TW201041980A - Dye composition - Google Patents

Abstract

The dye composition (A-1) of this invention comprises a compound represented by a formula (1) and a compound represented by a formula (2). The coloring photosensitive resin of the invention comprises a dye composition (A-1), an alkali soluble resin (B), a photopolymerizable compound (C), a photopolymerization initiator (D) and a solvent (E).

Description

201041980 VI. Description of the Invention: TECHNICAL FIELD OF THE INVENTION The present invention relates to a dye composition. [Prior Art] A fine coloring pattern has been used to form a desired azo dye, and various azo dyes and lanthanoid dyes are used for example (for example, Patent Document 1, Patent Document 2, etc.). . In recent years, the industry expects color filters to be more highly contrasted. [Patent Document 1] [Patent Document 1] Japanese Patent Laid-Open Publication No. Hei. No. Hei. No. Hei. A dye composition capable of producing a color filter of higher contrast is provided. That is, the present invention provides the following [1] to [1 8]. Q [1]. A dye composition comprising a compound represented by the formula (1) and a compound represented by the formula (2):

146860.doc 201041980 ($(1) and (2), 16 R1~R15 stand independently of the atom, -R16, -OH, -OR, -C02H, ς〇., -S03Na, -S03K Or -S03H, and the group of R~Rl5 represents -so3-, R is not a number of 〇! 饱和 one of the saturated hydrocarbon groups, the oxygen atom contained in the saturated hydrocarbon group can also be used to prepare The atomic, hydroxy or alkoxy group having a number of turns of 1 to 10 is substituted for the _CH2_ contained in the saturated sulphur Φ yumandi group. It can also be substituted into _〇... -CO- or -NR17-, only 17 志A red hydrocarbon does not contain an atom or a saturated hydrocarbon group having a carbon number of 1 to 1 fluorene, and R independently represents a hydrogen atom, _Rl6, _〇H, _〇r16, -S〇3, -S03Na, -S03K, - S03H, -s〇2n(R^)R^,.s〇2NHR,^ and at least one of !1~^ towels represent _s〇2n(ri8)r19 or 's〇2nhr18, ^ and R 9 are independently represented An alkyl group having a carbon number of 1 to 10, a city group having a carbon number of 3 to 30, an aromatic hydrocarbon group having a carbon number of 6 to 1 G, or a heterocyclic group having a carbon number of one or more, or Bonding to each other to form a carbon number of the heterocyclic ring '(tetra) group and the hydrogen atom contained in the group may also be dentate atom 1 Substituted by a phenyl group or a phenyl group, the calcining group and the -ch2- contained in the alkyl group may be substituted into _〇...C0·, shed or 丨6_, the aromatic smoki group and the aromatic heterocyclic group. The hydrogen atom contained in it can also be

R -C02H ' -COjR1 sub' -R generation)

OH, -OR - Να -CH=CH2 or _CH=CHR16 [2]. For example, the dye composition of the formula (3) further comprises a compound represented by the formula (3): 146860.doc (3) 201041980

(In the formula (3), R41 to R" are 〇r, and 6 γ〇„j independently represents a hydrogen atom, _Rb, _0H, -OR > -C02H ' -CO^R16 〇. f31 such as 丨 〇 2N (Rl ) Rl9 or -S02NHR18). ❹ m. The dye composition of [1] or [2], in the formula (1), R1~ respectively, the cats j represents a hydrogen atom, 16, or -so3h, 3 R1 to R15 Table, 3, and at least - represents -so3h. The dye composition of any one of [1] to [3] wherein in the formula (7), Rh to R35 independently represent a gas atom, _^6, _team, -so3h, -so2n(r18)r1, _s 〇2Nhr18, R21 to R35 - means P, and at least - means -S〇2n(r18)r19 ❹ or -so2nhr18. [5] The dye composition according to any one of [2] to [4] wherein, in the formula (7), the hydrogen atom, -R16 or -S〇2NHR18, R41 to R55 are independently represented by ～1155. Two represent _s〇2NHRu. [6] The dye composition according to any one of [1] to [5] wherein the content of the compound represented by the formula (1) is 1 part by mass or more and 35 parts by mass relative to the mass fraction of the dye composition. Hereinafter, the content of the compound represented by the formula (2) is 65 parts by mass or more and 99 parts by mass or less. The dye composition according to any one of [2] to [6] wherein the content of the compound represented by the formula (1) is 1 part by mass based on 100 parts by mass of the dye composition. The content of the compound represented by the formula (2) is 65 parts by mass or more and 98 parts by mass or less, and the content of the compound represented by the formula (3) is 1 part by mass or more and 2 parts by mass or less. the following. [8] The dye-based photosensitive resin composition of the present invention, which comprises the dye composition (A)) according to any one of [1] to [7], an alkali-soluble resin (B), and a photopolymerizable compound (c) , photopolymerization initiator (D) and solvent (E). [9] The colored photosensitive resin composition according to [8], which further comprises a pigment (a-2). [1] The colored photosensitive resin composition according to [9], wherein the pigment (A-2) is a pigment containing C.I. Pigment Blue 15:6. [11] The colored photosensitive resin composition according to [10], wherein the mass ratio of the dye composition (A-1) to the C.I. Pigment Blue 15:6 is 3: 97 to 5 〇 : 5 〇. [12] A coating film formed by using the dye composition of any one of [7] to [7]. [13] A color filter formed by using the dye composition of any one of [丨] to [7]. [14]. A color filter such as [π], which is formed by photolithography. [15] The use of the dye composition of any one of [1] to [7] for producing a color filter. [16]. A coloring composition comprising the dye of any one of (1) to [7] 146860.doc 201041980 composition (A-1) and pigment (Ad). [17] The coloring composition according to [16], wherein the pigment (A_2) is a pigment containing ci pigment blue 15:6. [18] The coloring composition according to [17], wherein the dye composition (the mass ratio of the pigment blue to the pigment blue 15: 6 is 3: 97 to 50: 50. [Embodiment] The dye composition of the invention ( A-1) includes a compound represented by the formula (hereinafter sometimes referred to as "compound (1)") and a compound represented by formula (2) (hereinafter, sometimes referred to as "compound (2)") In the present specification, 'there are differences depending on the carbon number, but the following substituents are the same in any of the chemical structural formulas unless otherwise specified. Further, linear or Substituents for both of the branches also include any of them.

(In the formulae (1) and (2), R1 to R15 each independently represent a hydrogen atom, -R16, -OH, -ORb, -C02H, -C02R16, -S(V, _s〇3Na, -S03K or - S03H, and 146860.doc -7- 201041980 R] - Rl5 - a group represents -so3-. & Rl6 represents a saturated hydrocarbon group having a carbon number of 1 to 10, and the hydrogen atom contained in the saturated hydrocarbon group may also be The i-atom, the meridine or the alkoxy group having a carbon number of 1 () is substituted for the saturation: the _CH2_ contained in the group may be substituted with _〇_, _C〇-NR17-.

Rl7 represents a hydrogen atom or a saturated hydrocarbon group having a carbon number of 1 to 10. R21 to R35 independently represent a hydrogen atom, _Rl6, _〇H, _〇r16, _c〇2H, -C〇2R16, -s〇3--S03Na, -S03K, -S03H, -S02N(R18)r19 or - One of at least one of R2 to R35 represents _s〇3_, and the base represents -so2n(r18)r19 or _s〇2NHRi8 and R21~R35 R 8 and R19 independently represent carbon number i~1 An alkyl group of hydrazine, a cycloalkyl group having a carbon number of 3 to fluorene, an aromatic hydrocarbon group having a carbon number of 6 to 10, or an aromatic heterocyclic group having a carbon number of 5 to 1 Å, or φ may be bonded to each other (4) to form a carbon. a heterocyclic ring having a number of 2 to 1 (), a hydrogen atom contained in the pendant group and the ring group may be substituted by a silane atom, a trans group or a phenyl group, and the alkyl group and the cycloalkyl group are contained The _CH2_ may also be taken as 0 C 〇-, -NH- or -NR16-, and the aromatic hydrocarbon group and the hydrogen atom contained in the aromatic heterocyclic group may also be a functional atom, _Rl6, _ 〇h, -OR16, -N02, -CH=CH^-CH=CHR〗 6 Substituted). The number of positive (+) charges and the number of negative (one) charges in each of the compounds of the formulae (1) and (2) are the same. Here, the saturated hydrocarbon group may be an alkyl group, a cycloalkyl group, an alkyl group having an alkyl group and an alkyl group having a cycloalkyl group, which are arbitrarily combined. As the alkyl group, a mercapto group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a fluorenyl group-methyl group, and 2 146860.doc 201041980 are exemplified. Methylpropyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2-ethylhexyl, decyl, decyl, dimethylpropyl, 1,2-dimethyl Propyl, 2,2-dimethylpropyl and the like. • Examples of the cyclodextrin group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and a tricyclodecyl group. Examples of the dentate atom include a fluorine atom, a chlorine atom, and a desert atom. Examples of the alkoxy group include a methoxy group, an ethoxy group, a n-propoxy group, an iso-oxyoxy-n-butoxy group, a 1-methylpropoxy group, a 2-methylpropoxy group, and a third butoxy group. , "Gytyloxy, 2-methylbutoxy, 3-methylbutoxy, dimethyl dimethyloxy, !, 2-dimethylpropoxy, 22 dimethyl propyl Oxyl-pentyloxy, n-hexyloxy, heptyloxy, octyloxy, -2-ethylhexyloxy, decyloxy, decyloxy, etc. Examples of the aromatic hydrocarbon group include an aryl group and an aralkyl group. Examples of the aryl group include a phenyl group, a naphthyl group, a biphenyl group, a fluorenyl group, and a phenanthryl group. Examples of the aralkyl group include a benzyl group, a phenethyl group, and a benzene group. a propyl group, a triphenyl fluorenyl group, a naphthylmethyl group, a naphthylethyl group, etc. as an aryl group having a phenyl group, a tolyl group, a xylyl group, a cumene benzoate 2,6-ethylphenyl group In addition to the 2-methyl- 6-ethylphenyl group, the above-mentioned substituents may be arbitrarily combined. Examples of the oxime-heterocyclic ring include the following heterocyclic rings:

NH

146860.doc 201041980

N

As a heterocyclic ring, it can be a 夭# J is a fragrant heterocyclic ring, and also a ring. The horse does not have a mixture of aromatics.

List the following heterocycles, etc.:

The position and the position described above may be any combination of the above-mentioned rings. The above-mentioned alkoxy group etc. are mentioned as -OR16'. As -CO2R16, can be listed as a strong 氦 氦 轴 轴 轴 尽 J J J · methoxy methoxy methoxy methoxy methoxy methoxy methoxy methoxy methoxy methoxy methoxy methoxy methoxy methoxy methoxy methoxy methoxy methoxy methoxy methoxy methoxy methoxy methoxy methoxy methoxy methoxy methoxy methoxy methoxy methoxy methoxy , pentyloxy (tetra), isopentyloxy (tetra), neofilyl, cyclopentyloxy, hexyloxycarbonyl, cyclohexyloxycarbonyl, heptyloxycarbonyl, cycloheptyloxycarbonyl, octyloxycarbonyl , 2-ethylhexyloxycarbonyl, cyclooctyloxycarbonyl, decyloxycarbonyl, decyloxycarbonyl, tricyclodecyloxycarbonyl, methoxypropoxy, ethoxypropoxycarbonyl, Hexyloxypropoxycarbonyl, 2-ethylhexyloxypropoxycarbonyl, methoxyhexyloxycarbonyl, and the like. Examples of -S〇2NHR18 include an amine sulfonyl group, an N-(methyl)amine sulfonyl group, an N-(ethyl)amine sulfonyl group, an N-(propyl)amine sulfonyl group, and N-( Isopropyl) sulfonamide, N-(butyl)amine sulfonyl, N-(isobutyl)amine sulfonyl, N-146860.doc 10-201041980 (mercapto)amine emulsifier, N_ (isopentyl)amine sulfonyl, N_(neopentyl)amine sulfonyl, N-(cyclopentyl)amine sulfonyl, n-(hexyl)amine sulfonyl, N-(cyclohexyl)amine sulfonate Sulfhydryl, N-(heptyl)amine sulfonyl, N-(cycloheptyl)amine sulfonyl, N-(octyl)amine hydrazino, N-(2-ethylhexyl)amine sulfonate, N-(l,5-dimethylhexyl)amine continuation base, N_(cyclooctyl)amine sulfonyl, N-methyl fluorenyl, N-(fluorenyl)amine sulfonyl, N_ (tricyclodecyl)amine sulfonyl, N_(methoxypropyl)amine sulfonyl, N-(ethoxypropyl)amine sulfonyl, N-(propoxypropyl)amine sulfonyl , N-(isopropoxypropyl)amine sulfonyl, N-(hexyloxypropyl)amine sulfonyl, N-(2-ethylhexyloxypropyl)amine sulfonyl, N_ (methoxy Alkyl sulfonyl, n_(3_phenylmercaptopropyl) Sulfo acyl and the like. Further, examples of -ShNHRi8 include a group represented by the following formula. Here, the following formula t ′ χι denotes a halogen atom. Χ3 represents an alkyl group having a carbon number of 1 to 3 or an alkoxy group having a carbon number of 3, and the hydrogen atom of the alkyl group and the alkoxy group may be substituted by a halogen atom. X2 represents an alkyl group having a carbon number of 3, an alkoxy group having a carbon number of 〇 3, a sulfonium atom or a schlossyl group, and the nitrogen atom of the alkyl group and the methoxy group may be substituted by a halogen atom. The alkyl group which may be substituted by a halogen atom and has a carbon number of 3 may be a perfluoromethyl group or the like in addition to the above alkyl group. The above-mentioned alkoxy group, particularly a methoxy group, an ethoxy group, a propoxy group or the like, may be mentioned as a methoxy group having a carbon number of (i) which may be substituted by an imine atom.

146860.doc -11- 201041980

Nhso2

Nhso2

Nhso2

NHS〇2 y 9 9 nhso2 nhso2 nhs

/-^2nHS〇2 I nhso2 Μθ nhs〇2 C0

NHS〇2 146860.doc -12· 201041980 Η〇·

NHSO〇 nhso2 •HO〆

HO j HO’, |^, NHS〇2 'nhso2 〇h HO" , NHS〇2 h〇,\/N\/\/NHS02

?H HO NHf°2 NHS〇2

Nhso2

HO ΜβΟ-ΝΗ^ ❹ ,〇, "NHSO? ^ ^ nhso2 , o’\^, nhso2 >fa nhL2 NHS〇2 , nhso2

, nhso2 〇, NHS〇2

oiHM

〇, z〇

I nhso2 '〇, o2shn

〇 〇 〇 o

〇2SHN

〇, 〇 Ίν‘ X I H NHS〇2 〇 Λ

NHS〇2 -X3 〇

I

〇 NHS〇2 丫, NHS〇2 NHS〇2 〇

〇nc^A NHS〇2

〇NHS〇2 MeO人Nhi〇2 〇〇NHS〇2 NHS〇2 146860.doc -13- 201041980 X1/\^NHS〇2 X1'^v/^'NHS〇2 II CF3CH2NHS〇2 CF3(CF2)7CH2NHS 〇2

Cl ci-v^v^A^nhso2 NHk NHk NhL2 NH^& ib-f3 heart~ nhs〇2 nhs〇2

Cl \\ TCI2 nhso2 -ci3 nhso2 I NHS〇2 nhs〇2 B "F, 丄 /Br B"- 丨:TB"2

Cl

F

Cl

Cl Br NHS〇2

F3c cf3

Br

I nhso2

Cl II J 丨I , 〇f3 f3c. I nhso2

NHS〇2 cf3

Br 〇cf3 o2n NHS〇2

CF.

Br Cl

N〇2 nhso2

NO· 2 NHS〇2 ^OMe

N〇2 o2n nhso2

N〇2 nhso2 o2n

Cf3 NHk N〇2

Cl

NHSOo

Cl I NHS〇2 Cl f3C'

Nhso2 〇Me

, NHS〇2 -X2 .〇.

NHS〇2

Nhso2

q. >—N -nhso2

SI 6 u02 146860.doc • 14- 201041980

NHS02 wherein, as -S02NHR18, R18 is preferably an alkyl group having 1 to 10 carbon atoms. As -so2n(r18)r19, the following bases can be cited:

Examples of the hetero ring formed by bonding R18 and R19 to each other include a group represented by the following formula:

146860.doc -15· 201041980

Ο

Wherein, as R18 and a cycloalkyl group having 5 to 7 R, hydrazine, preferably an alkyl group having a carbon number of 1 to 10, a phenylallyl group, a phenyl group, and an aralkyl group having a carbon number of 8 to 10, 146,860 .doc •16- 201041980 The base of the base and the aryl group, the carbon number is 2~8, the brightest is the branched carbon group with a carbon number of 6~8, especially the 2-ethyl group. Heji. In the compound (1), Ri~ preferably 〇3-, -s〇3Na, _s is called a chlorine atom, 4 5U3H, and han 1~Rl5 is Ο or 〇3H, and the one in R~R Further, R1 to Rl5 are particularly preferably independently a hydrogen atom, 丨6 _S〇3 or ·SO; one of H,me is nR1~Rl5t<ns〇3H. Further, compound (1) More preferably, it is represented by the following formula (la)

(1a) (In the formula (la), ❹ ^ independently represents a hydrogen atom or a carbon group having a carbon number of 1 to 1 G, and R independently represents a hydrogen atom, cn ^ L, a plurality of S.S〇3, _S03Na, _s〇3K : or _ 3. Among them, one R2' means _S(V).

146860.doc •17· 201041980 S03H ^ -S〇3Na > -S03K ' -S02N(R18)R19 4 S02NHR18, and f ^ 8 : In compound (7), R21 to R35 are preferably independently hydrogen atoms, - At least one of R1, -SO, ·, -SHu. R *_S〇2N(R18)R19 or so2nhr18. R21 ~ r35 16 R Particularly good 疋 are independently hydrogen atom, 35 S〇3 _S〇3H, -S〇2N(r18)R19 or -S02丽R18, and at least one of R~R towels is _s〇 2N (Rl8) Rl9 or Perry Ri8. Further, the yttrium compound (2) is more preferably a compound represented by the following formula (2a)' (R21) 2

(R21.)2 R 22 (2a) (In the formula (2a), the '2 knife is independently a hydrogen atom or an alkyl group having a carbon number of 1 to 10, and R independently represents a hydrogen atom, _scv, training, .SO #, -so3h, -S〇2N(Rl8)Rl9 or _s〇禅Ri8, where -r22 means 夕 m 2 means ·8〇2Ν(Ι118)Κ_19 or _s〇2NHR18). The compound (2), the following compound (2-1), the compound (2.2), and the compound (2-3) are exemplified. The compound (2-1) is a compound prepared under the formula of τ 4 female, that is, in the formula (2), R21 to R35 independently represent hydrogen moon, , , , -R, _OH, -OR16, -co2h, -C02R16, - S03, -s〇3Na, ς r2] r35, -so3h or -S02N(R18)r!9, and one of them represents _S〇3·, and one of R2丨~R35 represents a woman@ Compound. The compound (2-1) is preferably a compound in which W5 independently represents a hydrogen atom, _r16, _S (V, Na, -S03K, -S03H or -S〇2N(R18)R19, and wherein R to R represents _s〇3-, and one of r21 to R35 represents a compound of -S02NR18R19. ', Compound (2-2) is as follows The compound, that is, in the formula (2), independently represents a hydrogen atom, _Ri6, _〇h, _〇Ru, _co2r16, Ο Ο -S03-, -S03Na, -S03K, -S03H or -SC^. NHR18, and one of R21 to R35 represents a compound of _s〇3-, and R_so2nhr18. The compound (2-2) is preferably a compound of the following: R21 to R35 each independently represent a hydrogen atom, _Ris 21 to R35 One of the representations is in the formula (2), '-S〇3-, _s〇3Na, -S03K, -S03H or -S02NHR18, and one of R21 to R35 represents -so3' R21~R35 One of them represents a compound of _s〇2NHRl8. The compound (2-3) is a compound in which, in the formula (2), ^^~foot 35 independently represents a hydrogen atom, _Rl6, _〇H, _〇 Rl6, CO#, _c〇2Ri6, -SO', -S03Na, -S〇3K, -S〇3H, _s〇2N(Rl8)Rl9 or -S02NHR18' R2i~R35 one of _S(V, and at least two of R21~R35 Represents _s〇2N(Ru)Rl9 or -s〇2>jhr18

The compound D compound (2-3) is preferably a compound in which, in the formula (2), the RR knife independently represents a halogen atom, -R16, _S03·, -S03N£i, -so3K, -so3H, - So2n(r18)r19 or _s〇2NHr18, and 146860.doc -19- 201041980 one of the r21~r towels represents _s〇3-, and at least two of R21~R35 represent -S02N(R18)R19 or- Compound of S02NHR18. As the compound (2), for example, the following compounds can be mentioned:

These compounds can also be used, for example, by the method disclosed in Japanese Patent No. 2003-20(4) No. 3 or according to the method. σ When the dye composition of the present invention contains only the compound (1) and the compound (7) as a dye, it is contained in an amount of 1 part by mass or more based on 1 part by mass of the dye composition (1), and 曰 = compound (1). "1 part by mass or more and 2 parts by mass", particularly preferably: more than or equal to 15 parts by mass of the compound (2), preferably more than 65 parts by mass, and 99 parts by mass of the compound (2). The amount of the component is not less than 99 parts by weight, and furthermore than 146860.doc -20-201041980, the compound (1) i parts by mass or more, 35 parts by weight, (2) 65 parts by weight, and 99 parts by mass or less. The dye composition may further comprise a compound (hereinafter, sometimes referred to as "compound (3)"):

(3) (In the formula (3), R41 to R55 independently represent a hydrogen atom, -Rl6...〇H, _〇r16, _C〇2H, ·0〇2Κ16, -so2n(r18)r丨9 or _s〇 2NHRl8). The compound (3) is preferably a compound 16 in which, in the formula (7), a compound which independently represents a hydrogen atom, _R16 or _s〇2Nhr18, and at least two of R41 to R55 represents _s〇2NHRl8. .

Further, the compound (3) is preferably a compound represented by the following formula (3a):

(3a) (In the formula (3a), R41' independently represents a hydrogen atom or an alkyl group having a carbon number of 丨~1〇-s〇2N(r)Rl9 or -so2nhr18). 146860.doc -21- 201041980 4乍 is a compound (3), and examples thereof include the following compounds:

When the dye composition of the invention contains the compound (1), the compound (7), and the compound (3) as a dye, it is preferable to contain the compound (1) in an amount of 1 part by mass or more and 15 parts by mass based on the dye composition (10 parts by mass). In the following, it is more preferable that the compound (1) is contained in an amount of not less than 2 parts by mass and not more than 1 part by weight. Further, the compound (7) is preferably 65 parts by mass or more and % by mass in an amount of 7 parts by mass or more and 95 parts by mass or less. The compound (7) is more than 2 parts by mass or less, more preferably 3 parts by mass or less. Further, the compound (1) is preferably used in an amount of 15 parts by mass or less, the compound (2) is 65 parts by mass or more, and the compound (3) is i part by mass or more and parts by mass or less. The compound (7) and the compound (3) can be obtained, for example, by the usual method of using a pigment or a dye intermediate chlorodiindole in the usual manner to obtain a pigment or a pigment having _S〇2C1. The substance reacts with the material indicated by _NHR below. Further, it can be produced by chlorinating a pigment produced by the method disclosed in Japanese Patent Application Laid-Open No. Hei 3-78702, page 3, right upper barrier, and lower left column. It is allowed to react with an amine. The coloring composition of the attacking moon comprises the above dye composition (A-1) and pigment 146860.doc • 22- 201041980 (Α-2) 〇HUm, 15.6' and other blue pigments; CI pigment purple is contained It is selected from C. “Material violet ^8^ color pigment, etc. Among them, 'better of at least one kind of pigment, especially good is 5:3, 15:6 in the heart..., there is L pigment blue 15 : 6 The "° early use alone" can also be used in combination of two or more. Ο Ο = To be ancient, the following treatments can be applied to organic pigments: rosin treatment, = lead: surface treatment with pigment bases such as acid groups or test groups, grafting treatment of pigment surfaces such as acid = sputum The micronization treatment by a sulfur method or the like, or the use of a cleaning treatment for removing impurities, such as treatment by impurities such as an ion exchange method. 1 The best choice for organic pigments is from the top to the top ten. For example, a pigment-based, anionic, non-based, polyester-based, polyamine-based pigment can be used as a pigment dispersant. Interfacial Activity of the System, Acrylic Acid, etc. The pigment dispersants may be used singly or in combination of two. When the pigment dispersant is used, the amount thereof is preferably 1 part by mass or less, more preferably 0.05 part by mass or less, and 0.5 part by mass or less per mol of the pigment (A·2). If the amount of the pigment component (4) is within the range, then it is preferable to obtain the phthalocyanine dispersion of 146860.doc -23-201041980. The content ratio (mass ratio) of the dye composition (A-1) to the pigment (A-2) is preferably 1:99 to 99:1, more preferably 1:99 to 60:40, and further preferably Yes 3: 97~50: 50' and then better is 5: 95~40: 60. By setting such a ratio, it is easy to achieve the optimization of the transmission spectrum, and it is possible to obtain a coating and a pattern having high contrast and high brightness, and the heat resistance and chemical resistance are improved. It is particularly preferred that the mass ratio of the dye composition (A-1) to C.1_Pigment Blue 15:6 is 3: 97 to 50:50. The colored photosensitive resin composition of the present invention comprises the above dye composition (A-1), an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator (D), and a solvent (E). The dye composition (A-Di content is 〇3 to 3〇% by mass, preferably 丨2 to 〇% by mass, more preferably 1 to 15% by mass based on the solid content of the colored photosensitive resin composition. In the case where the pigment (A-2) is contained, the amount of the dye composition (6) and the pigment (()) is from 0 to 3 mass% with respect to the solid content of the coloring photosensitive resin composition. 'It is preferably 丨~仂% by mass, more preferably 1 to 30% by mass. Further, when the pigment (A-2) is C. Ϊ•Pigment Blue 15:6, the dye::(A-1) and c.!•Pigment Blue 15:6 are combined with the coloring sensitivity' The solid content of the resin composition is [% by mass, preferably in an amount of 3% to ≤% by mass), more preferably 5 to _% by volume, and even more preferably H) to 25 146860.doc • 24-201041980 Here, the solid content component refers to the total of the components other than the solvent in the colored photosensitive resin composition. The testable resin (B) is not particularly limited, and any resin can be used. For example, the alkali soluble (b) contains a constituent unit having an m group. As the structural unit having a rebel group, it is preferred to have a (meth)acrylic acid derived from a mouth unit, and (meth)acrylic acid means a acrylic acid and/or a methyl propyl benzoic acid. In all the structural units constituting the test-soluble resin (B), the content of the structural unit derived from (meth)acrylic acid is preferably 16 mol% or more, 4 mol% or less, more preferably 18 Mole% or more, 38 mol% or less. When the content of the structural unit derived from (meth)acrylic acid is within this range, the solubility in the non-pixel portion becomes good at the time of development. Further, there is a tendency that the residue does not remain in the non-pixel portion after development. Examples of the other monomer other than the structural unit derived from the Q-constituting unit of (meth)acrylic acid, which is an alkali-soluble resin-imprinted resin, include an aromatic vinyl compound, an unsaturated carboxylic acid ester, and an unsaturated carboxylic acid. Acid aminoalkyl esters, unsaturated acid glycidyl esters, acid retarded vinyl esters, unsaturated ethers, vinyl cyanide compounds, unsaturated amides, unsaturated quinones, a diene, a macromonomer having a monopropenylfluorenyl group or a monomethacrylinyl group at the end of a polymer molecular chain, a unit represented by the formula (π), and a unit represented by the formula (III) . 146860.doc -25- 201041980

(III) (In the formula (III), R" and R55 each independently represent a nitrogen atom or a methyl group. R54 and R56 each independently represent a hydrogen atom or an alkyl group having a carbon number of 6). As an alkali-soluble resin (B) Specifically, methacrylic acid / benzyl methacrylate copolymer, methacrylic acid / benzyl methacrylate / styrene copolymer, methacrylic acid / benzyl methacrylate / methyl Isodecyl acrylate copolymer, methacrylic acid/styrene/benzyl methacrylate/N-phenyl cis-butane-imine copolymer, methyl acrylate/component represented by formula (H) (wherein 'in the formula (II), 'R53 represents a methyl group, R54 represents a hydrogen atom) / benzyl methacrylate copolymer, a constituent represented by the formula (II) (wherein 'in the formula (II) R53 represents a fluorenyl group, R54 represents a gas atom) / benzyl methacrylate copolymer, methacrylic acid / a constituent represented by the formula (III) (wherein, in the formula (III), 'R55 represents a methyl group, R56 represents a hydrogen atom)/styrene copolymer/trimethyl decyl acrylate copolymer, represented by formula (IV) Soluble resin (B) and the like.

146860.doc -26 - 201041980 an alkali-soluble resin (B) having a constituent represented by the formula (π), for example, methacrylic acid / a constituent represented by the formula (II) (wherein, in the formula (II) The 'R represents a mercapto group/benzyl methacrylate copolymer can be obtained by polymerizing methacrylic acid with benzyl methacrylate to obtain a copolymer, and then obtaining the copolymer obtained by the formula (v) The compound represented by the reaction is carried out.

(In the formula (V), the meaning of R54 is the same as above). Methacrylic acid / a constituent represented by the formula (III) (wherein, in the formula (R), R55 represents a methyl group) / a styrene copolymer / a tricyclodecyl methacrylate copolymer can be made The compound represented by the formula (VI) is obtained by reacting a copolymer of benzyl methacrylate, methacrylic acid and tricyclodecyl monomethacrylate. 〇 (vi) Ο Copolymerization is usually carried out in a solvent using a polymerization initiator. As the polymerization initiator, for example, an azo compound such as 2,2,-azobisisobutyronitrile or 2,2'-azobis(methyl-2-methylpropionate) can be used. A peroxide such as benzoquinone or a third butyl peroxide. . The solvent may be any one as long as it dissolves each monomer. For example, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, propylene glycol monomethyl ether acetate vinegar, propylene glycol monoethyl ether acetate or the like may be used. A glycol ether vinegar, and a solvent exemplified as the solvent (E) described in 146860.doc -27. 201041980. The reaction temperature may be determined by the decomposition temperature of the polymerization initiator or the boiling point of the body. Further, the mixture may be used as an alkali-soluble tree (B) which is sensitive to the side chain of the copolymer obtained as described above by using a compound having a polymerizable group. At this time, it is also possible to add a polymerizable group to the catalyst in the bed 1 factory. w相肀之之. Further, for example, it may be mentioned as a catalyst. For example, it may be added to prevent side reactions, such as hydroquinone. An additive such as tris(diamidodecyl)phenol. Further, examples of the additive include the following copolymers as the alkali-soluble resin (B) [K1] to [K4]. [K1] an unsaturated carboxylic acid and/or an unsaturated carboxylic anhydride (B1) (hereinafter sometimes abbreviated as (B1)") and a monomer (B2) having a ring-shaped structure having a hindrance of 2 to 4 ( The following "sometimes abbreviated as "(B2)") polymerized copolymer. [K2] A copolymer obtained by polymerizing (Bl), (B2) and a monomer (B3). Here, the monomer (B3) (hereinafter sometimes abbreviated as "_") is a monomer which can be copolymerized with (and / or (B2) and is not (B1) and/or (B2). [K3 A copolymer obtained by reacting a copolymer of (B1) and (B3) (a part of a carboxyl group and a cyclic ether derived from (B2) having a carbon number of 2 to 4). [K4] ( a copolymer of B1) and (B3), wherein 'preferably a copolymer obtained by polymerizing at least (B1) and (B2). As (B1) ', for example, an aliphatic unsaturated carboxylic acid and/or a fat may be mentioned. Family 146860.doc •28- 201041980 Saturated carboxylic anhydrides, etc. Specifically, unsaturated monocarboxylic acids such as acrylic acid, mercaptoacrylic acid, butenoic acid, maleic acid, fumaric acid, and citrine Unsaturated ditoxaic acids such as acid, mesaconic acid and itaconic acid; and anhydrides of such unsaturated dicarboxylic acids; succinic acid mono [2-(methyl) propylene methoxyethyl] ester, phthalic acid a monovalent or higher polycarboxylic acid such as mono [2-(methyl) propylene methoxyethyl]carboxylate; and a mono[(meth) propylene decyloxyalkyl] ester;

Ο 5-carboxybicyclo[2.2.1]hept-2-ene, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene, 5-carboxy-5-methylbicycloalene, 5-carboxyl _ Ethylbicyclo[2_2.1]hept-2-ene, 5-carboxymethylbicyclo[2.2.1]hept-2-ene, 5-carboxy-6-ethylbicyclo[2_2·^_2-ene, 5, 6_Dimercaptobicyclo[mu olefinic anhydride (bicycloheptan #dimethyl anhydride), etc. containing a & group or a carboxylic anhydride bicyclo [2.2.1] hept-2-semiclass; and acrylic acid α-m fluorenyl) cool Equivalent to unsaturated acrylates having a thiol group and a thiol group in the molecule. a" Among them, acrylic acid, methacrylic acid or maleic anhydride is preferred in terms of copolymerization reactivity and solubility. These may be used singly or in the present specification as long as they are not used in advance; or two or more types are used. The compound, the component, the agent, and the like can be used singly and separately. , or a combination of two or more, such that (B2), for example, has at least 146,860 of a group consisting of an oxyethane group, an epoxy propyl group, and an I-ether structure (for example, selected from a ring). Doc •29· 201041980 A base), and, more preferably, a monomer having an unsaturated bond is (10) more preferably a ring having a carbon number of 2 to 4 as a carbon-carbon unsaturated bond. (4) Preferably, the monomer having a carbon number is a field ether structure and a (meth) acryloxy group. The turtle shape of ',, ' is (B2)', for example, having an oxirane group. a monomer, a monomer having a propylene group, a monomer having a tetrahydron-n-butyl group, etc. The monomer having the above oxirane group, for example, means having an aliphatic group selected from the group consisting of aliphatic

A polymerizable compound of at least one of a group consisting of an epoxy group and an alicyclic epoxy group. The monomer having a nonyloxy group is preferably a compound having at least one group selected from the group consisting of an aliphatic cycloalkyl group and an alicyclic oxiran group, and having an unsaturated bond. . The term "meta-metal oxide group" refers to a group having a structure in which a chain-type dilute hydrocarbon is epoxidized.

Specific examples of the compound having an aliphatic oxiranyl group include glycidyl (meth) acrylate, β fluorenyl glycerol (meth) acrylate, and β-ethyl condensed (meth) acrylate. A compound represented by the following formula (VI) and the like disclosed in Japanese Laid-Open Patent Publication No. Hei 7-248625.

146860.doc -30- 201041980 rRI~R6, independently as a hydrogen atom or a carbon atom having a number of 1 to 10 and a mother oxime, m 丨 is an integer of 1 to 5). = t(VI), for example, o-ethyl sulphate, glycidyl hydrazine, m-vinyl glycidyl bond, j-glycidol, α-methyl, acetyl sulfhydryl Glycidol test, diethylene glycol 2? base shrinkage (4), α_methyl-shrinkage of ethylglycosylation base, by oxygen its dimethylglycidyloxymethyl stupid ethylene, 2, dimethyl glycidyl / by Oxymethyl methyl ethene, 25--dimensional glycidoxymethyl styrene, benzoyl glyceryloxymethyl styrene, 2,3,4-triglycidoxy methoxy, " 5-triglycidyloxy-inchyl styrene, 2,3,6-triglycidoxymethyl styrene, 3 4 —, _ —glycidyl benzyl methyl stupid ethylene 2,4,6- Diglycidyloxymethyl stupid ethylene and the like. The alicyclic oxiranyl group refers to the structure of the structure. U is a monomer having an alicyclic epoxy group, and examples thereof include a monomer of an oxyethylene group, and an aliphatic polycyclic epoxy group called an aliphatic monocyclic ring. The epoxy group is a group having a structure in which a cyclic olefin is epoxidized. Also; = formula: Oxygen ethoxy group, refers to a group having a polycyclic ring and having a structure. The monomer having an epoxy group is preferably:: having at least one selected from the group consisting of an aliphatic monocyclic epoxy group and an aliphatic polycyclic epoxy group and having an unsaturated bond. The compound is a compound having at least one species selected from the group consisting of aliphatic monocyclic epoxy groups and aliphatic polycyclic formulas and having a (meth)propane-oxygen 146860.doc •31 - 201041980 group. The above-mentioned monocyclic ring-shaped olefin, hexanylene, cyclooctene, and the like. Its compound. For example, cyclopentene and hydrazine are preferably a monomer having a carbon number of 5 to 7 as a (tetra) group of monocyclic epoxy group, specifically, < Cyclohexene (1,2-epoxy-4 vinylcyclohexanone) (for example, CeUoxide 2000; DaiceUt Industrial Co., Ltd. manufactures 2,4-epoxycyclohexylmethyl _, _ heart (6) Manufactured by the postal industry (stock), 3,4_epoxycyclohexyl methacrylate (for example, Cyclomer MHH); manufactured by Daice Hb Industrial Co., Ltd.). Examples of the polycyclic ring-type flue gas include dicyclopentene, tricyclodecene, norbornene, iso-nene, bicyclooctene, bicyclononene, bicyclo-decene, and tricyclic ten- Alkene, double ring twelve rare, tricyclic twelve rare and so on. Among them, preferred are compounds having a carbon number of 8 to 12. Examples of the monomer having an aliphatic polycyclic epoxy group include, for example, 3,4-epoxy acetal acid acrylate, 3,4-epoxynorbornyl methacrylate, and VII) at least one of a compound represented by the compound represented by the formula (VIII) and the like.

Rr, 〇I II 71 H2C=C—C—Ο—X71 (VII) [In the formulae (VII) and (VIII), R71 and R72 independently represent a hydrogen atom or a carbon number which may also be substituted by a hydroxyl group is 1 ~4 alkyl. X and X respectively represent a single bond, -χ73_, * _χ73_〇_χ74 146860.doc -32- 201041980 X73 and X74 indicate a carbon number of 1 to 6 * -X73-S-X74_, * -χ73_ΝΗ_χ74_. Burn the second base. * indicates a bond with 0]. The alkane such as butyl or tert-butyl is R71 and π, and specific examples thereof include a gas atom; a methyl group, an ethyl group, a n-propyl group, an isopropyl group, an n-butyl group, and a decyl group;

^Methyl, 1-hydroxyethyl, 2-hydroxyethyl, hydrazine-hydroxypropyl, 2-hydroxypropyl, % propyl-propyl-based methylethyl, 2-cysyl small methyl ethyl The base is substituted with a butyl group, a butyl group, a 3-butyl group, a butyl group or a butyl group. Among them, preferred are a hydrogen atom, a methyl group, a methylol group, a hydroxyethyl group, and a 2-ethyl group. More preferred are hydrogen atoms and methyl groups. Examples of the alkanediyl group include a methylene group, an exoethyl group, a 1,2-propanediyl group, a 1,3-propanediyl group, a 14-butanediyl group, a 15 pentanediyl group, and a 16 hexyldiyl group. The preferred ones for X' are: a single bond, a methylene group, a methyl group CH2_〇-(* indicates a bond with 0), and a *-ch2ch2-o- group. More preferably, it is exemplified: Single bond, * -ch2ch2-〇-based. The compound represented by the formula (νπ) and at least one compound of the group consisting of the chemical group represented by the formula (VIII) are preferably selected from the compounds represented by the following formula (VII). And at least one of the groups consisting of the compounds represented by the formula (vm').

146860.doc • 33 - 201041980 In the formulae (VII,) and (VIII,), the meanings of R7丨' and r72, and human κ κ are the same as those of the above R71 and R72, respectively. Examples of the compound represented by the formula (νπ) include a compound represented by the formula (5) 1) to the formula (VII-15). Preferred are the formula (Μ), the formula (Vn-3), the formula (Vn-5), the formula (VII_7), the formula (VII_9), and the formula (νπ ιι) to the formula (νπ-15). More preferably, it is a formula (vn-i), a formula (VII_7), a formula (VII 9), and a formula (VII-15). H2c:ch H2C:CH—C—O—CH: H2C=CH—C—〇一〇2% Η2〇:ΟΗ—C—〇一C2H4—0 ch3o I II H2C—C—ό 一〇h2c=c— C—o—ch2 CH^ Ο

H2C:CH—C—〇—C2hj4~s CH2OH O H2C=C —-Q—.q H2C=C——CO-C2H4· CH30 I II H2C=C—0—O—C2H4—〇〇o H2C:CH —C—0—印广j CH30 I II H2C=C—c~o ～c2H4—s CH30 H2C=C—C—0—c2h4』 _i2^

(ΥΠ-13)

C2H4OH o H2C=C——S—. (ΥΠ-15)

Examples of the compound represented by the formula (VIII) include a compound represented by the formula (vni-1) to the formula (νιπ-15). Preferably, it is a formula (νιπ ι), a formula (νιπ-3), a formula (VIII_5), a formula (VIII_7), an s(VIIl 9), a formula (vm_ 146860.doc -34- 201041980 11)~ a formula (VIII- 15). More preferred are the formula (vm i), the formula (10) i 7), the formula (VIII-9), and the formula (VIII-15).

〇 II H^C=CH-C—Ο h2c=ch η —C—Ο —

Ch3o I II H2〇=C—C—O—CH H2C=CH-C—0—CH H2C=CH-C—0—C2H4 C2H4—ο CH3o I II H2C=C—C—Ο—〇2Η4. ch30 I II H2C=C—CO—C2H4-〇

C2H4OH o : -15^ —~I. H2C=CH-C-〇~c2H4-Sr^>' (vm-2) 0 ^ || H2C=CK-C — 0-c2h4』_^n (Vin-4) H2C=C-c-〇~ C2H4_s_^ ν-Λ (Vin-6) ?t h2c=c-c-〇-c2H4_h_^ CaHsO ^^(Vin-8) Hfi=C-C—〇CVin-10) CHPH o H2〇=C--e -ο

(Vm-i4)

The compound represented by the formula (VII) and at least one compound of the group consisting of the compound represented by the formula (v) may be used singly. It may be mixed at any ratio. In the case of mixing, The mixing ratio is in terms of molar ratio, preferably formula (VII): formula (VIII) is 5: 95 to 95:5, more preferably 10: 90 to 90: 10, and further preferably m 80~ 80 : 20 0 The monomer having an oxypropylene group, for example, means a polymerizable compound having an oxypropylene group. The monomer having an oxypropylene group preferably has a ring 146860.doc -35 - 201041980 oxypropane The compound of the group and the unsaturated bond is more preferably a compound having an oxypropylene group and having a (meth) propylene oxime group. As the monomer having an oxypropylene group, specifically, a hong methyl group is exemplified. 3-Methyl propylene methoxymethyl oxetane, 3-methyl _3 propylene methoxymethyl epoxide, 3-ethyl-3-methyl propyl decyloxymethyl Propylene oxide, 3-ethyl-3-propyl decyloxymethyl propylene oxide, 3 methyl _3_mercapto propylene oxyethyl epoxide, 3·methyl _3_ Return Oxyethyl propylene oxide, 3-ethyl-3-mercapto propylene methoxyethyl propylene oxide or 3 ethyl propyl oxyethyl epoxide or the like. So-called monomer having tetrahydrofuranyl group For example, it means a polymerizable compound having a tetrahydrofuranyl group. The monomer having a tetrahydrofuranyl group is preferably a compound having a tetrahydrofuranyl group and an unsaturated bond, more preferably having a tetrahydrofuranyl group and having a (fluorenyl) acrylonitrile group. The compound having an oxy group. Specific examples of the monomer having a tetrahydrofuran group include tetrahydroanthracene acrylate (for example, Viscoat V# 150, manufactured by Osaka Organic Chemical Industry Co., Ltd.), tetrahydrofurfuryl methacrylate. Examples of the copolymerizable monomer (B3) include methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl sulfonate (meth)acrylate, and (meth)acrylic acid. Dibutyl acrylate, (decyl) butyl acrylate, etc. (alkyl) acrylates; (fluorenyl) cyclohexyl acrylate, 2-mercaptocyclohexyl (meth) acrylate, Tricyclo[5·2.1·02,6]癸-8-yl (meth)acrylate (in this technique) In the field, as a customary name 'called (fluorenyl) dicyclopentanyl acrylate), (fluorenyl) dicyclopentyloxyethyl acrylate, isobutyl (meth) acrylate or the like (fluorenyl) acrylic ring 146B60 .doc •36- 201041980 alkyl esters; phenyl (meth) acrylate, benzyl (meth) acrylate (meth) acrylate; diethyl maleate, anti-butene Dihydroacids such as diethyl acid and diethyl itaconate; hydroxyalkyl esters such as 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate; .1]hept-2-ene, 5-methylbicyclo[2.2_1]hept-2-ene, 5-ethyl-bicyclo[2.2.1]hept-2-ene, 5-hydroxybicyclo[2.2.1] Hept-2-ene, 5-hydroxyindenylbicyclo[2.2.1]hept-2-ene, 5-(2,-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5-nonyloxybicyclo [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(hydroxyindenyl)bicyclo[2 21]hept-2-ene, 5,6-bis(2,-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5,6-dimethoxy Bicyclo[2.2.1]hept-2-ene, 5,6-diethoxybicyclo [2 2 hept-2-ene, 5-hydroxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-ethylbis-Q ring [2.2·1]hept-2-ene, 5-hydroxyindenyl-5-fluorenylbicyclo[2.2.^heptene·5, 2,butoxycarbonylbicyclo[2.2_1]hept-2-ene, 5-cyclohexyloxycarbonylbicyclo[2.2.1 Hept-2-ene, 5-phenoxycarbonylbicyclo[2.2.1]heptene, 5,6-bis(t-butoxycarbonyl)bicycloindole.2.1]hept-2-ene, 5,6- a bicyclic unsaturated compound such as bis(cyclohexyloxycarbonyl)bicyclo[2.2.1]hept-2-ene; Ν-methyl maleimide, Ν-ethyl maleimide,丙基-m-butyleneimine and the like 烷基-alkyl maleimide; Ν-cyclopentyl maleimide, Ν-cyclohexyl maleimide, Ν-ring Octyl maleimide and the like 环·cycloalkyl maleimide; 146860.doc -37· 201041980 N-adamantyl maleimide, N_(tetra) maleimide, etc. Crosslinked carbocyclic group-substituted maleimide; N-phenyl-butyleneimine and other fluorenyl aryl succinimide; N·benzyl succinimide, etc. Nonyl aralkyl methacrylimide; N-butyl Imino-3, maleimide benzoate, butadimine, 4 cis butyl imidate, N-butanediamine _6_ maleicene Amino hexanoimide derivatives such as amine hexanoate, N-butyl succinimide, maleimide propionate, N-(9-acridinyl) maleimide, and benzene Ethylene, α-methylstyrene, m-methylstyrene, p-methylstyrene, vinyl anthracene, p-methoxystyrene, acrylonitrile, methacrylonitrile, vinyl chloride, ethylene diene, propylene Guanidine, methacrylamide, vinyl acetate, 1,3-butadiene, isoprene, 2,3-dimethyl-, i-butadiene, and the like. Among them, in terms of copolymerization reactivity and solubility, styrene, fluorene-phenyl maleimide, fluorene-cyclohexylmethyleneimine, hydrazine-benzyl are preferred. A cis-butenylenediamine, a bicyclo[2 2 fluorene]hept-2-ene, and the like. The copolymer [Κ1]~[Κ4] can be referred to, for example, the literature "Experimental method for polymer synthesis" (Dazu Takashi, issue: Chemical Tongren (share), first edition, first print", March 1, 1972 It is manufactured by the method disclosed in the publication and the cited documents disclosed in the document. Specifically, the monomers (Β1) and (Β2) constituting the copolymer, a specific amount (Β3), a polymerization initiator, and a solvent are optionally charged in a reaction vessel, and the oxygen is replaced by nitrogen. In the absence of oxygen, the mixture was mixed, and 146860.doc -38-201041980 was heated and kept warm, thereby obtaining a polymer. The polymerization conditions such as the charging method, the reaction temperature and the time can be appropriately adjusted in consideration of the production equipment, the amount of heat generated by the polymerization, and the like. As the polymerization initiator and solvent used herein, any of a polymerization initiator and a solvent which are generally used in the field can be used. For example, a polymerization initiator, a solvent, and the like exemplified in the present specification can be used. Further, the obtained copolymer may be directly used as a solution after the reaction, or may be a solution which is concentrated or diluted, or may be used as a solid (powder) extract by a method such as reprecipitation. In particular, in the above polymerization, by using the following solvent as a solvent, the solution after the reaction can be used as it is, so that the production step can be simplified. The ratio of the respective monomers constituting the copolymer [κι] is preferably in the following range with respect to the total number of moles of the monomers constituting the copolymer [κι]. (Bl) 5 to 95 moles. /. It is better that 1〇~9〇 Moer% (Β2) 5~95 Moer%, and even better is 1〇~9〇 Mo Er. ο χ The ratio of the respective monomers constituting the copolymer [Κ2] to the total number of moles of the monomers constituting the copolymer [Κ2] is preferably in the following range. (Β1) 2~40mol%, more preferably 5~35mol% (Β2) 2~95mol%, more preferably 5~8〇mol% (Β3)1~65mol% The better is 1~6G Moll%. The copolymer [Κ3] can be produced via a two-stage process. First, the above method is similarly obtained by copolymerizing (Β1) with (Β3) to obtain a copolymer. In this case, the ratio of each monomer is relative to the total of 146860.doc-39·201041980 constituting the copolymer. The number of ears is preferably in the range of (Bl) 5 to 50 mol%, preferably 1 to 45 mol%. (B3) 50 to 95 mol%, preferably 55 ～9〇摩尔%. A person, a part of the carboxylic acid and/or carboxylic anhydride derived from (B1) of the copolymer of (B1) and (B3) is reacted with a cyclic ether derived from (B2). To this end, the environment inside the flask was continuously replaced with nitrogen, and (B2), a reaction catalyst, a polymerization inhibitor, and the like were placed in a flask, and then the reaction was continued for hours at, for example, 60 130 C. The charging method, the reaction temperature. And the time-specific reaction element can be appropriately adjusted in consideration of the manufacturing equipment or the amount of heat generated by the polymerization, etc. The number of moles of (B2) at this time is preferably 5 to 80 with respect to the number of moles of (B1). Molar, more preferably 1〇~75mol%, particularly preferably η~mol%., Reaction catalyst, for example, is suitable for use as a carboxyl group and epoxy B. The reaction catalyst of an alkyl group, a propylene oxide group or a tetrahydrofuranyl group. Specifically, it is exemplified by tris(dimethylaminomethyl)phenol, etc. The amount of the reaction catalyst used is relative to, for example, (Β1) to (Β3). The total amount of the polymerization inhibitor is preferably from 1 to 5% by mass. The polymerization inhibitor may, for example, be a benzoic acid or the like. The amount of the polymerization inhibitor used is, for example, the total amount of (Β1) to (Β3). Preferably, on a mass basis, 〇.〇〇1 to 5%. The ratio of the ratio of each unit constituting the copolymer [Κ4] to the total amount of the monomer of the copolymer [Κ4] is higher than that of the woman. In the following range. (Bl) 2 to 40 mol%, more preferably 5 to 35 mol% 146860.doc 201041980 (Β2) 60 to 98 mol%, and more preferably 65 to 95 mol%. The polystyrene-equivalent weight average molecular weight of the copolymer [Κ1] to [Κ4] is preferably 3,0〇〇~1〇〇, 〇〇〇, more preferably 5〇〇〇~5〇〇〇分散 The dispersion (molecular weight distribution), [weight average molecular weight (Mw) / number average molecular weight (?η)] of the copolymer [Κ1] to [Κ4] are preferably 〇, more preferably 1 · 2 to 4.0 〇 Ο

The polystyrene-equivalent weight average molecular weight of the alkali-soluble resin (yttrium) is preferably 5,000 to 35, _, more preferably 6, _~3 〇, _, particularly preferably 7,000 to 28,000. When the molecular weight is in the above range, the hardness of the coating film is increased, the residual film ratio is also high, the solubility of the unexposed portion to the developer is good, and the resolution tends to increase. Further, the weight average molecular weight is a value measured by, for example, a Gpc method (gei_permeation chr〇 matography), and specifically, a value measured by the measurement conditions disclosed in the examples. Wait. The acid value of the alkali-soluble resin (B) is preferably from 5 Torr to 15 Torr, more preferably from 6 Torr to 135 Å, particularly preferably from 7 G to 135. Here, the acid value is determined by the amount of potassium hydroxide required for neutralizing the testable resin (B) (IV), which can be usually obtained by using (4) an aqueous potassium hydroxide solution. The content of the alkali-soluble resin (B) is preferably from 7 to 65% by mass, more preferably %, particularly preferably from 17 to 55% by mass, based on the solid content of the colored photosensitive resin implanted person. The resin (8) has a tendency to form a pattern and have a resolution and a disability.卞丄丌 146860.doc -41- 201041980 The photopolymerizable compound (c) is a compound which can be polymerized by using an active radical, an acid or the like which is generated by irradiating light to the photopolymerization initiator (D). Specially limited. For example, a compound having a polymerizable carbon-carbon unsaturated bond or the like can be mentioned. The photopolymerizable compound (C) is preferably a trifunctional or higher functional photopolymerizable compound. Examples of the trifunctional or higher polyfunctional photopolymerizable compound include pentaerythritol tetrapropene _, quaternary tetrakis tetramethyl acrylate vinegar, dipentaerythritol pentoxide vinegar, and dipentaerythritol pentamethyl methacrylate. , dipentaerythritol hexaacrylic acid, and dipentaerythritol hexamethyl acrylate acid. Each of the above-mentioned convergent compounds (C) may be used singly or in combination of two or more. The content of the photopolymerizable compound (C) is preferably 7 to ^% by mole, more preferably 13 to 60% by mass of the solid content of the photosensitive resin composition of the 荽τ color. Good is 17~55皙 Jin. / ^ 疋 Μ 里 / 〇. When the content of the photopolymerizable compound (C) is in the above range, the film is sufficiently cured in the presence of η6+, and the film thickness ratio before and after development is increased, and the taper is harder. The undercut and the adhesion are improved. The colored photosensitive tree (D) of the present invention. The fat composition contains a photopolymerization initiator. The photopolymerization initiator (9) may, for example, be an active agent or an acid generator. Active Free Beauty Native Products ^ Μ ή^ . "• Produce scorpion hunting by illuminating light to produce loyal free radicals. In addition, the acid-producing stalk preparation agent produces acid by irradiation with light. The above-mentioned active radical compound, for example, may be exemplified by an acetophenone-based female heart, a fragrant compound, a poor-benzo-methyl sulfonium compound, a 9-oxysulfide μ 146860.doc • 42-201041980-based compound, Three tillage compounds, lanthanide compounds, and the like. Examples of the acetophenone-based compound include diethoxyacetophenone, 2-methyl-2-morpholinyl-indole-(4-methylsulfanylphenyl)propane oxime, and 2-dimethyl group. Amino-1-(4- morpholinylphenyl)_2-benzylbutane-nonanone, 2-hydroxy-2-methyl-1-phenylpropanone, benzoin dimethyl ketal. 2_Hydroxy-2-methylhydroxyethoxy)phenyl]propane _^, hydrazine hydroxycyclohexyl phenyl ketone, 2-yl-2-methylmethylethyl phenyl) propyl hydride The oligomer or the like of ruthenium is preferably 2-methyl-2-carboline-yl-(indenylmethylsulfanylphenyl)propan-1-one. Examples of the benzoin-based compound include benzoin, benzoin, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, and the like.

Examples of the benzophenone-based character A-based compound include, for example, benzhydryl, methyl ortho-benzoylbenzoate, 4-stupyl-a-indenyl, and 4-benzoic acid. Methionyl _4, _ decyl-phenylene sulfide, 3,3',4,4'-tetra (p.: r-dana, butyl-peroxycarbonyl) benzophenone, 2, 4, 6-trimethyldiphenyl fluorenone and the like. ❹ Examples of the above-mentioned 9-oxothiopurine galaline compound include 2-isopropyl-9-oxathione, 4-isopropyl-9-oxyxan, 2,4-diethyl-9- Oxime, 2,4_dichloro_9_oxythiazepine, 丨_, etc. Gas propoxy-9-oxopurine as the above-mentioned three-tillage compound, for example, a group of 6-(4-decyloxyphenyl) wells, 2, and 4_bis (three-gas methylol group) Naphthyl)-1,3,5·tris, 2,4_bis(dichloromethyl)·6-(4_ethene oxime)--6-(4-decyloxy stupid ethylene Base)-1,3,5-three tillage, 2,4-bis(trichloromethyl-2-yl)vinyltriazine, 2 = (5-methylfuran bis(dimethylmethyl)-6-[ 2-(furan-2-146860.doc -43· 201041980 base) vinyl]·1,3,5-three wells, 2,4_bis(trichloromethyl)-Η2, (4) February female base-2 -Methylphenyl)ethenyl]-1,3,5-three Β well, 2,, and (trichloromethyl, -6-[2-(3,4-dimethoxyphenyl) Vinyl]·13,5-three tillage, etc. As the above-mentioned lanthanoid compound, for example, it can be listed as a specific example of a cow's υ 醯 醯 醯 肟 人物 可 可 苯 苯 苯 苯 苯 苯 苯 苯 醢 醢Base-protected phenyl)butane-1-one-2-imine, Ν_Benzene, melon _ 丞 丞 基 硫 硫 ) ) ) 辛 -1- -1- -1- -1- -1- -1- -1- -1- -1- -1- -1- -1- Oxygenated _ 丨 『 『 『 『 『 『 『 『 『 『 『 『 『 『 『 『 『 『 『 『 『 『 『 『 『 『 『 『 『 『 『 『 『 『义一-Η9-ethyl winter {2•methyl-, 3-dimethyl-2,4-dioxolyl methoxy)phenyl hydrazone}-911-carbazol-3-yl ] Ethylene 丨 丨 亚 imine and so on. Further, as the living radical generating agent, for example, 2,46-trimethylsulfonyldiphenylphosphine oxide, 2,2,_bis (o-stupyl tetraphenyl-1,2' may also be used. -biimidazole, 10•butyl·2·gasacridone, 2_ethylhydrazine, benzoin, 9,10-phenanthrenequinone, camphorquinone, methyl phenylglyoxylate, di-titanium compound, etc. As the acid generator, for example, 4-hydroxyl quinone dioxime p-toluene acid salt, 4 _ phenyl dimethyl hexafluoroantimonate, 4 =0 oxyphenyl fluorenyl group铳 甲 磺酸 sulfonate, 4 醯 ethoxy phenyl fluorenyl _ 基 录 六 六 请 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 Phenyl hydrazine, styrene salt, diphenyl sulfonium hexahydrate, rust salt, or county ketone salt, benzoin toluene, etc. The radical generating agent is exemplified by the above compounds, and there are also compounds which generate an acid while generating an active radical, for example, 146860.doc • 44 - 201041980 The tri-grain photopolymerization initiator can also be used as an acid generator. Start The content of the agent (D) is preferably 0.1 to 30 mass%, more preferably 1 to 20 mass%, based on the total amount of the alkali-soluble resin (Β) and the photopolymerizable compound (C). When the content of the polymerization initiator is within the above range, high sensitivity is achieved, exposure time is shortened, and productivity is improved.

Further, the colored photosensitive resin composition of the present invention may further contain a photopolymerization initiation aid (F). The photopolymerization initiation aid is usually used in combination with a photopolymerization initiator (D) to promote polymerization of a polymerizable photopolymerizable compound by a photopolymerization initiator, or a sensitizer. Examples of the photopolymerization initiation aid (F) include an amine compound, an alkoxy quinone compound, and a 9-oxothioxanium star compound. Examples of the amine-based compound include triethanolamine, methyldiamine, triisopropanolamine, 4-dimethylaminobenzoate, and dimethylaminobenzoic acid, 4 - Dimercaptoalkyl benzoic acid isophthalic acid acetonate, 2-didecylaminoethyl benzoate, 4-dimethylamino benzyl ethyl hexanoate, N,N-dimethyl-p-toluidine, 4,41_bis(dimethylamino)benzamide (commonly known as micbutone), 4,4, bis(diethylamino)benzophenone, 4,4, _bis ( Ethyl mercaptoamine)diphenylmethylnet, etc., of which 4,4,-bis(diethylamino)benzophenone is preferred. Examples of the alkoxy oxime-based compound include 9-dimethoxy onion, 2-ethyl-9,10-dimethoxy onion, and 9,1 〇diethoxy oxime: 2-ethyl group. Diethoxy hydrazine, 9,1Q·dibutoxy f, 2 ethyl _91 〇 dibutoxy fluorene, and the like. As the above-mentioned 9-oxo-sulfur such as a galaxial compound, for example, 2 -isopropyl 146860.doc -45·201041980 2,4-diethyl-9-oxothiopropoxy-9-oxo-sulfur P-p-star -9-oxo-sulfur tr-P star, 4-isopropyl-9-oxysulfur P-p-p-rhodium, 2,4-dichloro-9-oxathione, 1-chloro-4, and the like. Two or more kinds of photopolymerization start aids (F) may be used alone or in combination. In addition, as a photopolymerization initiation aid (F), a commercially available photopolymerization initiation aid (F) can be used, for example, the product name "eab_f" (manufactured by Hosei Chemical Industry Co., Ltd.) )Wait. The combination of the photopolymerization initiator (D) and the photopolymerization initiation aid (F) of the coloring photosensitive resin composition of the present invention may, for example, be diethoxyphenidene M, 4, or (Diethylamino)diphenylhydrazine_, 2_methyl_2·Minyl-1-(4-indolethiophenyl)propane-indole-one/seven-bis(diethylamino) Diphenyl, steel, 2-carbyl-2-methyl-i-phenylpropan-di-propyl, bis(diethylamino)benzophenone, benzoin quinone/4, 4, _ bis (diethylamino) diphenylate, 2-yl-2-methyl-HR-based ethoxy) phenyl] propyl saponin / 4, 4 '- double (two Aminophenyl)diphenylfluorene g, hydroxycyclohexyl phenyl ketone oxime, bis(diethylamino)benzophenone, 2-hydroxy-2-methylmethylvinyl)phenyl]propane - 1-ketone oligomer/4,4,_bis(diethylamino)benzophenone, 2-mercapto-2-dimethylamino group (heart-flavored stupid base) The same as /4'4'-bis(diethylamino) dioxin and the like, preferably methyl-2-carbolinyl-1-(4-sulfonylphenyl)propane bis ( Diethylamino)benzophenone. 1 In the case of using the photopolymerization initiation assistant (F), the amount thereof is preferably from 〇〇1 to mol, per 1 mol of the photopolymerization initiator (D), more preferably It is 0.01~5 m. '146B60.doc -46- 201041980 The colored photosensitive resin composition of the present invention contains a solvent (E). The solvent (E)' is not particularly limited, and a solvent generally used in the field can be used. For example, it can be derived from esters (solvents containing _c〇〇_), ethers other than esters (solvents containing _〇_), ketones other than esters (solvents containing -CO-), alcohols, aromatics It is selected from the group consisting of a hydrocarbon, a guanamine, N-methylpyrrolidone, dimethyl sulfoxide and the like. Examples of the above esters include decyl lactate, ethyl lactate, butyl lactate, decyl 2-hydroxyisobutyrate, ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, and acetic acid. Amyl ester, butyl propionate, isopropyl@曰, ethyl butyrate, butyl butyrate, methyl glycolate, methoxyacetic acid vinegar, decyloxyacetate, butyl methoxyacetate , ethoxyacetic acid methyl ester, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, 3 ethoxy propyl Ethyl ethoxide, decyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-methoxypropionate, 2-ethoxyl Ethyl propionate, 2-methoxy-2-methylpropionic acid formazan, 2-ethoxy-2-phenylpropionic acid ethyl ester, methyl pyruvate, ethyl pyruvate, propyl pyruvate , acetamidine acetate, ethyl acetate, 2-sided oxygen, methyl butyrate, ethyl 2-oxobutanoate, 3-methoxybutyl acetate, 3-methyl-3-hydrazine acetate Oxy-butyl ester, cyclohexanol acetate, 丫_^_lactone, and the like. Examples of the ethers include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, and monoethyl alcohol monoethyl ether. Diethylene glycol monobutyl ether, propylene glycol monoterpene ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxybutyl 146860.doc -47- 201041980 alcohol, 3-methoxy-3- Methyl butanol; tetrahydrofuran, tetrahydropyran, M-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, = ethylene glycol methyl ether, diethylene glycol dipropyl ether, two Ethylene glycol dibutyl mystery, propylene glycol monomethyl-acetic acid [propylene glycol monoethyl acetate acetic acid brewing, propylene glycol monopropyl acetate acetic acid §, methyl cellosolve acetate vinegar, ethyl cellosolve acetic acid hydrazine, ethyl carbitol Acetate, butyl carbitol acetate, alum ether, phenethyl ether, methyl benzoate, and the like. Examples of the ketones include, for example, 4· mercapto-4·methyl·2-pentanone, acetone 2-butanone, 2-heptanone, 3—glyoxime, cardio-, 4-methyl-2. _pentanone, cyclopentanone, cyclohexanone, isophorone and the like. Examples of the above alcohols include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerin. Examples of the aromatic hydrocarbons include benzene, toluene, xylene, and mesitylene. Examples of the above guanamines include dimethyl ketoamine, hydrazine, hydrazine-dimethylacetamide, and hydrazine-methylpyrrolidone. Solvents such as β may be used singly or in combination of two or more. The content of the solvent (8) in the coloring-pure pure resin composition is preferably a negative I / 〇, more preferably 75 to 92 mass 0, in terms of mass fraction with respect to coloring & light 1 ± sulphate 1 GG mass %. /〇. In other words, the solvent () is adjusted so that the solid content is adjusted to 5 to 30% by mass, preferably 8 to 25% by mass, based on 1% by mass of the coloring photosensitive resin composition. m. When the content of the right solvent (E) is in the above range, the flatness at the time of coating becomes good, and when the color calender is formed, the color 146860.doc -48-201041980 is sufficient, and thus the display characteristics become Good tendencies, so it is better. The coloring photosensitive resin composition of the present invention may further contain a surfactant (G). The surfactant (G) may be at least one selected from the group consisting of a polyfluorene-based surfactant, a fluorine-based surfactant, and a polyoxo-based surfactant having a fluorine atom. The polyoxosiloxane surfactant may, for example, be a surfactant having a decane bond. Specifically, Toray Silicone DC3PA, Toray Silicone SH7PA, Toray Silicone DC11PA, Toray Silicone SH21PA, Toray Silicone SH28PA, Toray Silicone SH29PA, Toray Silicone SH30PA, Polyether Modified Emu Oil SH8400 (trade name: Toray Silicone; Toray Dow Corning (manufacturing), KP321, KP322, KP323, KP324, KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF-4446, TSF4452, TSF4460 ( Momentive Performance Materials Japan contract company) and so on. The fluorine-based surfactant may, for example, be an interface activator having a fluorine-blocking chain. Specific examples include Fluorad (trade name) FC430, Fluorad FC431 (manufactured by Sumitomo 3M Co., Ltd.), Megafac (trade name) F142D, Megafac F171, Megafac F172, Megafac F173, Megafac F177, Megafac F183, and Megafac R30 ( DIC (manufactured by DIC), Eftop (trade name) EF301, Eftop EF303, Eftop EF351, Eftop EF352 (manufactured by Mitsubishi Materials Electronic Chemicals), Surflon (trade name) S381, Surflon S382, Surflon 146860.doc -49- 201041980 SC101, Surflon SC105 (manufactured by Asahi Glass Co., Ltd.), E5844 (manufactured by Daikin Fine Chemical Co., Ltd.), BM l〇〇〇, BMll (all trade names: manufactured by BM Chemie Co., Ltd.). The polyfluorene-based surfactant having a fluorine atom may, for example, be a surfactant having an anthracycline bond or a fluorocarbon chain. Specifically, it can be listed as Megafac (registered trademark) R〇8, Megafac bl2〇, Megafac F475, Megafac F477, Megafac F443 (made by mc). These surfactants may be used singly or in combination of two or more. The content of the surfactant (G) is preferably 〇1 to 〇丨% by mass, more preferably 0.00005 to 0.01% by mass, based on the mass fraction of the coloring photosensitive resin composition. When the content of the surfactant (9) is within the above range, the flatness of the coating film tends to be good, which is preferable. The colored photosensitive resin composition of the present invention is preferably a negatively colored photosensitive resin composition. The colored photosensitive resin composition of the present invention can preferably form a color filter, a coating film or a colored pattern, and can obtain a good color pattern such as color density, brightness, contrast, sensitivity ▲, resolution, heat resistance, and the like. The color 遽=2' can be made in a well-known manner to the optical film having the (four) color ray s w as a component thereof, and the array 2 can be used to have the color filter, the coating film or the coloring. A display device such as a film and/or an array substrate, for example, a liquid crystal display device, an organic EL (Eleetr〇lumineseenee light device), a solid-state image, and a color map. Like all related machines 146860.doc •50· 201041980

A method of forming a color filter or a color pattern by using the colored photosensitive resin composition of the present invention, for example, a method of applying the colored photosensitive resin composition of the present invention to a substrate or another resin layer (for example, in advance on a substrate) a method of removing or drying a volatile component such as a solvent to form a coloring layer, and exposing the colored layer to a mask, and then performing development; and using the film on the other colored photosensitive resin composition layer formed thereon; A method of an inkjet machine that requires photolithography. The film thickness of the coating film at this time is not limited to (4), and can be appropriately adjusted depending on the material to be used, the use, and the like, for example, Q1 to 3G (four), preferably 2 〇 μηι, more preferably 1 to 6 μηι. Examples of the coating method of the colored photosensitive resin composition include an extrusion coating method, a direct gravure coating method, and a reverse gravure coating method. , CAP (Calcium Phosphate), coating method, and the like. Further, a immersion coater "ip coater", a bar coater (bar (3) also), a spin coater (sph coater), a slit type & rotary coater (siit & spin) can also be used. Curry, slit coater (sometimes also known as die coater (die c〇ater), curtain type flat coater (curtain fl〇wc〇ater), non-rotating coating Coating is carried out by a coater such as a spmless coater. Among them, it is preferably applied by a spin coater. Examples of the solvent removal/drying include natural drying, air drying, and reduced-pressure drying. The specific drying temperature is preferably 10~12〇t, more preferably 146860.doc •51 · 201041980 25-100 C. The drying time is preferably i〇 second to 60 minutes, more preferably 3 seconds. ~30 minutes. Drying under reduced pressure is preferably carried out at a temperature of from 50 to 150 Pa at a temperature ranging from 2 Torr to 25 ° C. EXAMPLES Hereinafter, the dye combination of the present invention will be described in more detail by way of examples. a coloring photosensitive resin composition and a color filter. In the examples, "0/〇" and "parts" unless otherwise specified, % by mass and parts by mass. Synthesis Example 1: Synthesis of Dye A1 41 parts of a gas mixture and 28 parts of dimethyl decylamine were mixed in a vessel equipped with a cooling tube and a stirring device. The temperature was 2 于 at 10 ° C. Add 7 7 parts of sulfinium chloride to the mixed solution at the end of the minute. After the completion of the dropwise addition, react for 3 〇 minutes in a state of heat retention. Add 57 parts of Acid Red 289 to the reaction mixture over 15 minutes (Chinese-Chinese chemical product) )), and reacted at 35t for 3 hours. Further, 4 parts of sulfite gas was added to the reaction mixture, and then reacted at 35t: for 15 hours. The reaction mixture was cooled at 1 Torr. 2 _ethylhexylamine, followed by dropwise addition of 89 parts of triethylamine. After the dropwise addition, the reaction was carried out for 5 hours at room temperature. The reaction mixture was concentrated and 2 parts of methanol was added, and then concentrated again until the amount of liquid It became about half. Further, 29 parts of sterol and 2 parts of acetic acid were added and reacted for 30 minutes. The reactant was poured into 3 parts of 6 parts of ion-exchanged water to be crystallized. 〇% methanol aqueous solution, 1000 parts of 70 ° C deionized water, 300 parts (10) The crystals obtained after filtration were washed successively with deionized water, and dried under reduced pressure at 6 ° C for one day to obtain 51 parts of dye A1 as a purplish red solid. 146860.doc • 52· 201041980 by LC-MS (Liquid chromatography-mass spectrometry, liquid chromatography-mass spectrometry) Chemically identifies each compound represented by the formulas (1), (2), and (3) contained in the dye A1. The results of the LC-MS analysis are shown below. Further, the measurement conditions of LC-MS are as follows.

Device: Shimadzu LC-10A Column: Wakosil II 3C18HG (3 μηι, 3 mm#xl50 mm) Mobile phase A liquid '· 0. l%TMAB (Trimethylamine borane, trimethylamine borane) / water: acetonitrile (9: 1 B solution: 0.1% TMAB / water: acetonitrile (1: 9) Gradient (solution B) B initial concentration: 20% 20% - (30 minutes) - 60% - (5 minutes) - 100% (keep 10 minutes) )

Wavelength: 25 0 nm Official column temperature · 40 degrees Flow: 0.5 mL/min Injection volume: 5 pL

MASS unit: HP LC/MSD ionization: ESI+ Scanning range: 100-1500 Fragmentor: 120 V Drying Gas: 350 °C Compound (1): Measured value ([M+H] + ) : 655.2 146860.doc -53- 201041980 Calculated value (Exact Mass): 654.2

Compound (2-1): Found ([M+H]+): 682.2 Calculated (Exact Mass): 681.2

Compound (2-2): Found ([M+H]+): 766.3 Calculated (Exact Mass): 765.3

Compound (2-3): Found ((Μ + Η)+ ) : 957.4 Calculated (Exact Mass): 956.4

Compound (3): Found (M+): 877.5, 146860.doc -54· 201041980 Calculated (Exact Mass) : 877.4

Ο Calculate the area ratio of each peak by the area percentage method of Lee: C for each compound of the formula (1) '(7) and (3), and find the total (10) parts relative to the compounds according to the following formula The content of each compound. The results are shown in Table 1. [Number 1] Content = - turbidity of the peak in the T1 to T2 period during the epidemic period. #保持时间X1 00 Compound (1) Holding time: 14.0~16_0 minutes Compound (2-1) Holding time: 16〇 ~25〇 minutes compound (2-2) retention time: 25.0~26.5 minutes compound (2-3) retention time: 26.5~31.0 minutes compound (3) retention time: 31.0~41.0 minutes Synthesis Example 2: Synthesis of dye A2 A container equipped with a cooling tube and a stirring device was mixed with 410 parts of chloroform and 28 parts of one methyl methamine. At 1〇. 37 parts of sulfite gas was added dropwise to the mixed solution over 20 minutes. After the completion of the dropwise addition, the reaction was carried out for 3 minutes in a state of heat retention. 57 parts of Acid Red 289 (manufactured by Sino-foreign Chemicals Co., Ltd.) was added to the reaction mixture over 15 minutes, and reacted at 35 ° C for 3 hours. Further, 4 parts of sulfite chloride was added to the reaction mixture of 146860.doc -55 - 201041980, and then reacted at 35 ° C for 丄 hours. The reaction mixture was cooled, and 34 parts of 2-ethylhexylamine was added dropwise at 10 ° C, followed by dropwise addition of 89 parts of triethylamine. After the dropwise addition, the reaction was carried out at room temperature. The reaction mixture was concentrated, and after adding 200 parts of methanol, it was concentrated again until the amount of liquid became about half to half. Further, 26 parts of sterol and hydrazine acetic acid were added and reacted for 30 minutes. The reactants were injected into 396 parts of ion exchange water and the skin was crystallized. The crystals obtained after filtration were washed sequentially with 3 parts of a 5 〇 0/〇 aqueous methanol solution, 1000 parts of deionized water at 70 ° C, and 3 parts of deionized water. It was dried under reduced pressure at 6 ° C for one day to obtain 65 parts of dye A2 as a purple-red solid. Each compound contained in A2 was chemically identified in the same manner as in Synthesis Example 1 and the content was calculated. The results are shown in Table 1. Synthesis Example 3: Synthesis of Dye A3 220 parts of acetonitrile and 28 parts of dimethylformamide were mixed in a vessel equipped with a cooling tube and a stirring device. To the mixed solution, 35 parts of sulfite chlorine was added dropwise at 1 ° C for 2 minutes. After the completion of the dropwise addition, the reaction was carried out for 3 minutes in a state of heat retention. 57 parts of Acid Red 289 (manufactured by Sino-foreign Chemicals Co., Ltd.) was added to the reaction mixture over 15 minutes, and reacted at 35 ° C for 3 hours. The reaction mixture was cooled, and 34 parts of 2-ethylhexylamine was added dropwise at 1 ° C, followed by dropwise addition of 69 parts of triethylamine. After the dropwise addition, the mixture was reacted at room temperature for 5 hours. The reaction mixture was concentrated. After adding 200 parts of methanol, it was concentrated again until the amount of liquid became about half. Further, 290 parts of methanol and 16 parts of acetic acid were added and reacted for 30 minutes. The reactant was poured into 306 parts of ion-exchanged water to be crystallized. The crystal obtained by filtration was washed successively with 300 parts of 50% aqueous methanol solution, 800 parts of 5% hydrochloric acid water 146860.doc -56-201041980 solution, and 300 parts of deionized water, and then dried under reduced pressure at 60X: Thereafter, 44 parts of the dye A3 as a purplish red solid were obtained. Each compound contained in A3 was chemically identified in the same manner as in Synthesis Example 1 and the content was calculated. The results are shown in Table 1. Synthesis Example 4: Synthesis of Dye A4 410 parts of chloroform and 28 parts of dimethyl decylamine were mixed in a vessel equipped with a cooling tube and a stirring device. 37 parts of sulfite gas was added dropwise to the mixed solution at 1 rc for 2 minutes. After the completion of the dropwise addition, the reaction was carried out for 3 minutes in a state of heat retention. 57 parts of Acid Red were added to the reaction mixture over 15 minutes. 289 (manufactured by Sino-foreign Chemicals Co., Ltd.), and reacted at 35 ° C for 3 hours. Then, 4 parts of sulfite chlorine was further added, and the reaction was continued for 1 hour at 0 μm. Thereafter, the reaction mixture was cooled at 1 34 parts of 2-ethylhexylamine was added dropwise at 〇 °c, followed by dropwise addition of 89 parts of triethylamine. After the dropwise addition, the mixture was reacted at room temperature for 5 hours, and the reaction mixture was concentrated to add 2 parts of sterol. Thereafter, the concentration was again concentrated until the amount of the liquid became about half. Further, 260 parts of methanol and 25 parts of the injured I were added and reacted for 3 minutes. The reactant was poured into 415 parts of ion-exchanged water to be crystallized. The crystal obtained after filtration was washed sequentially with 3 parts of a 5〇% hydrazine aqueous solution, 8〇〇5/Qjja_S water/glutle solution, and 3 parts of deionized water, and then 6 〇. Drying under reduced pressure at ° C for one day gave 42 parts of the dye composition A4 as a purple-red solid. 1 Chemically determine the content of each compound contained in A4 in the same manner, and calculate the content. The results are shown in Table 5. Synthesis Example 5: Synthesis of Dye A5 146860.doc -57- 201041980 With cooling tube and stirring device Mix 41 parts of the gas and 28 parts of decyl decylamine in a container. Add 1 part of sulfoxide to the mixed solution for 20 minutes. After the addition, The state of the heat preservation was reacted for 3 minutes, and 57 parts of Acid Red 289 (manufactured by Sino-foreign Chemical Co., Ltd.) was added to the reaction mixture over 15 minutes, and reacted at 351 for 3 hours. Thereafter, the reaction mixture was cooled at l〇t 33 parts of 2-ethylhexylamine was added dropwise, followed by dropwise addition of 69 parts of triethylamine. After the dropwise addition, the mixture was reacted at room temperature for 5 hours. The reaction mixture was concentrated, and 200 parts of methanol was added thereto, followed by concentration again. The amount of liquid was changed to about half. Further, 290 parts of sterol and 16 parts of acetic acid were added and reacted for 30 minutes. The reactant was poured into 3 parts of 6 parts of ion-exchanged water to be crystallized. % sterol aqueous solution, 200 parts of 20 ° C deionized water The crystals obtained after filtration were washed, and then dried under reduced pressure at 60 ° C for one day to obtain 53 parts of dye A5 as a purplish red solid. Chemicals of each compound contained in A5 were chemically synthesized in the same manner as in Synthesis Example 1. The content was determined and calculated. The results are shown in Table 1. Synthesis Example 6: Synthesis of Dye A6 In a vessel equipped with a cooling tube and a stirring device, 410 parts of a gas mixture and 28 parts of dimethylformamide were mixed. 37 parts of sulfite gas was added dropwise to the mixed solution at 10 ° C for 20 minutes. After the completion of the dropwise addition, the reaction was carried out for 3 minutes in the state of heat retention. 57 parts of Acid Red 289 were added to the reaction mixture over 15 minutes. (manufactured by Chugao Chemical Co., Ltd.) and reacted at 35 ° C for 3 hours. Then, 4.1 parts of sulfite gas was further added at 35. (: Continue the reaction for 1 hour and 5 hours. Thereafter, the reaction mixture was cooled at 1 Torr. (: 34 parts of 2-ethylhexyl 146860.doc -58-201041980 amine was added dropwise followed by 69 parts by weight) After the dropwise addition, the mixture was reacted at room temperature for 15 hours, and the reaction mixture was concentrated, and after adding 2 parts of decyl alcohol, it was concentrated again until the amount of liquid became about half. Further, 29 parts of sterol was added and 16 parts of acetic acid and reacted for 30 minutes. The reactants were injected into 3 〇 6 parts of the ion master water to crystallize them. Using 3 parts of 5 〇% aqueous methanol solution, 5 〇 0 parts of 50 ° C Deionized water, 300 parts of 2 Torr of deionized water were sequentially washed and filtered, and the crystals obtained after filtration were dried under reduced pressure at 6 ° C for one day to obtain 51 parts of dye A6 as a purplish red solid.

Each compound contained in A6 was chemically identified in the same manner as in Synthesis Example 1, and the content was calculated. The results are shown in Table 1. [Table 1] Dye compound (unit: part) (1) (2-1) (2-2) (2-3) Total of (2) (3) A1 4 4 65 15 84 12 A2 7 6 66 15 87 6 A3 1 13 28 39 10 77 86 10 4 A4 10 8 ~ —----- 64 14 A5 λ 6 — 4 63 14 83 13 A6 2 4 63 15 ____ 82 16 Synthesis Example 7: Synthesis of Resin B1 at 0.02 L/min flows into the L-flask with the reflux cooler, the dropping funnel and the turbulence machine to form a nitrogen atmosphere, and then adds 22 parts of lactic acid acetamidine, and then smashes it while adding 敎7〇c. Then, it was dissolved in 84 parts of methacrylic acid, 336 in + 1 && parts of acrylic 3,4-epoxy tricyclic 146860.doc •59- 201041980 [5.2.1.02·6 a solution of hydrazine-based vinegar (mixed with a compound represented by the formula (I) with a compound represented by the formula (I) at a molar ratio of 50:50) and 14 parts of ethyl lactate to form a solution' and then used The dropping funnel was added to the flask maintained at 70 ° C for 4 hours on the other hand. On the other hand, using another dropping funnel 'for 4 hours, 30 parts of the polymerization initiator 2, 2'-couple was used. Nitrogen bis(2,4-dioxyl valeronitrile) A solution obtained by dissolving 95 parts of ethyl lactate was added dropwise to the flask, and after the dropwise addition of the solution of the polymerization initiator, it was kept at 7 Torr for 4 hours, and then cooled to room temperature to obtain a weight. The resin solution B1 having an average molecular weight of "(7) of 8.〇xl〇3, a degree of dispersion of 2.5, a solid content of 48%, and an acid value of 5〇mg_KOH/g.

The measurement of the weight average molecular weight in terms of polystyrene in the above resin was carried out under the following conditions using the GPC method. Device: HLC-8120GPC (made by Tosoh Co., Ltd.)

Column: TSK-GELG2000HXL Column temperature: 40 °C Solvent: THF (tetrahydrofuran, four gas 〇 〇 South) Flow rate: 1.0 mL / min The concentration of solids in the tested liquid: 〇·〇〇1~〇〇ι % Injection volume: 50 μί 146860.doc -60· 201041980

Detector: RI (refractive index detector) calibration standard material; TSK STANDARD POLYSTYRENE F-40, F-4, Fl, A-2500, A-500 (made by Tosoh Co., Ltd.) Example 1 [Preparation of Colored Photosensitive Resin Composition 1] (A) Colorant: CI Pigment Blue 15 : 6 20 parts of acrylic pigment dispersant 5 parts

137 parts of propylene glycol monoterpene ether acetate were mixed, and the pigment was sufficiently dispersed using a bead mill, and then (A) coloring agent: dye A1 3 parts (B) Resin: resin solution B1 65 parts (C) Photopolymerizable compound: Dipentaerythritol hexaacrylate (KAYARADDPHA; manufactured by Sakamoto Chemical Co., Ltd.) 31 parts (D) Photopolymerization initiator: N-benzylideneoxy-1-(4-phenylsulfanylphenyl) octyl Alkan-1-one-2-imine (Irgacure OXE-01; Ciba (manufactured by Ciba)) 9 parts (E) solvent; -4-hydroxy-4-mercapto-2-pentanone 229 parts mixed The colored photosensitive resin composition 1 was obtained. [Formation of Pattern] The colored photosensitive resin composition 1 was applied onto a glass substrate (Eagle 2000; manufactured by Corning Co., Ltd.) of 2 pairs, and then prebaked at 100 ° C for 3 minutes. After cooling, the distance between the substrate coated with the colored photosensitive resin composition and the mask made of quartz glass having a pattern of 146860.doc -61 - 201041980 was set to 100 μm, and then the exposure machine was used under an atmospheric environment ( TME-150RSK; manufactured by Topcon) irradiated light at an exposure of 150 mJ/cm2 (based on 365 nm). After irradiating the light, the coating film was immersed and developed in an aqueous developing solution containing 0.12% of a nonionic surfactant and 0.04% of potassium hydroxide at 23 ° C for 80 seconds, washed with water, and then placed in an oven at 220. Post-baking was carried out at ° C for 20 minutes to obtain a coating film. After standing to cool, the film thickness of the obtained coating film was measured using a film thickness measuring device (DEKTAK3; manufactured by Sakamoto Vacuum Technology Co., Ltd.), and it was 2.2 μm. (Examples 2 to 6) A colored photosensitive resin composition and a coating film were obtained in the same manner as in Example 1 except that the dye oxime 1 was changed to the dyes shown in Tables 2 and 3. [Contrast evaluation] The coating film on the obtained glass substrate was sandwiched between two polarizing plates (POLAX-38S; manufactured by Luceo), and a contrast measuring device (CT-1; Tsuboaka motor) was used. Manufactured, brightness meter (BM-5A; manufactured by Topcon Technohouse), and cold cathode tube F 10 as a light source, the brightness of the transmitted light in the parallel polarizer and the brightness in the crossed polarizer The ratio of the luminance in the parallel polarizer to the luminance in the crossed polarizer (parallel polarizer/straight polarizer) is set to contrast, and the case where the contrast ratio is 6000 or more is determined as 〇. The results are shown in Table 2. [Table 2] Example 1 Example 2 Example 3 Example 4 Example 5 Example 6 Dye A1 A2 A3 A4 A5 A6 Contrast 〇〇〇〇〇〇 146860.doc -62- 201041980 Industrial availability according to The present invention provides a dye composition which provides a color filter of higher contrast.

146860.doc -63-

Claims (1)

201041980 VII. Patent application scope: 1. A dye composition: a: a compound represented by the formula (n), a compound represented by the formula (2), and a compound represented by the formula (2): R1 u "ft' R3-V^R5 (In the formulas (1) and (2), R to R each independently represent a hydrogen atom, r16, _〇H -co2h, -co2R", _s〇3-, _s〇3Na Rl~Rl5 - the base represents -S03-, -S03K or -OR16, -S03H, R represents a carbon number of 1 to 10 a hydrocarbon group, the nitrogen atom contained in the saturated smoky group may be substituted by a sulphur atom m or an alkoxy group having a carbon number of 10, and the CH2• contained in the money and the smoky group may be substituted into _0_, -CO- or -NR17-,r17 矣-^ ® V. 4-' .K represents an atom or a slave number of 1 to 10 one-valent saturated hydrocarbon group, and R to R 5 independently represent a hydrogen atom, _rU -OH , -OR16, -co2h, -co2Ri6, _s〇3·, -S02N(R18)R19^ -S〇2NHR -S03Na, -S03K, -S03H, 8, r21~R35 One of the base representations 146860.doc 201041980 - S 〇 3, and R21 〜 R35 巾 夕 5 , |, at least one of which represents _S 〇 2N (Ri8) Rl9 _so2nhr18, R18 and R19 respectively represent the carbon number of the 〇1〇6 base, the carbon number is The % alkyl carbon number is 6 to 10 monovalent aromatic hydrocarbon groups or a valence aromatic heterocyclic group having a carbon number of 5 to H), or may be bonded to each other to form a carbon number of 2 to H). a ring, the alkyl group and the hydrogen atom contained in the ring group may also be a * atom, a hydroxyl group or The base substitution, the alkyl group and the -ch2_ contained in the cycloalkyl group may also be substituted into _〇...c〇... or the dish 16_ , the aromatic hydrocarbon group and the heterocyclic group of the group The hydrogen atom may also be substituted by a functional atom, #, 郁, 趟丨6, _ _2, or _CH=CHR16. 2_ The dye composition of claim 1 'which further comprises the formula (3) Compounds indicated: (3) (In the formula, Μ independently represents a hydrogen atom, _Rl6, _OH, -(10), Cq2h, -C〇2R16, _s〇2N(r18)r, s〇2nhr18). 3. A dye composition according to the formula, wherein in the formula (1), R1 to R15 each independently represent a hydrogen atom, -Rl6, _scv or _s〇3H, and one of R to Han 5 represents B stone.丨Δ J, ^ ^ 3 and at least—represents -so3h. 4. If the dye composition of the first item is not identified, it is represented by the formula (2), and R21 to R35 are respectively 146860.doc 201041980, respectively, representing a hydrogen atom, _R16, _s〇3-, _s〇 or -S02NHR18, ' 'S02N(R18)R19 5. 6. One of R to R35 represents a dye composition of _s, such as μ, wherein the chlorine atom, -R16 or _S〇2NHRl8 is independently represented in the formula (3), and the Han 41 represents two -S〇2NHR18 . The dye composition of claim 1, wherein at least 35 parts by mass of the compound represented by the formula (1) with respect to the dye ', and at least - means that at least the composition 100 of each of R1 to R55 is 1 temporary county _ ^ , ^ 1 negative 以上 or more, the content of the compound represented by the formula (2) is 65 parts by mass or less. Buying a smear on the U, 99 quality: The dye composition of claim 2, wherein the content of the compound represented by the formula (1) is more than i part by mass, 15 mass relative to the dye. Below, 98 f The content of the compound represented by the formula (2) is 65 parts by mass or more, and the amount of the compound represented by the formula 0) is 丨 parts by mass or more and parts by weight or less. 8. A colored photosensitive resin composition comprising the dye according to claim i, 'and a mouthful (A-1), an alkali-soluble resin, a photopolymerizable compound (c), a photopolymerization initiator (D), and Solvent (E). 9. The colored photosensitive resin composition of claim 8, which further comprises a pigment 2). 146860.doc 201041980 ίο. 11. 12. 13. 14. 15. 16. 17. 18. The color-sensitive photosensitive resin composition of claim 9, wherein the pigment (A_2) contains C. Ϊ·Pigment Blue 15 : 6 The pigment. For example, the color sensitive resin composition of the applicant is used, wherein the mass ratio of the dye composition (A-1) to the C.L pigment blue 15:6 is 3: 97 to 5: 5 〇. A coating which is formed using a dye composition as claimed. A color filter, which is formed using the dye composition as claimed. For example, the color filter and the light sheet of the request item U are formed by the light micro-f彡 method. - Use of a dye composition as claimed in claim i for the manufacture of a color filter. A coloring composition which comprises the dye composition of claim i (Α_υ and pigment (Α-2). The colored composition of claim 16 is contained, for example, wherein the pigment (Α-2) contains C. l pigment Blue 15: 6 pigment. Such as the coloring composition of the request 7, wherein the dye composition of the work pigment blue 15: 6 mass ratio is 3: 97~5〇: 5q. 146860.doc 201041980 Fourth, the designated representative map: ( a) The representative representative of the case is: (none) (2) The symbolic symbol of the representative figure is simple: 5. If there is a chemical formula in this case, please disclose the chemical formula that best shows the characteristics of the invention: 146860.doc -2-