌裝置的燒瓶中投入由式(A-II-2)表示的化合物2.0份、氯化鎂六水合物3.4份、二甲基亞碸40.0份、離子交換水16.0份，在80℃下攪拌了2小時。將反應混合物冷卻到室溫後，滴入離子交換水161.3份、氯化鎂六水合物53.8份的溶液中，在40℃下攪拌了30分鐘。將得到的懸浮液過濾，將濾取的固體用離子交換水20.0份、50.0份清洗2次。將得到的固體在60℃下減壓下乾燥，得到了由式(A-II-4)表示的化合物1.9份。 Put 2.0 parts of the compound represented by the formula (A-II-2), 3.4 parts of magnesium chloride hexahydrate, 40.0 parts of dimethyl sulfide, and 16.0 parts of ion exchange water into a flask with a cooling tube and a stirring device, at 80°C Stirred for 2 hours. After the reaction mixture was cooled to room temperature, a solution of 161.3 parts of ion-exchanged water and 53.8 parts of magnesium chloride hexahydrate was dropped, and the mixture was stirred at 40°C for 30 minutes. The obtained suspension was filtered, and the filtered solid was washed twice with 20.0 parts and 50.0 parts of ion exchange water. The obtained solid was dried under reduced pressure at 60°C to obtain 1.9 parts of a compound represented by formula (A-II-4).

實施例4 Example 4

除了將氯化鎂六水合物變為氯化鋅以外，進行與實施例3同樣的反應，合成了由式(A-II-5)表示的化合物。 Except that magnesium chloride hexahydrate was changed to zinc chloride, the same reaction as in Example 3 was performed to synthesize a compound represented by formula (A-II-5).

實施例5 Example 5

除了將氯化鎂六水合物變為氯化鋇二水合物以外，進行與實施例3同樣的反應，合成了由式(A-II-6)表示的化合物。 Except that magnesium chloride hexahydrate was changed to barium chloride dihydrate, the same reaction as in Example 3 was performed to synthesize a compound represented by formula (A-II-6).

[化學式47]

[Chemical formula 47]

實施例6 Example 6

除了將由式(BP-1)表示的化合物變為由式(BP-2)表示的化合物以外，與實施例1同樣地得到了由式(A-III-2)、式(A-II-7)、式(A-II-8)表示的化合物的30：52：9混合物(摩爾基準)。將該混合物稱為色料(A-II-9)。應予說明，式中，-SO₃ ^-和-SO₂-N^--SO₂-CF₃意味著將圓括弧內的部分結構中所含的氫原子的任一個取代。 Except that the compound represented by the formula (BP-1) was changed to the compound represented by the formula (BP-2), in the same manner as in Example 1, the formula (A-III-2) and the formula (A-II-7 ) 30:52:9 mixture of the compound represented by the formula (A-II-8) (on a molar basis). This mixture is called a colorant (A-II-9). In addition, in the formula, -SO ₃ ^- and -SO ₂ -N ^-- SO ₂ -CF ₃ mean that any one of the hydrogen atoms contained in the partial structure in parentheses is substituted.

由式(A-III-2)表示的化合物的鑒定(質量分析)離子化模式=ESI+：m/z=931.5[M]⁺準確質量：930.3 Identification (mass analysis) of the compound represented by formula (A-III-2) Ionization mode=ESI+: m/z=931.5[M] ⁺ exact mass: 930.3

由式(A-II-7)表示的化合物的鑒定(質量分析)離子化模式=ESI+：m/z=1063.5[M]⁺準確質量：1061.3 Identification (mass analysis) of the compound represented by formula (A-II-7) Ionization mode=ESI+: m/z=1063.5[M] ⁺ exact mass: 1061.3

由式(A-II-8)表示的化合物的鑒定(質量分析)離子化模式=ESI+：m/z=1193.5[M]⁺準確質量：1192.2 Identification (mass analysis) of the compound represented by formula (A-II-8) Ionization mode=ESI+: m/z=1193.5[M] ⁺ exact mass: 1192.2

實施例7 Example 7

除了將由式(BP-1)表示的化合物變為由式(BP-2)表示的化合物以外，與實施例2同樣地得到了由式(A-II-8) 表示的化合物。 Except that the compound represented by the formula (BP-1) was changed to the compound represented by the formula (BP-2), the formula (A-II-8) was obtained in the same manner as in Example 2. Represents the compound.

實施例8 Example 8

除了將由式(A-II-2)表示的化合物變為由式(A-II-8)表示的化合物以外，進行與實施例3同樣的反應，合成了由式(A-II-10)表示的化合物。 Except that the compound represented by formula (A-II-2) was changed to the compound represented by formula (A-II-8), the same reaction as in Example 3 was performed to synthesize the compound represented by formula (A-II-10) compound of.

實施例9 Example 9

除了將由式(A-II-2)表示的化合物變為由式(A-II-8)表示的化合物以外，進行與實施例4同樣的反應，合成了由式(A-II-11)表示的化合物。 Except that the compound represented by formula (A-II-2) was changed to the compound represented by formula (A-II-8), the same reaction as in Example 4 was performed to synthesize the compound represented by formula (A-II-11) compound of.

實施例10 Example 10

除了將由式(A-II-2)表示的化合物變為由式(A-II-8)表示的化合物以外，進行與實施例5同樣的反應，合成了由式(A-II-12)表示的化合物。 Except that the compound represented by formula (A-II-2) was changed to the compound represented by formula (A-II-8), the same reaction as in Example 5 was performed to synthesize the compound represented by formula (A-II-12) compound of.

比較例1、2 Comparative examples 1, 2

按照日本特開2015-38201號公報中記載的方法合成了由式(A-X-1)表示的化合物(以下也稱為化合物(A-X-1))和由式(A-X-2)表示的化合物(以下也稱為化合物(A-X-2))。 The compound represented by formula (AX-1) (hereinafter also referred to as compound (AX-1)) and the compound represented by formula (AX-2) (hereinafter referred to as compound (AX-1)) were synthesized according to the method described in Japanese Patent Application Laid-Open No. 2015-38201 Also called compound (AX-2)).

[合成例1] [Synthesis Example 1]

在具有回流冷凝器、滴液漏斗和攪拌機的燒瓶內流入適量的氮而使其成為氮氣氛，裝入丙二醇單甲基醚乙酸酯100份，邊攪拌邊加熱到85℃。接下來，使用滴液泵歷時約5小時在該燒瓶內滴入了使甲基丙烯酸19份、丙烯酸3,4-環氧三環[5.2.1.0^2,6]癸烷-8-基酯和丙烯酸3,4-環氧三環[5.2.1.0^2,6]癸烷-9-基酯的混合物(含有比以摩爾比計為50：50)(商品名“E-DCPA”、株式會社大賽璐製造)171 份溶解於丙二醇單甲基醚乙酸酯40份中的溶液。另一方面，使用另外的滴液泵歷時約5小時在燒瓶內滴入了使聚合引發劑2,2’-偶氮二(2,4-二甲基戊腈)26份溶解於丙二醇單甲基醚乙酸酯120份中的溶液。聚合引發劑的滴入結束後，在同溫度下保持約3小時，然後冷卻到室溫，得到了固體成分43.5%的共聚物(樹脂(B-1))的溶液。得到的樹脂(B-1)的重均分子量為8000，分散度為1.98，固體成分換算的酸值為53mg-KOH/g。 An appropriate amount of nitrogen was poured into a flask equipped with a reflux condenser, a dropping funnel, and a stirrer to make a nitrogen atmosphere, 100 parts of propylene glycol monomethyl ether acetate was charged, and the mixture was heated to 85°C while stirring. Next, 19 parts of methacrylic acid, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decane-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decane-8-yl ester and methacrylic acid were dropped into the flask for about 5 hours using a drip pump. Acrylic acid 3,4-epoxy tricyclo[5.2.1.0 ^2,6 ]decane-9-yl ester mixture (the content ratio is 50:50 in molar ratio) (trade name "E-DCPA", Co., Ltd. Made by Lu) 171 parts of solution dissolved in 40 parts of propylene glycol monomethyl ether acetate. On the other hand, 26 parts of polymerization initiator 2,2'-azobis(2,4-dimethylvaleronitrile) was dissolved in propylene glycol monomethyl by dripping into the flask for about 5 hours using another drip pump. A solution in 120 parts of base ether acetate. After the dripping of the polymerization initiator was completed, it was kept at the same temperature for about 3 hours, and then cooled to room temperature to obtain a solution of a copolymer (resin (B-1)) with a solid content of 43.5%. The weight average molecular weight of the obtained resin (B-1) was 8000, the degree of dispersion was 1.98, and the acid value in terms of solid content was 53 mg-KOH/g.

[合成例2] [Synthesis Example 2]

在具有回流冷凝器、滴液漏斗和攪拌機的燒瓶內流入適量的氮而使其成為氮氣氛，裝入丙二醇單甲基醚乙酸酯280份，邊攪拌邊加熱到80℃。接下來，使用滴液泵歷時約5小時在該燒瓶內滴入了使丙烯酸38份、丙烯酸3,4-環氧三環[5.2.1.0^2,6]癸烷-8和9-基酯的混合物(含有比以摩爾比計為50：50)(商品名“E-DCPA”、株式會社大賽璐製造)289份溶解於丙二醇單甲基醚乙酸酯125份中的溶液。另一方面，使用另外的滴液泵歷時約6小時在燒瓶內滴入了使聚合引發劑2,2-偶氮二(2,4-二甲基戊腈)33份溶解於丙二醇單甲基醚乙酸酯235份中的溶液。聚合引發劑的滴入結束後，在同溫度下保持約4小時，然後冷卻到室溫，得到了固體成分35.1%的共聚物(樹脂(B-2))。得到的樹脂(B-2)的重均分子量為9200，分散度為2.08，固體成分換算的酸值為77mg-KOH/g。 An appropriate amount of nitrogen was poured into a flask equipped with a reflux condenser, a dropping funnel, and a stirrer to make a nitrogen atmosphere, 280 parts of propylene glycol monomethyl ether acetate was charged, and the mixture was heated to 80°C while stirring. Next, 38 parts of acrylic acid and 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decane-8 and 9-yl ester of acrylic acid were dropped into the flask for about 5 hours using a dropping pump. A solution in which 289 parts of the mixture (the content ratio is 50:50 in molar ratio) (trade name "E-DCPA", manufactured by Daicel Co., Ltd.) was dissolved in 125 parts of propylene glycol monomethyl ether acetate. On the other hand, a separate drip pump was used to drop 33 parts of the polymerization initiator 2,2-azobis(2,4-dimethylvaleronitrile) into the flask over about 6 hours. A solution in 235 parts of ether acetate. After the dripping of the polymerization initiator was completed, it was kept at the same temperature for about 4 hours, and then cooled to room temperature to obtain a copolymer (resin (B-2)) with a solid content of 35.1%. The weight average molecular weight of the obtained resin (B-2) was 9,200, the degree of dispersion was 2.08, and the acid value in terms of solid content was 77 mg-KOH/g.

樹脂的聚苯乙烯換算的重均分子量(Mw)和數均分子量(Mn)的測定採用GPC法在以下的條件下進行。 The measurement of the weight average molecular weight (Mw) and number average molecular weight (Mn) in terms of polystyrene of the resin was performed under the following conditions by the GPC method.

裝置：HLC-8120GPC(東曹(株)製造) Device: HLC-8120GPC (manufactured by Tosoh Corporation)

柱：TSK-GELG2000HXL Column: TSK-GELG2000HXL

柱溫度：40℃ Column temperature: 40℃

溶劑：THF Solvent: THF

流速：1.0mL/min Flow rate: 1.0mL/min

被檢液固體成分濃度：0.001~0.01質量% The concentration of solid content of the tested liquid: 0.001~0.01% by mass

注入量：50μL Injection volume: 50μL

檢測器：RI Detector: RI

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

將上述得到的聚苯乙烯換算的重均分子量和數均分子量之比(Mw/Mn)作為分散度。 Divide the weight average molecular weight and number average of the polystyrene obtained above The ratio of particles (Mw/Mn) is taken as the degree of dispersion.

[著色固化性樹脂組合物的製備] [Preparation of colored curable resin composition]

實施例11~20和比較例3~4 Examples 11~20 and Comparative Examples 3~4

按照以下的組成將各成分混合，得到了著色固化性樹脂組合物。 The components were mixed in the following composition to obtain a colored curable resin composition.

表14中，各成分表示以下的化合物。 In Table 14, each component represents the following compound.

(A-II-2)：由式(A-II-2)表示的化合物 (A-II-2): Compound represented by formula (A-II-2)

(A-II-3)：色料(A-II-3) (A-II-3): Pigment (A-II-3)

(A-II-4)：由式(A-II-4)表示的化合物 (A-II-4): Compound represented by formula (A-II-4)

(A-II-5)：由式(A-II-5)表示的化合物 (A-II-5): Compound represented by formula (A-II-5)

(A-II-6)：由式(A-II-6)表示的化合物 (A-II-6): Compound represented by formula (A-II-6)

(A-II-8)：由式(A-II-8)表示的化合物 (A-II-8): Compound represented by formula (A-II-8)

(A-II-9)：色料(A-II-9) (A-II-9): Pigment (A-II-9)

(A-II-10)：由式(A-II-10)表示的化合物 (A-II-10): Compound represented by formula (A-II-10)

(A-II-11)：由式(A-II-11)表示的化合物 (A-II-11): Compound represented by formula (A-II-11)

(A-II-12)：由式(A-II-12)表示的化合物 (A-II-12): Compound represented by formula (A-II-12)

(A-X-1)：由式(A-X-1)表示的化合物 (A-X-1): Compound represented by formula (A-X-1)

(A-X-2)：由式(A-X-2)表示的化合物 (A-X-2): Compound represented by formula (A-X-2)

(B-1)：樹脂(B-1)(固體成分換算) (B-1): Resin (B-1) (calculated as solid content)

(C-1)：二季戊四醇六丙烯酸酯(KAYARAD(註冊商標)DPHA；日本化藥(株)製造) (C-1): Dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.)

(D-1)：N-苯甲醯氧基-1-(4-苯基硫烷基苯基)辛烷-1-酮-2-亞胺(Irgacure(註冊商標)OXE-01；BASF公司製造；O-醯基肟化合物) (D-1): N-Benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine (Irgacure (registered trademark) OXE-01; BASF Corporation Manufacturing; O-acetoxime compound)

(E-1)：丙二醇單甲基醚乙酸酯 (E-1): Propylene glycol monomethyl ether acetate

(E-2)：N-甲基吡咯烷酮 (E-2): N-methylpyrrolidone

(E-3)：乳酸乙酯 (E-3): Ethyl lactate

(F-1)：聚醚改性矽油(固體成分換算)(

SH8400；東麗道康寧(株)製造) (F-1): Polyether modified silicone oil (conversion of solid content) (

SH8400; manufactured by Toray Dow Corning Co., Ltd.)

[濾色器的製作] [Making of Color Filter]

在2英寸見方的玻璃基板(# 1737；康寧公司製造)上採用旋塗法塗布了該著色固化性樹脂組合物後，在100℃下預烘焙3分鐘，形成了著色組合物層。冷却後，使用曝光機(TME-150RSK；

(株)製造)，在大氣氣氛下、以150mJ/cm²的曝光量(365nm基準)曝光。應予說明，没有使用光掩模。通過將曝光後的著色組合物層在烘箱中、180℃下進行20分鐘後烘焙，從而製作濾色器(膜厚2.0μm)。 The colored curable resin composition was applied on a 2-inch square glass substrate (# 1737; manufactured by Corning Incorporated) by spin coating, and then pre-baked at 100°C for 3 minutes to form a colored composition layer. After cooling, use the exposure machine (TME-150RSK;

(Manufactured by Co., Ltd.), exposed to an exposure amount of 150 mJ/cm ² (based on 365 nm) in an atmospheric atmosphere. It should be noted that no photomask was used. The coloring composition layer after exposure was post-baked in an oven at 180°C for 20 minutes to produce a color filter (film thickness 2.0 μm).

[吸光度的測定] [Measurement of absorbance]

將得到的化合物或色料0.35g在氯仿中溶解，使體積成為250cm³，將其中的2cm³用氯仿稀釋，使體積成為100cm³(濃度：0.028g/L)，使用分光光度計(石英池、光路長；1cm)測定了吸收光譜。按照以下的標準對換算為0.028g/L的最大吸收波長下的吸光度進行了評價。 Dissolve 0.35 g of the compound or colorant in chloroform to make the volume 250cm ³ , dilute 2cm ^{3 of it} with chloroform to make the volume 100cm ³ (concentration: 0.028g/L), use a spectrophotometer (quartz cell , Optical path length; 1cm) The absorption spectrum was measured. The absorbance at the maximum absorption wavelength converted to 0.028 g/L was evaluated according to the following criteria.

A：2.0以上 A: 2.0 or more

B：1.5以上且不到2.0 B: 1.5 or more and less than 2.0

C：不到1.5 C: less than 1.5

[耐溶劑性評價] [Evaluation of Solvent Resistance]

將著色感光性樹脂組合物的塗布膜在N-甲基吡咯烷酮中在室溫下浸漬40分鐘，使用測色機(OSP-SP-200；OLYMPUS公司製造)測定塗布膜的浸漬前後的色差(△Eab*)，按照以下的標準進行了評價。應予說明，△Eab* 值為由根據CIE1976(L*，a*，b*)空間表色系的以下的色差公式求出的值(日本色彩學會編新編色彩科學手冊(昭和60年)第266頁)。 The coating film of the colored photosensitive resin composition was immersed in N-methylpyrrolidone at room temperature for 40 minutes, and the color difference (△) before and after the immersion of the coating film was measured using a color measuring machine (OSP-SP-200; manufactured by OLYMPUS) Eab*), evaluated according to the following criteria. It should be stated that △Eab* The value is calculated from the following color difference formula based on the CIE1976 (L*, a*, b*) space table color system (The Color Science Handbook (Showa 60), page 266, edited by the Color Society of Japan).

△Eab*={(△L*)2+(△a*)2+(△b*)2}1/2 △Eab*={(△L*)2+(△a*)2+(△b*)2}1/2

A：不到5.0 A: Less than 5.0

B：5.0以上且不到10.0 B: 5.0 or more and less than 10.0

C：10.0以上 C: 10.0 or more

[電壓保持率的測定] [Measurement of voltage holding rate]

將得到的化合物0.025g和液晶(MCL-6608、

株式會社製造)1g混合，在樣品瓶中在120℃下加熱了50分鐘。將混合物轉移到離心分離用管中，使用MICRO SIX(

株式會社製造)進行了2次30分鐘的離心分離。將混合物的上清部分封入液晶評價用單元(KSRT-05/BIIIMINTS05X、E.H.C.Co.，Ltd.製造)，使用液晶物性評價裝置(6254型東陽

株式會社製造)在下述的測定條件下測定電壓保持率，按照下述的標準進行了評價。 The obtained compound 0.025g and liquid crystal (MCL-6608,

Co., Ltd.) 1 g was mixed and heated in a sample bottle at 120°C for 50 minutes. Transfer the mixture to a centrifuge tube and use MICRO SIX (

Co., Ltd.) centrifuged twice for 30 minutes. The supernatant portion of the mixture was enclosed in a liquid crystal evaluation unit (KSRT-05/BIIIMINTS05X, manufactured by EHC Co., Ltd.), and a liquid crystal property evaluation device (type 6254 Toyo

Co., Ltd.) The voltage holding ratio was measured under the following measurement conditions, and the evaluation was performed according to the following criteria.

測定條件 Measurement conditions

‧施加電壓脈衝振幅：5V ‧Applied voltage pulse amplitude: 5V

*電壓保持率：1000毫秒後的液晶單元電位差/在0毫秒施加的電壓的值 *Voltage retention rate: the potential difference of the liquid crystal cell after 1000 milliseconds/the value of the applied voltage at 0 milliseconds

評價標準 evaluation standard

A：95%以上 A: More than 95%

B：85%以上且不到95% B: More than 85% and less than 95%

C：不到85% C: Less than 85%

實施例21~24、比較例5、6 Examples 21-24, Comparative Examples 5 and 6

[分散液製作方法] [Method of Making Dispersion]

將表17中所示的各成分稱量後，放入0.4μm的氧化鋯珠粒600份，使用塗料調理器(LAU公司製造)振盪1小時，製作了分散液1~6。 After each component shown in Table 17 was weighed, 600 parts of 0.4 μm zirconia beads were put in, and they were shaken for 1 hour using a paint conditioner (manufactured by LAU) to prepare dispersions 1 to 6.

表17中，各成分表示以下的化合物。 In Table 17, each component represents the following compound.

分散劑1：DISPERBYK-162(固體成分38%的丙二醇單甲基醚乙酸酯溶液) Dispersant 1: DISPERBYK-162 (Propylene glycol monomethyl ether acetate solution with 38% solid content)

分散樹脂1：樹脂(B-2)的丙二醇單甲基醚乙酸酯溶液(固體成分35.1%) Dispersing resin 1: Resin (B-2) propylene glycol monomethyl ether acetate solution (solid content 35.1%)

[著色固化性樹脂組合物的製作方法] [Production method of colored curable resin composition]

將表18中所示的各成分混合，得到了著色固化性樹脂組合物。 The components shown in Table 18 were mixed to obtain a colored curable resin composition.

表18中，各成分表示以下的化合物。 In Table 18, each component represents the following compound.

(F-1)：聚醚改性矽油(固體成分換算)(

SH8400; manufactured by Toray Dow Corning Co., Ltd.)

[電壓保持率的測定] [Measurement of voltage holding rate]

在3英寸見方的玻璃基板(# 1737；康寧公司製造)上採用旋塗法塗布該著色固化性樹脂組合物後，在100℃ 預烘焙3分鐘，形成了著色組合物層。冷却後，使用曝光機(TME-150RSK；

(株)製造)在大氣氣氛下以150mJ/cm²的曝光量(365nm基準)曝光。應予說明，没有使用光掩模。通過將曝光後的著色組合物層在烘箱中、230℃下進行20分鐘後烘焙，從而制作了塗膜(膜厚2.0μm)。通過將該塗膜從玻璃基板刮掉，從而得到了粉體。將得到的粉體0.025g和液晶(MCL-6608、

株式會社製造)1g混合，在樣品瓶中在120℃下加熱了50分鐘。將混合物轉移到離心分離用管中，採用MICRO SIX(

株式會社製造)在下述的測定條件下測定電壓保持率，按照下述的標準進行了評價。 After coating the colored curable resin composition on a 3-inch square glass substrate (# 1737; manufactured by Corning Corporation) by spin coating, it was pre-baked at 100° C. for 3 minutes to form a colored composition layer. After cooling, use the exposure machine (TME-150RSK;

(Product made by Co., Ltd.) Exposure was performed in an atmospheric atmosphere at an exposure amount of 150 mJ/cm ² (365 nm standard). It should be noted that no photomask was used. The coloring composition layer after exposure was post-baked in an oven at 230°C for 20 minutes to produce a coating film (film thickness 2.0 μm). By scraping off the coating film from the glass substrate, a powder was obtained. The obtained powder 0.025g and liquid crystal (MCL-6608,

測定條件 Measurement conditions

‧施加電壓脈衝振幅：5V ‧Applied voltage pulse amplitude: 5V

評價標準 evaluation standard

A：95%以上 A: More than 95%

B：85%以上且不到95% B: More than 85% and less than 95%

C：不到85% C: Less than 85%

產業上的可利用性 Industrial availability

本發明的化合物的吸光度、電壓保持率優異，並且採用使用了該化合物的著色組合物，能夠製造耐溶劑性優異的濾色器。 The compound of the present invention has excellent absorbance and voltage retention, and a coloring composition using the compound can be used to produce a color filter having excellent solvent resistance.

Claims

一種由式(A-I)表示的化合物：

式(A-I)中，R⁴¹~R⁴⁴各自獨立地表示氫原子、碳數1~20的飽和烴基、可具有取代基的碳數6~20的芳香族烴基或可具有取代基的碳數7~30的芳烷基，該芳香族烴基和該芳烷基可具有的取代基可以是-SO₃ ^-或-SO₂-N^--SO₂-R^f，該碳數1~20的飽和烴基中，該飽和烴基中所含的氫原子可以被取代或未取代的胺基或鹵素原子取代，該飽和烴基的碳數為2~20的情況下，該飽和烴基中所含的亞甲基可被替換為氧原子或-CO-，不過，該碳數2-20的飽和烴基中，鄰接的亞甲基不會同時被替換為氧原子，末端的亞甲基不會被替換為氧原子或-CO-，R⁴¹與R⁴²可結合並與它們結合的氮原子一起形成環，R⁴³與R⁴⁴可結合並與它們結合的氮原子一起形成環，R⁴⁷~R⁵⁴各自獨立地表示氫原子、鹵素原子、硝基、羥基、-SO₃ ^-、-SO₂-N^--SO₂-R^f、或碳數1~8的烷基，構成該烷基的亞甲基可以被替換為氧原子或-CO-，R⁴⁸與R⁵² 可相互結合而形成-NH-、-S-、或-SO₂-，不過，該烷基中，鄰接的亞甲基不會同時被替換為氧原子，末端的亞甲基不會被替換為氧原子或-CO-，環T¹表示碳數3~10的芳香族雜環，該碳數3~10的芳香族雜環可具有以下作為取代基：碳數1~20的飽和烴基、取代或未取代的胺基或可具有取代基的碳數6~20的芳香族烴基，該芳香族烴基可具有的取代基可以為-SO₃ ^-或-SO₂-N^--SO₂-R^f，M^r+表示氫離子、r價的金屬離子或者取代或未取代的銨離子，k表示由式(A-I)表示的化合物具有的-SO₃ ^-的個數和-SO₂-N^--SO₂-R^f的個數之和，且k表示2~7的整數，r表示1以上的整數，R^f表示碳數1~12的氟烷基，不過，由式(A-I)表示的化合物具有至少1個-SO₂-N^--SO₂-R^f。 A compound represented by formula (AI):

In the formula (AI), R ⁴¹ to R ⁴⁴ each independently represent a hydrogen atom, a saturated hydrocarbon group with 1 to 20 carbons, an optionally substituted aromatic hydrocarbon group with 6 to 20 carbons, or a substituted carbon number 7 ~30 aralkyl group, the aromatic hydrocarbon group and the substituent that the aralkyl group may have may be -SO ₃ ^- or -SO ₂ -N ^-- SO ₂ -R ^f , the saturated hydrocarbon group having 1 to 20 carbon atoms In the saturated hydrocarbon group, the hydrogen atom contained in the saturated hydrocarbon group may be substituted by a substituted or unsubstituted amine group or halogen atom. When the saturated hydrocarbon group has 2 to 20 carbon atoms, the methylene group contained in the saturated hydrocarbon group may be It is replaced by an oxygen atom or -CO-. However, in this saturated hydrocarbon group with 2-20 carbon atoms, adjacent methylene groups will not be replaced by oxygen atoms at the same time, and the terminal methylene groups will not be replaced by oxygen atoms or -CO-, R ⁴¹ and R ⁴² can be combined with their combined nitrogen atom to form a ring, R ⁴³ and R ⁴⁴ can be combined with their combined nitrogen atom to form a ring, R ⁴⁷ ~ R ⁵⁴ each independently represents hydrogen atom, a halogen atom, a nitro group, a hydroxyl _{^{_{group, -SO 3 -, -SO 2 -N}}} - methylene -SO ₂ -R ^f, or an alkyl group having 1 to 8 carbon atoms constituting the alkyl group may be replaced Oxygen atom or -CO-, R ⁴⁸ and R ⁵² can combine with each other to form -NH-, -S-, or -SO ₂ -, but in this alkyl group, adjacent methylene groups will not be replaced with oxygen at the same time Atom, the methylene group at the end will not be replaced with an oxygen atom or -CO-. Ring T ¹ represents an aromatic heterocyclic ring with 3 to 10 carbon atoms. The aromatic heterocyclic ring with 3 to 10 carbon atoms may have the following substitutions Group: a saturated hydrocarbon group with 1 to 20 carbons, a substituted or unsubstituted amine group, or an optionally substituted aromatic hydrocarbon group with 6 to 20 carbons. The substituent that the aromatic hydrocarbon group may have may be -SO ₃ ^- or -SO ₂ -N ^-- SO ₂ -R ^f , M ^r+ represents hydrogen ion, r-valent metal ion or substituted or unsubstituted ammonium ion, and k represents -SO ₃ ^- of the compound represented by formula (AI) The sum of the number and the number of -SO ₂ -N ^-- SO ₂ -R ^f , and k represents an integer of 2-7, r represents an integer of 1 or more, and R ^f represents a fluoroalkyl group with carbon number 1-12, However, the compound represented by the formula (AI) has at least one -SO ₂ -N ^-- SO ₂ -R ^f .

如請求項1之化合物，其中，M^r+為r價的金屬離子。 Such as the compound of claim 1, wherein Mr ⁺ is an r-valent metal ion.

如請求項1之化合物，其中，由上述T¹表示的芳香族雜環為由下述式(A-t1)表示的環：

式(A-t1)中，環T²表示碳數3~10的芳香族雜環，R⁴⁵和R⁴⁶各自獨立地表示氫原子、可具有取代基的碳數1~20的飽和烴基、可具有取代基的碳數6~20的芳香族烴基或可具有取代基的碳數7~30的芳烷基，該飽和烴基的碳數為2~20的情況下，該飽和烴基中所含的亞甲基可被替換為氧原子或-CO-，不過，該碳數2~20的飽和烴基中，鄰接的亞甲基不會同時被替換為氧原子，末端的亞甲基不會被替換為氧原子或-CO-，R⁴⁵與R⁴⁶可結合並與它們結合的氮原子一起形成環，R⁵⁵表示碳數1~20的飽和烴基、或可具有取代基的碳數6~20的芳香族烴基，k1表示0或1，*表示與碳陽離子的鍵合端。 The compound of claim 1, wherein the aromatic heterocyclic ring represented by the above T ¹ is a ring represented by the following formula (A-t1):

In the formula (A-t1), ring T ² represents an aromatic heterocyclic ring having 3 to 10 carbons, R ⁴⁵ and R ⁴⁶ each independently represent a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbons that may have a substituent, and A substituted aromatic hydrocarbon group with 6 to 20 carbons or an optionally substituted aralkyl group with 7 to 30 carbons. When the saturated hydrocarbon group has 2 to 20 carbon atoms, the saturated hydrocarbon group contains The methylene group can be replaced with an oxygen atom or -CO-. However, in this saturated hydrocarbon group with 2 to 20 carbon atoms, the adjacent methylene group will not be replaced with an oxygen atom at the same time, and the terminal methylene group will not be replaced It is an oxygen atom or -CO-, R ⁴⁵ and R ⁴⁶ can be combined and form a ring together with the nitrogen atom to which they are combined, R ⁵⁵ represents a saturated hydrocarbon group with 1 to 20 carbons, or a substituted group with 6 to 20 carbons In the aromatic hydrocarbon group, k1 represents 0 or 1, and * represents the bonding terminal to the carbocation.

一種著色組合物，其包含如請求項1至3中任一項之化合物。 A coloring composition comprising the compound of any one of claims 1 to 3.

一種濾色器，其係由如請求項4之著色組合物形成。 A color filter formed from the coloring composition of claim 4.

一種顯示裝置，其包含如請求項5之濾色器。 A display device including the color filter of claim 5.