CN104880910A - Coloring composition, coloring cured film and display device - Google Patents
Coloring composition, coloring cured film and display device Download PDFInfo
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- CN104880910A CN104880910A CN201510088646.4A CN201510088646A CN104880910A CN 104880910 A CN104880910 A CN 104880910A CN 201510088646 A CN201510088646 A CN 201510088646A CN 104880910 A CN104880910 A CN 104880910A
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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
- G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
- G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
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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
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Abstract
The invention discloses a coloring composition, a coloring cured film and a display device. The invention aims at providing a coloring composition which is suitable for forming a coloring cured film having excellent heat resistance and high contrast ratio. The coloring composition herein is a coloring composition containing a (A) coloring agent and a (B) polymer compound, wherein the coloring agent has a portion which generates fluorescence and a polymer which absorbs the fluorescence.
Description
Technical field
The present invention relates to coloured composition, color solidification film and display element, more specifically, the coloured composition that the formation relating to the color solidification film used in the color liquid crystal display device of transmission-type or reflection-type, solid-state imager, organic EL display element, Electronic Paper etc. uses, use the color solidification film that this coloured composition is formed, and possess the display element of this color solidification film.
Background technology
When using colored radiation-sensitive composition to manufacture color filter, known following method, namely, on substrate coating pigment decentralized colored radiation-sensitive composition and after drying, irradiate (following to dry coating pattern form desirably, be called " exposure ") radioactive ray developing, obtain the method (for example, referring to patent documentation 1 ~ 2) of each color pixel thus.In addition, the optical polymerism composition that known utilization is dispersed with carbon black forms the method (for example, referring to patent documentation 3) of black matrix.In addition, the also colored resin composition of known use pigment-dispersing type, utilizes ink-jetting style to obtain the method (for example, referring to patent documentation 4) of each color pixel.
In recent years, the high-contrast of active demand liquid crystal display cells, the high-precision refinement of solid-state imager, in order to realize these demands, have studied the technology using dyestuff as colorant.But, in general, with use pigment as colorant situation compared with, use dyestuff when, often there is problem in thermotolerances etc.Under such background, as the coloured composition that can form the excellent colored pattern such as thermotolerance, such as, propose in patent documentation 5 containing the coloured composition of pigment polymer as colorant.
Prior art document
Patent documentation
Patent documentation 1: Japanese Unexamined Patent Publication 2-144502 publication
Patent documentation 2: Japanese Unexamined Patent Publication 3-53201 publication
Patent documentation 3: Japanese Unexamined Patent Publication 6-35188 publication
Patent documentation 4: Japanese Unexamined Patent Publication 2000-310706 publication
Patent documentation 5: Japanese Unexamined Patent Publication 2013-28764 publication
Summary of the invention
But judge the colored pattern using the coloured composition as recorded in patent documentation 5 to be formed according to the research of the present inventor etc., contrast is extremely low, is not suitable for the middle each color pixels used such as color filter.
Therefore, problem of the present invention is to provide and is suitable for excellent heat resistance and the coloured composition of the formation of the color solidification film of high-contrast.In addition, problem of the present invention is to provide the color solidification film using this coloured composition to be formed and the display element possessing it.
The present inventor etc., through further investigation, found that by using the polymkeric substance at the position having and produce fluorescence and the position absorbing this fluorescence as colorant, can solve above-mentioned problem.
Namely, the invention provides a kind of coloured composition, wherein, containing (A) colorant and (B) polymerizable compound, (A) colorant contains the polymkeric substance (hereinafter referred to as " polymkeric substance (A1) ") at the position having and produce fluorescence and the position absorbing this fluorescence.
In addition, the invention provides a kind of coloured composition, wherein, containing (A) colorant and (B) polymerizable compound, (A) colorant contains polymkeric substance, and this polymkeric substance has at least 1 chromophore be selected from xanthene chromophore and cyanine chromophore and at least 1 chromophore be selected from triarylmethane chromophore and anthraquinone chromophores.
In addition, the invention provides the color solidification film using above-mentioned coloured composition to be formed and the display element possessing this color solidification film.Here, " color solidification film " refers in display element, solid-state imager each color pixel used, black matrix, black separator etc.
If use coloured composition of the present invention, then excellent heat resistance can be formed and the color solidification film of high-contrast.
Therefore, coloured composition of the present invention can extremely be applicable to make the display elements such as color liquid crystal display device, organic EL display element, Electronic Paper, the solid-state imagers such as cmos image sensor.
Embodiment
Below, the present invention is described in detail.
Coloured composition
Below, the constituent of coloured composition of the present invention is described in detail.
-(A) colorant-
Coloured composition of the present invention contains polymkeric substance (A1) as colorant.
As polymkeric substance (A1) as long as have the position producing fluorescence and the position absorbing this fluorescence, just be not particularly limited, preferably (following containing the ethylenically unsaturated monomers with the position producing fluorescence, be called " unsaturated monomer (a1) ") with the multipolymer of ethylenically unsaturated monomers (hereinafter referred to as " unsaturated monomer (a2) ") with the position absorbing this fluorescence.Here, the multipolymer containing unsaturated monomer (a1) and unsaturated monomer (a2) refers to have unsaturated monomer (a1) and unsaturated monomer (a2) polymkeric substance as structural unit.
As the position producing fluorescence, such as, xanthene chromophore, cyanine chromophore can be enumerated.In addition, as the position absorbing fluorescence, such as, triarylmethane chromophore, anthraquinone chromophores can be enumerated.
As unsaturated monomer (a1), such as, the compound represented by following formula (1-1) can be enumerated.In addition, as unsaturated monomer (a2), such as, the compound represented by following formula (1-2) can be enumerated.
(in formula (1-1),
R
1represent hydrogen atom or methyl independently of each other.
X
1the divalent group representing Direct Bonding, substituted or non-substituted divalent alkyl independently of each other or this divalent alkyl and the linking group of more than 1 containing the atom beyond carbon atom and hydrogen atom are combined.
P represents the position producing fluorescence.
G represents the integer of more than 1.)
(in formula (1-2),
R
2represent hydrogen atom or methyl.
X
2the divalent group representing Direct Bonding, substituted or non-substituted divalent alkyl or this divalent alkyl and the linking group of more than 1 containing the atom beyond carbon atom and hydrogen atom are combined.
Q represents the position absorbing fluorescence.
H represents the integer of more than 1.)
R
1and R
2can suitably select hydrogen atom or methyl.
As X
1and X
2divalent alkyl, such as, divalent aliphatic alkyl, divalent ester ring type alkyl, divalent aromatic hydrocarbyl can be enumerated.Should illustrate, in this instructions, " ester ring type alkyl " refers to the concept not comprising the aliphatic alkyl without ring texture.Divalent aliphatic alkyl can be the arbitrary form in straight chain and side chain, and in addition, divalent aliphatic alkyl and divalent ester ring type alkyl can be saturated hydrocarbyls, also can be unsaturated alkyls.In addition, in this instructions, " ester ring type alkyl ", " aromatic hydrocarbyl " refer to the group not only comprising and be only made up of ring structure, also comprise the concept this ring structure replacing further and has the group of divalent aliphatic alkyl, in this structure, at least comprise ester ring type hydrocarbon or aromatic hydrocarbon.
As divalent aliphatic alkyl, such as, can enumerate alkane 2 basis, olefin 2 base, its carbon number is preferably 1 ~ 20, is more preferably 2 ~ 12, and more preferably 2 ~ 6.As concrete example, such as, methylene can be enumerated, ethane-1, 1-bis-base, ethane-1, 2-bis-base, propane-1, 1-bis-base, propane-1, 2-bis-base, propane-1, 3-bis-base, propane-2, 2-bis-base, butane-1, 2-bis-base, butane-1, 3-bis-base, butane-1, 4-bis-base, pentane-1, 4-bis-base, pentane-1, 5-bis-base, hexane-1, 5-bis-base, hexane-1, 6-bis-base, 2-methylpropane-1, 2-bis-base, 2, 2-dimethylpropane-1, 3-bis-base, ethene-1, 1-bis-base, ethene-1, 2-bis-base, propylene-1, 2-bis-base, propylene-1, 3-bis-base, propylene-2, 3-bis-base, 1-butene-1, 2-bis-base, 1-butene-1, 3-bis-base, 1-butene-1, 4-bis-base, 2-amylene-1, 5-bis-base, 3-hexene-1, 6-bis-base etc.
As divalent ester ring type alkyl, such as, can enumerate cycloalkylidene, sub-cycloalkenyl group, its carbon number is preferably 3 ~ 20, and more preferably 3 ~ 12.As concrete example, such as, the monocyclic hydrocarbon cyclic bases such as cyclopropylidene, sub-cyclobutyl, cyclopentylene, cyclohexylidene, sub-cyclobutane base, cyclopentenylidene, cyclohexadienylidene can be enumerated, 1, the sub-norbornies such as the sub-norborny of 4-, 2,5-sub-norbornies, 1, the bridged cyclic hydrocarbon groups etc. such as the sub-adamantyl of 5-, 2,6-sub-adamantyls.
As divalent aromatic hydrocarbyl, such as, arlydene can be enumerated, the arlydene of monocycle to 3 ring of preferred carbon number 6 ~ 14.As concrete example, such as, phenylene, biphenylene, naphthylene, phenanthryl, anthrylene etc. can be enumerated.
In addition, for divalent group divalent alkyl and the linking group of more than 1 containing the atom beyond carbon atom and hydrogen atom combined, as linking group, such as ,-O-,-S-,-SO can be enumerated
2-,-CO-,-COO-,-OCO-,-CONR
3-(R
3represent the alkyl of hydrogen atom or carbon number 1 ~ 6) ,-NR
3-(R
3identical with above-mentioned implication), can have a kind or two or more.The bonding position of linking group is arbitrary, such as, can have between the end of divalent alkyl or C-C key, wherein, preferably have between an end or C-C key.Instructions walks to the total carbon atom number of the part of said carbon number meaning except forming the carbon atom of this linking group in the 5th page of the 12nd row for the 4th page the 23rd.
As the concrete example of divalent alkyl between C-C key with above-mentioned linking group, such as ,-CH can be enumerated
2-CH
2-CH
2-COO-CH
2-CH
2-,-CH
2-CH (-CH
3)-CH
2-COO-CH
2-CH
2-,-CH
2-CH
2-CH
2-OCO-CH
2-CH
2-,-CH
2-CH
2-CH
2-CH
2-COO-CH
2-CH (CH
2-CH
3)-CH
2-CH
2-CH
2-CH
2-,-CH
2-CH
2-CH
2-O-CH
2-CH (CH
2-CH
3)-CH
2-CH
2-CH
2-CH
2-,-(CH
2)
5-COO-(CH
2)
11-CH
2-,-CH
2-CH
2-CH
2-C-(COO-CH
2-CH
3)
2-,-CH
2-CH
2-O-CH
2-CH
2-,-CH
2-CH
2-CH
2-O-CH
2-CH
2-,-(CH
2-CH
2-O)
n-CH
2-(n is the integer of 1 ~ 8) ,-(CH
2-CH
2-CH
2-O)
m-CH
2-(m is the integer of 1 ~ 5) ,-CH
2-CH (CH
3)-O-CH
2-CH
2-,-CH
2-CH-(OCH
3)-,-CH
2-CH
2-COO-CH
2-CH
2-O-CH
2-CH (CH
2-CH
3)-CH
2-CH
2-CH
2-CH
2-,-CH
2-CH
2-CH
2-O-CO-CH
2-CH (CH
2-CH
3)-CH
2-CH
2-CH
2-CH
2-,-CH
2-CH
2-COO-CH
2-CH
2-O-CH
2-CH
2-O-CH
2-CH (CH
2-CH
3)-CH
2-CH
2-CH
2-CH
2-,-CH
2-CH
2-NH-COO-CH
2-CH
2-,-CH
2-CH
2-OCO-CH
2-etc., but be not limited to these.
In addition, as there is divalent alkyl and above-mentioned linking group bonding and the concrete example of the group of the ring structure formed, such as, following group can be enumerated, but being not limited to these.
As the substituting group with divalent alkyl, halogen atom, nitro, hydroxyl, substituted or non-substituted alkoxy, substituted or non-substituted aryloxy group etc. can be enumerated.As halogen atom, fluorine atom, chlorine atom, bromine atoms, atomic iodine can be enumerated.Alkoxy can be the arbitrary form in straight chain and side chain, carbon number preferably 1 ~ 6.As concrete example, such as, methoxyl, ethoxy, propoxyl group, butoxy etc. can be enumerated.As aryloxy group, the aryloxy group of preferred carbon number 6 ~ 14, such as, can enumerate phenoxy group, benzyloxy etc.In addition, as the substituting group of alkoxy and aryloxy group, halogen atom, nitro, hydroxyl, amino, carboxyl, sulfanyl etc. can be enumerated.In addition, when divalent alkyl is divalent aromatic hydrocarbyl, can be substituted or non-substituted alkyl, substituted or non-substituted thiazolinyl replace.The carbon number of alkyl and thiazolinyl preferably 1 ~ 6, as the concrete example of alkyl, such as, methyl, ethyl, propyl group, isopropyl, butyl, isobutyl, sec-butyl, the tert-butyl group, hexyl etc. can be enumerated, in addition, as the concrete example of thiazolinyl, such as, vinyl, 1-propenyl, 1-butenyl group, 1-pentenyl, 1-hexenyl, 2-ethyl-2-butenyl group etc. can be enumerated.Should illustrate, as the substituting group of alkyl and thiazolinyl, the substituting group identical with the substituting group of above-mentioned divalent alkyl can be enumerated.
As P, as long as from the group of compound producing fluorescence, be just not particularly limited, but preferably xanthene chromophore or cyanine chromophore.Preferably there is as the compound represented by above-mentioned formula (1-1) at least 1 the chromophoric ethylenically unsaturated monomers be selected from xanthene chromophore and cyanine chromophore.Should illustrate, xanthene chromophore or cyanine chromophore are the residues losing g hydrogen atom from xanthene compound or cyanine compound and obtain, be can with g X of above-mentioned formula (1-1)
1the residue connected.
As Q, as long as carry out the group of the compound of self-absorption fluorescence, be just not particularly limited, but preferred triarylmethane chromophore or anthraquinone chromophores.As the compound represented by above-mentioned formula (1-2), preferably there is at least 1 the chromophoric ethylenically unsaturated monomers be selected from triarylmethane chromophore and anthraquinone chromophores.Should illustrate, triarylmethane chromophore or anthraquinone chromophores are the residues losing h hydrogen atom from triaryl methane compounds or anthraquinone compounds and obtain, be can with h X of above-mentioned formula (1-2)
2the residue connected.
G and h represents the integer of more than 1 independently of each other, preferably 1 or 2.
As xanthene compound, cyanine compound, triaryl methane compounds, anthraquinone compounds, color index (C.I. can be enumerated; The Society of Dyers and Colourists corporation issues) in be classified as the dyestuff of dyestuff (Dye).As these dyestuffs, any one in acid dyes, direct dyes, basic-dyeable fibre, salt forming dye, oil-soluble dyes, disperse dyes, reactive dye, mordant dye, reducing dye, sulfur dye etc. can be used, from the viewpoint of can easily excellent, the compound that represented by above-mentioned formula (1-1) of generation of reactive, the compound that represented by above-mentioned formula (1-2), preferably use acid dyes, oil-soluble dyes, basic-dyeable fibre.
As acid dyes, being the dyestuff being classified as C.I. acidity in color index, as direct dyes, is be classified as the direct dyestuff of C.I. in color index.As oil-soluble dyes, being the dyestuff being classified as C.I. solvent in color index, as basic-dyeable fibre, is the dyestuff being classified as C.I. alkalescence in color index.
Below, xanthene compound, cyanine compound, triaryl methane compounds, anthraquinone compounds are described.
As xanthene compound, preferably there is the compound of the structure represented by following formula (2), as concrete example, such as, the xanthene system basic-dyeable fibres such as C.I. alkaline purple 10 (rhodamine B) can be enumerated.
(in formula (2),
R
11, R
12, R
13and R
14represent hydrogen atom, substituted or non-substituted alkyl, the group between the C-C key of this alkyl with the linking group of the atom beyond containing carbon atom and hydrogen atom or substituted or non-substituted heterocyclic group independently of each other.
R
15and R
16represent hydrogen atom or substituted or non-substituted alkyl independently of each other.
R
17expression-SO
3 -,-SO
3h ,-SO
3m ,-SO
3r
18,-CO
2 -,-CO
2h ,-CO
2m ,-CO
2r
19,-SO
2nHR
20or-SO
2nR
21r
22.
R represents the integer of 0 ~ 5, when r is the integer of more than 2, and multiple R
17can be identical, also can be different.
R
18, R
19and R
20represent substituted or non-substituted alkyl independently of each other or there is the group of linking group of the atom beyond containing carbon atom and hydrogen atom between the C-C key of this alkyl.
R
21and R
22represent substituted or non-substituted alkyl independently of each other or there is the group of linking group or the R of the atom beyond containing carbon atom and hydrogen atom between the C-C key of this alkyl
21with R
22mutual bonding and the substituted or non-substituted heterocyclic group formed.
M represents sodium atom or potassium atom.〕
As R
11~ R
16and R
18~ R
22in alkyl, such as, aliphatic alkyl, ester ring type alkyl, aromatic hydrocarbyl can be enumerated.
Aliphatic alkyl can be saturated also can be undersaturated, such as, can enumerate alkyl, thiazolinyl, alkynyl.The carbon number of aliphatic alkyl preferably 1 ~ 30, more preferably 1 ~ 15, particularly preferably 1 ~ 8.In addition, aliphatic alkyl can be straight-chain also can be branched.As alkyl, such as, except above-mentioned concrete example, heptyl, octyl group, nonyl, decyl, undecyl, 1-methyldecyl, dodecyl, 1-methylundecyl, 1-ethyl decyl, tridecyl, myristyl, tertiary dodecyl, pentadecyl, 1-heptyl octyl group, cetyl, octadecyl etc. can be enumerated.Such as, as thiazolinyl, except above-mentioned concrete example, 2-octenyl, (4-vinyl)-5-hexenyl, 2-decene base etc. can be enumerated.In addition, as alkynyl, such as, ethinyl, 1-propinyl, 1-butynyl, 1-pentynyl, 3-pentynyl, 1-hexin base, 2-ethyl-2-butynyl, 2-octyne base, (4-ethinyl)-5-hexin base, 2-decynyl etc. can be enumerated.
As ester ring type alkyl, the ester ring type alkyl of preferred carbon number 3 ~ 30.Ester ring type alkyl can be saturated also can be undersaturated, such as, can enumerate naphthenic base, cycloalkenyl group, fused polycycle alkyl, bridged cyclic hydrocarbon group, volution alkyl, ring-type terpene alkyl etc.More specifically, the naphthenic base such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, tert-butylcyclohexyl, suberyl, ring octyl group can be enumerated; The cycloalkenyl groups such as 1-cyclohexenyl group;
The fused polycycle alkyl such as three ring decyls, decahydro-2-naphthyl, adamantyl; Three ring [5.2.1.0
2,6] bridged cyclic hydrocarbon group such as decane-8-base, pentacyclopentadecandimethanol base, isobornyl, dicyclopentenyl, three cyclopentenyls; From volution alkyl such as the 1 valency groups that volution [3,4] heptane, volution [3,4] octane lose 1 hydrogen atom and obtain; From right
the ring-type terpene alkyl etc. such as the 1 valency group that Wan, thujane, carane etc. lose 1 hydrogen atom and obtain.In above-mentioned naphthenic base and cycloalkenyl group, more preferably carbon number is 3 ~ 12.
As aromatic hydrocarbyl, the aryl of preferred carbon number 6 ~ 20, the more preferably aryl of carbon number 6 ~ 10.Here, " aryl " refers to monocycle ~ 3 ring type aromatic hydrocarbyl, such as, can enumerate phenyl, naphthyl, anthryl, phenanthryl, Azulene base, 9-fluorenyl etc., wherein, and preferred phenyl, naphthyl.
In addition, R
11, R
12, R
13, R
14, R
18, R
19, R
20, R
21and R
22in alkyl can have the linking group of the atom beyond containing carbon atom and hydrogen atom between C-C key, when there is linking group, preferably there is between the C-C key of aliphatic alkyl the group of above-mentioned linking group.As the concrete example of linking group, group same as described above can be enumerated.
Heterocyclic group can be monocyclic type heteroaromatic, also can be polycyclic heterocycle.Heterocyclic group can be unsaturated ring, also can be saturated rings, in addition, can have the heteroatoms (such as, nitrogen-atoms, oxygen atom, sulphur atom) of identical type or different types of more than 2 in ring.As heterocyclic group, the heterocyclic group of preferred carbon number 3 ~ 10, such as, pyrrolidinyl can be enumerated, imidazolidinyl, pyrazolidinyl, morpholinyl, thio-morpholinyl (テ オ モ Le ホ リ ニ Le base), piperidyl, piperidino, piperazinyl, the nitrogenous ester ring type heterocyclic groups such as homopiperazine base (ホ モ ピ レ ラ ジ ニ Le base), 1, other ester ring type heterocyclic groups such as 3-dioxolanes-2-base, pyridine radicals, pyrazinyl, pyrimidine radicals, pyridazinyl, quinolyl, isoquinolyl, phthalazinyl, phthalazinyl, quinoxalinyl, imidazole radicals, pyrazolyl, triazolyl, tetrazole radical, thiazolyl, benzothiazolyl,
other aromatic heterocyclic groups such as the nitrogenous aromatic heterocyclic group such as azoles base, indyl, indazolyl, benzimidazolyl, phthalimide-based, thienyl, furyl, pyranose, purine radicals.
As R
21and R
22mutual bonding and the heterocyclic group formed, can enumerate the group identical with above-mentioned heterocyclic group.
As R
11~ R
16and R
18~ R
22in the substituting group of alkyl, halogen atom, hydroxyl, cyano group, formoxyl, carboxyl, nitro, amino, two (C can be enumerated
1-8alkyl) amino, ammonia diaryl base, C
1-8alkoxy, C
6-10aryloxy group, C
2-8alkoxy carbonyl, C
1-8alkyl sulfenyl, C
6-10artyl sulfo, three (C
1-8alkyl) silicyl, sulfydryl, allyl, C
1-8alkyl sulphonyl, C
1-8alkylsulfamoyl group, heterocyclic group, aromatic hydrocarbyl etc., ester ring type alkyl, heterocyclic group and aromatic hydrocarbyl can be replaced by aliphatic alkyl.These substituting groups can have substituting group further.Should illustrate, substituent position and number are arbitrary, and when having the substituting group of more than 2, this substituting group can be the same or different.Should illustrate, as R
11~ R
14the substituting group of heterocyclic group and R
21with R
22mutual bonding and the substituting group of the heterocyclic group formed, can enumerate and R
11~ R
16and R
18~ R
22in the identical group of the substituting group of alkyl.
Wherein, as R
11, R
12, R
13and R
14, the alkyl of preferred hydrogen atom, carbon number 1 ~ 8 or the aryl of carbon number 6 ~ 10.
As R
15and R
16, the alkyl of preferred hydrogen atom or carbon number 1 ~ 8.
As R
17, preferably-SO
3h ,-SO
3r
18,-CO
2h ,-CO
2r
19,-SO
2nHR
20or-SO
2nR
21r
22, in addition, as R
18, R
19, R
20, R
21and R
22, the alkyl of preferred carbon number 1 ~ 8.
R preferably 1 or 2.
As the concrete example of xanthene compound with the structure represented by above-mentioned formula (2), such as, the compound with the structure represented by following formula can be enumerated.
When the structure represented by above-mentioned formula (2) is cationic, there is the xanthene compound of this structure there is negative ion in electroneutral mode.As negative ion, such as, halide ion, boron anion, phosphate radical anion, carboxylate anion, sulfate anion, organic sulfonic acid root negative ion, nitrogen negative ion, methide anion, hydroxide ion etc. can be enumerated.
In addition, when the structure represented by above-mentioned formula (2) is anionic property, the xanthene compound with this structure is that electroneutral mode has kation.As kation, such as, can enumerate proton, metal cation,
kation etc.As metal cation, such as, the divalent metal cations such as 1 valency metal cation such as lithium ion, sodion, potassium ion, rubidium ion, cesium ion, magnesium ion, calcium ion, strontium ion, barium ion can be enumerated.As
kation, can enumerate ammonium cation,
kation etc.As the concrete example of ammonium cation, the kation etc. in the compound recorded in the paragraph (0045) of Japanese Unexamined Patent Publication 2011-138094 publication can be enumerated, as
cationic concrete example, can enumerate the middle kations recorded such as paragraph (0038) ~ (0040) of Japanese Unexamined Patent Publication 2013-190776 publication.
As cyanine compound, preferably there is the compound of the structure represented by following formula (3), as concrete example, such as, basic-dyeable fibre such as system such as cyanine such as C.I. alkali red 1:1 2 grade can be enumerated.
(in formula (3),
R
31and R
32represent substituted or non-substituted alkyl independently of each other.
R
33~ R
35represent hydrogen atom, halogen atom, substituted or non-substituted alkyl independently of each other.Multiple R
33and R
34can be the same or different.
Ring Z
1with ring Z
2represent substituted or non-substituted aromatic hydrocarbon ring independently of each other.
G
1and G
2represent-O-,-S-or-CR independently of each other
36r
37-.Wherein, R
36and R
37represent substituted or non-substituted alkyl independently of each other.
S represents the integer of 1 ~ 3.〕
As R
31~ R
37in alkyl, such as, aliphatic alkyl, ester ring type alkyl, aromatic hydrocarbyl can be enumerated.As concrete example, the alkyl identical with the alkyl in formula (2) can be enumerated, also can enumerate identical substituting group for substituting group.
Ring Z
1with ring Z
2in aromatic hydrocarbon ring can be monocyclic aromatic hydrocarbon ring, also can be polycycle aromatic hydrocarbon ring, carbon number preferably 6 ~ 20, more preferably 6 ~ 10.As concrete example, such as, phenyl ring, cyclohexyl biphenyl, naphthalene nucleus, Azulene ring, anthracene nucleus, phenanthrene ring, pyrene ring, aphthacene ring, Sanya phenyl ring etc. can be enumerated.As the substituting group of aromatic hydrocarbon ring, the group identical with the substituting group of the alkyl in formula (2) can be enumerated.
Wherein, as R
31and R
32in alkyl, the alkyl of preferred carbon number 1 ~ 12, the more preferably alkyl of carbon number 1 ~ 8, the particularly preferably alkyl of carbon number 1 ~ 6.
As R
33~ R
35, preferred hydrogen atom.
As ring Z
1with ring Z
2, preferred phenyl ring.
As G
1and G
2, preferably-O-,-CR
36r
37-, as R
36and R
37, the alkyl of preferred carbon number 1 ~ 8, the more preferably alkyl of carbon number 1 ~ 4, particularly preferably methyl, ethyl.
S preferably 1 or 2, more preferably 1.
As the concrete example of cyanine compound with the structure represented by above-mentioned formula (3), such as, the compound with the structure represented by following formula can be enumerated.
When the structure represented by above-mentioned formula (3) is cationic, there is the cyanine compound of this structure there is negative ion in electroneutral mode.In addition, when the structure represented by above-mentioned formula (3) is anionic property, there is the cyanine compound of this structure there is kation in electroneutral mode.As such negative ion and cationic concrete example, such as, the ion same with illustrative Ion Phase in above-mentioned formula (2) can be enumerated.
As triaryl methane compounds, such as, diamido triarylmethane based dye, triaminotriarylmethane methane series dyestuff can be enumerated, there is the rosolic acid based dye etc. of OH base.Wherein, from the viewpoint of excellent hue, than other dyestuff daylight fastness excellences, preferred diamido triarylmethane based dye, triaminotriarylmethane methane series dyestuff.As preferred triaryl methane compounds, the compound with the structure represented by following formula (4) can be enumerated.Should illustrate, there is various resonant structure in the structure represented by following formula (4), and in this instructions, these resonant structures are the structure be equal to the structure represented by following formula (4).
(in formula (4),
Y represents hydrogen atom, substituted or non-substituted alkyl or-NR
59r
60.
R
41~ R
44and R
59~ R
60represent hydrogen atom or substituted or non-substituted alkyl independently of each other.
R
45~ R
52represent hydrogen atom, halogen atom, substituted or non-substituted alkyl or-COOR'.Wherein, R' represents hydrogen atom or substituted or non-substituted alkyl.
Ar represents and replaces or non-substituted aromatic hydrocarbyl.〕
As Y, R
41~ R
52, R
59~ R
60with the alkyl in R', such as, aliphatic alkyl, ester ring type alkyl, aromatic hydrocarbyl can be enumerated.As concrete example, the alkyl identical with the alkyl in formula (2) can be enumerated, also can enumerate identical substituting group for substituting group.
The preferred carbon number of aromatic hydrocarbyl of Ar is 6 ~ 20, and more preferably carbon number is 6 ~ 10.As concrete example, such as, phenylene, naphthylene, biphenylene, anthrylene etc. can be enumerated.As the substituting group of aromatic hydrocarbyl, such as, the substituting group identical with the substituting group of the alkyl in formula (2) can be enumerated, wherein, preferred halogen atom.
Wherein, as R
41~ R
44, R
59~ R
60and R', the alkyl of preferred hydrogen atom or carbon number 1 ~ 8.
As R
45~ R
52, the alkyl of preferred hydrogen atom, halogen atom or carbon number 1 ~ 8.
The preferred phenylene of Ar, naphthylene.
The alkyl of the preferred hydrogen atom of Y or carbon number 1 ~ 8.
In the present invention, from the view point of thermotolerance and solvent resistance, the kation particularly preferably represented by following formula (4-1) or (4-2) in the structure represented by above-mentioned formula (4).
(in formula (4-1) and (4-2),
Y
1represent alkyl or the-NR of hydrogen atom, halogen atom, carbon number 1 ~ 8 independently of each other
61r
62.
R
53~ R
56and R
61~ R
62represent the alkyl of hydrogen atom or carbon number 1 ~ 8 independently of each other.
R
57and R
58represent the alkyl of hydrogen atom, halogen atom or carbon number 1 ~ 8 independently of each other.〕
As R
53~ R
56, the more preferably alkyl of carbon number 1 ~ 4, particularly preferably methyl, ethyl.
As R
57and R
58, the alkyl of preferred hydrogen atom, halogen atom or carbon number 1 ~ 4.
As R
61~ R
62, the alkyl of preferred hydrogen atom or carbon number 1 ~ 6.
As Y
1, the alkyl of preferred hydrogen atom or carbon number 1 ~ 4.
As the concrete example of triaryl methane compounds with the structure represented by above-mentioned formula (4), such as, the compound with the structure represented by following formula can be enumerated.
When the structure represented by above-mentioned formula (4) is cationic, there is the triaryl methane compounds of this structure there is negative ion in electroneutral mode.In addition, when the structure represented by above-mentioned formula (4) is anionic property, there is the triaryl methane compounds of this structure there is kation in electroneutral mode.As such negative ion and cationic concrete example, such as, the ion same with illustrative Ion Phase in above-mentioned formula (2) can be enumerated.
As anthraquinone compounds, preferably there is the compound of the structure represented by following formula (5-1) or (5-2), as concrete example, such as, the anthraquinone system oil-soluble dyes such as C.I. solvent green 3 can be enumerated.
(in formula (5-1),
R
71and R
72represent hydrogen atom or substituted or non-substituted alkyl independently of each other.〕
(in formula (5-2),
R
81and R
82represent hydrogen atom or substituted or non-substituted alkyl.
R
83represent substituted or non-substituted divalent alkyl.〕
R
84, R
85and R
86represent substituted or non-substituted alkyl independently of each other.〕
As R
71, R
72, R
81, R
82and R
84~ R
86in alkyl, such as, aliphatic alkyl, ester ring type alkyl, aromatic hydrocarbyl can be enumerated.As concrete example, the group that in formula (2), illustrative group is identical can be enumerated, also can enumerate identical group for substituting group.
As R
83in divalent alkyl, divalent aliphatic alkyl, divalent ester ring type alkyl, divalent aromatic hydrocarbyl can be enumerated.As concrete example, the alkyl identical with illustrative alkyl in the divalent alkyl that (1-2) relates to formula (1-1) can be enumerated, also can enumerate identical substituting group for substituting group.
Wherein, as R
71and R
72, the alkyl of preferred hydrogen atom, substituted or non-substituted carbon number 1 ~ 6 or the aryl of substituted or non-substituted carbon number 6 ~ 10, more preferably hydrogen atom or substituted or non-substituted phenyl.As the substituting group of alkyl, halogen atom, hydroxyl, cyano group etc. can be enumerated, in addition, as the substituting group of aryl, phenyl, the alkyl etc. of halogen atom, hydroxyl, cyano group, carbon number 1 ~ 6 can be enumerated.
As R
81, R
82, R
84, R
85and R
86, the alkyl of preferred hydrogen atom or substituted or non-substituted carbon number 1 ~ 6, the more preferably alkyl of hydrogen atom or substituted or non-substituted carbon number 1 ~ 4.As the substituting group of alkyl, substituting group same as described above can be enumerated.
As R
83, the alkane 2 basis of preferred carbon number 1 ~ 20, the more preferably alkane 2 basis of carbon number 2 ~ 8.As the substituting group of alkane 2 basis, such as, the X with above-mentioned formula (1-1) and (1-2) can be enumerated
1and X
2the identical substituting group of substituting group.
As the concrete example of anthraquinone compounds with the structure represented by above-mentioned formula (5-1) or (5-2), such as, the compound with the structure represented by following formula can be enumerated.
In addition to that mentioned above, as xanthene compound, such as, also can use
C.I. the xanthene system acid dyes such as CI 45430 (erythrosine), C.I. acid red 52 (acid rhodamine), C.I. acid red 87 (eosin G), C.I. acid red 92 (acid phloxin PB), C.I. acid red 289, C.I. acid red 388, rose red b (edible red No. 5), acid Rhodamine G, C.I. acid violet 9;
C.I. the xanthene system oil-soluble dyes such as solvent red 35, C.I. solvent red 36, C.I. solvent red 42, C.I. solvent red 43, C.I. solvent red 44, C.I. solvent red 45, C.I. solvent red 46, C.I. solvent red 47, C.I. solvent red 48, C.I. solvent red 49, C.I. solvent red 72, C.I. solvent red 73, C.I. solvent red 109, C.I. solvent red 140, C.I. solvent red 141, C.I. solvent red 23 7, C.I. solvent red 24 6, C.I. solvent violet 2, C.I. solvent violet 10;
C.I. the xanthene system basic-dyeable fibre etc. such as alkali red 1:1 (rhodamine 6G CP), red 8 (Rhodamine Gs) of C.I. alkalescence.
In addition, as cyanine compound, such as, the cyanine system basic-dyeable fibres such as C.I. Basic Red 13, C.I. alkali red 1:1 4, C.I. alkaline purple 7, C.I. basic yellow 11, C.I. basic yellow 13, C.I. basic yellow 21, C.I. Basic Yellow 28, C.I. basic yellow 51 can also be used.
In addition, as triaryl methane compounds, such as, also can use
C.I. Blue VRS, C.I. acid blue 3, C.I. acid blue 5, C.I. Acid Blue 7, C.I. acid blue 9, C.I. Blue VRS 1, C.I. Blue VRS 5, C.I. Blue VRS 7, C.I. Blue VRS 9, C.I. acid blue 22, C.I. acid blue 24, C.I. acid blue 38, C.I. acid blue 48, C.I. Acid Blue 75, C.I. acid blue 83, C.I. acid blue 90, C.I. acid blue 91, C.I. acid blue 93, C.I. acid blue 9 3:1, C.I. Blue VRS 00, C.I. Blue VRS 03, C.I. Blue VRS 04, C.I. Blue VRS 09, C.I. Blue VRS 10, C.I. Blue VRS 19, C.I. Blue VRS 47, C.I. acid blue 269, C.I. Blue VRS 23, C.I. acid blue 213, C.I. direct indigo plant 41, C.I. acid violet 17, C.I. acid violet 19, C.I. acid violet 21, C.I. acid violet 23, C.I. acid violet 25, C.I. acid violet 38, C.I. acid violet 49, C.I. acid dyes such as system such as triarylmethane such as acid violet 72 grade,
C.I. the triarylmethane system basic-dyeable fibre such as alkaline purple 1 (methyl violet), C.I. alkaline purple 3 (crystal violet), C.I. basic violet 14 (fuchsin (Magenta)), C.I. alkali blue 1 (alkaline cyanine 6G), C.I. alkali blue 5 (alkaline cyanine EX), C.I. Blue 7 (Victoria pure blue BO), C.I. alkali blue 26 (victoria blue B conc.), C.I. Viride Nitens 1 (BG GX), C.I. Viride Nitens 4 (peacock green);
C.I. direct blue 41 direct dyess such as system such as triarylmethane such as grade etc.
In addition, as anthraquinone compounds, such as, also can use
C.I. acid blue 23, C.I. acid blue 25, C.I. acid blue 27, C.I. acid blue 35, C.I. Acid Blue 40, C.I. acid blue 41, C.I. acid blue 43, C.I. acid blue 45, C.I. acid blue 47, C.I. acid blue 49, C.I. acid blue 51, C.I. acid blue 53, C.I. acid blue 55, C.I. acid blue 56, C.I. Acid blue 62, C.I. acid blue 68, C.I. acid blue 69, C.I. Acid Blue 78, C.I. acid blue 80, C.I. acid blue 81:1, C.I. Blue VRS 1, C.I. Blue VRS 24, C.I. Blue VRS 27, C.I. Blue VRS 27:1, C.I. Blue VRS 40, C.I. Blue VRS 50, C.I. Blue VRS 75, C.I. acid blue 215, C.I. acid blue 230, C.I. acid blue 277, C.I. acid blue 3 44, C.I. acid violet 41, C.I. acid violet 42, C.I. acid violet 43, C.I. ACID GREEN 25, C.I. acid dyes such as system such as anthraquinone such as acid green 27 grade,
C.I. direct purple 17 direct dyess such as grade;
C.I. the anthraquinone system oil-soluble dyes etc. such as solvent red 172, C.I. solvent red 222, C.I. solvent violet 60.
Be not particularly limited as the compound represented by above-mentioned formula (1-1), the synthetic method of compound that represented by above-mentioned formula (1-2), known method can be used.Such as, can obtain as follows: utilize common methodology of organic synthesis to import the group with ethylenic unsaturated group at the basic framework of the above-mentioned dyestuff with functional group, or to dyestuff synthesis material import there is the group of ethylenic unsaturated group after, synthetic dyestuffs.More specifically, can with reference to the record of Japanese Unexamined Patent Publication 2013-178478 publication, Japanese Unexamined Patent Publication 2013-173850 publication, Japanese Unexamined Patent Publication 2013-210621 publication, Japanese Unexamined Patent Publication 2013-028764 publication etc.
Then, by by the compound represented by above-mentioned formula (1-1) and the compound copolymerization represented by above-mentioned formula (1-2), polymkeric substance (A1) can be manufactured.Copolyreaction can use known method, such as, can adopt the method identical with (C) described later resin glue.
In polymkeric substance (A1), the ratio of the content producing the position of fluorescence and the content at the position absorbing this fluorescence is in mol ratio (the former/the latter) preferably 99/1 ~ 50/50, more preferably 97/3 ~ 60/40, further preferably 95/5 ~ 70/30, further preferably 90/10 ~ 70/30.In addition, when polymkeric substance (A1) is the multipolymer containing unsaturated monomer (a1) and unsaturated monomer (a2), when the molal quantity of unsaturated monomer (a1) being set to p, the molal quantity of unsaturated monomer (a2) being set to q, preferably the mol ratio (p/q) of these monomers is in above-mentioned scope.
Particularly, when polymkeric substance (A1) is the multipolymer containing unsaturated monomer (a1) and unsaturated monomer (a2), the copolymerization ratios (p/q) of unsaturated monomer (a1) and unsaturated monomer (a2) by quality ratio preferably 97/3 ~ 40/60, more preferably 95/5 ~ 65/35, further preferably 90/10 ~ 70/30.
Polymkeric substance (A1) can have beyond unsaturated monomer (a1) and unsaturated monomer (a2) other can the ethylenically unsaturated monomers (hereinafter also referred to as " unsaturated monomer (a3) ") of copolymerization as structural unit.
As the concrete example of such unsaturated monomer (a3), such as, can enumerate
(methyl) acrylic acid, maleic acid, maleic anhydride, mono succinate (2-(methyl) acryloyl-oxyethyl) ester, ω-carboxy-polycaprolactone list (methyl) acrylate, the ethylenically unsaturated monomers with carboxyl to vinyl benzoic acid and so on;
The N-position substituted maleimide amine of N-phenylmaleimide, N-N-cyclohexylmaleimide and so on;
Styrene, α-methyl styrene, 4-Vinyl phenol, to hydroxy-alpha-methyl styrene, aromatic ethenyl compound to vinylbenzyl glycidyl 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 (degree of polymerization 2 ~ 10) methyl ether (methyl) acrylate, polypropylene glycol (degree of polymerization 2 ~ 10) methyl ether (methyl) acrylate, single (methyl) acrylate of polyglycol (degree of polymerization 2 ~ 10), single (methyl) acrylate of polypropylene glycol (degree of polymerization 2 ~ 10), (methyl) cyclohexyl acrylate, (methyl) isobornyl acrylate, (methyl) acrylic acid three ring [5.2.1.0
2,6] decane-8-base ester, (methyl) acrylic acid dicyclopentenyl ester, glycerine list (methyl) acrylate, (methyl) acrylic acid 4-hydroxy phenyl ester, p-cumylphenol (methyl) acrylate of ethylene-oxide-modified (methyl) acrylate, (methyl) glycidyl acrylate, (methyl) acrylic acid 3,4-expoxycyclohexyl methyl esters, 3-((methyl) acryloyloxymethyl) oxetanes, 3-((methyl) acryloyloxymethyl)-3-Ethyloxetane and so on,
Cyclohexyl vinyl ether, isobornyl vinyl ether, three ring [5.2.1.0
2,6] decane-8-base vinyl ether, pentacyclopentadecandimethanol base vinyl ether, 3-(vinyloxy methyl)-3-Ethyloxetane and so on vinyl ether;
The macromonomer at the end of polymer molecular chain with list (methyl) acryloyl group of polystyrene, poly-methyl (methyl) acrylate, poly-normal-butyl (methyl) acrylate, polysiloxane and so on.
Wherein, from the view point of thermotolerance, solvent resistance, suppression migration property, dispersiveness, as unsaturated monomer (a3), preferably there is the ethylenically unsaturated monomers of carboxyl, (methyl) acrylate.
When polymkeric substance (A1) is further containing the multipolymer of unsaturated monomer (a3) as structural unit, the copolymerization ratios of the unsaturated monomer (a3) in the entire infrastructure unit of polymkeric substance (A1) is preferably with under type.That is, the copolymerization ratios of unsaturated monomer (a3) is preferably 30 ~ 97 quality %, more preferably 40 ~ 95 quality % in entire infrastructure unit, is particularly preferably 50 ~ 90 quality %.By making unsaturated monomer (a3) copolymerization with such scope, easily obtain the coloured composition of thermotolerance, solvent resistance, suppression migration property, excellent dispersion.
Polymkeric substance (A1) (following by gel permeation chromatography, referred to as GPC) (eluting solvent: tetrahydrofuran) weight-average molecular weight (Mw) of polystyrene conversion of measuring is generally 1000 ~ 100000, be preferably 3000 ~ 50000, more preferably 3000 ~ 10000.By becoming such mode, contrast, thermotolerance, solvent resistance, suppression migration property can be made, become good by membrane property, electrical specification, pattern form, resolution.
In addition, the weight-average molecular weight (Mw) of polymkeric substance (A1) is preferably 1.0 ~ 5.0 with the ratio (Mw/Mn) of number-average molecular weight (Mn), is more preferably 1.0 ~ 3.0.Should illustrate, Mn mentioned here is the number-average molecular weight of the polystyrene conversion measured by GPC (eluting solvent: tetrahydrofuran).
Coloured composition of the present invention can be used in combination by other colorants beyond polymkeric substance (A1).As other colorants, be not particularly limited, can suitably select color, material according to purposes.As other colorants, can enumerate pigment, the dyestuff beyond polymkeric substance (A1), other colorants can be used alone or combine two or more and use.Wherein, from obtaining the high pixel aspect of brightness, contrast and colouring power, as pigment, preferred organic pigment, in addition, as dyestuff, preferably has organic dye.As organic dyestuff, such as, instructions can be enumerated and walk to the dyestuff recorded in the 20th page of the 7th row for the 18th page the 14th.
As organic pigment, such as, the compound as described below being classified as pigment can be enumerated in color index.
C.I. paratonere 166, C.I. paratonere 177, C.I. paratonere 224, C.I. paratonere 242, C.I. paratonere 254, C.I. paratonere 264;
C.I. pigment Green 7, C.I. pigment green 36, C.I. naphthol green 58, C.I. naphthol green 59;
C.I. pigment blue 15: 6, C.I. pigment blue 16, C.I. alizarol saphirol 80;
C.I. pigment Yellow 14, C.I. pigment yellow 83, C.I. pigment Yellow 12 9, C.I. pigment yellow 13 8, C.I. pigment yellow 13 9, C.I. pigment yellow 150, C.I. pigment yellow 17 9, C.I. pigment yellow 180, C.I. pigment yellow 185, C.I. pigment yellow 211, C.I. pigment yellow 215;
C.I. pigment orange 38;
C.I. pigment Violet 23.
In addition, can enumerate represented by following formula red pigment,
The mordant pigment recorded in Japanese Unexamined Patent Publication 2001-081348 publication, Japanese Unexamined Patent Publication 2010-026334 publication, Japanese Unexamined Patent Publication 2010-237384 publication, Japanese Unexamined Patent Publication 2010-237569 publication, Japanese Unexamined Patent Publication 2011-006602 publication, Japanese Unexamined Patent Publication 2011-145346 publication etc.
In the present invention, can other pigment mixed arbitrarily be undertaken refining by recrystallization method, reprecipitation method, solvent cleaning method, sublimed method, vaccum heating method or their combination and use.In addition, these pigment, according to desired, can carry out modification with resin to its particle surface and use.As the resin particle surface of pigment being carried out modification, such as, the resin of vehicle resin or the commercially available various pigment dispersion recorded in Japanese Unexamined Patent Publication 2001-108817 publication can be enumerated.As the resin-coated method of carbon blacksurface, such as, the method recorded in Japanese Unexamined Patent Publication 9-71733 publication, Japanese Unexamined Patent Publication 9-95625 publication, Japanese Unexamined Patent Publication 9-124969 publication etc. can be adopted.In addition, primary particle miniaturization can be used by so-called salt mill (ソ Le ト ミ リ Application グ) by organic pigment.As the method for salt mill, such as, method disclosed in Japanese Unexamined Patent Publication 8-179111 publication can be adopted.
In addition, in the present invention, can further containing known spreading agent and dispersing aid together with any other colorants mixed.As known spreading agent, such as, carbamate system spreading agent, polyethyleneimine system spreading agent, polyoxyethylene alkyl ether system spreading agent, polyoxyethylene alkyl phenyl ether system spreading agent, polyethylene glycol di system spreading agent, sorbitan fatty acid ester system spreading agent, Polyester spreading agent, dispersant containing acrylic etc. can be enumerated, in addition, as dispersing aid, pigment derivative etc. can be enumerated.
Such spreading agent can be obtained by commercial sources, such as, as dispersant containing acrylic, can enumerate Disperbyk-2000, Disperbyk-2001, BYK-LPN6919, BYK-LPN21116 (more than, BYK-Chemie (BYK) Inc.) etc., as carbamate system spreading agent, Disperbyk-161 can be enumerated, Disperbyk-162, Disperbyk-165, Disperbyk-167, Disperbyk-170, Disperbyk-182 (more than, BYK-Chemie (BYK) Inc.), Solsperse76500 (Lubrizol Co., Ltd. system) etc., as polyethyleneimine system spreading agent, Solsperse24000 (Lubrizol Co., Ltd. system) etc. can be enumerated, as Polyester spreading agent, Adisper PB821 can be enumerated, AdisperPB822, Adisper PB880, Adisper PB881 (more than, Ajinomoto Fine-Techno Co., Ltd. system) etc. and BYK-LPN21324 (BYK-Chemie (BYK) Inc.) etc.
In addition, as pigment derivative, specifically, the sulfonic acid etc. of copper phthalocyanine, diketopyrrolo-pyrrole, quinophthalone can be enumerated.
During containing other colorants, containing of other colorants is proportional, relative to total content preferably below the 70 quality % of colorant, more preferably below 50 mass parts.Lower limit is not particularly limited, and is more than 0.01 quality %.
From the viewpoint of the pixel or the black matrix of light-proofness excellence, the black separator that form the high colour purity excellence of thermotolerance, solvent resistance, suppression migration property and brightness, (A) colorant containing proportional be usually 3 ~ 70 quality % in the solid constituent of coloured composition, be preferably 5 ~ 60 quality %, more preferably 5 ~ 30 quality %.Here solid constituent refers to the composition beyond solvent described later.
-(B) polymerizable compound-
In the present invention, polymerizable compound refers to the compound of the polymerisable group with more than 2.As polymerisable group, such as, ethylenic unsaturated group, Oxyranyle, epoxypropane base, N-alkoxy methyl amino etc. can be enumerated.In the present invention, as polymerizable compound, the compound of the compound preferably with (methyl) acryloyl group of more than 2 or the N-alkoxy methyl amino with more than 2.
As the concrete example of compound of (methyl) acryloyl group with more than 2, multifunctional (methyl) acrylate that aliphatic polyhydroxy compound and (methyl) acrylic acid are obtained by reacting can be enumerated, by multifunctional (methyl) acrylate of caprolactone modification, by alkylen oxide-modified multifunctional (methyl) acrylate, make to have polyfunctional carbamate (methyl) acrylate that (methyl) acrylate of hydroxyl and polyfunctional isocyanate are obtained by reacting, make to have multifunctional (methyl) acrylate etc. with carboxyl that (methyl) acrylate of hydroxyl and anhydride reaction obtain.
Here, as aliphatic polyhydroxy compound, such as, the divalent aliphatic polyhydroxy compound of ethylene glycol, propylene glycol, polyglycol, polypropylene glycol and so on can be enumerated; Aliphatic polyhydroxy compounds more than 3 valencys of glycerine, trimethylolpropane, pentaerythrite, dipentaerythritol and so on.As above-mentioned (methyl) acrylate with hydroxyl, such as, (methyl) acrylic acid 2-hydroxy methacrylate, trimethylolpropane two (methyl) acrylate, pentaerythrite three (methyl) acrylate, dipentaerythritol five (methyl) acrylate, glycerine dimethacrylate etc. can be enumerated.As above-mentioned polyfunctional isocyanate, such as, toluene diisocyanate, hexamethylene diisocyanate, MDI, isophorone diisocyanate etc. can be enumerated.As acid anhydrides, such as, the tetra-atomic acid dianhydride of the acid anhydrides, pyromellitic acid anhydride, biphenyl tetracarboxylic dianhydride, benzophenone tetracarboxylic dianhydride and so on of the dibasic acid of succinic anhydride, maleic anhydride, glutaric anhydride, itaconic anhydride, phthalic anhydride, hexahydrophthalic anhydride and so on can be enumerated.
In addition, as by multifunctional (methyl) acrylate of caprolactone modification, such as, the compound recorded in paragraph (0015) ~ (0018) of Japanese Unexamined Patent Publication 11-44955 publication can be enumerated.As above-mentioned by alkylen oxide-modified multifunctional (methyl) acrylate, bisphenol-A two (methyl) acrylate of at least a kind of modification be selected from oxirane and epoxypropane can be enumerated, be selected from isocyanuric acid three (methyl) acrylate of at least a kind of modification in oxirane and epoxypropane, be selected from trimethylolpropane tris (methyl) acrylate of at least a kind of modification in oxirane and epoxypropane, be selected from pentaerythrite three (methyl) acrylate of at least a kind of modification in oxirane and epoxypropane, be selected from pentaerythrite four (methyl) acrylate of at least a kind of modification in oxirane and epoxypropane, be selected from dipentaerythritol five (methyl) acrylate of at least a kind of modification in oxirane and epoxypropane, be selected from dipentaerythritol six (methyl) acrylate etc. of at least a kind of modification in oxirane and epoxypropane.
In addition, as the compound of N-alkoxy methyl amino with more than 2, such as, the compound etc. with melamine structure, benzoguanamine structure, urea structure can be enumerated.Should illustrate, melamine structure, benzoguanamine structure refer to that the triazine ring with more than 1 or phenyl replace the chemical constitution of triazine ring as basic framework, are the concepts comprising melamine, benzoguanamine or their condensation product.As the concrete example of compound of N-alkoxy methyl amino with more than 2, N can be enumerated, N, N ', N ', N ", N "-six (alkoxy methyl) melamine, N, N, N ', N '-four (alkoxy methyl) benzoguanamine, N, N, N ', N '-four (alkoxy methyl) glycoluril etc.
In these polymerizable compounds, multifunctional (methyl) acrylate preferably making the aliphatic polyhydroxy compound of more than 3 valencys and (methyl) acrylic acid be obtained by reacting, by multifunctional (methyl) acrylate of caprolactone modification, polyfunctional carbamate (methyl) acrylate, there is multifunctional (methyl) acrylate, the N of carboxyl, N, N ', N '; N "; N "-six (alkoxy methyl) melamine, N, N, N ', N '-four (alkoxy methyl) benzoguanamine.The surface smoothness of, dyed layer high from the intensity of dyed layer is excellent and not easily produce the aspects such as dirt, film be residual the substrate in unexposed portion and on light shield layer and consider, in multifunctional (methyl) acrylate making the aliphatic polyhydroxy compound of more than 3 valencys and (methyl) acrylic acid be obtained by reacting, particularly preferably trimethylolpropane triacrylate, pentaerythritol triacrylate, Dipentaerythritol Pentaacrylate, dipentaerythritol acrylate; In multifunctional (methyl) acrylate with carboxyl, the compound particularly preferably making pentaerythritol triacrylate and succinic anhydride be obtained by reacting, the compound that Dipentaerythritol Pentaacrylate and succinic anhydride are obtained by reacting.
In the present invention, (B) polymerizable compound may be used singly or as a mixture of two or more.
The content of (B) polymerizable compound in the present invention is relative to (A) colorant 100 mass parts preferably 10 ~ 1000 mass parts, more preferably 20 ~ 800 mass parts, preferably 100 ~ 700 mass parts, particularly preferably 200 ~ 400 mass parts further.By becoming such mode, curability can be made, alkali development becomes good.
-(C) resin glue-
Coloured composition of the present invention can contain resin glue (wherein, not comprising polymkeric substance (A1)).Thereby, it is possible to improve the alkali-soluble of coloured composition, the cohesiveness, storage stability etc. to substrate.As resin glue, only otherwise being equivalent to polymkeric substance (A1) is just not particularly limited, preferably there is the resin of the acidic functionality such as carboxyl, phenolic hydroxyl group.Wherein, the polymkeric substance preferably with carboxyl is (following, be called " polymkeric substance containing carboxyl "), such as, the ethylenically unsaturated monomers can enumerating the carboxyl with more than 1 is (following, be called " unsaturated monomer (c1) ") can the multipolymer of ethylenically unsaturated monomers (hereinafter referred to as " unsaturated monomer (c2) ") of copolymerization with other.
As unsaturated monomer (c1), such as, can enumerate (methyl) acrylic acid, maleic acid, maleic anhydride, mono succinate (2-(methyl) acryloyl-oxyethyl) ester, ω-carboxy-polycaprolactone list (methyl) acrylate, to vinyl benzoic acid etc.
These unsaturated monomers (c1) may be used singly or as a mixture of two or more.
In addition; as unsaturated monomer (c2); such as; illustrative N-position substituted maleimide amine in unsaturated monomer (a3), aromatic ethenyl compound, (methyl) acrylate, vinyl ether can be enumerated, there is at the end of polymer molecular chain the macromonomer etc. of list (methyl) acryloyl group; as concrete example, group same as described above can be enumerated.
Unsaturated monomer (c2) may be used singly or as a mixture of two or more.
In the multipolymer of unsaturated monomer (c1) with unsaturated monomer (c2), the copolymerization ratios of the unsaturated monomer (c1) in this multipolymer is preferably 5 ~ 50 quality %, more preferably 10 ~ 40 quality %.By making unsaturated monomer (c1) copolymerization in such scope, the coloured composition of alkali development and excellent storage stability can be obtained.
As the concrete example of unsaturated monomer (c1) with the multipolymer of unsaturated monomer (c2), such as, multipolymer disclosed in Japanese Unexamined Patent Publication 7-140654 publication, Japanese Unexamined Patent Publication 8-259876 publication, Japanese Unexamined Patent Publication 10-31308 publication, Japanese Unexamined Patent Publication 10-300922 publication, Japanese Unexamined Patent Publication 11-174224 publication, Japanese Unexamined Patent Publication 11-258415 publication, Japanese Unexamined Patent Publication 2000-56118 publication, Japanese Unexamined Patent Publication 2004-101728 publication etc. can be enumerated.
In addition; in the present invention; such as; disclosed in Japanese Unexamined Patent Publication 5-19467 publication, Japanese Unexamined Patent Publication 6-230212 publication, Japanese Unexamined Patent Publication 7-207211 publication, Japanese Unexamined Patent Publication 9-325494 publication, Japanese Unexamined Patent Publication 11-140144 publication, Japanese Unexamined Patent Publication 2008-181095 publication etc., be used in side chain and there is the polymkeric substance containing carboxyl of the polymerism unsaturated links such as (methyl) acryloyl group as resin glue.
Resin glue in the present invention (following by gel permeation chromatography, referred to as GPC) (eluting solvent: tetrahydrofuran) weight-average molecular weight (Mw) of polystyrene conversion of measuring is generally 1000 ~ 100000, is preferably 3000 ~ 50000.By becoming such mode, thus the residual film ratio of tunicle, pattern form, thermotolerance, electrical specification, resolution are further enhanced, and in addition, dry foreign matter during coating can be suppressed to produce with high level.
In addition, the weight-average molecular weight (Mw) of the resin glue in the present invention is preferably 1.0 ~ 5.0 with the ratio (Mw/Mn) of number-average molecular weight (Mn), is more preferably 1.0 ~ 3.0.Should illustrate, Mn mentioned here refers to the number-average molecular weight of the polystyrene conversion measured by GPC (eluting solvent: tetrahydrofuran).
Resin glue in the present invention can be manufactured by known method, such as, method disclosed in Japanese Unexamined Patent Publication 2003-222717 publication, Japanese Unexamined Patent Publication 2006-259680 publication, International Publication No. 2007/029871 pamphlet etc. can be utilized to control its structure, Mw, Mw/Mn.
In the present invention, (C) resin glue may be used singly or as a mixture of two or more.
In the present invention, the content of (C) resin glue, relative to (A) colorant 100 mass parts, is generally 10 ~ 1000 mass parts, is preferably 20 ~ 500 mass parts.By becoming such mode, alkali development, the storage stability of coloured composition, colorimetric properties can be improved further.
-(D) Photoepolymerizationinitiater initiater-
Coloured composition of the present invention can contain Photoepolymerizationinitiater initiater.Thereby, it is possible to give radiation-sensitive to coloured composition.The Photoepolymerizationinitiater initiater used in the present invention is the compound being produced the spike that can cause the polymerization of above-mentioned polymerizable compound by the exposure of the radioactive ray such as luminous ray, ultraviolet, far ultraviolet, electron beam, X ray.
As such Photoepolymerizationinitiater initiater, such as, 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, multinuclear quinone based compound, diazonium based compound, acid imide sulphonic acid ester (imidosulfonates) based compound etc.
In the present invention, Photoepolymerizationinitiater initiater may be used singly or as a mixture of two or more.As Photoepolymerizationinitiater initiater, be preferably selected from least a kind in thioxanthones based compound, acetophenone based compound, bisglyoxaline based compound, triazine based compound, O-acyl group oxime compound.
In the present invention in preferred Photoepolymerizationinitiater initiater, as the concrete example of thioxanthones based compound, thioxanthones, CTX, 2-methyl thioxanthones, ITX, ITX, 2 can be enumerated, 4-bis-clopenthixal ketone, 2,4-dimethyl thioxanthone, 2,4-diethyl thioxanthone, 2,4-diisopropylthioxanthone etc.
In addition, as the concrete example of acetophenone based compound, 2-methyl isophthalic acid-(4-(methyl mercapto) phenyl)-2-morpholino propane-1-ketone, 2-benzyl-2-dimethylamino-1-(4-morphlinophenyl) butane-1-ketone, 2-(4-methyl-benzyl)-2-(dimethylamino)-1-(4-morphlinophenyl) butane-1-ketone etc. can be enumerated.
In addition, as the concrete example of bisglyoxaline based compound, two (the 2-chlorphenyl)-4 of 2,2'-can be enumerated, 4', 5,5'-tetraphenyl-1,2'-bisglyoxaline, 2, two (2, the 4-dichlorophenyl)-4,4', 5 of 2'-, 5'-tetraphenyl-1,2'-bisglyoxaline, 2,2'-two (2,4,6-trichlorophenyl)-4,4', 5,5'-tetraphenyl-1,2'-bisglyoxaline etc.
Should illustrate, when using bisglyoxaline based compound as Photoepolymerizationinitiater initiater, preferred and use hydrogen donor from the viewpoint of improving sensitivity." hydrogen donor " mentioned here refers to can to the compound of the free radical supply hydrogen atom produced by bisglyoxaline based compound by exposure.As hydrogen donor, such as, 2-mercaptobenzothiazole, 2-sulfydryl benzo can be enumerated
the amine system hydrogen donors such as the mercaptan system hydrogen donors such as azoles, 4,4'-two (dimethylamino) benzophenone, 4,4'-two (diethylamino) benzophenone.In the present invention, hydrogen donor may be used singly or as a mixture of two or more, but from the viewpoint of improving sensitivity further, is preferably combinationally used by the amine system hydrogen donor of the mercaptan system hydrogen donor of more than a kind and more than a kind.
In addition, as the concrete example of triazine based compound, can 2 be enumerated, 4, 6-tri-(trichloromethyl)-s-triazine, 2-methyl-4, two (the trichloromethyl)-s-triazine of 6-, 2-(2-(5-methylfuran-2-base) vinyl)-4, two (the trichloromethyl)-s-triazine of 6-, 2-(2-(furans-2-base) vinyl)-4, two (the trichloromethyl)-s-triazine of 6-, 2-(2-(4-diethylamino-2-aminomethyl phenyl) vinyl)-4, two (the trichloromethyl)-s-triazine of 6-, 2-(2-(3, 4-Dimethoxyphenyl) vinyl)-4, two (the trichloromethyl)-s-triazine of 6-, 2-(4-methoxyphenyl)-4, two (the trichloromethyl)-s-triazine of 6-, 2-(4-ethoxystyrene base)-4, two (the trichloromethyl)-s-triazine of 6-, 2-(4-n-butoxyphenyl)-4, two (the trichloromethyl)-s-triazine of 6-etc. have the triazine based compound of halogenated methyl.
In addition, as the concrete example of O-acyl group oxime compound, 1-(4-(thiophenyl) phenyl)-1 can be enumerated, 2-octanedione 2-(O-benzoyl oxime), 1-[9-ethyl-6-(2-methyl benzoyl)-9H-carbazyl-3-base]-ethyl ketone 1-(O-acetyl oxime), 1-(9-ethyl-6-(2-methyl-4-tetrahydrofuran base methoxybenzoyl base)-9H-carbazyl-3-base)-ethyl ketone 1-(O-acetyl oxime), 1-(9-ethyl-6-{2-methyl-4-(2, 2-dimethyl-1, 3-dioxolanyl) methoxybenzoyl base }-9H-carbazyl-3-base)-ethyl ketone 1-(O-acetyl oxime) etc.As the commercially available product of O-acyl group oxime compound, NCI-831, NCI-930 (more than, Inc. of Asahi Denka Co., Ltd.) etc. can be used.
When using the Photoepolymerizationinitiater initiater except the bisglyoxaline based compounds such as acetophenone based compound in the present invention, can be used together sensitizer.As such sensitizer; such as; can 4 be enumerated; two (dimethylamino) benzophenone, 4 of 4'-; two (diethylamino) benzophenone of 4'-, 4-diethyl amino benzoylformaldoxime, 4-dimethylamino propiophenone, EDMAB, 4-dimethylaminobenzoic acid 2-Octyl Nitrite, 2,5-two (4-diethylamino benzal) cyclohexanone, 7-diethylamino-3-(4-diethylamino benzoyl) cumarin, 4-(diethylamino) chalcone etc.
In the present invention, the content of Photoepolymerizationinitiater initiater relative to (B) polymerizable compound 100 mass parts preferably 0.01 ~ 120 mass parts, particularly preferably 1 ~ 100 mass parts.By becoming such mode, curability can be made, become good by membrane property.
-solvent-
Coloured composition of the present invention contains other compositions of above-mentioned (A) and (B) composition and interpolation arbitrarily, usually coordinates organic solvent to be prepared into fluid composition.
As organic solvent, as long as will (A) and (B) composition, the dispersion of other compositions of coloured composition be formed or dissolve and do not react with these compositions, there is appropriate volatility, just can suitably choice for use.
In such organic solvent, such as, can enumerate
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, diethylene glycol list positive propyl ether, diethylene glycol mono-n-butyl ether, triethylene glycol monomethyl ether, Triethylene glycol ethyl ether, propylene glycol monomethyl ether, dihydroxypropane single-ether, propylene glycol list positive propyl ether, propylene glycol mono-n-butyl ether, dipropylene glycol monomethyl ether, DPE, dipropylene glycol list positive propyl ether, dipropylene glycol mono-n-butyl ether, Tripropylene glycol monomethyl Ether, (gathering) alkylene glycol monoalkyl ethers such as tripropylene glycol list ether,
The lactic acid alkyl ester such as methyl lactate, ethyl lactate;
(ring) alkylols such as methyl alcohol, ethanol, propyl alcohol, butanols, isopropyl alcohol, isobutyl alcohol, the tert-butyl alcohol, octanol, 2-Ethylhexyl Alcohol, cyclohexanol;
The keto-alcohols such as diacetone alcohol;
(gathering) the alkylene glycol monoalkyl ethers acetic acid esters such as 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, acetic acid 3-methoxybutyl, acetic acid 3-methyl-3-methoxybutyl;
The glycol ethers such as diethylene glycol dimethyl ether, diethylene glycol MEE, diethylene glycol diethyl ether;
The cyclic ethers such as tetrahydrofuran;
The ketone such as methyl ethyl ketone, cyclohexanone, 2-HEPTANONE, 3-heptanone;
The diacetate esters such as propylene-glycol diacetate, 1,3-BDO diacetate esters, 1,6-hexane diol diacetate esters;
The alkoxyl carboxylates such as 3-methoxy methyl propionate, 3-methoxypropionate, 3-ethoxypropanoate, 3-ethoxyl ethyl propionate, ethoxy ethyl acetate, 3-methyl-3-methoxybutyl propionic ester;
The fatty acid alkyl esters 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, propyl butyrate, isopropyl isobutyrate, the positive butyl ester of butyric acid, methyl pyruvate, ethyl pyruvate, pyruvic acid n-propyl, methyl acetoacetate, ethyl acetoacetate, 2-Oxobutyric acid ethyl ester;
The aromatic hydrocarbon such as toluene, dimethylbenzene;
Acid amides or the lactams etc. such as DMF, DMA, 1-METHYLPYRROLIDONE.
In these organic solvents, from dissolubility, pigment-dispersing, the viewpoints such as coating are set out, preferred propylene glycol monomethyl ether, dihydroxypropane single-ether, ethylene glycol monomethyl ether acetate, propylene glycol methyl ether acetate, propylene glycol monoethyl ether acetate, 3-methoxybutyl acetic acid esters, diethylene glycol dimethyl ether, diethylene glycol MEE, cyclohexanone, 2-HEPTANONE, 3-heptanone, 1, 3-butylene glycol diacetate esters, 1, 6-hexanediol diacetate esters, ethyl lactate, 3-methoxypropionate, 3-ethoxypropanoate, 3-ethoxyl ethyl propionate, 3-methyl-3-methoxybutyl 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 etc.
In the present invention, organic solvent can be used alone or two or more use of mixer.
The content of organic solvent, is not particularly limited, and the total concentration of each composition except the organic solvent of coloured composition preferably becomes the amount of 5 ~ 50 quality %, more preferably becomes the amount of 10 ~ 40 quality %.By becoming such mode, coloured composition dispersiveness, the colorant dispersion had good stability and coating can be obtained, having good stability.
-adjuvant-
Coloured composition of the present invention can contain various adjuvant as required.
As adjuvant, such as, the filling agent such as glass, aluminium oxide can be enumerated, the macromolecular compounds such as polyvinyl alcohol (PVA), poly-(fluoroalkyl) class, the surfactants such as fluorine system surfactant, silicone based surfactants, vinyltrimethoxy silane, vinyltriethoxysilane, vinyl three (2-methoxy ethoxy) silane, N-(2-amino-ethyl)-3-amino propyl methyl dimethoxysilane, N-(2-amino-ethyl)-3-TSL 8330, APTES, 3-glycidoxypropyltrime,hoxysilane, 3-glycidoxypropyl dimethoxysilane, 2-(3, 4-expoxycyclohexyl) ethyl trimethoxy silane, 3-chloropropylmethyldimethoxysilane, 3-r-chloropropyl trimethoxyl silane, 3-methacryloxypropyl trimethoxy silane, the closely sealed promoter such as 3-mercaptopropyi trimethoxy silane, the antioxidants such as 2,2-thiobis (4-methyl-6-tert-butylphenol), 2,6-bis--tert-butyl phenols, 2-(the 3-tert-butyl group-5-methyl-2-hydroxy phenyl) ultraviolet light absorber such as-5-chlorobenzotriazole, alkoxy benzophenone class, the condensation such as sodium polyacrylate preventing agent, malonic acid, hexane diacid, itaconic acid, citraconic acid, fumaric acid, mesaconic acid, 2-ethylaminoethanol, the residue improver such as 3-amino-1-propyl alcohol, 5-amino-1-amylalcohol, 3-amino-1,2-PD, 2-amino-1,3-propanediol, amino-1, the 2-butylene glycol of 4-, the developability improvers etc. such as mono succinate (2-(methyl) acryloyl-oxyethyl) ester, phthalic acid list (2-(methyl) acryloyl-oxyethyl) ester, ω-carboxy-polycaprolactone list (methyl) acrylate.
Color solidification film and forming method thereof
Color solidification film of the present invention uses coloured composition of the present invention to be formed, and specifically, refers in display element, solid-state imager each color pixel used, black matrix, black separator etc.
Below, color solidification film used in the color filter to formation display element, solid-state imager and forming method thereof is described.
As the method manufacturing color filter, the first, can following methods be enumerated.First, light shield layer (black matrix) is formed in the mode dividing the part forming pixel as required on a surface of a substrate.Then, be such as coated with the fluid composition of blue radiation-sensitive coloured composition of the present invention on the substrate, then bake and bank up with earth in advance and solvent is evaporated, form film.Then, after photomask exposes this film, use alkaline-based developer to develop, removing is dissolved in the unexposed portion of film.Thereafter, by after cure, the pel array of the blue pattern of pixels (color solidification film) that is arranged being formed to specify.
Then, use each radiation-sensitive coloured composition of green or redness, carry out the coating of each radiation-sensitive coloured composition as described above, bake and bank up with earth in advance, expose, develop and after cure, form green pel array and red pel array on the same substrate successively.Thus, color filter substrate being configured with blueness, green and this trichromatic pel array red is obtained.Wherein, in the present invention, the order forming each color pixel is not limited to said sequence.
Above-mentioned black matrix can be formed by utilizing photoetching process to make to become desired pattern by the metallic film of the chromium etc. of sputtering, evaporation film-forming, also by using the radiation-sensitive coloured composition being dispersed with black colorant, can be formed in the same manner as forming the situation of above-mentioned pixel.
As the substrate used when forming color filter, such as, glass, organosilicon, polycarbonate, polyester, aromatic polyamide, polyamidoimide, polyimide etc. can be enumerated.
In addition, these substrates, the pre-service suitable according to the desired agent treated, Cement Composite Treated by Plasma, ion plating, sputtering, gas-phase reaction method, vacuum evaporation etc. can implementing to utilize silane coupling agent etc. to carry out.
When substrate is coated with radiation-sensitive coloured composition, the rubbing method that spray-on process, rolling method, spin-coating method (spin coat method), slot die rubbing method (slot coated method), stick coating method etc. are suitable can be adopted, particularly preferably adopt spin-coating method, slot die rubbing method.
Bake and bank up with earth in advance and be generally 70 ~ 110 DEG C, about 1 ~ 10 minute.
Coating thickness is generally 0.6 ~ 8 μm with dried film thickness gauge, is preferably 1.2 ~ 5 μm.
As the light source of the radioactive ray used when forming at least a kind of being selected from pixel and black matrix, such as, the LASER Light Source etc. such as the 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, argon laser, YAG laser, XeCl excimer laser, N_2 laser can be enumerated.As exposure light source, also ultraviolet LED can be used.Optimal wavelength is at the radioactive ray of the scope of 190 ~ 450nm.
The usual preferably 10 ~ 10000J/m of exposure of radioactive ray
2.
In addition, as above-mentioned alkaline-based developer, such as, preferred sodium carbonate, sodium bicarbonate, NaOH, potassium hydroxide, Tetramethylammonium hydroxide, choline, 1, the aqueous solution of 8-diazabicyclo-[5.4.0]-7-undecylene, 1,5-diazabicyclo-[4.3.0]-5-nonene etc.
Such as the water-miscible organic solvent such as methyl alcohol, ethanol, surfactant etc. can be added in right amount in alkaline-based developer.Should illustrate, usually wash after alkaline development.
As development treatment method, spray development method, spray development method, dipping (dip) development method can be used, revolve and cover submergence (puddle) development method etc.Under the preferred normal temperature of development conditions 5 ~ 300 seconds.
After the condition of curing be generally 180 ~ 280 DEG C at about 10 ~ 60 minutes.
The thickness of the pixel of such formation is generally 0.5 ~ 5 μm, is preferably 1.0 ~ 3 μm.
In addition, as the second method manufacturing color filter, can adopt disclosed in Japanese Unexamined Patent Publication 7-318723 publication, Japanese Unexamined Patent Publication 2000-310706 publication etc. and utilize ink-jetting style to obtain the method for each color pixel.In the method, first, the next door having shade function concurrently is formed on a surface of a substrate.Then, utilize ink discharge device in the next door formed, spray the fluid composition of such as blue Thermocurable coloured composition, then bake and bank up with earth in advance and solvent is evaporated.Then, after as required this film being exposed, by after cure and make it solidify, form blue pattern of pixels.
Then, use each Thermocurable coloured composition of green or redness, form green pattern of pixels and red pattern of pixels as described above on the same substrate successively.Thus, the color filter being configured with blueness, green and red trichromatic pattern of pixels on substrate is obtained.Wherein, in the present invention, the order forming each color pixel is not limited to above-mentioned order.
Should illustrate, next door not only plays shade function, and also play the function for making the assorted Thermocurable coloured composition be ejected in septal area that colour mixture not occur, compared with the black matrix used in the first above-mentioned method, thickness is thicker.Therefore, next door uses black radiation-ray sensitive composition to be formed usually.
The substrate used when forming color filter, the light source of radioactive ray, in addition, bake and bank up with earth in advance, after method, the condition of curing identical with the first above-mentioned method.Like this, the thickness of the pixel utilizing ink-jetting style to be formed and the height equal extent in next door.
After the pattern of pixels obtained like this forms diaphragm as required, sputtering is utilized to form nesa coating.After forming nesa coating, can separator be formed further and make color filter.Separator uses radiation-ray sensitive composition to be formed usually, also can make the separator (black separator) with light-proofness.At this moment, use the radiation-sensitive coloured composition being dispersed with black colorant, coloured composition of the present invention can be applicable to the formation of above-mentioned black separator.
Radiation-sensitive coloured composition of the present invention can be applicable to the formation of the arbitrary color solidification film in each color pixel used in above-mentioned color filter, black matrix, black separator etc.
Comprise the color filter of the color solidification film of the present invention formed like this, brightness and colour purity high, therefore exceedingly useful in color liquid crystal display device, colour pick-up tube element, color sensor, organic EL display element, Electronic Paper etc.Should illustrate, the color solidification film that the use radiation-sensitive coloured composition of the present invention that display element described later at least possesses more than 1 is formed.
Display element
Display element of the present invention possesses color solidification film of the present invention.As display element, color liquid crystal display device, organic EL display element, Electronic Paper etc. can be enumerated.
Possessing the color liquid crystal display device of color solidification film of the present invention, can be transmission-type also can be reflection-type, can adopt suitable structure.Such as, can adopt and form color filter on the substrate different from the driving substrate being configured with thin film transistor (TFT) (TFT), driving substrate and the substrate being formed with color filter are across the opposed structure of liquid crystal layer.In addition, the substrate that is formed with color filter on the surface of the driving substrate being configured with thin film transistor (TFT) (TFT) and the substrate being formed with ITO (indium oxide doped with tin) electrode or IZO (potpourri of indium oxide and zinc paste) electrode also can be adopted across the opposed structure of liquid crystal layer.The structure of the latter can significantly improve aperture opening ratio, has and can obtain becoming clear and the advantage of the liquid crystal display cells of fine.Should illustrate, when adopting the structure of the latter, black matrix, black separator can be formed in the substrate-side and either party being formed in the substrate-side of ITO electrode or IZO electrode being formed with color filter.
Possess the color liquid crystal display device of color solidification film of the present invention, except cold cathode fluorescent tube (CCFL:Cold Cathode Fluorescent Lamp), can also possess with White LED is the backlight unit of light source.As White LED, such as, display predetermined colors in combination LED, green LED and blue led can be enumerated, be obtained the White LED of white light by colour mixture; Combined blue LED, red LED and green-emitting phosphor, obtain the White LED of white light by colour mixture; Combined blue LED, red light-emitting phosphor and green-emitting phosphor body, obtain the White LED of white light by colour mixture; The White LED of white light is obtained by the colour mixture of blue led and YAG system fluorophor; Combined blue LED, orange luminescence fluorophor and green-emitting phosphor body, obtain the White LED of white light by colour mixture; Combination ultraviolet LED, red light-emitting phosphor, green-emitting phosphor body and blue-light-emitting fluorescent material, obtain the White LED etc. of white light by colour mixture.
Possess in the color liquid crystal display device of color solidification film of the present invention and can apply TN (twisted-nematic (Twisted Nematic)) type, STN (supertwist is to row (Super TwistedNematic)) type, IPS (plane conversion (In-Planes Switching)) type, VA (vertical orientated (Vertical Alignment)) type, the liquid crystal mode that OCB (optical compensation curved arrangement (OpticallyCompensated Birefringence)) type etc. are suitable.
In addition, the organic EL display element possessing color solidification film of the present invention can adopt suitable structure, such as, can enumerate structure disclosed in Japanese Unexamined Patent Publication 11-307242 publication.
In addition, the Electronic Paper possessing color solidification film of the present invention can adopt suitable structure, such as, can enumerate structure disclosed in Japanese Unexamined Patent Publication 2007-41169 publication.
Solid-state imager
Solid-state imager of the present invention possesses color solidification film of the present invention.In addition, solid-state imager of the present invention can adopt suitable structure.Such as, as an embodiment, the coloured composition of the application of the invention, forms colored pixels (color solidification film) by same as described above operating on the semiconductor substrates such as CMOS substrate, can make the solid-state imager of color separated, colorrendering quality excellence.
Embodiment
Below, enumerate embodiment to be specifically described further embodiments of the present invention.But the invention is not restricted to following embodiment.
The synthesis > of < colorant
(synthesis example 1)
The there-necked flask of the 100mL putting into stirrer, be provided with backflow cooling tube and thermometer is fully carried out nitrogen displacement, and load cyclohexanone 15.0g, nitrogen flows down and is heated to interior temperature 80 ± 2 DEG C.On the other hand, using the methacrylic acid of the methyl methacrylate of the following shown pigment monomer (A3) of the following shown pigment monomer (A1) of mixing 4.00g, 0.50g, 6.00g, 4.50g, 2.18g as 2 of polymerization initiator, 2 '-azo two (2,4-methyl pentane nitrile) (Wako Pure Chemical Industries, Ltd.'s system, trade name V-65), the cyclohexanone of 45.0g and the solution made remains on interior temperature 80 ± 2 DEG C, use pump dropping in 2 hours.After dropping terminates, at this temperature Keep agitation 1 hour again.Thereafter, reactant liquor is cooled to room temperature, is added drop-wise in a large amount of hexanes.By the coloring solid that obtains at 50 DEG C of drying under reduced pressure, obtain 13.9g polymkeric substance (1).The Mw of the polymkeric substance (1) obtained is 5100.Polymkeric substance (1) is equivalent to polymkeric substance (A1).
Synthesis example 2 ~ 10
In synthesis example 1, by the kind and the amount that change the monomer used in polymerization table 1 Suo Shi, in addition, carry out in the same manner as synthesis example 1, obtain polymkeric substance (2) ~ (10).The structure of pigment monomer (A1) ~ (A4) as above.Polymkeric substance (2) ~ (4) and polymkeric substance (9) ~ (10) are equivalent to polymkeric substance (A1).Polymkeric substance (5) ~ (8) are not polymkeric substance (A1).
The symbol used in table 1 is as follows.
MMA: methyl methacrylate
MA: methacrylic acid
In addition, in table 1 " p/q " represent the molal quantity of the compound represented by formula (1-1) used in polymerization is set to p, the mol ratio when molal quantity of the compound represented by formula (1-2) being set to q.
In addition, pigment monomer (A1) ~ (A4) synthesizes with reference to following publication respectively.
Pigment monomer (A1): according to the 2-in-1 one-tenth of synthesis example recorded in paragraph (0145) ~ (0146) of Japanese Unexamined Patent Publication 2013-178478 publication.Be equivalent to that there is the chromophoric ethylenically unsaturated monomers of xanthene.
Pigment monomer (A2): according to the embodiment 1-1 synthesis recorded in paragraph (0096) ~ (0097) of Japanese Unexamined Patent Publication 2013-173850 publication.Be equivalent to that there is the chromophoric ethylenically unsaturated monomers of cyanine.
Pigment monomer (A3): according to the manufacture synthesis of the dye monomer (A1-1) recorded in paragraph (0149) ~ (0150) of Japanese Unexamined Patent Publication 2013-210621 publication.Be equivalent to that there is the chromophoric ethylenically unsaturated monomers of triarylmethane.
Pigment monomer (A4): " monomer 1 " recorded in the paragraph (0501) of Japanese Unexamined Patent Publication 2013-028764 publication.Be equivalent to the ethylenically unsaturated monomers with anthraquinone chromophores.
The preparation > of < colourant solution
Preparation example 1
Make polymkeric substance (1) 10 weight portion obtained be dissolved in propylene glycol monomethyl ether 90 weight portion, make colourant solution (A-1).
Preparation example 2 ~ 14
In preparation example 1, by kind and the amount of the solute of change table 2 Suo Shi, solvent, in addition, carry out in the same manner as preparation example 1, prepare colourant solution (A-2) ~ (A-14).Should illustrate, in table 2, propylene glycol monomethyl ether is recited as " PGME ".
[table 2]
The synthesis > of < resin glue
Synthesis example 1
In the flask possessing cooling tube and stirring machine, load propylene glycol methyl ether acetate 100 mass parts and carry out nitrogen displacement.Be heated to 80 DEG C, at such a temperature, propylene glycol methyl ether acetate 100 mass parts, methacrylic acid 20 mass parts, styrene 10 mass parts, benzyl methacrylate 5 mass parts, 2-hydroxyethyl methacrylate 15 mass parts, 2-Ethylhexyl Methacrylate 23 mass parts, N-phenylmaleimide 12 mass parts, mono succinate (2-acryloyl-oxyethyl) 15 mass parts and 2 are dripped with 1 hour, 2'-azo two (2,4-methyl pentane nitrile) mixed solution of 6 mass parts, keep this temperature polymerizations 2 hours.Thereafter, make the temperature to 100 DEG C of reaction solution, polymerization 1 hour, obtains resin glue solution (solid component concentration 33 quality %) thus further.The Mw of the resin glue obtained is 12200, Mn is 6500.Using this resin glue as " resin glue (C1) ".
The preparation of < coloured composition and evaluation >
The preparation of coloured composition
Embodiment 1
Will as the colourant solution of (A) colorant (A-1) 16.5 mass parts, as resin glue (C1) solution 23.3 mass parts of (C) resin glue, as the dipentaerythritol acrylate of (B) polymerizable compound and potpourri (Nippon Kayaku K. K's system of Dipentaerythritol Pentaacrylate, trade name KAYARAD DPHA) 9.9 mass parts, as 2-benzyl-2-dimethylamino-1-(4-morphlinophenyl) butane-1-ketone (the trade name Irgacure369 of (D) Photoepolymerizationinitiater initiater, Ciba Specialty Chemicals Inc.) 1.8 mass parts and NCI-930 (Inc. of Asahi Denka Co., Ltd.) 0.1 mass parts, as fluorine system surfactant Megafac F-554 (Dainippon Ink Chemicals's system) 0.05 mass parts and mix as the propylene glycol methyl ether acetate of solvent, prepare the coloured composition (S-1) of solid component concentration 20 quality %.
The evaluation of contrast
After using spin coater to be coated with the coloured composition obtained on the glass substrate, carry out 10 minutes baking and banking up with earth in advance with the heating plates of 80 DEG C, form the film of thickness 2.5 μm.
Then, after this substrate cool to room temperature, use high-pressure sodium lamp, not across photomask with 2000J/m
2exposure the exposure of each film is comprised to the radioactive ray of each wavelength of 365nm, 405nm and 436nm.Thereafter, with the pressure 1kgf/cm that develops
2(nozzle diameter 1mm) sprayed the developer solution be made up of 0.04 quality % potassium hydroxide aqueous solution of 23 DEG C to this substrate with 90 seconds.Thereafter, clean this substrate with ultrapure water, after air-dry, cure after carrying out 30 minutes further in the cleaning oven of 200 DEG C, form evaluation cured film thus.
The substrate being formed with cured film is clipped with 2 deflecting plate, irradiate from rear side fluorescent light (wavelength coverage 380 ~ 780nm), rotate the deflecting plate of front face side simultaneously, utilize nitometer LS-100 (Minolta Co., Ltd. system) measure through the maximal value of light intensity and minimum value.And value maximal value obtained divided by minimum value spends ratio as a comparison.Evaluation result is shown in table 3.Should illustrate, contrast ratio is that the larger expression of numerical value is better.
The evaluation of thermotolerance
Use spin coater that coloured composition (S-1) is coated on the SiO that surface is formed with the stripping preventing sodion
2after on the soda-lime glass substrate of film, carry out 2 minutes baking and banking up with earth in advance with the heating plates of 90 DEG C, form the film of thickness 2.5 μm.
Then, after this substrate is cooled to room temperature, high-pressure sodium lamp is used across photomask with 400J/m
2exposure the exposure of each film is comprised to the radioactive ray of each wavelength of 365nm, 405nm and 436nm.Thereafter, 1kgf/cm is pressed to these substrates to develop
2(nozzle diameter 1mm) sprays the developer solution be made up of 0.04 quality % potassium hydroxide aqueous solution of 23 DEG C, carries out spray development in 90 seconds.Thereafter, clean this substrate with ultrapure water, after air-dry, cure after carrying out 30 minutes further in the cleaning oven of 200 DEG C, on substrate, form dot pattern thus.
To the dot pattern obtained, use color analysis instrument (Otsuka Electronics Co., Ltd. MCPD2000), with the chromaticity coordinate value (x, y) in illuminant-C, 2 degree of visual field mensuration CIE color specification systems and values (Y).
Then, after aforesaid substrate is added cure 90 minutes at 230 DEG C, measure chromaticity coordinate value (x, y) and values (Y), evaluate and adding the color change and Δ E of curing front and back
*ab.Its result, by Δ E
*the average evaluation that the value of ab is less than 3.0 is "○", and being less than the average evaluation of 5.0 for " △ " by more than 3.0, is "×" by the average evaluation of more than 5.0.Evaluation result is shown in table 3.Should illustrate, Δ E can be said
*ab value is less, and thermotolerance is better.
Embodiment 2 ~ 6 and comparative example 1 ~ 6
In embodiment 1, by the kind and the amount that change each composition table 3 Suo Shi, in addition, carry out similarly to Example 1, prepare coloured composition (S-2) ~ (S-12).Then, use coloured composition (S-2) ~ (S-12) to replace coloured composition (S-1), in addition, evaluate similarly to Example 1.Show the result in table 3.
Claims (6)
1. a coloured composition, wherein, containing (A) colorant and (B) polymerizable compound,
(A) colorant contains polymkeric substance, and this polymkeric substance has the position producing fluorescence and the position absorbing this fluorescence.
2. a coloured composition, wherein, containing (A) colorant and (B) polymerizable compound,
(A) colorant contains polymkeric substance, and this polymkeric substance has and is selected from
at least 1 chromophore in ton chromophore and cyanine chromophore and be selected from least 1 chromophore in triarylmethane chromophore and anthraquinone chromophores.
3. coloured composition according to claim 1 and 2, wherein, described polymkeric substance is selected from containing having
at least 1 chromophoric ethylenically unsaturated monomers in ton chromophore and cyanine chromophore is selected from the multipolymer of at least 1 chromophoric ethylenically unsaturated monomers in triarylmethane chromophore and anthraquinone chromophores as the ethylenically unsaturated monomers of structural unit with having.
4. coloured composition according to claim 1 and 2, wherein, further containing (C) resin glue.
5. a color solidification film, uses the coloured composition according to any one of claim 1 ~ 4 to be formed.
6. a display element, possesses color solidification film according to claim 5.
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| CN106918999A (en) * | 2015-12-28 | 2017-07-04 | 东友精细化工有限公司 | Photosensitive composition, colored filter and image display device |
| CN107092165A (en) * | 2016-02-17 | 2017-08-25 | 住友化学株式会社 | Colored curable resin composition, colour filter and the display device comprising the colour filter |
| CN108572515A (en) * | 2017-03-13 | 2018-09-25 | Jsr株式会社 | Coloured composition, coloring cured film, colored filter, display element, light receiving element, light-emitting component and pigment compound |
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| JP6350335B2 (en) * | 2014-02-27 | 2018-07-04 | Jsr株式会社 | Colored composition, colored cured film, and display element |
| JP6543275B2 (en) * | 2015-01-29 | 2019-07-10 | 富士フイルム株式会社 | Colored composition, color filter, pattern forming method, method of manufacturing color filter, solid-state imaging device, and image display device |
| JP2017088667A (en) * | 2015-11-04 | 2017-05-25 | Jsr株式会社 | Composition for forming colored cured film, colored cured film, method for forming colored cured film, and method for manufacturing display element |
| KR102361511B1 (en) * | 2015-12-18 | 2022-02-10 | 동우 화인켐 주식회사 | Colored photosensitive resin composition, color filter and image display device using the same |
| KR102498588B1 (en) | 2016-08-30 | 2023-02-10 | 동우 화인켐 주식회사 | Colored photosensitive resin composition, color filter, and image display apparatus comprising the same |
| KR102503367B1 (en) | 2016-11-16 | 2023-02-24 | 동우 화인켐 주식회사 | Colored photosensitive resin composition, color filter and image display device produced using the same |
| KR101998729B1 (en) * | 2016-12-27 | 2019-07-10 | 삼성에스디아이 주식회사 | Novel compound, photosensitive resin composition including the same and color filter |
| KR101998777B1 (en) | 2017-01-13 | 2019-07-10 | 동우 화인켐 주식회사 | Colored photosensitive resin composition, color filter and image display device produced using the same |
| KR20220121054A (en) | 2021-02-24 | 2022-08-31 | 동우 화인켐 주식회사 | Colored photosensitive composition, color filter, and image display device comprising the same |
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| CN104880910B (en) | 2020-01-03 |
| TWI704413B (en) | 2020-09-11 |
| KR102349690B1 (en) | 2022-01-12 |
| TW201543149A (en) | 2015-11-16 |
| JP2015178603A (en) | 2015-10-08 |
| JP6327173B2 (en) | 2018-05-23 |
| KR20150101934A (en) | 2015-09-04 |
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