CN102346370A - Coloring composition, color filter and display element - Google Patents
Coloring composition, color filter and display element Download PDFInfo
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- CN102346370A CN102346370A CN201110213042XA CN201110213042A CN102346370A CN 102346370 A CN102346370 A CN 102346370A CN 201110213042X A CN201110213042X A CN 201110213042XA CN 201110213042 A CN201110213042 A CN 201110213042A CN 102346370 A CN102346370 A CN 102346370A
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/201—Filters in the form of arrays
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
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- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optical Filters (AREA)
- Materials For Photolithography (AREA)
Abstract
Provided are a coloring composition, a color filter, and a display element. The coloring composition, with excellent heat resistance performance, contains a colorant. The coloring composition contains A colorant, B binder resin, and C cross-linking agent, with the A colorant comprising the colorant indicated in the formula (1). X plus represents cation chromophore while Z minus represents organic acid conjugate base having halogenated thioetherification.
Description
Technical field
The present invention relates to coloured composition, color filter and display element; In more detail, relate to the color filter of the color liquid crystal display device that is used for transmission-type or reflection-type well, solid-state imager, organic EL display element, electronic paper etc. colorant, contain the coloured composition of this colorant, the display element that has the color filter of the dyed layer that contains this colorant and have this color filter.
Background technology
When using colored radiation-sensitive composition to make color filter; Known behind the colored radiation-sensitive composition and drying of coating pigment decentralized on the substrate; With dry coating according to needed pattern form irradiation radioactive ray (below be called " exposure "); And develop, thereby obtain the method (patent documentation 1～2) of pixel of all kinds.In addition, the also known utilization optical polymerism composition that is dispersed with carbon black forms the method (patent documentation 3) of black matrix.And then the colored resin composition of also known use pigment-dispersing type obtains the method (patent documentation 4) of pixel of all kinds through ink-jetting style.
Yet for the high brightnessization that realizes display element and the height of high-purityization or solid-state imager become more meticulous, known valid is to use dyestuff as colorant.The use of the triarylmethane based dye of ad hoc structure for example, has been proposed in the patent documentation 5.
The prior art document
Patent documentation
Patent documentation 1: japanese kokai publication hei 2-144502 communique
Patent documentation 2: japanese kokai publication hei 3-53201 communique
Patent documentation 3: japanese kokai publication hei 6-35188 communique
Patent documentation 4: TOHKEMY 2000-310706 communique
Patent documentation 5: TOHKEMY 2008-304766 communique
Summary of the invention
But the thermotolerance of the triarylmethane based dye that proposes in the patent documentation 5 is insufficient, if through the heating after such exposure above 200 ℃, the development (back baking) operation, then lose the dominance to the colorimetric properties of pigment.From above background, the exploitation of the dyestuff of strong request excellent heat resistance.
Therefore, problem of the present invention provides excellent heat resistance, contains the coloured composition of colorant.And then problem of the present invention provides possesses color filter that the dyed layer that uses this coloured composition to form forms and the display element that possesses this color filter.
Inventor of the present invention furthers investigate, and the result finds to have than the basic-dyeable fibre of the strong organic acid conjugate base of common sulfonic acid acidity as cationic moiety through containing, and can solve above-mentioned problem.
That is, the present invention provides a kind of coloured composition, and this coloured composition is to contain (A) colorant, (B) resin glue and (C) coloured composition of crosslinking chemical, and the colorant (below, be also referred to as " in line with toner ") that contains following formula (1) expression is as (A) colorant.
X
+Z
- (1)
[in the formula (1), X
+Expression cationic chromophore, Z
-Expression has the organic acid conjugate base of halo alkyl.]
In the present invention, said Z
-Be preferably the negative ion of following formula (1a) expression or the negative ion of following formula (1b) expression.
R
1-SO
3 - (1a)
[in the formula (1a), R
1Expression can have the halo alkyl of linking group, and said linking group contains carbon atom, hydrogen atom and the atom except halogen atom.]
R
2-SO
2-N
--SO
2-R
2 (1b)
[in the formula (1b), R
2Expression independently of each other can have the halo alkyl of linking group, and said linking group contains carbon atom, hydrogen atom and the atom except halogen atom, R
2Bonding and form ring each other.]
In addition, the present invention provides possesses the color filter that the dyed layer that uses above-mentioned coloured composition to form forms, and the display element that possesses this color filter.Wherein, " dyed layer " is meant each color pixel that is used for color filter, black matrix, spacing body night (black spacer) etc.
Thermotolerance in line with toner is extremely excellent.Use contains the coloured composition of the present invention in line with toner, even pass through the heating process of high temperature, also can form the dyed layer of the colorimetric properties that kept excellent.
Therefore, the coloured composition that contains in line with toner can be used for using the look decomposition of color filter, solid-state imager to use color filter, organic EL display element to use color filter, electronic paper to use the making of color filter as the various color filters of representative with color liquid crystal display device extremely well.In addition, in line with toner can also be used for well the plastic shaping thing painted, the colorant, the colorant that is used for color toner that are used for jetted ink, be used for the colorant of electrophoretic display device etc.
Embodiment
Below, be elaborated to of the present invention.
Coloured composition
Below, the constituent of coloured composition of the present invention is elaborated.
-(A) colorant-
Coloured composition of the present invention be characterised in that contain in line with toner, be that the colorant of above-mentioned formula (1) expression is as (A) colorant.In line with toner is that (maximal value of the molar absorptivity among the 380nm～780nm) is generally the compound more than 3000, and is different with acidic smooth acid producing agent is known as absorbing ultraviolet ray triaryl matte perfluoro alkyl sulfonic acid ester etc. in the visible region.
At first, to the Z in the formula (1)
-Describe.
Z
-Just have no particular limits so long as have the organic acid conjugate base of halo alkyl,, can enumerate the sulfonic acid (SO that for example has the halo alkyl as organic acid with halo alkyl
3H), thionyl imide acid (SO
2NHSO
2-) etc.Inventor of the present invention infers through at alkali stain, that is, with kation as importing the stronger organic acid conjugate base of acidity in the chromophoric colorant as anionicsite, thereby ions bind power strengthens, the thermotolerance of colorant improves.
As Z
-Object lesson, can enumerate the negative ion of following formula (1a) expression, the negative ion of following formula (1b) expression etc.
R
1-SO
3 -(1a) R
2-SO
2-N
--SO
2-R
2 (1b)
The definition of the mark in then, explanation formula (1a) and the formula (1b).
R
1And R
2Expression can have the halo alkyl of the linking group that contains carbon atom, hydrogen atom and the atom except halogen atom; As the alkyl that forms its skeleton, for example can enumerate (1) aliphatic alkyl, (2) ester ring type alkyl, (3) and have the ester ring type alkyl and have aliphatic alkyl as substituent aliphatic alkyl (below be called " ester ring type hydrocarbyl substituted aliphatic alkyl "), (4) aromatic hydrocarbyl, (5) and have aromatic hydrocarbyl as substituent aliphatic alkyl (below be called " aromatic hydrocarbyl replacement aliphatic alkyl ") etc. as substituent aromatic hydrocarbyl (below be called " aliphatic alkyl substituted aromatic alkyl "), (6).Consider from the deliquescent viewpoint organic solvent, as forming R
1And R
2The alkyl of skeleton be preferably following characteristic group.
That is, as above-mentioned (1) aliphatic alkyl, preferred alkyl is preferably 1～20, is preferably 1～8 especially as its carbon number.In addition, as above-mentioned (2) ester ring type alkyl, preferred ester ring type saturated hydrocarbyl is preferably 3～20, is preferably 3～12 especially as its carbon number.In addition,, be preferably ester ring type saturated hydrocarbyl substituted alkyl, be preferably 4～20, preferred especially 6～14 as its total carbon atom number as above-mentioned (3) ester ring type hydrocarbyl substituted aliphatic alkyl.In addition, as above-mentioned (4) aromatic hydrocarbyl, preferred carbon number is 6～14 (more preferably carbon number 6～10), is preferably phenyl especially.In addition,, be preferably alkyl-substituted phenyl, be preferably 7～30, be preferably 7～20 especially as its total carbon atom number as above-mentioned (5) aliphatic alkyl substituted aromatic hydrocarbon.In addition, replace aliphatic alkyl, be preferably aralkyl,, be preferably 7～30, be preferably 7～20 especially as its total carbon atom number as above-mentioned (6) aromatic hydrocarbyl.Should explain that the alkyl in this section can be the straight chain shape, also can be branched.
Wherein, as forming R
1And R
2The alkyl of skeleton; Preferably (1) aliphatic alkyl, (3) ester ring type hydrocarbyl substituted aliphatic alkyl, (4) aromatic hydrocarbyl, (5) aliphatic alkyl substituted aromatic alkyl or (6) aromatic hydrocarbyl replace aliphatic alkyl; More preferably alkyl, ester ring type saturated hydrocarbyl substituted alkyl, phenyl, alkyl-substituted phenyl, aralkyl, special preferred alkyl.In addition, in the formula (1b), R
2Bonding and form the alkyl of divalent each other.
In addition, consider from the stable on heating viewpoint of colorant, at R
1And R
2In, as the halogen in the halo alkyl, preferred fluorine.Can think, through selecting fluorine, become the stronger organic acid conjugate base of acidity, form the stronger salt of ions bind power, thereby can improve thermotolerance in line with the anionicsite of toner as substituting group.
In addition, at R
1And R
2In, as the linking group that contains carbon atom, hydrogen atom and the atom except halogen atom, can enumerate-O-,-S-,-CO-,-COO-,-CONH-,-SO
2-etc.Therefore, make progress thus that said carbon number is the total carbon atom number that means the part except the carbon atom that constitutes this linking group in several the 3rd section.
In the present invention, consider from the stable on heating viewpoint of colorant, as R
1And R
2, be preferably the following formula (1-1) or (1-2) group of expression, be preferably formed the group of following formula (1-1) expression of the stronger organic acid conjugate base of acidity especially.
[in the formula (1-1), R
19Expression hydrogen atom, fluorine atom, alkyl, fluoro-alkyl, ester ring type alkyl, alkoxy, fluoroalkyl, R
20COOR
21-or R
20COOR
21CFH-(R
20Expression alkyl, ester ring type alkyl, heteroaryl, or replace or non-substituted aryl R
21Expression methylene or alkylidene), n representes the integer more than 1, " * " representes binding site (combination hand).]
[in the formula (1-2), R
14～R
18Represent hydrogen atom, fluorine atom, hydroxyl, alkyl, fluoro-alkyl or alkoxy independently of each other, " * " representes binding site.Wherein, R
14～R
18In at least one be fluorine atom or fluoro-alkyl.]
In the formula (1-1), as R
19, preferred fluorine atom, fluoro-alkyl, ester ring type alkyl, fluoroalkyl, R
20COOR
21-or R
20COOR
21CFH-, preferred especially fluorine atom, ester ring type alkyl, perfluoro alkoxy, R
20COOCH
2CH
2-or R
20COOCH
2CH
2CFH-.
R
20Expression alkyl, ester ring type alkyl, heteroaryl, or replace or non-substituted aryl, alkyl can be the straight chain shape, also can be branched, and the carbon number of alkyl is preferably 1～12 (more preferably 1～8).The ester ring type alkyl can be the bridging ester ring type alkyl of 2～4 rings, and the carbon number of ester ring type alkyl is preferably 3～20 (more preferably 3～12).As heteroaryl, preferably by containing heteroatomic 5～10 yuan of groups that heteroaromatic constitutes that are selected from more than 1 in nitrogen-atoms, oxygen atom and the sulphur atom.As aryl, being preferably carbon number is the aryl of 6～14 (more preferably carbon number is 6～10), is preferably phenyl especially.In addition, as substituting group, can enumerate carbon number for example and be 1～6 alkyl, carbon number and be 1～6 alkoxy, halogen atom or trifluoromethyl; Substituent position and number are arbitrarily; Have more than 2 under the substituent situation, this substituting group can be identical, also can be different.
In addition, R
21Expression methylene or alkylidene, preferred methylene or carbon number are 2～6 alkylidene, consider from the aspect of easy manufacturing, preferred especially ethylidene.
In addition, the upper limit of n is preferably 10, more preferably 8.
In addition, in formula (1-2), preferred R
14～R
18In at least 3 be fluorine atom or fluoro-alkyl.In addition, in formula (2), preferred R
2Combine each other and form fluoro alkylidene, particularly perfluoro alkylidene.
As above-mentioned formula (1-1) or (1-2) expression anionic typical example, can enumerate the negative ion shown in for example following compound group a and the compound group b.
[compound group a]
Then, to the X in the formula (1)
+Describe.
X
+So long as the cationic chromophore, promptly as X
+Z
-And the kation that forms alkali stain does not just have special qualification, and for example can enumerate triarylmethane and be chromophore, methine and be chromophore, azo and be chromophore, diarylmethanes and be chromophore, quinone imines and be chromophore, anthraquinone chromophores, phthalocyanine is that chromophore, xanthene are chromophore etc.
As above-mentioned triarylmethane is chromophore, the chromophore of preferred following formula (2) expression.Should explain that have various resonant structures in the kation of following formula (2) expression, but in this manual, exist in the kation of various expression under the situation of resonant structure, the kation of representing with this formula is equal material.
[in the formula (2), Ar representes aromatic hydrocarbon ring, R
3And R
4Represent that independently of each other hydrogen atom or carbon number are 1～8 alkyl, R
5And R
6Represent that independently of each other hydrogen atom, carbon number are 1～8 alkyl or phenyl, R
7Expression hydrogen atom, carbon number be 1～8 alkyl ,-COOR ' (R ' expression hydrogen atom or carbon number be 1～8 alkyl) or chlorine atom, R
8And R
11Represent that independently of each other hydrogen atom or carbon number are 1～8 alkyl or R
8And R
11Represent sulphur atom together, R
9And R
10Represent that independently of each other hydrogen atom, carbon number are 1～8 alkyl or chlorine atom, Y representes the group of hydrogen atom or following formula (3) expression.]
[in the formula (3), R
12And R
13Represent that independently of each other hydrogen atom or carbon number are 1～8 alkyl.]
As the aromatic hydrocarbon ring among the Ar, preferred carbon number is the aromatic hydrocarbon ring of 6～20 (more preferably carbon number is 6～10), specifically, can enumerate phenyl ring, naphthalene nucleus, cyclohexyl biphenyl, anthracene nucleus.
R as above-mentioned formula (2)
3～R
11(comprise R
7In-R ' of COOR ') and the R of above-mentioned formula (3)
12And R
13In carbon number be 1～8 alkyl, can enumerate for example methyl, ethyl, propyl group, isopropyl, butyl, sec-butyl, the tert-butyl group, isobutyl, amyl group, tertiary pentyl, hexyl, heptyl, octyl group, iso-octyl, uncle's octyl group, 2-ethylhexyl etc.
In the present invention, consider from the viewpoint that improves brightness and excitation, in the kation of above-mentioned formula (2) expression, the kation of preferred especially following formula (4) expression.
[in the formula (4), R
3, R
4, R
5, R
6, R
12And R
13With the R in above-mentioned formula (2) and (3)
3, R
4, R
5, R
6, R
12And R
13Synonym.]
In above-mentioned formula (4), as R
3, R
4, R
12And R
13, preferred carbon number is the alkyl of 1～8 (more preferably carbon number is 1～6); In addition, as R
5, preferred carbon number is the alkyl or phenyl of 1～8 (more preferably carbon number is 1～6); And then, as R
6, preferred carbon number is the alkyl or the hydrogen atom of 1～8 (more preferably carbon number is 1～6).
As the cationic typical example of above-mentioned formula (2) expression, can enumerate the kation shown in for example following compound group c and the compound group d, wherein, preferred compound c2, compound c 3, compound c 4.
[compound group c]
As above-mentioned methine is chromophore, the chromophore of preferred following formula (5-1)～(5-3) expression.
[in the formula (5-1)～(5-3), R
31Expression hydrogen atom or halogen atom, R
32, R
33, R
34And R
35Represent that independently of each other carbon number is 1～6 alkyl, R
36Expression replaces or non-substituted carbon number is 1～6 alkyl, and G representes-CH=CH-,-CH=CH-NR
37-(R
37Expression hydrogen atom or carbon number are 1～6 alkyl) ,-CH=N-NR
37-(R
37With above-mentioned synonym) or-N=N-NR
37-(R
37With above-mentioned synonym), R
aExpression replaces or non-substituted aromatic hydrocarbyl or replacement or non-substituted heterocyclic radical.]
As R
a, the group of preferred following formula (5a)～(5g) expression.
[in formula (5a)～(5g), R
38And R
45Represent that independently of each other carbon number is 1～6 alkyl, R
39Expression replacement or non-substituted carbon number are 1～6 alkyl, R
40, R
42, R
43And R
44Represent that independently of each other hydrogen atom or carbon number are 1～6 alkyl, R
41And R
46Represent that independently of each other hydrogen atom, halogen atom, carbon number are that 1～6 alkoxy, replacement or non-substituted carbon number are 1～6 alkyl, nitro, hydroxyl or cyanic acid.]
As the substituting group of abovementioned alkyl, can enumerate halogen atom, cyanic acid, hydroxyl etc.
As the cationic typical example of above-mentioned formula (5-1)～(5-3) expression, can enumerate the kation shown in the for example following compound group e.
As above-mentioned azo is chromophore, the chromophore of preferred following formula (6-1)～(6-6) expression.
[in the formula (6-1)～(6-6), R
51, R
52, R
53, R
54, R
55And R
57Expression replacement independently of each other or non-substituted carbon number are 1～6 alkyl, R
56And R
60Represent that independently of each other hydrogen atom, halogen atom, carbon number are that 1～6 alkyl, carbon number are 1～6 alkoxy, nitro, hydroxyl or cyanic acid, R
58The expression carbon number is 1～6 alkyl, R
59Expression forms the group of quaternary ammonium, R
bExpression replaces or non-substituted aromatic hydrocarbyl, or replace or non-substituted heterocyclic radical.]
As above-mentioned R
59, preferred-NR
61C
mH
2mN
+R
62R
63R
64(m is 1～5 integer, R
61Expression hydrogen atom or carbon number are 1～6 alkyl, R
62, R
63And R
64Represent that independently of each other carbon number is 1～6 alkyl) ,-COC
mH
2mN
+R
62R
63R
64(m, R
62, R
63And R
64With above-mentioned synonym) ,-C
mH
2mN
+(NH
2) R
74R
75(m and above-mentioned synonym, R
74And R
75Represent that independently of each other carbon number is 1～6 alkyl), perhaps following formula (6-i) or the group of (6-ii) representing.
[formula (6-i) and (6-ii) in, R
61With m and above-mentioned synonym.]
As above-mentioned R
b, group, replacement or the non-substituted phenyl of preferred following formula (6a)～(6e) expression.
[in formula (6a)～(6d), R
65Expression hydrogen atom, carbon number are 1～6 alkyl, phenyl, benzyl, R
66Expression hydrogen atom or replacement or non-substituted carbon number are 1～6 alkyl, R
67Expression hydrogen atom, carbon number are 1～6 alkyl or phenyl, R
68Expression hydrogen atom or carbon number are 1～6 alkyl, R
69Expression hydrogen atom or carbon number are 1～6 alkyl, R
70～R
73Represent that independently of each other hydrogen atom, halogen atom, carbon number are that 1～6 alkyl, carbon number are 1～6 alkoxy, nitro, hydroxyl or cyanic acid.]
As the substituting group of abovementioned alkyl, can enumerate halogen atom, hydroxyl, cyanic acid ,-CONH
2Base etc.As the substituting group of above-mentioned phenyl, can enumerate halogen atom, carbon number and be 1～6 alkyl, carbon number and be 1～6 alkoxy, hydroxyl, cyanic acid, nitro etc.
As the cationic typical example of above-mentioned formula (6-1)～(6-6) expression, can enumerate the kation shown in for example following compound group f or the compound group g.
[compound group f]
As above-mentioned diaryl is chromophore, preferred following formula (7-1) or the chromophore of (7-2) representing.
[in formula (7-1) with (7-2), R
81, R
82, R
83, R
84, R
86, R
87, R
88And R
89Represent that independently of each other carbon number is 1～6 alkyl, R
85, R
90And R
91Represent that independently of each other hydrogen atom or carbon number are 1～6 alkyl.]
As the cationic typical example of above-mentioned formula (7-1)～(7-2) expression, can enumerate the kation shown in the for example following compound group h.
As above-mentioned quinone imines is chromophore, the chromophore of preferred following formula (8-1)～(8-3) expression.
[in formula (8-1)～(8-3), R
101, R
102, R
103, R
104, R
105, R
106, R
108, R
109, R
110, R
111, R
114, R
115, R
116, R
117And R
118Represent that independently of each other hydrogen atom, replacement or non-substituted carbon number are that 1～6 alkyl, carbon number are 1～6 alkoxy, phenyl or benzyl, R
107And R
113Represent that independently of each other carbon number is that 1～6 alkyl or carbon number are 6～20 aryl, R
112Expression-NR
119R
120(R
119And R
120Expression independently of each other replaces or non-substituted carbon number is 1～6 alkyl), hydroxyl, nitro or cyanic acid, Q representes oxygen atom or sulphur atom.]
As the substituting group of abovementioned alkyl, can enumerate halogen atom, hydroxyl, cyanic acid etc.
As the cationic typical example of above-mentioned formula (8-1)～(8-3) expression, can enumerate the kation that for example following compound group i representes.
As above-mentioned anthraquinone chromophores, preferred following formula (9-1) or the chromophore of (9-2) representing.
[in formula (9-1) with (9-2), R
131, R
135And R
136Represent that independently of each other hydrogen atom, replacement or non-substituted carbon number are 1～6 alkyl, or replace or non-substituted phenyl R
132, R
133, R
134, R
138, R
139And R
140Represent that independently of each other carbon number is 1～6 alkyl, R
137Expression methylene or replacement or non-substituted alkylidene.]
As the substituting group of abovementioned alkyl or phenyl, can enumerate carbon number and be 1～6 alkyl, halogen atom, hydroxyl, cyanic acid etc.In addition, as the substituting group of above-mentioned alkylidene, can enumerate hydroxyl, cyanic acid or nitro etc.
As above-mentioned formula (9-1) or (9-2) expression cationic typical example, can enumerate the kation shown in the for example following compound j.
As above-mentioned phthalocyanine is chromophore, the chromophore of preferred following formula (10) expression.
CuPC-T (10)
[in formula (10), CuPc representes the copper phthalocyanine residue, T represent following formula (10a) or (10b) shown in group.]
[in formula (10a) with (10b), R
151, R
152, R
153, R
154, R
155, R
156, R
157And R
158Represent that independently of each other hydrogen atom, carbon number are 1～6 alkyl or phenyl, p representes 2～8 integer independently of each other, m and above-mentioned synonym.]
As the cationic typical example of above-mentioned formula (10) expression, can enumerate the kation shown in the for example following compound group k.
As above-mentioned xanthene is chromophore, the chromophore of preferred following formula (11) expression.
[in the formula (11), R
159, R
160, R
161And R
162Represent independently of each other hydrogen atom ,-R
166Or carbon number is 6～10 aromatic hydrocarbyl.Wherein, the contained hydrogen atom of this aromatic hydrocarbyl can by halogen atom ,-R
166,-OH ,-OR
166,-SO
3H ,-SO
3M ,-CO
2H ,-CO
2R
166,-SO
3R
166,-SO
2NHR
167Or-SO
2NR
167R
168Replace.
R
163And R
164Represent that independently of each other hydrogen atom or carbon number are 1～8 alkyl.
R
165Expression-SO
3H ,-SO
3M ,-CO
2H ,-CO
2R
166,-SO
3R
166,-SO
2NHR
167Or-SO
2NR
167R
168
Q representes 0～5 integer.Q is under the situation of the integer more than 2, a plurality of R
165Can be the same or different.
R
166The expression carbon number is 1～10 saturated hydrocarbyl.Wherein, the contained hydrogen atom of this saturated hydrocarbyl can be replaced by halogen atom, in addition the contained methylene of saturated hydrocarbyl can by oxygen atom, carbonyl or-NR
166-replace.
R
167And R
168Represent independently of each other carbon number be alkyl, the carbon number of 1～10 straight or branched be 3～30 naphthenic base or-Q, perhaps represent R
167And R
168Mutual bonding and to form carbon number be 1～10 heterocyclic radical.Wherein, the contained hydrogen atom of this alkyl and naphthenic base can by hydroxyl, halogen atom ,-Q ,-CH=CH
2Or-CH=CHR
166Replace, perhaps the contained methylene of this alkyl and naphthenic base can by oxygen atom, carbonyl or-NR
166-replacing, this heterocyclic radical institute hydrogen atoms can be by-R
166,-OH or-Q replaces.
M representes sodium atom or potassium atom.
Q representes that carbon number is that 6～10 aromatic hydrocarbyl or carbon number are 5～10 aromatic heterocycle.Wherein, the contained hydrogen atom of this aromatic hydrocarbyl and aromatic heterocycle can be by-OH, R
166,-OR
166,-NO
2,-CH=CH
2,-CH=CHR
166Or halogen atom replaces.]
R
166In saturated hydrocarbyl so long as carbon number is 1～10, can be in straight chain, side chain and the ring-type any one, can also have bridged linkage.Specifically; Can enumerate alkyl such as methyl, ethyl, propyl group, isopropyl, butyl, isobutyl, amyl group, isopentyl, neopentyl, hexyl, heptyl, octyl group, 2-ethylhexyl, nonyl, decyl; Naphthenic base such as cyclopentyl, cyclohexyl, suberyl, ring octyl group, bridging ester ring type alkyl such as three ring decyls.The contained hydrogen atom of saturated hydrocarbyl can be replaced by halogen atom, as halogen atom, can enumerate fluorine atom, chlorine atom, bromine atoms etc.The contained methylene of saturated hydrocarbyl can by oxygen atom, carbonyl or-NR
10-replace.For example, by the substituted group of oxygen atom, can enumerate methoxy-propyl, ethoxycarbonyl propyl, own oxygen base propyl group, methoxyl hexyl, ethoxycarbonyl propyl etc. as the contained methylene of saturated hydrocarbyl.
As R
159, R
160, R
161, R
162With the aromatic hydrocarbyl among the Q,, can enumerate for example phenyl, naphthyl etc. so long as carbon number is 6～10 just not have special qualification.In addition, the halogen atom of enumerating as the substituting group that can be used as this aromatic hydrocarbyl can be enumerated fluorine atom, chlorine atom, bromine atoms etc.
As R
159, R
160, R
161, R
162And R
165In-SO
3R
166, can enumerate methane sulfonyl, ethane sulfonyl, hexane sulfonyl, decane sulfonyl etc.
As R
159, R
160, R
161, R
162And R
165In-CO
2R
166, can enumerate methoxycarbonyl group, carbethoxyl group, the third oxygen carbonyl, the different third oxygen carbonyl, butoxy carbonyl, isobutyl boc, penta oxygen carbonyl, isoamyl oxygen carbonyl, new penta oxygen carbonyl, ring penta oxygen carbonyl, own oxygen carbonyl, hexamethylene oxygen carbonyl, heptan oxygen carbonyl, ring oxygen carbonyl in heptan, hot oxygen carbonyl, the own oxygen carbonyl of 2-ethyl, the hot oxygen carbonyl of ring, ninth of the ten Heavenly Stems oxygen carbonyl, last of the ten Heavenly stems oxygen carbonyl, three ring oxygen carbonyls in the last of the ten Heavenly stems, methoxy propyl oxygen carbonyl, ethoxy-c oxygen carbonyl, the own oxygen base third oxygen carbonyl, the 2-ethyl hexyl oxy third oxygen carbonyl, the own oxygen carbonyl of methoxyl etc.
As R
159, R
160, R
161, R
162And R
165In-SO
2NHR
167Can enumerate sulfamoyl, methane sulfamoyl, ethane sulfamoyl, propane sulfamoyl, different propane sulfamoyl, butane sulfamoyl, isobutane sulfamoyl, pentane sulfamoyl, isopentane sulfamoyl, neopentane sulfamoyl, cyclopentane sulfamoyl, hexane sulfamoyl, cyclohexane sulfamoyl, heptane sulfamoyl, cycloheptane sulfamoyl, octane sulfamoyl, 2-ethyl hexane sulfamoyl, 1,5-dimethylhexane sulfamoyl, cyclooctane sulfamoyl, nonane sulfamoyl, decane sulfamoyl, tristane sulfamoyl, methoxy propane sulfamoyl, ethoxy propane sulfamoyl, propoxyl group propane sulfamoyl, isopropoxy propane sulfamoyl, own oxygen base propane sulfamoyl, 2-ethyl hexyl oxy propane sulfamoyl, methoxyhexane sulfamoyl, 3-phenyl-1-methylpropane sulfamoyl etc.
As R
159, R
160, R
161, R
162And R
165In-SO
2NHR
167With-SO
2NR
167R
168, can also enumerate the group that following substituting group group a representes to substituting group group u.
In above-mentioned substituting group group d, X
1The expression halogen atom.As X
1In halogen atom, can enumerate fluorine atom, chlorine atom and bromine atoms.
In above-mentioned substituting group group h, X
3The expression carbon number is that 1～3 alkyl or carbon number are 1～3 alkoxy, and the hydrogen atom of this alkyl or alkoxy can be replaced by halogen atom.
As carbon number is 1～3 alkyl, can enumerate methyl, ethyl, propyl group, isopropyl etc.As the alkyl that by the substituted carbon number of halogen atom is 1～3, can enumerate perfluoro-methyl etc.
As carbon number is 1～3 alkoxy, can enumerate methoxyl, ethoxy, propoxyl group etc.
[substituting group group i]
In above-mentioned substituting group group 1, X
2The expression carbon number is that 1～3 alkyl, carbon number are 1～3 alkoxy, halogen atom or nitro, and the hydrogen atom of this alkyl and alkoxy can be replaced by halogen atom.
As halogen atom, can enumerate and above-mentioned X
1Identical atom as being 1～3 alkyl by the substituted carbon number of halogen atom, can being 1～3 alkoxy by the substituted carbon number of halogen atom, can be enumerated and above-mentioned X in addition
3Identical group.
Among the above-mentioned substituting group group q, X
2With above-mentioned synonym.
Among the above-mentioned substituting group group u, X
3With above-mentioned synonym.
As above-mentioned-SO
2NHR
167,-SO
2NR
167R
168In R
167, R
168Preferred carbon number be 6～8 branched-chain alkyl, carbon number be 5～7 ester ring type alkyl, allyl, carbon number be 8～10 aralkyl, carbon number be 2～8 hydroxyl alkyl, carbon number be 2～8 contain alkoxyalkyl, aryl; More preferably carbon number is 6～8 branched-chain alkyl, preferred especially 2-ethylhexyl.
As R
159, R
160, R
161And R
162In carbon number be the substituting group of 6～10 aromatic hydrocarbyl, preferred carbon number be 1～4 alkyl, aryl, alkyl-substituted phenyl ,-SO
3R
166Or-SO
2NHR
167, more preferably ethyl, propyl group, 3,5-dimethylphenyl ,-SO
3R
166Or-SO
2NHR
167
As R
159, R
160, R
161And R
162In have an object lesson that substituent carbon number is 6～10 aromatic hydrocarbyl, can enumerate aminomethyl phenyl, 3,5-dimethylphenyl, trimethylphenyl, ethylphenyl, hexyl phenyl, decyl phenyl, fluoro phenyl, chlorophenyl, bromo phenyl, hydroxy phenyl, methoxyphenyl, Dimethoxyphenyl, ethoxyl phenenyl, own oxygen base phenyl, last of the ten Heavenly stems oxygen base phenyl, trifluoromethyl etc.
Preferred R
159And R
160In at least one or R
161And R
162In at least one be that carbon number is 1～4 alkyl or can substituted carbon number is 6～10 aromatic hydrocarbyl.
More preferably R
159And R
160In at least one and R
161And R
162In at least one be can substituted carbon number to be 6～10 aromatic hydrocarbyl.
R
165Be preferably carboxyl, carbethoxyl group, sulfonic group, 2-ethyl hexyl oxy propane sulfamoyl, 1,5-dimethylhexane sulfamoyl, 3-phenyl-1-methylpropane sulfamoyl or isopropoxy propane sulfamoyl.
As the kation of above-mentioned formula (11) expression, preferred following formula (11-1), (11-2), (11-3) or the kation of (11-4) representing.
[in the formula (11-1), R
159a, R
160a, R
161aAnd R
162aRepresent independently of each other hydrogen atom ,-R
166Or the aromatic hydrocarbyl of carbon number 6～10, the contained hydrogen atom of this aromatic hydrocarbyl can by halogen atom ,-R
166,-OH ,-OR
166,-SO
3H-,-SO
3Na ,-CO
2H ,-CO
2R
166,-SO
3R
166,-SO
2NHR
167Or-SO
2NR
167R
168Replace.
R
165aExpression-SO
3H ,-SO
2NHR
167Or-SO
2NR
167R
168
R
165bThe expression hydrogen atom ,-SO
3H ,-SO
2NHR
167Or-SO
2NR
167R
168
R
166, R
167Or R
168With above-mentioned synonym.]
[in the formula (11-2), R
159b, R
160b, R
161bAnd R
162bRepresent independently of each other hydrogen atom ,-R
166bOr carbon number is 6～10 aromatic hydrocarbyl, the contained hydrogen atom of this aromatic hydrocarbyl can by halogen atom ,-R
166b,-OH ,-OR
166b,-SO
3 -,-SO
3Na ,-CO
2H ,-CO
2R
166b,-SO
3H ,-SO
3R
166bOr-SO
2NHR
178Replace.
R
163bAnd R
164bRepresent that independently of each other hydrogen atom or carbon number are 1～8 alkyl.
R
165cExpression-SO
3Na ,-CO
2H ,-CO
2R
166b,-SO
3H or SO
2NHR
178
R
166bThe expression carbon number is 1～10 saturated hydrocarbyl, and the contained hydrogen atom of this saturated hydrocarbyl can be by-OR
166bOr halogen atom replaces.
R
178The expression hydrogen atom ,-R
166b,-CO
2R
166bOr carbon number is 6～10 aromatic hydrocarbyl, and the contained hydrogen atom of this aromatic hydrocarbyl can be by-R
166bOr-OR
166bReplace.
Q and above-mentioned synonym.]
[in the formula (11-3), R
159cAnd R
161cRepresent phenyl independently of each other, the contained hydrogen atom of this phenyl can by halogen atom ,-R
166b,-OR
166b,-CO
2R
166b,-SO
3R
166bOr-SO
2NHR
178Replace.
R
165dExpression-SO
2NHR
178
R
165eThe expression hydrogen atom or-SO
2NHR
178
R
166bAnd R
178With above-mentioned synonym.]
[in the formula (11-4), R
159dAnd R
161dRepresent phenyl independently of each other, the contained hydrogen atom of this phenyl can be by-R
166bOr-SO
2NHR
178Replace.
R
165fExpression-SO
2NHR
178
R
166bAnd R
178With above-mentioned synonym.]
As the cationic typical example of above-mentioned formula (11) expression, can enumerate the kation that for example following compound group m and compound group n represent.
As other X
+The cationic chromophore of expression can be enumerated the kation shown in the for example following compound group p.
[compound group p]
Can utilize known method manufacturing in line with toner, for example can utilize with the identical method of embodiment of TOHKEMY 2003-206415 communique and make.As the embodiment of TOHKEMY 2003-206415 communique, utilize the salt exchange reaction to make under the situation in line with toner; Need the negative ion of above-mentioned formula (1a) expression or the anionic salt of above-mentioned formula (1b) expression; As this salt; Can utilize commercially available article, also can use [0149]～[0153] section product that the method for putting down in writing is synthesized into through known method, for example TOHKEMY 2008-7410 communique.In addition; Embodiment as TOHKEMY 2003-206415 communique; The basic-dyeable fibre that with the anionicsite is halide ion is as initiation material; When utilizing the salt exchange reaction to make,, preferably make with extra care so that halide ion is not residual as far as possible from the stable on heating viewpoint that further raising obtains in line with toner in line with toner.It is in the various organic solvents of representative that the colorant that obtains like this can be dissolved in ketone such as cyclohexanone, has excellent thermotolerance in addition.In addition, in order further to improve thermotolerance, halide ion contained in the coloured composition of the present invention is also preferably the least possible.That is, after in other compositions of stating, also preferably use the least possible composition of content of halide ions.
Can use separately or use in line with toner mixing more than 2 kinds.
For example, X
+For triarylmethane is under the chromophoric situation; To be dissolved in organic solvent in line with toner; Then demonstrate green grass or young crops～redness; So through with this colorant separately, or suitably mix with other colorant and to use, then go for for example being used to form the coloured composition of the dyed layer of blue pixel, red pixel, black.
As in line with the colorant beyond the toner, can suitably select color, material according to purposes.Specifically; As in line with the colorant beyond the toner, can use in pigment, dyestuff and the natural colouring matter any, but owing to constitute the demanding excitation of dyed layer, brightness, contrast, light-proofness etc. of color filter; Therefore, preferably use pigment and/or dyestuff.
As above-mentioned pigment, organic pigment and inorganic pigment all can, as organic pigment, can enumerate for example pigment index (C.I.; The distribution of The Society of Dyers and Colourists company) is categorized as the compound of pigment in.Particularly, can enumerate the compound that is endowed following pigment index (C.I.) name.
C.I. pigment Yellow 12; C.I. pigment yellow 13; C.I. pigment Yellow 14; C.I. pigment yellow 17; C.I. pigment yellow 20; C.I. pigment yellow 24; C.I. pigment yellow 31; C.I. pigment yellow 55; C.I. pigment yellow 83; C.I. pigment yellow 93; C.I. pigment yellow 109; C.I. pigment yellow 110; C.I. pigment yellow 13 8; C.I. pigment yellow 13 9; C.I. pigment yellow 150; C.I. pigment yellow 153; C.I. pigment yellow 154; C.I. pigment yellow 155; C.I. pigment yellow 166; C.I. pigment yellow 168; C.I. pigment yellow 180; C.I. pigment yellow 211;
C.I. pigment orange 5, C.I. pigment orange 13, C.I. pigment orange 14, C.I. pigment orange 24, C.I. pigment orange 34, C.I. pigment orange 36, C.I. pigment orange 38, C.I. pigment orange 40, C.I. pigment orange 43, C.I. pigment orange 46, C.I. pigment orange 49, C.I. pigment orange 61, C.I. pigment orange 64, C.I. pigment orange 68, C.I. pigment orange 70, C.I. pigment orange 71, C.I. pigment orange 72, C.I. pigment orange 73, C.I. pigment orange 74;
C.I. paratonere 1; C.I. paratonere 2; C.I. paratonere 5; C.I. paratonere 17; C.I. pigment red 31; C.I. pigment red 32; C.I. pigment red 41; C.I. pigment red 122; C.I. pigment red 123; C.I. paratonere 144; C.I. pigment red 149; C.I. paratonere 166; C.I. paratonere 168; C.I. paratonere 170; C.I. paratonere 171; C.I. paratonere 175; C.I. paratonere 176; C.I. paratonere 177; C.I. paratonere 178; C.I. paratonere 179; C.I. paratonere 180; C.I. paratonere 185; C.I. paratonere 187; C.I. paratonere 202; C.I. paratonere 206; C.I. Pigment Red 207; C.I. paratonere 209; C.I. pigment red 21 4; C.I. paratonere 220; C.I. paratonere 221; C.I. paratonere 224; C.I. paratonere 242; C.I. paratonere 243; C.I. paratonere 254; C.I. paratonere 255; C.I. paratonere 262; C.I. paratonere 264; C.I. paratonere 272;
C.I. pigment violet 1, C.I. pigment violet 19, C.I. pigment Violet 23, C.I. pigment violet 29, C.I. pigment violet 32, C.I. pigment violet 36, C.I. pigment violet 38;
C.I. pigment blue 1, C.I. pigment blue 15, C.I. pigment blue 15: 3, C.I. pigment blue 15: 4, C.I. pigment blue 15: 6, C.I. pigment blue 60, C.I. alizarol saphirol 80;
C.I. pigment Green 7, C.I. pigment green 36, C.I. naphthol green 58;
C.I. pigment brown 23, C.I. pigment brown 25;
C.I. pigment black 1, C.I. pigment black 7.
In addition; As above-mentioned inorganic pigment, for example can enumerate titanium dioxide, barium sulphate, lime carbonate, the flowers of zinc, lead sulfate, yellow lead, zinc yellow, iron oxide red (red iron oxide (III)), cadmium red, ultramarine, Prussian blue, chrome oxide green, cobalt green, umber, titanium black, synthesize iron oxide black, carbon black etc.
Among the present invention, also can pigment be made with extra care and use through recrystallization method, reprecipitation method, solvent wash method, sublimed method, vaccum heating method or these combination.In addition, pigment can carry out modification with resin to its particle surface as required and use.Particle surface as with pigment carries out modified resins, can enumerate resin that the vehicles resin put down in writing in the TOHKEMY 2001-108817 communique for example or commercially available various pigment dispersing use etc.As the resin-coated method of carbon blacksurface, can adopt the for example method of middle record such as japanese kokai publication hei 9-71733 communique, japanese kokai publication hei 9-95625 communique, japanese kokai publication hei 9-124969 communique.In addition, organic pigment preferably uses the primary particle miniaturization through so-called salt mill method.For example can adopt disclosed method in the japanese kokai publication hei 08-179111 communique as salt mill method.
As above-mentioned dyestuff, can in various oil-soluble dyes, direct dyes, acid dyes, metal complex dyestuff etc., suitably select, for example, can enumerate the compound that for example is endowed following pigment index (C.I.) name.
C.I. solvent yellow 4, C.I. solvent yellow 14, C.I. solvent yellow 15, C.I. solvent yellow 24, C.I. solvent yellow 82, C.I. solvent yellow 88, C.I. solvent yellow 94, C.I. solvent yellow 98, C.I. solvent yellow 16 2, C.I. solvent yellow 179;
C.I. solvent red 45, C.I. solvent red 49;
C.I. solvent orange 2, C.I. solvent orange 7, C.I. solvent orange 11, C.I. solvent orange 15, C.I. solvent orange 26, C.I. solvent orange 56;
C.I. solvent blue 35, C.I. solvent blue 37, C.I. solvent blue 59, C.I. solvent blue 67;
C.I. Indian yellow 17, C.I. Indian yellow 29, C.I. Indian yellow 40, C.I. Indian yellow 76;
C.I. acid red 91, C.I. acid red 92, C.I. acid red 97, C.I. azogeramine 14, C.I. azogeramine 38, C.I. acid red 151;
C.I. acid orange 51, C.I. acid orange 63;
C.I. acid blue 80, C.I. acid blue 83, C.I. acid blue 90;
C.I. acid green 9, C.I. acid green 16, C.I. ACID GREEN 25, C.I. acid green 27.
In the present invention, other colorant can use separately or with mixing more than 2 kinds.
In the present invention, X
+For methine is under the chromophoric situation, preferably will in line with toner and green other colorant and with and process the coloured composition that is used to form green pixel.At this moment, as the green colourant of other colorant, preferred green organic pigment is preferably selected from least a kind in C.I. pigment Green 7, C.I. pigment green 36, the C.I. naphthol green 58, preferred especially C.I. naphthol green 58.
In the present invention, X
+For xanthene is under the chromophoric situation; Preferably will in line with toner and red other colorant and with and process the coloured composition that is used to form red pixel, perhaps will in line with toner and blue other colorant and with and process the coloured composition that is used to form blue pixel.
To also use and process under the situation of the coloured composition that is used to form red pixel in line with toner and other red colorant; Red stain as other colorant; Preferred red organic pigment; Be preferably selected from least a kind in C.I. paratonere 166, C.I. paratonere 177, C.I. paratonere 224, C.I. paratonere 242, the C.I. paratonere 254, be preferably selected from least a kind in C.I. paratonere 177 and the C.I. paratonere 254 especially.
At this moment, in all coloring agent, in line with proportionally being preferably 1～30 quality % containing of toner, further being preferably 3～15 quality %.In addition, at this moment, can also further use yellow, orange colorant such as C.I. pigment yellow 13 8, C.I. pigment yellow 13 9, C.I. pigment yellow 150, C.I. pigment orange 38.
In addition; And use in line with toner and process under the situation of the coloured composition that is used to form blue pixel with other blue colorant; Blue colorant as other colorant; Preferred blue organic pigment and/or organic dyestuff; Be preferably selected from C.I. pigment blue 1, C.I. alizarol saphirol 2, C.I. alizarol saphirol 3, C.I. alizarol saphirol 9, C.I. pigment blue 10, C.I. pigment blue 14, C.I. pigment blue 15: 3, C.I. pigment blue 15: 6, at least a kind in C.I. alizarol saphirol 62, C.I. Blue 7, the C.I. alkali blue 11, preferred especially C.I. pigment blue 15: 6.
At this moment, in all coloring agent, in line with proportionally being preferably 3～70 quality % containing of toner, further being preferably 3～50 quality %.In addition, at this moment, the colorant of purples such as all right further use C.I. pigment Violet 23.
Consider from the aspect that forms the excellent black matrix of excellent pixel of brightness height and excitation or light-proofness, (A) colorant contain proportional be 5～70 quality % in the solid constituent of coloured composition usually, be preferably 5～60 quality %.Here the composition beyond the solvent of stating after said solid constituent is meant.
In the present invention, use as colorant under the situation of pigment, as required, can use with spreading agent, dispersing aid.As above-mentioned spreading agent, can use for example suitable spreading agents such as kation system, negative ion system, nonionic system, but the preferred polymers spreading agent.Specifically, can enumerate the polyurethane series spreading agent, polyethyleneimine is that spreading agent, polyoxyethylene alkyl ether are that spreading agent, polyoxyethylene alkyl phenyl ether are that spreading agent, polyethylene glycol di are that spreading agent, sorbitan fatty acid ester are that spreading agent, polyester are spreading agent, acrylic acid series spreading agent etc.
Such spreading agent can obtain through being purchased; For example can enumerate Disperbyk-2000, Disperbyk-2001, BYK-LPN6919, BYK-LPN21116, BYK-LPN21324 (above BYK Chemie corporate system) as the acrylic acid series spreading agent; Disperbyk-161, Disperbyk-162, Disperbyk-165, Disperbyk-167, Disperbyk-170, Disperbyk-182 (above BYK Chemie corporate system), Solsperse76500 (Lubrizol (strain) corporate system) as the polyurethane series spreading agent; As polyethyleneimine is the Solsperse24000 (Lubrizol (strain) corporate system) of spreading agent; As polyester is spreading agent, Ajisper PB821, Ajisper PB822, Ajisper PB880, Ajisper PB881 (Ajinomot o Fine Techno Co., Ltd. system) etc.
In addition,, for example pigment derivative can be enumerated, particularly, the sulfonic acid of copper phthalocyanine, diketopyrrolopyrrolecocrystals, Kui phthalein ketone etc. can be enumerated as above-mentioned dispersing aid.In addition, the content of spreading agent and dispersing aid can suitably decision in the scope that does not hinder the object of the invention.
-(B) resin glue-
Coloured composition of the present invention contains (B) resin glue.Thus, can make coloured composition alkali-developable, the cohesive of substrate is improved.Do not have special qualification as such resin glue, but preferably have the resin of acidic functionalities such as carboxyl, phenol property hydroxyl.Wherein, The polymkeric substance (below be called " carbonyl bearing polymer ") that preferably has carboxyl can be enumerated the multipolymer of the ethylene unsaturated monomer that for example has the carboxyl more than 1 (below be called " unsaturated monomer (b1) ") and other polymerisable ethylene unsaturated monomer (below be called " unsaturated monomer (b2) ").
As above-mentioned unsaturated monomer (b1), for example can enumerate (methyl) acrylic acid, maleic acid, maleic anhydride, mono succinate [2-(methyl) acryloxy ethyl] ester, ω-carboxyl polycaprolactone list (methyl) acrylic ester, to vinyl benzoic acid etc.
These unsaturated monomers (b1) can use separately or use mixing more than 2 kinds.
In addition, as above-mentioned unsaturated monomer (b2), for example can enumerate:
The N-substituted maleimide amine of N-phenylmaleimide, N-cyclohexyl maleimide and so on; Styrene, AMS, para hydroxybenzene ethene, to hydroxyl-AMS, to the aromatic ethenyl compound of vinyl benzyl glycidol ether, acenaphthylene and so on;
(methyl) methyl acrylate; (methyl) n-butyl acrylate; (methyl) 2-EHA; (methyl) acrylic acid 2-hydroxy methacrylate; (methyl) allyl acrylate; (methyl) benzyl acrylate; Polyglycol (n=2～10) methyl ethers (methyl) acrylic ester; Polypropylene glycol (n=2～10) methyl ethers (methyl) acrylic ester; Single (methyl) acrylic ester of polyglycol (n=2～10); Single (methyl) acrylic ester of polypropylene glycol (n=2～10); (methyl) cyclohexyl acrylate; (methyl) IBOA; Three ring [5.2.1.0
2,6] decane-8-base (methyl) acrylic ester, dicyclopentenyl (methyl) acrylic ester, glycerine list (methyl) acrylic ester, (methyl) acrylic acid 4-hydroxylphenyl ester, to oxirane modification (methyl) acrylic ester, (methyl) glycidyl acrylate, (methyl) acrylic acid 3 of cumyl phenol, (methyl) acrylic ester of 4-epoxycyclohexyl methyl esters, 3-[(methyl) acryloyl-oxy ylmethyl] oxetanes, 3-[(methyl) acryloyl-oxy ylmethyl]-3-ethyl oxetanes and so on;
Cyclohexyl vinyl ether, isobornyl vinyl ether, three ring [5.2.1.0
2,6] vinyl ether of decane-8-base vinyl ether, pentacyclopentadecandimethanol base vinyl ether, 3-(ethene yloxymethyl)-3-ethyl oxetanes and so on;
Polystyrene, gather (methyl) methyl acrylate, the end that gathers the polymer molecular chain of (methyl) n-butyl acrylate, polysiloxane and so on has macromonomer of list (methyl) acryloyl group etc.
These unsaturated monomers (b2) can use separately or use mixing more than 2 kinds.
In the multipolymer of unsaturated monomer (b1) and unsaturated monomer (b2), the copolymerization ratio of the unsaturated monomer in this multipolymer (b1) is preferably 5～50 quality %, further is preferably 10～40 quality %.Through make unsaturated monomer (b1) copolymerization in such scope, can obtain the coloured composition of alkali-developable and excellent storage stability.
As the object lesson of the multipolymer of unsaturated monomer (b1) and unsaturated monomer (b2), for example can enumerate disclosed multipolymer among japanese kokai publication hei 7-140654 communique, japanese kokai publication hei 8-259876 communique, japanese kokai publication hei 10-31308 communique, japanese kokai publication hei 10-300922 communique, japanese kokai publication hei 11-174224 communique, japanese kokai publication hei 11-258415 communique, TOHKEMY 2000-56118 communique, the TOHKEMY 2004-101728 etc.
In addition; In the present invention, the carbonyl bearing polymer that can also be for example has polymerism unsaturated link such as (methyl) acryloyl group like open such use in japanese kokai publication hei 5-19467 communique, japanese kokai publication hei 6-230212 communique, japanese kokai publication hei 7-207211 communique, japanese kokai publication hei 09-325494 communique, japanese kokai publication hei 11-140144 communique, the TOHKEMY 2008-181095 communique etc. at side chain is as resin glue.
(the stripping solvent: the polystyrene conversion weight-average molecular weight of tetrahydrofuran) measuring (Mw) is generally 1000-100000 to the employing GPC of resin glue among the present invention, is preferably 3000-50000.If Mw is too small, the reductions such as residual film ratio of the tunicle that might obtain, or pattern form, thermotolerance etc. are impaired; And electrical characteristics worsen; On the other hand, if excessive, might reduce by the exploring degree; Or pattern form is impaired, and is easy to generate dry foreign matter when adopting the gap nozzle mode to be coated with.
In addition, among the present invention the weight-average molecular weight of resin glue with adopt GPC (the stripping solvent: the ratio (Mw/Mn) of the polystyrene conversion number-average molecular weight of tetrahydrofuran) measuring (Mn) is preferably 1.0～5.0, more preferably 1.0～3.0.
Resin glue among the present invention can adopt the known method manufacturing; Also can adopt for example middle disclosed method such as TOHKEMY 2003-222717 communique, TOHKEMY 2006-259680 communique, No. 07/029871 pamphlet of International Publication, control its structure, Mw, Mw/Mn.
In the present invention, resin glue can use separately or use mixing more than 2 kinds.
Among the present invention, with respect to (A) colorant 100 mass parts, the content of resin glue is generally 10～1000 mass parts, is preferably 20～500 mass parts.If the content of resin glue is very few, for example, might reduce by alkali-developable; Or the reduction of the storage stability of the coloured composition that obtains, on the other hand, if too much; Relatively colorant concentration reduces, so realize might becoming difficult as the aim colour concentration of film.
-(C) crosslinking chemical-
In the present invention, so-called (C) crosslinking chemical is meant the compound with the polymerizable groups more than 2.As polymerizable groups, can enumerate for example ethene property unsaturated group, epoxy ethyl, oxa-cyclobutyl, N-alkoxy methyl amino etc.In the present invention; As (C) crosslinking chemical; Preferably have (methyl) acryloyl group more than 2 compound, or have the amino compound of N-alkoxy methyl more than 2, the compound that especially preferably will have (methyl) acryloyl group more than 2 uses with the amino compound combination of N-alkoxy methyl that has more than 2.
As above-mentioned object lesson with compound of (methyl) acryloyl group more than 2, can enumerate multifunctional (methyl) acrylic ester, the alkylene oxide modification of multifunctional (methyl) acrylic ester of making the reaction of aliphatic polyhydroxy compound and (methyl) acrylic acid and obtaining, caprolactone modification multifunctional (methyl) acrylic ester, (methyl) acrylic ester with hydroxyl reacted with the polyfunctional isocyanate and multifunctional polyurethane (methyl) acrylic ester that obtains, make (methyl) acrylic ester with hydroxyl and anhydride reaction and multifunctional (methyl) acrylic ester of obtaining etc. with carboxyl.
Here; As above-mentioned aliphatic polyhydroxy compound; For example can enumerate 2 yuan the aliphatic polyhydroxy compound of monoethylene glycol, propylene glycol, polyglycol, polypropylene glycol and so on, the aliphatic polyhydroxy compound more than 3 yuan of glycerine, trimethylolpropane, pentaerythrite, dipentaerythritol and so on.As above-mentioned (methyl) acrylic ester, for example can enumerate (methyl) acrylic acid 2-hydroxyethyl ester, trimethylolpropane two (methyl) acrylic ester, pentaerythrite three (methyl) acrylic ester, dipentaerythritol five (methyl) acrylic ester, glycerine dimethylacrylate etc. with hydroxyl.As above-mentioned polyfunctional isocyanate, for example can enumerate toluene diisocyanate, hexamethylene diisocyanate, MDI, IPDI etc.As acid anhydrides; Can enumerate the for example acid anhydride of the dibasic acid of succinic anhydride, maleic anhydride, glutaric anhydride, itaconic anhydride, phthalic anhydride, hexahydrophthalic anhydride and so on, the tetra-atomic acid dianhydride of pyromellitic dianhydride, biphenyl tetracarboxylic dianhydride, benzophenone tetracarboxylic dianhydride and so on.
In addition, as multifunctional (methyl) acrylic ester of above-mentioned caprolactone modification, can enumerate the for example compound of [0015]～[0018] the section record of japanese kokai publication hei 11-44955 communique.As multifunctional (methyl) acrylic ester of above-mentioned alkylene oxide modification, can enumerate oxirane and/or epoxy pronane modification six (methyl) acrylic ester etc. of oxirane and/or epoxy pronane modification five (methyl) acrylic ester, the dipentaerythritol of oxirane and/or epoxy pronane modification four (methyl) acrylic ester, the dipentaerythritol of oxirane and/or epoxy pronane modification three (methyl) acrylic ester, the pentaerythrite of oxirane and/or epoxy pronane modification three (methyl) acrylic ester, the pentaerythrite of oxirane and/or epoxy pronane modification three (methyl) acrylic ester, the trimethylolpropane of oxirane and/or epoxy pronane modification two (methyl) acrylic ester, the cyamelide of bisphenol-A.
In addition, as the above-mentioned amino compound of N-alkoxy methyl that has more than 2, can enumerate for example have the melamine structure, the compound of benzene guanamine structure, urea structure etc.Should explain that so-called melamine structure, benzene guanamine structure are meant that the triazine ring or the phenyl that have more than 1 replace the chemical constitution of triazine ring as basic framework, are the notions that also comprises melamine, benzene guanamine or these condensation product.As the object lesson of compound, can enumerate N, N, N ', N '; N with the N-alkoxy methyl amino more than 2 ", N " and-six (alkoxy methyl) melamine, N, N, N '; N '-four (alkoxy methyl) benzene guanamine, N, N, N ', N '-four (alkoxy methyl) glycoluril etc.
In these polyfunctional monomers, preferably make aliphatic polyhydroxy compound and (methyl) acrylic acid reaction more than 3 yuan and multifunctional (methyl) acrylic ester, multifunctional polyurethane (methyl) acrylic ester of multifunctional (methyl) acrylic ester of obtaining, caprolactone modification, have multifunctional (methyl) acrylic ester, the N of carboxyl, N; N ', N ', N "; N "-six (alkoxy methyl) melamine, N; N, N ', N '-four (alkoxy methyl) benzene guanamine.From the colored layer, high strength, colored layer excellent surface smoothness, and the unexposed portion of the substrate and the light-shielding layer on the hard fouling (ground dirt), a residual film of the viewpoint, when the trivalent or higher aliphatic polyhydroxy compound with (meth) acrylic acid obtained by reacting a polyfunctional (meth) acrylates, particularly preferably trimethylolpropane triacrylate, pentaerythritol triacrylate, dipentaerythritol pentaacrylate, dipentaerythritol hexaacrylate , having a carboxyl group in the polyfunctional (meth) acrylates, particularly preferably pentaerythritol triacrylate with succinic anhydride obtained by reacting a compound that dipentaerythritol pentaacrylate succinic acid anhydride and reacting the compound obtained.
In the present invention, (C) crosslinking chemical can use separately or use mixing more than 2 kinds.
With respect to (A) colorant 100 mass parts, preferred 10～1000 mass parts of content of (C) crosslinking chemical among the present invention, preferred especially 20～500 mass parts.At this moment, if the content of multi-functional monomer is very few, then possibly can not get sufficient curable.On the other hand,, then coloured composition of the present invention is given under the situation of alkali-developable, had that alkali-developable reduces and be easy to generate residual etc. the tendency of dirt, film on unexposed the substrate or on the light shield layer if the content of multi-functional monomer is too much.
-(D) Photoepolymerizationinitiater initiater-
Can contain (D) Photoepolymerizationinitiater initiater in the coloured composition of the present invention.Thus, can give radiation-sensitive to coloured composition.(D) Photoepolymerizationinitiater initiater that uses among the present invention is the compound that produces the spike that can cause the polymerization of above-mentioned (C) crosslinking chemical through the exposure of luminous ray, ultraviolet ray, far ultraviolet, electron beam, X ray isoradial.
As such Photoepolymerizationinitiater initiater, for example can enumerate thioxanthones based compound, acetophenone based compound, bisglyoxaline based compound, triazine based compound, O-acyl group oxime compound,
salt based compound, benzoin based compound, benzophenone based compound, α-diketone based compound, encircle quinone based compound, diazonium based compound, acid imide sulphonic acid ester based compound etc. more.
Among the present invention, Photoepolymerizationinitiater initiater can use separately or use mixing more than 2 kinds.As Photoepolymerizationinitiater initiater, be preferably selected from least a kind in thioxanthones based compound, acetophenone based compound, bisglyoxaline based compound, triazine based compound, the O-acyl group oxime compound.
Among the present invention in the preferred Photoepolymerizationinitiater initiater; Concrete example as the thioxanthones based compound; Can enumerate thioxanthones, 2-clopenthixal ketone, 2-methyl thioxanthones, 2-isopropyl thioxanthone, 4-isopropyl thioxanthone, 2,4-two clopenthixal ketones, 2,4-dimethyl thioxanthones, 2; 4-diethyl thioxanthone, 2,4-diisopropyl thioxanthones etc.
In addition; As the concrete example of above-mentioned acetophenone based compound, can enumerate 2-methyl isophthalic acid-[4-(methyl mercapto) phenyl]-2-morpholino propane-1-ketone, 2-benzyl-2-dimethylamino-1-(4-morpholino phenyl) butane-1-ketone, 2-(4-methyl-benzyl)-2-(dimethylamino)-1-(4-morpholino phenyl) butane-1-ketone etc.
In addition, as the concrete example of above-mentioned bisglyoxaline based compound, can enumerate 2,2 '-two (2-chlorphenyl)-4,4 ', 5; 5 '-tetraphenyl-1,2 '-bisglyoxaline, 2,2 '-two (2, the 4-dichlorophenyl)-4,4 '; 5,5 '-tetraphenyl-1,2 '-bisglyoxaline, 2,2 '-two (2,4; The 6-trichlorophenyl)-4,4 ', 5,5 '-tetraphenyl-1,2 '-bisglyoxaline etc.
Have again, when using the bisglyoxaline based compound, can improve aspect the sensitivity as Photoepolymerizationinitiater initiater, preferred and use hydrogen donor.Here said " hydrogen donor " means the compound that can supply with hydrogen atom to the free radical that is produced by the bisglyoxaline based compound through exposure.As hydrogen donor; For example can enumerating, mercaptan such as 2-mercaptobenzothiazole, 2-sulfydryl benzo
azoles is hydrogen donor; 4; Amine such as 4 '-two (dimethylamino) benzophenone, 4,4 '-two (diethylamino) benzophenone are hydrogen donor.Among the present invention, hydrogen donor can use separately or use mixing more than 2 kinds, from can further improving the sensitivity aspect, is that hydrogen donor and the amine more than a kind are that the hydrogen donor combination is used with the mercaptan more than a kind preferably.
In addition, as the concrete example of above-mentioned triazine based compound, can enumerate 2; 4,6-three (trichloromethyl) s-triazine, 2-methyl-4, two (trichloromethyl) s-triazine of 6-, 2-[2-(5-methylfuran-2-yl) vinyl]-4; Two (trichloromethyl) s-triazine of 6-, 2-[2-(furans-2-yl) vinyl]-4; Two (trichloromethyl) s-triazine of 6-, 2-[2-(4-diethylamino-2-aminomethyl phenyl) vinyl]-4, two (trichloromethyl) s-triazine of 6-, 2-[2-(3, the 4-Dimethoxyphenyl) vinyl]-4; Two (trichloromethyl) s-triazine of 6-, 2-(4-methoxyphenyl)-4; Two (trichloromethyl) s-triazine of 6-, 2-(4-ethoxybenzene vinyl)-4, two (trichloromethyl) s-triazine of 6-, 2-(4-n-butoxy phenyl)-4, two (trichloromethyl) s-triazine etc. of 6-have the triazine based compound of halogenated methyl.
In addition, as the concrete example of O-acyl group oxime compound, can enumerate 1; The 2-acetyl caproyl, 1-[4-(thiophenyl) phenyl]-, 2-(O-benzoyl oximes), ethyl ketone; 1-[9-ethyl-6-(2-methyl benzoyl)-9H-carbazole-3-yl]-, 1-(O-acetyl group oxime), ethyl ketone, 1-[9-ethyl-6-(2-methyl-4-tetrahydrofuran base methoxybenzoyl base)-9H-carbazole-3-yl]-; 1-(O-acetyl group oxime), ethyl ketone, and 1-[9-ethyl-6-{2-methyl-4-(2,2-dimethyl-1; The 3-dioxolanyl) methoxybenzoyl base }-9H-carbazole-3-yl]-, 1-(O-acetyl group oxime) etc.
Among the present invention, when using Photoepolymerizationinitiater initiater beyond the bisglyoxaline based compound such as acetophenone based compound, also can and use sensitizer.As such sensitizer; For example can enumerate 4; 4 '-two (dimethylamino) benzophenone, 4; 4 '-two (diethylamino) benzophenone, 4-diethyl amino benzoylformaldoxime, 4-dimethylamino propiophenone, 4-dimethylaminobenzoic acid ethyl ester, 4-dimethylaminobenzoic acid 2-Octyl Nitrite, 2, two (the 4-diethylamino benzal) cyclohexanone of 5-, 7-diethylamino-3-(4-diethylamino benzoyl) cumarin, 4-(diethylamino) chalcone etc.
Among the present invention, with respect to (C) crosslinking chemical 100 mass parts, preferred 0.01～120 mass parts of the content of Photoepolymerizationinitiater initiater, preferred especially 1～100 mass parts.In this case, if the content of Photoepolymerizationinitiater initiater is very few, being solidified with that exposure produces possibly become insufficient, on the other hand, if too much, the tendency that the dyed layer that existence forms comes off from substrate when developing easily.
-(E) solvent-
Coloured composition of the present invention is to contain mentioned component (A)～(C) and the coloured composition of other composition of adding arbitrarily, cooperates solvent usually and processes fluid composition and prepare.
As above-mentioned solvent, as long as disperse or dissolve composition (A)～(C), other composition that constitutes coloured composition, and do not react with these compositions, have the volatility of appropriateness, can suitably select to use.
As such solvent, can enumerate for example (gathering) alkylene glycol monoalkyl ethers such as glycol monoethyl ether, ethylene glycol monoethyl ether, ethylene glycol propyl ether, ethylene glycol mono-n-butyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diglycol monotertiary positive propyl ether, diglycol monotertiary n-butyl ether, triethylene glycol monomethyl ether, triethylene glycol list ether, propylene glycol monomethyl ether, dihydroxypropane single-ether, propylene glycol list positive propyl ether, propylene glycol mono-n-butyl ether, dipropylene glycol monomethyl ether, DPG list ether, DPG list positive propyl ether, DPG mono-n-butyl ether, tripropylene glycol monomethyl ether, tripropylene glycol list ether;
Lactic acid alkyl ester such as methyl lactate, ethyl lactate class;
(ring) alkyl alcohols such as methyl alcohol, ethanol, propyl alcohol, butanols, isopropyl alcohol, isobutyl alcohol, the tert-butyl alcohol, octanol, 2-Ethylhexyl Alcohol, cyclohexanol;
Ketols such as DAA etc.;
Ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monomethyl ether acetic acid esters, diethylene glycol monoethyl ether acetic acid esters, propylene glycol methyl ether acetate, propylene glycol monoethyl ether acetate, dipropylene glycol monomethyl ether acetic acid esters, 3-methoxyl butylacetic acid ester, 3-methyl-(gathering) alkylene glycol monoalky lether acetate esters such as 3-methoxyl butylacetic acid ester;
Other ethers such as diethylene glycol dimethyl ether, diglycol methyl ethyl ether, diethyl carbitol, tetrahydrofuran;
Ketones such as methyl ethyl ketone, cyclohexanone, 2-heptanone, 3-heptanone;
Propylene glycol diacetate, oxalic acid 1,3 butylene glycol ester, oxalic acid 1, diacetate esters classes such as 6-hexanediol ester;
3-methoxypropionic acid methyl esters, 3-methoxy propyl acetoacetic ester, 3-ethoxy-propionic acid methyl esters, 3-ethoxyl ethyl propionate, ethoxy ethyl acetate, 3-methyl-alkoxyl carboxylate classes such as 3-methoxyl butyl propionic ester;
Other ester classes such as ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, isobutyl acetate, formic acid n-pentyl ester, isoamyl acetate, n-butyl propionate, ethyl butyrate, butyric acid n-propyl, isopropyl isobutyrate, the positive butyl ester of butyric acid, methyl pyruvate, ethyl pyruvate, pyruvic acid n-propyl, methyl acetoacetate, ethyl acetoacetate, 2-ketobutyric acid ethyl ester;
Toluene, xylene etc. are aromatic hydrocarbon based;
N, acid amides such as dinethylformamide, DMAC N,N, N-Methyl pyrrolidone or lactams etc.
Consider from the viewpoint of dissolubility, pigment-dispersing, coating etc.; Preferred propylene glycol monomethyl ether, dihydroxypropane single-ether, ethylene glycol monomethyl ether acetate, propylene glycol methyl ether acetate, propylene glycol monoethyl ether acetate, 3-methoxyl butylacetic acid ester, diethylene glycol dimethyl ether, diglycol methyl ethyl ether, cyclohexanone, 2-heptanone, 3-heptanone, oxalic acid 1 in these solvents; 3-butanediol ester, oxalic acid 1,6-hexanediol ester, ethyl lactate, 3-methoxy propyl acetoacetic ester, 3-ethoxy-propionic acid methyl esters, 3-ethoxyl ethyl propionate, 3-methyl-3-methoxyl butyl propionic ester, n-butyl acetate, isobutyl acetate, formic acid n-pentyl ester, isoamyl acetate, n-butyl propionate, ethyl butyrate, isopropyl isobutyrate, the positive butyl ester of butyric acid, ethyl pyruvate.
In the present invention, solvent can use separately or use mixing more than 2 kinds.
The content of solvent does not have special qualification; But consider from the viewpoint of the coating of the coloured composition that obtains, stability etc.; The total concentration of removing each composition after desolvating from this coloured composition is preferably the amount of 5～50 quality %, is preferably the amount of 10～40 quality % especially.
-adjuvant-
Coloured composition of the present invention also can contain various adjuvants as required.
As adjuvant, can enumerate for example filling agent such as glass, aluminium oxide; Polyvinyl alcohol (PVA), gather macromolecular compounds such as (fluoroalkyl acrylic ester) class; Fluorine is that surfactant, silicon are surfactants such as surfactant; Driving fit promoter such as vinyltrimethoxy silane, VTES, vinyl three (2-methoxy ethoxy) silane, N-(2-amino-ethyl)-3-aminopropyl methyl dimethoxysilane, N-(2-amino-ethyl)-3-TSL 8330,3-aminopropyltriethoxywerene werene, 3-glycidoxypropyltrimewasxysilane, 3-glycidoxypropyl methyl dimethoxysilane, 2-(3, the 4-epoxycyclohexyl) ethyl trimethoxy silane, 3-chloropropylmethyldimethoxysilane, 3-r-chloropropyl trimethoxyl silane, 3-methacryloxypropyl trimethoxy silane, 3-sulfydryl propyl trimethoxy silicane; 2, anti-oxidants such as 2-thiobis (4-methyl-6-tert butyl phenol), 2,6 di t butyl phenol; Ultraviolet light absorbers such as 2-(the 3-tert-butyl group-5-methyl-2-hydroxy phenyl)-5-chlorobenzotriazole, alkoxy benzophenone class; Anti-polycoagulant such as sodium polyacrylate; Malonic acid, hexane diacid, itaconic acid, citraconic acid, fumaric acid, mesaconic acid, 2-ethylaminoethanol, 3-amino-1-propyl alcohol, 5-amino-1-amylalcohol, 3-is amino-1, and 2-propylene glycol, 2-are amino-1, and ammediol, 4-are amino-1, residue improvers such as 2-butylene glycol; Mono succinate [2-(methyl) acryloxy ethyl] ester, phthalic acid list [2-(methyl) acryloxy ethyl] ester, ω-development property improvement agent such as carboxyl polycaprolactone list (methyl) acrylic ester; Disclosed siloxane oligomer etc. in the TOHKEMY 2008-242078 communique etc. with reactive functional groups.
Coloured composition of the present invention can utilize appropriate method to prepare, and as this preparation method, can enumerate for example middle disclosed method such as TOHKEMY 2008-58642 communique, TOHKEMY 2010-132874 communique.Use in line with under toner etc. and this situation of two kinds of pigment as colorant; Preferably as TOHKEMY 2010-132874 communique is disclosed; Make the dye solution that contains in line with toner etc. through behind the 1st filtrator; Dye solution that will be through the 1st filtrator and the dispersible pigment dispersion of preparation in addition etc. mix, and make the coloured composition that obtains through the 2nd filtrator, thus the method for preparing.In addition; Also preferably will contain in line with the dyestuff of toner etc. and above-mentioned (B)～(C) composition and above-mentioned (D) composition as required and additive component and be dissolved in (E) solvent; Make the solution that obtains through behind the 1st filtrator; Solution that will be through the 1st filtrator and the dispersible pigment dispersion of preparation in addition etc. mix, and make the coloured composition that obtains through the 2nd filtrator, thus the method for preparing.In addition; Also preferably make the dye solution that contains in line with toner etc. through behind the 1st filtrator; To mix, dissolve with above-mentioned (B)～(C) composition and as required above-mentioned (D)～(E) composition and additive component through the dye solution of the 1st filtrator, make the solution that obtains through the 2nd filtrator, solution that further will be through the 2nd filtrator and the other dispersible pigment dispersion for preparing etc. mix; Make the coloured composition that obtains through the 3rd filtrator, thus the method for preparing.
Color filter and manufacturing approach thereof
Color filter of the present invention possesses the dyed layer that contains in line with toner.
As the method for making color filter, first can enumerate following method.At first, on the surface of substrate, form light shield layer (black matrix) as required will form the part subregion of pixel.Secondly, after coating on this substrate for example contains the liquid composition in line with the radiation-ray sensitive composition of the blueness of toner, carry out prebake conditions and make solvent evaporation, formation is filmed.Secondly, through photomask to this film make public after, use alkaline developer to develop, the unexposed portion dissolving of filming is removed.Then, through carrying out the back baking, form the pel array that disposes the blue pixel pattern with predetermined arrangement.
Secondly; Use green or each red colored radiation-sensitive composition; With above-mentioned coating, prebake conditions, exposure, development and the back baking of likewise carrying out each colored radiation-sensitive composition, on same substrate, form green pel array and red pel array successively.Thus, obtain on substrate, disposing the color filter of redness, green and blue trichromatic pel array.But among the present invention, the order that forms pixel of all kinds is not limited to said sequence.
In addition; Black matrix can be through utilizing photoetching process to make to adopt sputter, vapor deposition the metallic film of chromium etc. of film forming become needed pattern and form; But also can use the colored radiation-sensitive composition that is dispersed with black colorant, likewise form during with the above-mentioned pixel of formation.Coloured composition of the present invention can also be used for the formation of this black matrix well.
The substrate that uses during as the formation color filter can be enumerated for example glass, silicon, polycarbonate, polyester, aromatic polyamide, polyamidoimide, polyimide etc.
In addition, to these substrates, also can implement to adopt the suitable pre-service such as agent treated, plasma treatment, ion plating, sputter, gas-phase reaction method, vacuum evaporation of silane coupling agent etc. as required.
When colored radiation-sensitive composition is coated on substrate, suitable rubbing methods such as spray-on process, rolling method, method of spin coating (spin-coating method), slit die rubbing method, scraping article rubbing method be can adopt, spin-coating method, slit die rubbing method especially preferably adopted.
Prebake conditions is carried out drying under reduced pressure and heat drying combination usually.Drying under reduced pressure proceeds to usually and reaches 50～200Pa.In addition, drying was about 1～10 minute under the condition of heat drying was generally 70～110 ℃.
For coating thickness, as dried thickness, be generally 0.6～8.0 μ m, be preferably 1.2～5.0 μ m.
The light source of the radioactive ray that use during as formation pixel and/or black matrix; Can enumerate for example lamp source such as xenon lamp, Halogen lamp LED, tungsten lamp, high-pressure sodium lamp, ultrahigh pressure mercury lamp, metal halide lamp, medium pressure mercury lamp, low pressure mercury lamp; LASER Light Sources such as argon laser, YAG laser, XeCl PRK, nitrogen laser, but optimal wavelength is at the radioactive ray of the scope of 190～450nm.
The general preferred 10～10000J/m of the exposure of radioactive ray
2
In addition, as above-mentioned alkaline developer, preference such as sodium carbonate, NaOH, potassium hydroxide, tetramethylammonium hydroxide, choline, 1,8-diazabicyclo-[5.4.0]-7-undecylene, 1, the WS of 5-diazabicyclo-[4.3.0]-5-nonene etc.
In above-mentioned alkaline developer, also can add an amount of water-miscible organic solvent such as for example methyl alcohol, ethanol etc., surfactant etc.Have, alkali is washed after developing usually again.
As the development treatment method, can adopt spray development method, spray development method, immersion development method, soak the formula of putting (covering liquid) development method etc.Development conditions was preferably carried out 5～300 seconds at normal temperature.
The condition of back baking is generally carried out under 120～280 ℃ about 10～60 minutes, but considered from the thermotolerance aspect in line with toner, and the temperature of back baking is preferably below 240 ℃, is preferably below 230 ℃ especially.
The thickness of the pixel that forms like this is generally 0.5～5.0 μ m, is preferably 1.0～3.0 μ m.
In addition, as second method of making color filter, disclosed employing ink-jetting style obtains the method for pixel of all kinds in also known japanese kokai publication hei 7-318723 communique, the TOHKEMY 2000-310706 communique etc.In the method, at first, on the surface of substrate, form the next door that has shade function concurrently.Then, will for example contain in the next door that fluid composition in line with the coloured composition of the blueness of toner is ejected into formation through ink discharge device after, carry out prebake conditions and make solvent evaporation.Then, with this film make public as required after, be cured through back baking, form the blue pixels pattern.
Then, use green or each red coloured composition, with above-mentioned green pattern of pixels and the red pattern of pixels of likewise on same substrate, forming successively.Thus, obtain on substrate, disposing simultaneously the color filter of redness, green and blue trichromatic pattern of pixels.But among the present invention, the order that forms pixel of all kinds is not limited to said sequence.
Have, above-mentioned next door not only has shade function again, also play to make the not function of colour mixture of the coloured composition of all kinds that is ejected in the subregion, therefore, and the black matrix that uses in above-mentioned first method, thickness is thick.Therefore, the next door uses the black radiation-ray sensitive composition to form usually.
The substrate that when forming color filter, uses, the light source of radioactive ray, and method, the condition of prebake conditions, back baking are identical with the first above-mentioned method.The thickness of the pixel that forms through ink-jetting style like this, and the height in next door are same degree.
On the pattern of pixels that obtains like this, form diaphragm as required after, utilize sputter to form nesa coating.After forming nesa coating, can also further form distance piece and form color filter.Distance piece can use radiation-ray sensitive composition to form usually, but also can process the distance piece (spacing body night) with light-proofness.At this moment, use the colored radiation-sensitive composition be dispersed with black colorant, coloured composition of the present invention also can perform well in the formation of this of spacing body night.
The brightness and the excitation of the color filter of the present invention that obtains like this are high, and be therefore exceedingly useful to color liquid crystal display device, colour pick-up tube element, color sensor, organic EL display element, electronic paper etc.
Display element
Display element of the present invention possesses color filter of the present invention.As display element, can enumerate color liquid crystal display device, organic EL display element, electronic paper etc.
The color liquid crystal display device that possesses color filter of the present invention can be taked suitable structure.For example can adopt: with the driving of disposing thin film transistor (TFT) (TFT) the other substrate different with substrate on form color filter, drive with substrate and substrate Jie who is formed with color filter by the relative structure of liquid crystal layer; And then also can adopt: disposing the substrate that is formed with color filter on the surface of driving with substrate of thin film transistor (TFT) (TFT), be situated between by the relative structure of liquid crystal layer with the substrate that is formed with ITO (indium oxide of the tin that mixed) electrode.The latter's structure has can significantly improve aperture opening ratio, obtain the advantage bright and liquid crystal display cells that height is meticulous.
The color liquid crystal display device that possesses color filter of the present invention except cold cathode fluorescent tube (CCFL:Cold Cathode Fluorescent Lamp), can also possess with the backlight unit of White LED as light source.As White LED; For example can enumerate and to use red LED, green LED and blue led and the White LED that obtains white light with spectrum independently; Display predetermined colors in combination LED, green LED and blue led obtain the White LED of white light through colour mixture; Combined blue LED, red LED and green-emitting phosphor obtain the White LED of white light through colour mixture; Combined blue LED, red-emitting phosphors and green-emitting phosphor obtain the White LED of white light through colour mixture; Through blue led and YAG is the White LED that the colour mixture of fluorophor obtains white light, and combined blue LED, fluorescent orange body and green-emitting phosphor obtain the White LED of white light through colour mixture, make up ultraviolet LED, red-emitting phosphors, green-emitting phosphor and blue emitting phophor and obtain White LED of white light etc. through colour mixture.
Display element of the present invention can be suitable for TN (Twisted Nematic; Twisted-nematic) type, STN (Super Twisted Nematic; Supertwist is to row) type, IPS (In-Planes Switching; The face intra) suitable liquid crystal mode such as type, VA (Vertical Alignment, vertical orientated) type, OCB (Optically Compensated Birefringence, optical compensation curved arrangement) type.
In addition, the organic EL display element that possesses color filter of the present invention can be taked suitable structure, can enumerate the for example disclosed structure of japanese kokai publication hei 11-307242 communique.
In addition, the electronic paper that possesses color filter of the present invention can be taked suitable structure, can enumerate the for example disclosed structure of TOHKEMY 2007-41169 communique.
Embodiment 1
Below enumerate embodiment, embodiment of the present invention is further specified.But the present invention is not limited to following embodiment.
< in line with the synthetic and evaluation of toner >
1. synthetic in line with toner
The synthetic example 1 of colorant
In the spiral pipe that has dropped into stirrer, add 1.4g (2.72mmol) C.I. Blue 7 (CI of the compound c 2 of above-claimed cpd group c
-Salt), 0.768g (4.08mmol) trifluoromethayl sulfonic acid potassium (with the pure medicine corporate system of light), 20mL chloroform and 10mL water, at room temperature stirred 7 hours.After water layer is removed in separation, wash 2 times organic layer, under reduced pressure concentrate, and then with the solid drying under reduced pressure that obtains, thereby the black-and-blue solid of 1.70g (yield 80.2%) obtained.With this as compd A.Compd A
1(solvent: deuterochloroform) compose as follows, affirmation is a target compound to H-NMR.
1H-NMR：δ8.25(d，1H)，7.18-7.51(m，8H)，6.75(brs，4H)，6.65(d，1H)，3.60(q，2H)，3.55(q，8H)，1.46(t，3H)，1.30(t，12H)
The synthetic example 2 of colorant
In colorant synthetics 1, replace trifluoromethayl sulfonic acid potassium to use nine fluorine butane potassium sulfonates (with the pure medicine corporate system of light), in addition, synthesize example 1 synthetic coloring matter likewise with colorant, through
1(solvent: deuterochloroform) measure, affirmation is a target compound to H-NMR.With this as compd B.Compd B
1The H-NMR spectrum as follows.
1H-NMR：δ8.26(d，1H)，7.15-7.55(m，8H)，6.75(brs，4H)，6.65(d，1H)，3.60(q，2H)，3.55(q，8H)，1.47(t，3H)，1.30(t，12H)
The synthetic example 3 of colorant
In colorant synthetics 1, replace trifluoromethayl sulfonic acid potassium to use two (trifluoromethane sulfonyl group) acid imide potassium, in addition, synthesize example 1 synthetic coloring matter likewise with colorant, through
1(solvent: deuterochloroform) measure, affirmation is a target compound to H-NMR.With this as Compound C.Compound C
1The H-NMR spectrum as follows.
1H-NMR：δ8.01(d，1H)，7.16-7.52(m，7H)，6.75(brs，4H)，6.68(d，1H)，6.19(t，1H)，3.55(q，10H)，1.45(t，3H)，1.30(t，12H)
The synthetic example 4 of colorant
In colorant synthetics 1, replaced C .I. Blue 7 uses the C.I. alkali blue 11 (Cl of the compound c 4 of above-claimed cpd group c
-Salt), in addition, synthesize example 1 synthetic coloring matter likewise with colorant, through
1(solvent: deuterochloroform) measure, affirmation is a target compound to H-NMR.
The synthetic example 5 of colorant
In colorant synthetics 1, replaced C .I. Blue 7 uses the C.I. Basic Violet16 (Cl of the Verbindung 2 of above-claimed cpd group e
-Salt), in addition, synthesize example 1 synthetic coloring matter likewise with colorant, through
1(solvent: deuterochloroform) measure, affirmation is a target compound to H-NMR.
The synthetic example 6 of colorant
In colorant synthetics 1, replaced C .I. Blue 7 uses C.I. alkali blue 41 (the methane sulfate of the compound f13 of above-claimed cpd group f), in addition, synthesizes example 1 synthetic coloring matter likewise with colorant, through
1(solvent: deuterochloroform) measure, affirmation is a target compound to H-NMR.
The synthetic example 7 of colorant
In colorant synthetics 1, replaced C .I. Blue 7 uses the C.I. alkali blue 3 (Cl of the compound i 4 of above-claimed cpd group i
-Salt), in addition, synthesize example 1 synthetic coloring matter likewise with colorant, through
1(solvent: deuterochloroform) measure, affirmation is a target compound to H-NMR.
The synthetic example 8 of colorant
In colorant synthetics 1, replaced C .I. Blue 7 uses the C.I. alkali blue 22 (Cl of the compound j1 of above-claimed cpd group j
-Salt), in addition, synthesize example 1 synthetic coloring matter likewise with colorant, through
1(solvent: deuterochloroform) measure, affirmation is a target compound to H-NMR.
The synthetic example 9 of colorant
In colorant synthetics 1, replaced C .I. Blue 7 uses the C.I. alkali red 1:1 3 (Cl of the Verbindung 1 of above-claimed cpd group e
-Salt), replace trifluoromethayl sulfonic acid potassium to use two (trifluoromethane sulfonyl group) acid imide potassium, in addition, synthesize example 1 synthetic coloring matter likewise with colorant, through
1(solvent: deuterochloroform) measure, affirmation is a target compound to H-NMR.
The synthetic example 10 of colorant
In colorant synthetics 1, replaced C .I. Blue 7 uses the C.I. basic yellow 25 (Cl of the compound f1 of above-claimed cpd group f
-Salt), replace trifluoromethayl sulfonic acid potassium to use two (trifluoromethane sulfonyl group) acid imide potassium, in addition, synthesize example 1 synthetic coloring matter likewise with colorant, through
1(solvent: deuterochloroform) measure, affirmation is a target compound to H-NMR.
The synthetic example 11 of colorant
In colorant synthetics 1, replaced C .I. Blue 7 uses the C.I. basic yellow 2 (Cl of the compound h2 of above-claimed cpd group h
-Salt), replace trifluoromethayl sulfonic acid potassium to use two (trifluoromethane sulfonyl group) acid imide potassium, in addition, synthesize example 1 synthetic coloring matter likewise with colorant, through
1(solvent: deuterochloroform) measure, affirmation is a target compound to H-NMR.
The synthetic example 12 of colorant
In colorant synthetics 1, replaced C .I. Blue 7 uses the red 2 (Cl of the compound i 1 of above-claimed cpd group i of C.I. alkalescence
-Salt), replace trifluoromethayl sulfonic acid potassium to use two (trifluoromethane sulfonyl group) acid imide potassium, in addition, synthesize example 1 synthetic coloring matter likewise with colorant, through
1(solvent: deuterochloroform) measure, affirmation is a target compound to H-NMR.
The synthetic example 13 of colorant
In colorant synthetics 1, replaced C .I. Blue 7 uses the C.I. alkaline orange 24 (Cl of the compound g3 of above-claimed cpd group g
-Salt), replace trifluoromethayl sulfonic acid potassium to use two (trifluoromethane sulfonyl group) acid imide potassium, in addition, synthesize example 1 synthetic coloring matter likewise with colorant, through
1(solvent: deuterochloroform) measure, affirmation is a target compound to H-NMR.
The synthetic example 14 of colorant
In colorant synthetics 1, replaced C .I. Blue 7 uses the C.I. basic yellow 21 (Cl of the Verbindung 9 of above-claimed cpd group e
-Salt), replace trifluoromethayl sulfonic acid potassium to use two (trifluoromethane sulfonyl group) acid imide potassium, in addition, synthesize example 1 synthetic coloring matter likewise with colorant, through
1(solvent: deuterochloroform) measure, affirmation is a target compound to H-NMR.With this as compd E.Compd E
1The H-NMR spectrum as follows.
1H-NMR：8.78(d，1H)，7.70(d，1H)，7.67(m?1H)，7.28-7.57(m，8H)，6.24(d，1H)，5.19(quintet，1H)，3.89(s?3H)，3.66(q，1H)，3.01(d，1H)，1.88(s，3H)，1.82(s，3H)，1.52(d，3H)
The synthetic example 15 of colorant
In the spiral pipe that has dropped into stirrer, add C.I. alkali red 1:1,0.766g (4.07mmol) trifluoromethayl sulfonic acid potassium (with the pure medicine corporate system of light), 20mL chloroform and 10mL water that the following formula of 1.3g (2.71mmol) is represented, at room temperature stirred 7 hours.After water layer is removed in separation, wash 2 times organic layer, under reduced pressure concentrate, and then, obtain the black-and-blue solid of 1.61g (yield 72%) thus the solid drying under reduced pressure that obtains.With this as compound G.Compound G's
1(solvent: deuterochloroform) compose as follows, affirmation is a target compound to H-NMR.
1H-NMR：8.25(dd，1H)，7.87(m，2H)，7.70(t，2H)，7.47(dd，1H)，6.94(d，3H)，6.81(s，2H)，3.95(q，2H)，3.50(quintet，4H)，2.10(s，6H)，1.27(t，6H)，0.85(t，3H，)
The synthetic example 16 of colorant
In colorant synthetics 15, replace trifluoromethayl sulfonic acid potassium to use nine fluorine butane potassium sulfonates (with the pure medicine corporate system of light), in addition, synthesize example 15 synthetic coloring matter likewise with colorant, through
1(solvent: deuterochloroform) measure, affirmation is a target compound to H-NMR.With this as compound H.Compound H
1The H-NMR spectrum as follows.
1H-NMR：8.32(d，1H)，7.78(m，2H)，7.28(dd，1H)，6.81(d，2H)，6.76(s，2H)，6.68(s，2H)，4.04(q，2H)，3.51(quintet，4H)，2.18(s，6H)，1.38(t，6H)，1.00(t，3H，)
The synthetic example 17 of colorant
In colorant synthetics 15, replace trifluoromethayl sulfonic acid potassium to use two (trifluoromethane sulfonyl group) acid imide potassium, in addition, synthesize example 15 synthetic coloring matter likewise with colorant, through
1(solvent: deuterochloroform) measure, affirmation is a target compound to H-NMR.With this as compound I.Compound I
1The H-NMR spectrum as follows.
1H-NMR：8.33(d，1H)，7.79(m，2H)，7.28(dd，1H)，6.81(d，2H)，6.76(d，2H)，5.94(d，2H)，4.04(q，2H)，3.50(quintet，4H)，2.15(s，6H)，1.39(t，6H)，1.01(t，3H，)
The synthetic example 18 of colorant
In colorant synthetics 15, replaced C .I. alkali red 1:1 uses the C.I. alkali red 1:1: 1, in addition, synthesize example 15 synthetic coloring matter likewise with colorant, through
1(solvent: deuterochloroform) measure, affirmation is a target compound to H-NMR.With this as compound J.Compound J's
1The H-NMR spectrum as follows.
1H-NMR：8.33(d，1H)，7.80(m?2H)，7.28(d，1H)，6.77(d，4H)，5.95(t，2H)，3.66(s?3H)，3.49(quintet，4H)，2.13(s，6H)，1.38(t，6H)
The synthetic example 19 of colorant
In colorant synthetics 17, the C.I. alkaline purple 10 that replaced C .I. alkali red 1:1 uses following formula to represent in addition, synthesizes example 17 synthetic coloring matter likewise with colorant, through
1(solvent: deuterochloroform) measure, affirmation is a target compound to H-NMR.With this as compound K.Compound K
1The H-NMR spectrum as follows.
1H-NMR：8.28(d，1H)，7.77(t，1H)，7.69(t，1H)，7.26(dd，2H)，7.02(d，2H)，6.76-6.83(m?4H)，5.95(t，2H)，3.58(q，8H)，1.30(t，12H)
The synthetic example 20 of colorant
In colorant synthetics 17, the C.I. alkali violet 11:1 that replaced C .I. alkali red 1:1 uses following formula to represent: 1, in addition, synthesize example 17 synthetic coloring matter likewise with colorant, through
1(solvent: deuterochloroform) measure, affirmation is a target compound to H-NMR.With this as compound L.Compound L
1The H-NMR spectrum as follows.
1H-NMR：8.31(d，1H)，7.77(dt，2H)，7.30(m，1H)，7.06(m?2H)，6.83(d，4H)，3.68(s?3H)，3.60(q，8H)，1.32(t，12H)
The synthetic example 21 of colorant
In colorant synthetics 17, replaced C .I. alkali red 1:1 uses C.I. alkalescence that following formula representes red 3, in addition, and with the synthetic example 17 of colorant synthetic coloring matter likewise, through
1(solvent: deuterochloroform) measure, affirmation is a target compound to H-NMR.
The synthetic example 22 of colorant
In colorant synthetics 17, replaced C .I. alkali red 1:1 uses C.I. alkalescence that following formula representes red 4, in addition, and with the synthetic example 17 of colorant synthetic coloring matter likewise, through
1(solvent: deuterochloroform) measure, affirmation is a target compound to H-NMR.
The synthetic example 23 of colorant
In colorant synthetics 17, the C.I. alkali violet 11:1 that replaced C .I. alkali red 1:1 uses following formula to represent in addition, synthesizes example 17 synthetic coloring matter likewise with colorant, through
1(solvent: deuterochloroform) measure, affirmation is a target compound to H-NMR.
2. in line with the evaluation of toner
The compd A that obtains in the synthetic example 1 of colorant dissolves in cyclohexanone more than the 10 quality %, and this solution presents blueness.The colorant that obtains in the synthetic example 2～23 of colorant all dissolves more than the 10 quality % in cyclohexanone.
In addition, the colorant that obtains in the synthetic example 1～23 of colorant, based on thermogravimetric amount-differential heat simultaneously the temperature of minimizing 5% quality of determination and analysis be more than 250 ℃.On the other hand, red 2, the C.I. alkaline orange 24 of C.I. Blue 7, C.I. alkali blue 11, C.I. Basic Violet16, C.I. alkali blue 41, C.I. alkali blue 3, C.I. alkali blue 22, C.I. alkali red 1:1 3, C.I. basic yellow 25, C.I. basic yellow 2, C.I. alkalescence, C.I. basic yellow 21, C.I. alkali red 1:1, C.I. alkali red 1:1: 1, red 4, the C.I. alkaline purple 10 of red 3, the C.I. alkalescence of C.I. alkalescence, C.I. alkali violet 11:1, C.I. alkali violet 11:1: 1, based on thermogravimetric amount-differential heat simultaneously the temperature of minimizing 5% quality of determination and analysis all less than 200 ℃.
< preparation of dispersible pigment dispersion >
Preparation example 1
Use the C.I. pigment blue 15 of 15 mass parts as colorant: 6; Use the BYK-LPN21116 (BYK Chemie corporate system) (solid component concentration=40 quality %) of 12.5 mass parts as spreading agent; Use the propylene glycol methyl ether acetate of 72.5 mass parts as solvent; Utilize ball mill to handle, preparation dispersible pigment dispersion (A-1).
Preparation example 2
Except replaced C .I. pigment blue 15: 6 use the C.I. pigment Violet 23s as the colorant, likewise carry out with preparation example 1, have prepared dispersible pigment dispersion (A-2).
Preparation example 3
Except replaced C .I. pigment blue 15: 6 use C.I. naphthol greens 58 as the colorant, likewise carry out with preparation example 1, have prepared dispersible pigment dispersion (A-3).
Preparation example 4
Except replaced C .I. pigment blue 15: 6 use C.I. pigment yellows 150 as the colorant, likewise carry out with preparation example 1, have prepared dispersible pigment dispersion (A-4).
Preparation example 5
Use the C.I. paratonere 177 of 15 mass parts as colorant; Use the BYK-LPN21116 (BYK Chemie corporate system) (solid component concentration=40 quality %) of 12.5 mass parts as spreading agent; Use the propylene glycol methyl ether acetate of 72.5 mass parts as solvent; Utilize ball mill to handle, preparation dispersible pigment dispersion (A-5).
Preparation example 6
Except replaced C .I. paratonere 177 uses C.I. paratonere 254 as the colorant, likewise carry out with preparation example 5, prepared dispersible pigment dispersion (A-6).
< preparation of dye solution >
Preparation example 7
With mixing of 5 mass parts, prepare dye solution A as the compd A of colorant and the propylene glycol methyl ether acetate as solvent of 95 mass parts.
Preparation example 8
With mixing of 5 mass parts, prepare dye solution B as the compd B of colorant and the propylene glycol methyl ether acetate as solvent of 95 mass parts.
Preparation example 9
With mixing of 5 mass parts, prepare dye solution C as the Compound C of colorant and the propylene glycol methyl ether acetate as solvent of 95 mass parts.
Preparation example 10
With mixing of 5 mass parts, prepare dye solution D as the C.I. Blue 7 of colorant and the propylene glycol monomethyl ether as solvent of 95 mass parts.
Preparation example 11
With mixing of 5 mass parts, prepare dye solution E as the compd E of colorant and the propylene glycol methyl ether acetate as solvent of 95 mass parts.
Preparation example 12
With mixing of 5 mass parts, prepare dye solution F as the C.I. basic yellow 21 of colorant and the propylene glycol methyl ether acetate as solvent of 95 mass parts.
Preparation example 13
With mixing of 20 mass parts, prepare dye solution G as the compound G of colorant and the propylene glycol monomethyl ether as solvent of 80 mass parts.
Preparation example 14
With mixing of 20 mass parts, prepare dye solution H as the compound H of colorant and the propylene glycol monomethyl ether as solvent of 80 mass parts.
Preparation example 15
With mixing of 20 mass parts, prepare dye solution I as the compound I of colorant and the propylene glycol monomethyl ether as solvent of 80 mass parts.
Preparation example 16
With mixing of 20 mass parts, prepare dye solution J as the compound J of colorant and the propylene glycol monomethyl ether as solvent of 80 mass parts.
Preparation example 17
With mixing of 20 mass parts, prepare dye solution K as the compound K of colorant and the propylene glycol monomethyl ether as solvent of 80 mass parts.
Preparation example 18
With mixing of 20 mass parts, prepare dye solution L as the compound L of colorant and the propylene glycol monomethyl ether as solvent of 80 mass parts.
Preparation example 19
With mixing of 20 mass parts, prepare dye solution M as the C.I. alkali red 1:1 of colorant and the propylene glycol monomethyl ether as solvent of 80 mass parts.
< synthesizing of resin glue >
In the beaker that possesses cooling tube and stirrer, the propylene glycol methyl ether acetate of 100 mass parts of packing into also carries out nitrogen replacement.Be heated to 80 ℃; Under this temperature; With 2 of mono succinate (the 2-acryloxy ethyl) ester of the N-phenylmaleimide of the methacrylic acid 2-Octyl Nitrite of the 2-hydroxyethyl methacrylate of the benzyl methacrylate of the styrene of the methacrylic acid of the propylene glycol methyl ether acetate that splashed into 100 mass parts in 1 hour, 20 mass parts, 10 mass parts, 5 mass parts, 15 mass parts, 23 mass parts, 12 mass parts, 15 mass parts and 6 mass parts; 2 '-azo two (2; The 4-methyl pentane nitrile) mixed solution keeps this temperature, polymerization 2 hours.Then, make the temperature of reaction solution be warming up to 100 ℃, and then polymerization 1 hour, thereby resin glue (solid component concentration=33 quality %) obtained.The resin glue that obtains is Mw=12200, Mn=6500.With this resin glue as " resin glue (B1) ".
< preparation of coloured composition and evaluation >
Embodiment 1
With the resin glue as resin glue (B1) solution of the dye solution A of the dispersible pigment dispersion (A-1) of 13.6 mass parts, 27.2 mass parts, 16.1 mass parts, make MW-30 (principal ingredient be N with chemical as Co., Ltd. three of the system M-402 (potpourris of dipentaerythritol acrylate and dipentaerythritol five acrylic ester) of Toagosei Co., Ltd of 5.5 mass parts of crosslinking chemical and 2.4 mass parts; N; N '; N '; N "; N "-six (methoxy) melamine; Weight average degree of polymerization 1.3), the 2-benzyl-2-dimethylamino-1-as Photoepolymerizationinitiater initiater (the 4-morpholino phenyl) butane-1-ketone (Ciba Specialty Chemicals corporate system, trade name IRGACURE369) of 2.2 mass parts and mix the coloured composition (CR1) of preparation solid component concentration 20 quality % as the propylene glycol methyl ether acetate of solvent.
On glass substrate, be coated with coloured composition (CR1) with spin coater after, carry out 10 minutes prebake conditions and form filming at 80 ℃ heating plates.Change the revolution of spin coater, carry out identical operations, formed different 3 of thickness and filmed.
Then, these substrates are cooled to room temperature after, use high-pressure sodium lamp, the unfavorable photomask of using, the radioactive ray of each wavelength that will comprise 365nm, 405nm and 436nm are with 2000J/m
2Exposure make public to respectively filming.Then, these substrates are pressed 1kgf/cm to develop
2The developer solution that the potassium hydroxide aqueous solution by 0.04 quality % that (nozzle diameter 1mm) ejection is 23 ℃ constitutes, thus the spray that carried out 90 seconds develops.Then, this substrate is cleaned with ultrapure water, the sector-style of going forward side by side is further carried out 30 minutes back baking after doing in 230 ℃ cleaning stove, uses cured film thereby form to estimate.
To 3 cured film that obtain, utilize color analyzer (big tomb electronics (strain) system MCPD2000), with illuminant-C, the 2 degree visuals field, measure chromaticity coordinate value in the CIE color specification system (x, y) and values (Y).In addition, the thickness with the cured film that obtains utilizes KLA-Tencor system Alpha-Step IQ to measure.According to measuring the result, obtain chromaticity coordinate value x, values (Y) and the thickness of chromaticity coordinate value y=0.080.Evaluation result is shown in table 1.The big more expression light transmission of values (Y) (brightness) is high more, and thickness thin list more shows that colouring power is high more.
The substrate that will be formed with cured film is with 2 deflecting plate clampings; (make the deflecting plate rotation of front face side in the time of wavelength coverage 380～780nm), utilize the maximal value and the minimum value of the light intensity of nitometer LS-100 (Minolta (strain) system) mensuration transmission from the back side illuminaton fluorescent light.And,, the value that maximal value gets divided by minimum value is spent as a comparison for each cured film.According to measuring the result, obtained the contrast of chromaticity coordinate value y=0.080.Evaluation result is shown in table 1.
Embodiment 2
With the resin glue as resin glue (B1) solution of the dye solution B of the dispersible pigment dispersion (A-1) of 15.5 mass parts, 24.3 mass parts, 16.1 mass parts, make MW-30 (principal ingredient be N with chemical as Co., Ltd. three of the system M-402 (potpourris of dipentaerythritol acrylate and dipentaerythritol five acrylic ester) of Toagosei Co., Ltd of 5.5 mass parts of crosslinking chemical and 2.4 mass parts; N; N '; N '; N "; N "-six (methoxy) melamine; Weight average degree of polymerization 1.3), the 2-benzyl-2-dimethylamino-1-as Photoepolymerizationinitiater initiater (the 4-morpholino phenyl) butane-1-ketone (Ciba Specialty Chemicals corporate system, trade name IRGACURE369) of 2.2 mass parts and mix the coloured composition (CR2) of preparation solid component concentration 20 quality % as the propylene glycol methyl ether acetate of solvent.
Except replacing showing signs of anger composition (CR1) the use coloured composition (CR2), carry out equally with embodiment 1, and estimate.Evaluation result is shown in table 1.
Embodiment 3
With the resin glue as resin glue (B1) solution of the dye solution C of the dispersible pigment dispersion (A-1) of 12.5 mass parts, 28.3 mass parts, 16.1 mass parts, make MW-30 (principal ingredient be N with chemical as Co., Ltd. three of the system M-402 (potpourris of dipentaerythritol acrylate and dipentaerythritol five acrylic ester) of Toagosei Co., Ltd of 5.5 mass parts of crosslinking chemical and 2.4 mass parts; N; N '; N '; N "; N "-six (methoxy) melamine; Weight average degree of polymerization 1.3), the 2-benzyl-2-dimethylamino-1-as Photoepolymerizationinitiater initiater (the 4-morpholino phenyl) butane-1-ketone (Ciba Specialty Chemicals corporate system, trade name IRGACURE369) of 2.2 mass parts and mix the coloured composition (CR3) of preparation solid component concentration 20 quality % as the propylene glycol methyl ether acetate of solvent.
Except replacing showing signs of anger composition (CR1) the use coloured composition (CR3), carry out equally with embodiment 1, and estimate.Evaluation result is shown in table 1.
Comparative example 1
With the resin glue as resin glue (B1) solution of the pigment solution (A-2) of the dispersible pigment dispersion (A-1) of 18.1 mass parts, 4.5 mass parts, 16.1 mass parts, as the 2-benzyl-2-dimethylamino-1-as Photoepolymerizationinitiater initiater (4-morpholino phenyl) butane-1-ketone (the Ciba Specialty Chemicals corporate system of Co., Ltd. three of the system M-402 of Toagosei Co., Ltd of 5.5 mass parts of crosslinking chemical and 2.4 mass parts and chemistry system MW-30,2.2 mass parts; Trade name IRGACURE369) and as the propylene glycol methyl ether acetate of solvent mix the coloured composition (CR4) of preparation solid component concentration 20 quality %.
Except replacing showing signs of anger composition (CR1) the use coloured composition (CR4), carry out equally with embodiment 1, and estimate.Evaluation result is shown in table 1.
Comparative example 2
With the resin glue as resin glue (B1) solution of the dye solution D of the dispersible pigment dispersion (A-1) of 18.1 mass parts, 24.2 mass parts, 16.1 mass parts, as the 2-benzyl-2-dimethylamino-1-as Photoepolymerizationinitiater initiater (4-morpholino phenyl) butane-1-ketone (the Ciba Specialty Chemicals corporate system of Co., Ltd. three of the system M-402 of Toagosei Co., Ltd of 5.5 mass parts of crosslinking chemical and 2.4 mass parts and chemistry system MW-30,2.2 mass parts; Trade name IRGACURE369) and as the propylene glycol methyl ether acetate of solvent mix the coloured composition (CR5) of preparation solid component concentration 20 quality %.
Except replacing showing signs of anger composition (CR1) the use coloured composition (CR5), carry out equally with embodiment 1, and estimate.Evaluation result is shown in table 1.
Embodiment 4
With the resin glue as resin glue (B1) solution of the dye solution E of the dispersible pigment dispersion (A-3) of 12.3 mass parts, 31.3 mass parts, 16.1 mass parts, as the 2-benzyl-2-dimethylamino-1-as Photoepolymerizationinitiater initiater (4-morpholino phenyl) butane-1-ketone (the Ciba Specialty Chemicals corporate system of Co., Ltd. three of the system M-402 of Toagosei Co., Ltd of 5.5 mass parts of crosslinking chemical and 2.4 mass parts and chemistry system MW-30,2.2 mass parts; Trade name IRGACURE369) and as the propylene glycol methyl ether acetate of solvent mix the coloured composition (CR6) of preparation solid component concentration 20 quality %.
Except replacing showing signs of anger composition (CR1) the use coloured composition (CR6), carry out equally with embodiment 1, and estimate.But, at this moment, obtained chromaticity coordinate value x, values (Y), thickness and the contrast of chromaticity coordinate value y=0.590.Evaluation result is shown in table 1.
Comparative example 3
With the resin glue as resin glue (B1) solution of the dispersible pigment dispersion (A-4) of the dispersible pigment dispersion (A-3) of 12.1 mass parts, 32.5 mass parts, 16.1 mass parts, as the 2-benzyl-2-dimethylamino-1-as Photoepolymerizationinitiater initiater (4-morpholino phenyl) butane-1-ketone (the Ciba Specialty Chemicals corporate system of Co., Ltd. three of the system M-402 of Toagosei Co., Ltd of 5.5 mass parts of crosslinking chemical and 2.4 mass parts and chemistry system MW-30,2.2 mass parts; Trade name IRGACURE369) and as the propylene glycol methyl ether acetate of solvent mix the coloured composition (CR7) of preparation solid component concentration 20 quality %.
Except replacing showing signs of anger composition (CR6) the use coloured composition (CR7), carry out equally with embodiment 4, and estimate.Evaluation result is shown in table 1.
Comparative example 4
With the resin glue as resin glue (B1) solution of the dye solution F of the dispersible pigment dispersion (A-3) of 12.1 mass parts, 30.2 mass parts, 16.1 mass parts, as the 2-benzyl-2-dimethylamino-1-as Photoepolymerizationinitiater initiater (4-morpholino phenyl) butane-1-ketone (the Ciba Specialty Chemicals corporate system of Co., Ltd. three of the system M-402 of Toagosei Co., Ltd of 5.5 mass parts of crosslinking chemical and 2.4 mass parts and chemistry system MW-30,2.2 mass parts; Trade name IRGACURE369) and as the propylene glycol methyl ether acetate of solvent mix the coloured composition (CR8) of preparation solid component concentration 20 quality %.
Except replacing showing signs of anger composition (CR6) the use coloured composition (CR8), carry out equally with embodiment 4, and estimate.Evaluation result is shown in table 1.
Embodiment 5
With the resin glue as resin glue (B1) solution of the dye solution G of the dispersible pigment dispersion (A-6) of the dispersible pigment dispersion (A-5) of 25.6 mass parts, 2.6 mass parts, 2.2 mass parts, 16.1 mass parts, 5.5 mass parts as the system M-402 (potpourris of dipentaerythritol acrylate and dipentaerythritol five acrylic ester) of Toagosei Co., Ltd of crosslinking chemical and the 2-benzyl-2-dimethylamino-1-as Photoepolymerizationinitiater initiater (4-morpholino phenyl) butane-1-ketone (the Ciba Specialty Chemicals corporate system of 2.2 mass parts; Trade name IRGACURE369), 0.2 mass parts is Dainippon Ink Chemicals system Megafac F-554 of surfactant and mixes the coloured composition (CR9) of preparation solid component concentration 20 quality % as the cyclohexanone of solvent as fluorine.
Except replacing showing signs of anger composition (CR1) the use coloured composition (CR9), carry out equally with embodiment 1, and estimate.But, at this moment, obtained chromaticity coordinate value y, values (Y), thickness and the contrast of chromaticity coordinate value x=0.655.Evaluation result is shown in table 1.
Embodiment 6
With the resin glue as resin glue (B1) solution of the dye solution H of the dispersible pigment dispersion (A-6) of the dispersible pigment dispersion (A-5) of 23.6 mass parts, 2.6 mass parts, 3.2 mass parts, 16.1 mass parts, 5.5 mass parts as the system M-402 (potpourris of dipentaerythritol acrylate and dipentaerythritol five acrylic ester) of Toagosei Co., Ltd of crosslinking chemical and the 2-benzyl-2-dimethylamino-1-as Photoepolymerizationinitiater initiater (4-morpholino phenyl) butane-1-ketone (the Ciba Specialty Chemicals corporate system of 2.2 mass parts; Trade name IRGACURE369), 0.2 mass parts is Dainippon Ink Chemicals system Megafac F-554 of surfactant and mixes the coloured composition (CR10) of preparation solid component concentration 20 quality % as the cyclohexanone of solvent as fluorine.
Except replacing showing signs of anger composition (CR9) the use coloured composition (CR10), carry out equally with embodiment 5, and estimate.Evaluation result is shown in table 1.
Embodiment 7
With the resin glue as resin glue (B1) solution of the dye solution I of the dispersible pigment dispersion (A-6) of the dispersible pigment dispersion (A-5) of 22.3 mass parts, 1.6 mass parts, 1.2 mass parts, 16.1 mass parts, 5.5 mass parts as the system M-402 (potpourris of dipentaerythritol acrylate and dipentaerythritol five acrylic ester) of Toagosei Co., Ltd of crosslinking chemical and the 2-benzyl-2-dimethylamino-1-as Photoepolymerizationinitiater initiater (4-morpholino phenyl) butane-1-ketone (the Ciba Specialty Chemicals corporate system of 2.2 mass parts; Trade name IRGACURE369), 0.2 mass parts is Dainippon Ink Chemicals system Megafac F-554 of surfactant and mixes the coloured composition (CR11) of preparation solid component concentration 20 quality % as the cyclohexanone of solvent as fluorine.
Except replacing showing signs of anger composition (CR9) the use coloured composition (CR11), carry out equally with embodiment 5, and estimate.Evaluation result is shown in table 1.
Embodiment 8
With the resin glue as resin glue (B1) solution of the dye solution J of the dispersible pigment dispersion (A-6) of the dispersible pigment dispersion (A-5) of 24.3 mass parts, 2.6 mass parts, 1.3 mass parts, 16.1 mass parts, 5.5 mass parts as the system M-402 (potpourris of dipentaerythritol acrylate and dipentaerythritol five acrylic ester) of Toagosei Co., Ltd of crosslinking chemical and the 2-benzyl-2-dimethylamino-1-as Photoepolymerizationinitiater initiater (4-morpholino phenyl) butane-1-ketone (the Ciba Specialty Chemicals corporate system of 2.2 mass parts; Trade name IRGACURE369), 0.2 mass parts is Dainippon Ink Chemicals system Megafac F-554 of surfactant and mixes the coloured composition (CR12) of preparation solid component concentration 20 quality % as the cyclohexanone of solvent as fluorine.
Except replacing showing signs of anger composition (CR9) the use coloured composition (CR12), carry out equally with embodiment 5, and estimate.Evaluation result is shown in table 1.
Embodiment 9
With the resin glue as resin glue (B1) solution of the dye solution K of the dispersible pigment dispersion (A-6) of the dispersible pigment dispersion (A-5) of 22.6 mass parts, 5.6 mass parts, 3.2 mass parts, 16.1 mass parts, 5.5 mass parts as the system M-402 (potpourris of dipentaerythritol acrylate and dipentaerythritol five acrylic ester) of Toagosei Co., Ltd of crosslinking chemical and the 2-benzyl-2-dimethylamino-1-as Photoepolymerizationinitiater initiater (4-morpholino phenyl) butane-1-ketone (the Ciba Specialty Chemicals corporate system of 2.2 mass parts; Trade name 1RGACURE369), 0.2 mass parts is Dainippon Ink Chemicals system Megafac F-554 of surfactant and mixes the coloured composition (CR13) of preparation solid component concentration 20 quality % as the cyclohexanone of solvent as fluorine.
Except replacing showing signs of anger composition (CR9) the use coloured composition (CR13), carry out equally with embodiment 5, and estimate.Evaluation result is shown in table 1.
Embodiment 10
With the resin glue as resin glue (B1) solution of the dye solution L of the dispersible pigment dispersion (A-6) of the dispersible pigment dispersion (A-5) of 24.2 mass parts, 4.6 mass parts, 2.2 mass parts, 16.1 mass parts, 5.5 mass parts as the system M-402 (potpourris of dipentaerythritol acrylate and dipentaerythritol five acrylic ester) of Toagosei Co., Ltd of crosslinking chemical and the 2-benzyl-2-dimethylamino-1-as Photoepolymerizationinitiater initiater (4-morpholino phenyl) butane-1-ketone (the Ciba Specialty Chemicals corporate system of 2.2 mass parts; Trade name IRGACURE369), 0.2 mass parts is Dainippon Ink Chemicals system Megafac F-554 of surfactant and mixes the coloured composition (CR14) of preparation solid component concentration 20 quality % as the cyclohexanone of solvent as fluorine.
Except replacing showing signs of anger composition (CR9) the use coloured composition (CR14), carry out equally with embodiment 5, and estimate.Evaluation result is shown in table 1.
Comparative example 5
With the resin glue as resin glue (B1) solution of the dispersible pigment dispersion (A-6) of the dispersible pigment dispersion (A-5) of 22.1 mass parts, 4.5 mass parts, 16.1 mass parts, as the 2-benzyl-2-dimethylamino-1-as Photoepolymerizationinitiater initiater (4-morpholino phenyl) butane-1-ketone (the Ciba Specialty Chemicals corporate system of Co., Ltd. three of the system M-402 of Toagosei Co., Ltd of 5.5 mass parts of crosslinking chemical and 2.4 mass parts and chemistry system MW-30,2.2 mass parts; Trade name IRGACURE369), 0.2 mass parts is Dainippon Ink Chemicals system Megafac F-554 of surfactant and mixes the coloured composition (CR15) of preparation solid component concentration 20 quality % as the propylene glycol methyl ether acetate of solvent as fluorine.
Except replacing showing signs of anger composition (CR9) the use coloured composition (CR15), carry out equally with embodiment 5, and estimate.Evaluation result is shown in table 1.
Comparative example 6
With the resin glue as resin glue (B1) solution of the dye solution M of the dispersible pigment dispersion (A-6) of the dispersible pigment dispersion (A-5) of 24.1 mass parts, 4.6 mass parts, 2.2 mass parts, 16.1 mass parts, as the 2-benzyl-2-dimethylamino-1-as Photoepolymerizationinitiater initiater (4-morpholino phenyl) butane-1-ketone (the Ciba Specialty Chemicals corporate system of Co., Ltd. three of the system M-402 of Toagosei Co., Ltd of 5.5 mass parts of crosslinking chemical and 2.4 mass parts and chemistry system MW-30,2.2 mass parts; Trade name IRGACURE369), 0.2 mass parts is Dainippon Ink Chemicals system Megafac F-554 of surfactant and mixes the coloured composition (CR16) of preparation solid component concentration 20 quality % as the cyclohexanone of solvent as fluorine.
Except replacing showing signs of anger composition (CR9) the use coloured composition (CR16), carry out equally with embodiment 5, and estimate.Evaluation result is shown in table 1.
Table 1
[table 1]
In table 1, " B15:6 " expression C.I. pigment blue 15: 6, " G58 " expression C.I. naphthol green 58, " V-23 " expression C.I. pigment Violet 23, " BB-7 " expression C.I. Blue 7, " Y150 " expression C.I. pigment yellow 150, " BY-21 " expression C.I. basic yellow 21, " R254 " expression C.I. paratonere 254, " R177 " expression C.I. paratonere 177, " BR1 " expression C.I. alkali red 1:1.
Claims (8)
1. a coloured composition is characterized in that, is to contain (A) colorant, (B) resin glue and (C) coloured composition of crosslinking chemical, and the colorant that contains following formula (1) expression is as said (A) colorant,
X
+Z
- (1)
In the formula (1), X
+Expression cationic chromophore, Z
-Expression has the organic acid conjugate base of halo alkyl.
2. coloured composition according to claim 1, wherein, said Z
-Be the negative ion of following formula (1a) expression or the negative ion of following formula (1b) expression,
R
1-SO
3 - (1a)
In the formula (1a), R
1Expression can have the halo alkyl of linking group, and said linking group contains carbon atom, hydrogen atom and the atom except halogen atom,
R
2-SO
2-N
--SO
2-R
2 (1b)
In the formula (1b), R
2Expression independently of each other can have the halo alkyl of linking group, and said linking group contains carbon atom, hydrogen atom and the atom except halogen atom, R
2Bonding and form ring each other.
3. coloured composition according to claim 1 and 2, wherein, said halo alkyl is the fluoro alkyl.
4. coloured composition according to claim 2, wherein, said R
1And R
2Be group, or the group of following formula (1-2) expression of following formula (1-1) expression,
In the formula (1-1), R
19Expression hydrogen atom, fluorine atom, alkyl, fluoro-alkyl, ester ring type alkyl, alkoxy, fluoroalkyl, R
20COOR
21-or R
20COOR
21CFH-, R
20Expression alkyl, ester ring type alkyl, heteroaryl, or replace or non-substituted aryl R
21Expression methylene or alkylidene, n representes the integer more than 1, * representes binding site,
In the formula (1-2), R
14～R
18Represent hydrogen atom, fluorine atom, hydroxyl, alkyl, fluoro-alkyl, alkoxy or alkyl sulphonyl independently of each other, * representes binding site, wherein, and R
14～R
18In at least one be fluorine atom or fluoro-alkyl.
5. coloured composition according to claim 1 and 2, wherein, said X
+Be that triarylmethane is that chromophore, methine are that chromophore, azo are that chromophore, diarylmethanes are that chromophore, quinone imines are that chromophore, anthraquinone chromophores or xanthene are chromophore.
6. coloured composition according to claim 1 and 2 wherein, further contains (D) Photoepolymerizationinitiater initiater.
7. a color filter is characterized in that, possesses to use the dyed layer that each described coloured composition forms in the claim 1～6.
8. a display element is characterized in that, possesses the described color filter of claim 7.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2010171749 | 2010-07-30 | ||
| JP2010-171749 | 2010-07-30 | ||
| JP2010239590 | 2010-10-26 | ||
| JP2010-239590 | 2010-10-26 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102346370A true CN102346370A (en) | 2012-02-08 |
| CN102346370B CN102346370B (en) | 2016-12-14 |
Family
ID=
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| JP2013140348A (en) * | 2011-12-09 | 2013-07-18 | Sumitomo Chemical Co Ltd | Red colored curable resin composition |
| CN104007615A (en) * | 2013-02-26 | 2014-08-27 | Jsr株式会社 | Coloring composition, coloring immobilizing membrane and display element |
| CN105246978A (en) * | 2013-06-05 | 2016-01-13 | Jsr株式会社 | Colored composition, colored cured film, and display element |
| CN105358628A (en) * | 2013-09-06 | 2016-02-24 | 富士胶片株式会社 | Colored composition, cured film, color filter, color-filter manufacturing method, solid-state imaging element, image display device, polymer, and xanthene dye |
| CN105573055A (en) * | 2014-10-30 | 2016-05-11 | 住友化学株式会社 | Colored curable resin composition |
| CN105826393A (en) * | 2015-01-06 | 2016-08-03 | 昆山国显光电有限公司 | Thin-film transistor and manufacturing method thereof |
| CN108699365A (en) * | 2016-03-09 | 2018-10-23 | Jsr株式会社 | Ink, printing process, printed article and ink agent used for textiles |
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| JP2013140348A (en) * | 2011-12-09 | 2013-07-18 | Sumitomo Chemical Co Ltd | Red colored curable resin composition |
| CN104007615A (en) * | 2013-02-26 | 2014-08-27 | Jsr株式会社 | Coloring composition, coloring immobilizing membrane and display element |
| CN104007615B (en) * | 2013-02-26 | 2020-03-13 | Jsr株式会社 | Coloring composition, colored cured film, and display element |
| CN105246978A (en) * | 2013-06-05 | 2016-01-13 | Jsr株式会社 | Colored composition, colored cured film, and display element |
| CN105246978B (en) * | 2013-06-05 | 2017-09-26 | Jsr株式会社 | Coloured composition, staining and curing film and display element |
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| CN105573055A (en) * | 2014-10-30 | 2016-05-11 | 住友化学株式会社 | Colored curable resin composition |
| CN105573055B (en) * | 2014-10-30 | 2020-11-17 | 住友化学株式会社 | Colored curable resin composition |
| CN105826393A (en) * | 2015-01-06 | 2016-08-03 | 昆山国显光电有限公司 | Thin-film transistor and manufacturing method thereof |
| CN105826393B (en) * | 2015-01-06 | 2019-03-26 | 昆山国显光电有限公司 | Thin film transistor and its manufacturing method |
| CN108699365A (en) * | 2016-03-09 | 2018-10-23 | Jsr株式会社 | Ink, printing process, printed article and ink agent used for textiles |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2012108469A (en) | 2012-06-07 |
| KR101921752B1 (en) | 2018-11-23 |
| JP5772263B2 (en) | 2015-09-02 |
| JP2012107192A (en) | 2012-06-07 |
| KR20120012393A (en) | 2012-02-09 |
| JP5919657B2 (en) | 2016-05-18 |
| TW201539133A (en) | 2015-10-16 |
| TWI509358B (en) | 2015-11-21 |
| TW201214045A (en) | 2012-04-01 |
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