CN103571233A - Salt for dye - Google Patents
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- CN103571233A CN103571233A CN201310300507.4A CN201310300507A CN103571233A CN 103571233 A CN103571233 A CN 103571233A CN 201310300507 A CN201310300507 A CN 201310300507A CN 103571233 A CN103571233 A CN 103571233A
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- 0 CCCC(C=C1)c(cccc2)c2C1=C(c(cc1)c(C)cc1N(CC)CC)*(c(F)c1)ccc1N(CC)CC Chemical compound CCCC(C=C1)c(cccc2)c2C1=C(c(cc1)c(C)cc1N(CC)CC)*(c(F)c1)ccc1N(CC)CC 0.000 description 6
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/02—Dyestuff salts, e.g. salts of acid dyes with basic dyes
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
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- Indole Compounds (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Abstract
Provided is a salt, which is characterized in that the salt is formed by negative ion expressed by the formula (1) and onium positive ion. In the formula (1), Z1 and Z2 respectively and independently express a group having two substituent groups, which are formed by releasing proton from a monovalent substituent group. The onium positive ion is a positive ion from anthocyanin dye, or a positive ion from triarylmethane dye, or a positive ion from xanthenes dye, or a positive ion from anthraquinone dye.
Description
Technical field
The present invention relates to as the useful salt of dyestuff.
Background technology
Dyestuff is for fields such as filamentary material, liquid crystal indicator, ink-jet and recording materials.
As such dyestuff, known for example have the represented compound of following formula (d-1), represented compound and represented compound (JP2008-106111-A, JP2011-100114-A and a Wuhan University Journal of formula (h-1) of formula (d-2), Li Xueban, Vol.51, the 6th phase, 699-703,2005).
Conventionally known above-claimed cpd, sometimes differs and fully meets surely the solvability in organic solvent.
Summary of the invention
The invention provides following [1]～[7].
[1], it is characterized in that, is the represented negatively charged ion of formula (1) and the cationic salt coming in the dyestuff of self energy and this negatively charged ion formation salt.
[in formula (1), Z
1and Z
2represent to have independently respectively two substituent groups, these two substituting groups are discharged proton and form for proton substituting group by 1 valency.]
[2] salt according to [1], wherein, described positively charged ion is positively charged ion from anthocyanin dye, from the positively charged ion of triarylmethane dye, from the positively charged ion of xanthene dye or from the positively charged ion of anthraquinone dye.
[3] according to the salt [1] or [2] described, wherein, Z
1and Z
2represent independently respectively any of group shown in following formula (a-1)～(a-10).
(in formula, R
21and R
22represent independently respectively hydrogen atom, can substituted carbonatoms 1～6 alkyl, can substituted carbonatoms 3～7 cycloalkyl or can substituted phenyl, R
23～R
92represent independently respectively the alkyl of hydrogen atom, carbonatoms 1～4, the alkoxyl group of carbonatoms 1～4, carbonatoms 1～4 haloalkyl, halogen atom, hydroxyl, amino or nitro.)
[4] according to the salt [3] described, wherein, Z
1and Z
2for formula (a-1), formula (a-5), formula (a-6) or the represented group of formula (a-8).
[5] according to the salt described in any one of [1]～[4], wherein, having two groups that formed for proton substituting group release proton by 1 valency is for 2 these protons of the substituent compound of proton, to supply with the group that substituents discharge respectively proton by having 21 valencys, there is the compound of 21 valency protons supply substituents for can there is substituent catechol, can have substituent 2, 3-dihydroxy naphthlene, can have substituent 2, 2 '-xenol, can there is substituent 3-hydroxy-2-naphthoic acid, can there is substituent 2-hydroxyl-1-naphthoic acid, can there is substituent 1-hydroxy-2-naphthoic acid, can there is substituent dinaphthol, can there is substituent Whitfield's ointment, can there is substituent benzilic acid or can there is substituent tussol.
[6], wherein, contain salt described in any one of [1]～[5] as its effective constituent.
[7], wherein, contain [6] described dyestuff.
Salt of the present invention, its solvability in organic solvent is excellent.
Embodiment
Salt of the present invention is the represented negatively charged ion of formula (1) and the cationic salt coming in the dyestuff of self energy and this negatively charged ion formation salt.
[in formula (1), Z
1and Z
2represent to have independently respectively two substituent groups, these two substituting groups are supplied with substituent by 1 valency proton and are discharged proton and form.]
Salt of the present invention-electric charge with+electric charge is identical.
As the dyestuff of salt can be formed with this negatively charged ion, there are for example anthocyanin dye, anthraquinone dye, triarylmethane dye, xanthene dye, phthalocyanine pigment, triarylmethane colouring matters, acridine dye, azines, thiazine dyes, oxazine dye, azomethine dyes and azoic dyestuff etc.Wherein, anthocyanin dye, triarylmethane dye, xanthene dye and anthraquinone dye are preferred.By the positively charged ion by from dyestuff, form such salt of the present invention, can demonstrate as the useful color characteristics of dyestuff.
As positively charged ion, have for example such as respectively from the ammonium cation of above-mentioned dyestuff, oxygen positively charged ion, sulfonium cation, phosphonium cation etc.
Below, to forming the positively charged ion of salt of the present invention, enumerating, become the dyestuff in its source and carry out particular instantiation.
From the positively charged ion of anthocyanin dye, for example there are for example the positively charged ion with cyanin skeleton that formula (1-1)～formula (1-42) represents respectively etc.In addition, in formula, " n-Pr " represents n-propyl, and " n-Bu " represents normal-butyl, and " s-Bu " represents sec-butyl.
As anthocyanin dye, there is for example the salt of positively charged ion that formula (1-1)～formula (1-42) represents respectively and above-mentioned balance anion.Balance anion has halide ions (for example, Cl for example
-, Br
-, I
-), perchloric acid negatively charged ion, salt acid anion, thiocyanic acid negatively charged ion, phosphorus hexafluoride negatively charged ion, antimony hexafluoride negatively charged ion, tetrafluoride boron anion, C
6h
5sO
3 -, CH
3-C
6h
4sO
3 -, CF
3sO
3 -deng.
As the dyestuff that the positively charged ion from triarylmethane dye is imported, there is for example C.I. alkalescence red 9, C.I. alkaline purple 1, C.I. alkalescence purple 2, C.I. alkaline purple 3, C.I. alkalescence purple 4, C.I. alkaline purple 13, C.I. basic violet 14, C.I. alkalescence purple 23, C.I. alkali blue 1, C.I. alkali blue 5, C.I. Blue 7, C.I. alkali blue 8, C.I. alkali blue 11, C.I. alkali blue 15, C.I. alkali blue 18, C.I. alkali blue 20, C.I. alkali blue 21, C.I. alkali blue 24, C.I. alkali blue 26, C.I. alkali green 1, C.I. alkali green 4 etc., and the dyestuff that represents respectively of following formula (g-1)～(g-7) etc.In addition, can become the dyestuff of these precursor, also for example have for example, C.I. solvent blue 5 (can become the precursor of C.I. Blue 7) etc.
As the dyestuff that positively charged ion from xanthene dye is imported, be xanthene dye, be the general name in molecule with the dyestuff of xanthene skeleton.Preferably on this xanthene skeleton, having at least one can substituted amino, and more preferably having two can substituted amino.The positively charged ion containing in salt of the present invention, preferably have can substituted amino nitrogen-atoms with the positively charged ion of the structure of positive charge, be more preferably imines positively charged ion.
Such xanthene dye, has rhodamine (Rosamine) based dye of eosin (Eosin) based dye, fluorescein (Fluorescein) based dye, rhodamine (Rhodamine) based dye, pyrrole Luo Hong (Pyronine) based dye, nothing 2 '-carboxyl etc. for example.In addition, can also exemplify as Synlett, 2010, No.1, rhodamine (Rosamine) based dye of rhodamine (Rhodamine) based dye that Sauerstoffatom that p.89-92 recorded, xanthene skeleton is replaced by sulphur atom, selenium atom or tellurium atom or nothing 2 '-carboxyl etc.
Xanthene dye has Cl conventionally
-or PF
6 -deng inorganic anion, or in molecule, there is carboxylate group (COO
-) or sulphonate-base (SO
3 -) etc. acidic groups.The former situation, xanthene dye is so-called basic dyestuff, from the positively charged ion of xanthene dye, normally from xanthene dye, has removed the positively charged ion of part or all (preferably whole) of inorganic anion.The latter's situation, xanthene dye is so-called inner salt, the positively charged ion of the structure that part or all (preferably whole) of normally having an acidic groups that such inner salt has from the positively charged ion of xanthene dye have been neutralized.Here, acidic groups for example, carboxylate group (COO
-) group that has been neutralized is carboxyl (COOH) or its salt (COONa etc.), sulphonate-base (SO
3 -) group that has been neutralized is sulfo group (SO
3h) or its salt (SO
3na etc.).
The concrete example of xanthene dye neutral and alkali dyestuff, has that C.I. alkali red 1:1, C.I. alkalescence is red 2, C.I. alkalescence is red 3, C.I. alkalescence is red 4, alkalescence is red 8, the dyestuff of alkali red 1:1 1, C.I. alkaline purple 10, C.I. alkali violet 11:1, C.I. alkalescence purple 25 and following formula (h-1)～(h-86) represent respectively etc. for example.
As the concrete example of inner salt in xanthene dye, there is for example dyestuff that C.I. medium red 27 and following formula (h-100)～(h-122) represent respectively etc.
Dyestuff as the positively charged ion from anthraquinone dye is imported, has C.I. alkali blue 22, C.I. Basic Blue 35, C.I. alkali blue 45, C.I. alkali blue 47 etc. for example.
Formula (1)
[in formula (1), Z
1and Z
2represent to have independently respectively two substituent groups, these two substituting groups are supplied with substituent by 1 valency proton and are discharged proton and form.]
In represented negatively charged ion, there are 2 and supply with that substituent discharges proton and the substituent groups that form by 1 valency proton, to discharge respectively the formed group of proton by 2 these confession proton substituting groups with the compound of 21 valency protons supply substituents, in formula (1), Jie is by 2 bonding positions that discharge this proton, Z
1, Z
2respectively with boron atom phase bonding.As 1 valency proton, supply with substituent, there can be exemplified carboxyl, hydroxyl etc.
Z
1, Z
2, there can be exemplified the group that following formula (a1)～(a10) represents.
(in formula, R
21and R
22represent independently respectively hydrogen atom, can substituted carbonatoms 1～6 alkyl, can substituted carbonatoms 3～7 cycloalkyl or can substituted phenyl, R
23～R
92represent independently respectively the alkyl of hydrogen atom, carbonatoms 1～4, haloalkyl, halogen atom, hydroxyl, amino or the nitro of the alkoxyl group of carbonatoms 1～4, carbonatoms 1～4.)
Z
1, Z
2the group that preferably formula (a-1), formula (a-5), formula (a-6) and formula (a-8) represent, the group that further preferably formula (a-1) and formula (a-8) represent, is further more preferably the represented group of formula (a-1).From manufacturing easy aspect, preferred Z
1with Z
2identical.In addition, in formula (1), Z
1, Z
2preferred and boron atomic linkage forms 5 rings, 6 rings or 7 rings that contain this boron atom respectively.
As the compound with 21 valency protons supply substituents, preferably can there is substituent catechol, can have substituent 2,3-dihydroxy naphthlene, can have and substituent 2,2 ' xenol, can there is substituent 3-hydroxy-2-naphthoic acid, can there is substituent 2-hydroxyl-1-naphthoic acid, can there is substituent 1-hydroxy-2-naphthoic acid, can there is substituent dinaphthol, can there is substituent Whitfield's ointment, can there is substituent benzilic acid or can there is substituent tussol.
As thering is described substituent Whitfield's ointment, for example have for example, Whitfield's ointment, 3-cresotinic acid, 3-tertiary butyl Whitfield's ointment, 3-aminosallcylic acid, 3-chloro-salicylic acid, 4-bromo ortho-oxybenzoic acid, 3-methoxyl group Whitfield's ointment, 3-Nitrosalicylic Acid, 4-trifluoromethyl Whitfield's ointment, 3, 5-di-tert-butyl salicylic acid, 3, 5-dibromosalicylic acid, 3, 5-dichlorosalicylic acid, 3, 5, 6-tri-chloro-salicylic acids, 3-hydroxyl Whitfield's ointment (another name: 2, 3-dihydroxyl M-nitro benzoic acid), 4-hydroxyl Whitfield's ointment (another name: 2, 4-dihydroxyl M-nitro benzoic acid), 5-hydroxyl Whitfield's ointment (another name: 2, 5-dihydroxyl M-nitro benzoic acid), 6-hydroxyl Whitfield's ointment (another name: 2, 6-dihydroxyl M-nitro benzoic acid) etc.
As thering is described substituent benzilic acid, for example have for example,
As thering is described substituent tussol, for example have for example,
Deng.
There are 2 and supply with that substituent discharges proton and the concrete example of the substituent groups that form by 1 valency proton, as with to salicylic
The same, can enumerate above-mentioned have 21 valency protons supply with in each example of compound of substituents, from 2 these protons, supply with substituents and eliminate respectively the group proton.
The represented negatively charged ion of formula (1), such as enumerating negatively charged ion (BC-1)～negatively charged ion (BC-28) etc.
[table 1]
Wherein, as the represented negatively charged ion of formula (1), preferred anionic (BC-1), negatively charged ion (BC-2), negatively charged ion (BC-3), negatively charged ion (BC-25), negatively charged ion (BC-26), negatively charged ion (BC-27), more preferably negatively charged ion (BC-1), negatively charged ion (BC-25), further preferred anionic (BC-1).If these negatively charged ion, the solvability of salt of the present invention in organic solvent has the tendency that becomes excellent.
Salt of the present invention, has salt (I-1)～salt (I-90) etc. for example.
[table 2]
| Salt | Positively charged ion from dyestuff | The negatively charged ion that formula (1) represents |
| Salt (I-1) | The positively charged ion that formula (1-2) represents | (BC-1) |
| Salt (I-2) | The positively charged ion that formula (1-10) represents | (BC-1) |
| Salt (I-3) | C.I. the positively charged ion of Blue 7 | (BC-1) |
| Salt (I-4) | C.I. the positively charged ion of alkaline purple 3 | (BC-1) |
| Salt (I-5) | C.I. the positively charged ion of alkali blue 18 | (BC-1) |
| Salt (I-6) | C.I. the positively charged ion of alkali blue 26 | (BC-1) |
| Salt (I-7) | C.I. the positively charged ion of alkaline purple 10 | (BC-1) |
| Salt (I-8) | C.I. the positively charged ion of alkali violet 11:1 | (BC-1) |
| Salt (I-9) | C.I. the positively charged ion of alkali red 1:1 | (BC-1) |
| Salt (I-10) | C.I. the positively charged ion of alkali blue 22 | (BC-1) |
| Salt (I-11) | The positively charged ion that formula (1-2) represents | (BC-2) |
| Salt (I-12) | The positively charged ion that formula (1-10) represents | (BC-2) |
| Salt (I-13) | C.I. the positively charged ion of Blue 7 | (BC-2) |
| Salt (I-14) | C.I. the positively charged ion of alkaline purple 3 | (BC-2) |
| Salt (I-15) | C.I. the positively charged ion of alkali blue 18 | (BC-2) |
| Salt (I-16) | C.I. the positively charged ion of alkali blue 26 | (BC-2) |
| Salt (I-17) | C.I. the positively charged ion of alkaline purple 10 | (BC-2) |
| Salt (I-18) | C.I. the positively charged ion of alkali violet 11:1 | (BC-2) |
| Salt (I-19) | C.I. the positively charged ion of alkali red 1:1 | (BC-2) |
| Salt (I-20) | C.I. the positively charged ion of alkali blue 22 | (BC-2) |
| Salt (I-21) | The positively charged ion that formula (1-2) represents | (BC-25) |
| Salt (I-22) | The positively charged ion that formula (1-10) represents | (BC-25) |
| Salt (I-23) | C.I. the positively charged ion of Blue 7 | (BC-25) |
| Salt (I-24) | C.I. the positively charged ion of alkaline purple 3 | (BC-25) |
| Salt (I-25) | C.I. the positively charged ion of alkali blue 18 | (BC-25) |
| Salt (I-26) | C.I. the positively charged ion of alkali blue 26 | (BC-25) |
| Salt (I-27) | C.I. the positively charged ion of alkaline purple 10 | (BC-25) |
| Salt (I-28) | C.I. the positively charged ion of alkali violet 11:1 | (BC-25) |
| Salt (I-29) | C.I. the positively charged ion of alkali red 1:1 | (BC-25) |
| Salt (I-30) | C.I. the positively charged ion of alkali blue 22 | (BC-25) |
[table 3]
Salt of the present invention can be by mixing dyestuff to make with an alkali metal salt of the negatively charged ion of formula (1) expression in solvent.As basic metal, lithium, sodium, potassium etc. have been enumerated.
The solvent using during mixing, there is for example N, dinethylformamide, N,N-dimethylacetamide, N-Methyl pyrrolidone, dimethyl sulfoxide (DMSO), acetonitrile, vinyl acetic monomer, toluene, methyl alcohol, ethanol, Virahol, acetone, tetrahydrofuran (THF), diox, water, chloroform etc.
Wherein, preferred DMF, N,N-dimethylacetamide, N-Methyl pyrrolidone, dimethyl sulfoxide (DMSO), methyl alcohol, ethanol, Virahol and water.If these solvents, the solubleness of an alkali metal salt of the negatively charged ion that dyestuff and formula (1) represent has the tendency uprising.
When solvent is water, for an alkali metal salt of the negatively charged ion of dyestuff and formula (1) expression is dissolved in solvent, also can add the acid of acetic acid or hydrochloric acid etc.
Mixing of an alkali metal salt of the negatively charged ion that dyestuff represents with formula (1), can be dissolved in both in above-mentioned solvent and carry out, and also can in the situation that not dissolving both, carry out.But, use to dissolve both solvents, and make it to dissolve and carry out, can obtain with high yield salt of the present invention.
The mixing temperature of an alkali metal salt of the negatively charged ion that dyestuff and formula (1) represent, preferably 0 ℃～150 ℃, more preferably 10 ℃～120 ℃, further preferably 20 ℃～100 ℃.
In addition, mixing time preferably 1 hour～72 hours, more preferably 2 hours～24 hours, further preferably 3 hours～12 hours.
When the solvent for mixing is when with the molten solvent of water, in this solution, add ion exchanged water, further stir 1～3 hour.Afterwards, if obtain precipitate by filtration, just can obtain salt of the present invention.As required, can also be with washing in ion exchanged water.
When the solvent for mixing is when with the immiscible solvent of water, in this solution, add ion exchanged water, further stir 1～3 hour.Afterwards, if obtain organic layer by separatory, just can obtain the solution that contains salt of the present invention.As required, can also be with washing in ion exchanged water.By the solution from containing salt of the present invention, except desolventizing, can obtain salt of the present invention.
Further, can also make salt of the present invention be dissolved in acetonitrile, ethyl acetate, toluene, methyl alcohol, ethanol, Virahol, acetone, chloroform equal solvent, by recrystallize, purify.
Dyestuff can be used commercially available product, for example, can use with thin Tian Fengzhu " theoretical manufacture dyestuff chemistry ", skill report hall, 396～402,357～366,369～377 and 235～241 pages, pine and occupy and just setting chief editor " functional pigmented synthetic and utilisation technology ", CMC publication, 89～96 Page, Synlett, 2010, No.1, p.89-92, J.Organic Chemistry, 2008, Vol.73, the dyestuff that the known method that 8711-8718 etc. record is manufactured.
An alkali metal salt of the negatively charged ion that formula (1) represents, can be used commercially available product, for example, can be according to JP4097704-B or JP4341251-B and Journal of The Electrochemical Society, the method manufacture that the Vol.148 phase 1,2001 is recorded.
The salt of the present invention obtaining like this, useful as dyestuff.In addition, salt of the present invention, because its solvability in organic solvent is high, so the dyestuff using in the special colour filter as display unit such as liquid crystal indicators is useful.
Dyestuff of the present invention is to take the dyestuff that salt of the present invention is effective constituent.
Coloured composition of the present invention, contains dyestuff of the present invention as tinting material (being sometimes referred to as below " tinting material (A) "), further preferably contains resin (B).Coloured composition of the present invention, more preferably contains polymerizable compound (C), polymerization starter (D) and solvent (E) further.
Tinting material (A), except dyestuff of the present invention, can also further contain pigment and/or the dyestuff different from dyestuff of the present invention.
The dyestuff different from dyestuff of the present invention, have for example in Colour Index (Colour Index) (The Society of Dyers and Colourists publication), be classified as solvent (Solvent), acid (Acid), alkalescence (Basic), active (reactive), directly (Direct), disperse the dyestuff of (Disperse) or reduction (Vat) etc.More specifically, there is for example the dyestuff of Colour Index as described below (C.I.) numbering, but be not limited to these.C.I. solvent yellow 25,79, and 81,82,83,89;
C.I. turmeric yellow 7,23, and 25,42,65,76;
C.I. reactive yellow 2,76, and 116;
C.I. directly yellow 4,28,44,86,132;
C.I. DISPERSE YELLOW 54,76;
C.I. solvent orange 41,54, and 56,99;
C.I. von Muller's indicator 56,74, and 95,108,149,162;
C.I. reactive orange 16;
C.I. direct orange 26;
C.I. solvent red 24,49,90,91,118,119,122,124,125,127,130,132,160,218;
C.I. Xylene Red 73,91, and 92,97,138,151,211,274,289;
C.I. acid violet 102;
C.I. solvent green 1,5;
C.I. acid green 3,5,9,25,28;
C.I. alkali green 1;
C.I. Vat green 1 etc.
As pigment, there are for example the pigment dyestuff or the mineral dye that in common colo(u)rant dispersion resist, use.Mineral dye has for example, and the metallic compound of metal oxide or metallic complex salt and so on particularly, has oxide compound or the complex metal oxides of the metal of iron, cobalt, aluminium, cadmium, lead, copper, titanium, magnesium, chromium, zinc, antimony etc. for example.In addition, as pigment dyestuff and mineral dye, there is for example particularly the compound that is classified as pigment (Pigment) in Colour Index (Colour Index) (The Society of Dyers and Colourists publication).More specifically, there is for example the pigment of Colour Index (C.I.) numbering as follows, but be not limited thereto.
C.I. Pigment Yellow 73 20,24,31,53,83,86,93,94,109,110,117,125,137,138,139,147,148,150,153,154,166,173 and 180;
C.I. pigment Orange 13,31,36,38,40,42,43,51,55,59,61,64,65 and 71;
C.I. Pigment Red 9,97,105,122,123,144,149,166,168,176,177,180,192,215,216,224,242,254,255 and 264;
C.I. pigment violet 14,19,23,29,32,33,36,37 and 38;
C.I. pigment Green 7,10,15,25,36,47 and 58 etc.
The content of tinting material (A), with respect to the solids component in coloured composition, is preferably 5～60 quality %.Here, solids component refers to the total of the composition of having removed the solvent in coloured composition.
The content of the dyestuff of the present invention containing in tinting material (A), is preferably 3～100 quality %.
Dyestuff and the pigment different from dyestuff of the present invention, can be used separately respectively or combine two or more and use together with dyestuff of the present invention.
Resin (B) is not particularly limited, can uses resin arbitrarily.Resin (B) is alkali soluble resin preferably, is more preferably and contains the resin of leading from (methyl) acrylic acid structural unit.Here, (methyl) vinylformic acid represents vinylformic acid and/or methacrylic ester.
Resin (B) concrete example has methacrylic acid/methacrylic acid benzene methyl multipolymer, methacrylic acid/methacrylic acid benzene methyl/styrol copolymer, methacrylic acid/methacrylic acid benzene methyl/isobornyl methacrylate multipolymer, methacrylic acid/styrene/methacrylic acid benzene methyl/N-phenyl maleic anhydride contracting imine copolymer, methacrylic acid/styrene/methacrylic acid glycidyl ester copolymer etc.
The polystyrene conversion weight-average molecular weight of resin (B), preferably 5,000～35,000, more preferably 6,000～30,000.
The acid number of resin (B), preferably 50～150mg-KOH/g, more preferably 60～135mg-KOH/g.
The content of resin (B), with respect to the solids component of coloured composition, is preferably 7～65 quality %, more preferably 13～60 quality %.
Polymerizable compound (C), so long as the compound of polymerization is carried out in the living radical that can produce by auto-polymerization initiator (D), acid etc., is not just particularly limited.For example, can enumerate the compound etc. of the ethene unsaturated link(age) with polymerizability.。
Described polymerizable compound (C), preferably has 3 polymerizable compounds of polymerizable groups above.The polymerizable compound with 3 above polymerizable groups, can exemplify pentaerythritol tetracrylate, pentaerythritol tetramethacrylate, five vinylformic acid dipentaerythritol ester, pentamethyl-vinylformic acid dipentaerythritol ester, six vinylformic acid dipentaerythritol ester, hexamethyl vinylformic acid dipentaerythritol ester etc.Described polymerizable compound (C), can be used singly or in combination of two or more thereof.
The content of polymerizable compound (C), with respect to the solids component of coloured composition, is preferably 5～65 quality %, more preferably 10～60 quality %.
Described polymerization starter (D) is that living radical produces agent, acid producing agent etc.Living radical produces agent by the effect generation living radical of heat or light.Described living radical produces agent, has for example alkyl phenones compound, thioxanthone compound, triaizine compounds, oxime compound etc.
Described alkyl phenones compound, has such as 2-methyl-2-morpholino base-1-(4-first sulfydryl phenyl) propane-1-ketone, 2-hydroxy-2-methyl-1-phenyl-propane-1-ketone, benzyl dimethyl ketal, 2-hydroxy-2-methyl-1-(4-(2-hydroxyl-oxethyl) phenyl) propane-1-ketone, 1-hydroxy-cyclohexyl phenyl ketone etc. for example.
As described thioxanthone compound, there are for example for example ITX, ITX, 2,4-diethyl thioxanthone, 2,4-bis-clopenthixal ketones, the chloro-4-propoxy-of 1-thioxanthone etc.
Described triaizine compounds, have for example 2, two (the trichloromethyl)-6-(4-p-methoxy-phenyl)-1 of 4-, 3, 5-triazine, 2, two (the trichloromethyl)-6-(4-methoxyl group naphthyl)-1 of 4-, 3, 5-triazine, 2, two (the trichloromethyl)-6-(4-methoxyl-styrene)-1 of 4-, 3, 5-triazine, 2, two (the trichloromethyl)-6-(2-(5-methyl furan-2-yl) vinyl)-1 of 4-, 3, 5-triazine, 2, two (the trichloromethyl)-6-(2-(furans-2-yl) vinyl)-1 of 4-, 3, 5-triazine, 2, two (the trichloromethyl)-6-(2-(4-diethylamino-2-aminomethyl phenyl) vinyl)-1 of 4-, 3, 5-triazine, 2, (2-(3 for two (the trichloromethyl)-6-of 4-, 4-Dimethoxyphenyl) vinyl)-1, 3, 5-triazine etc.
Described oxime compound; there is for example for example adjacent acyl group oxime compound; as its concrete example; have for example N-benzoyloxy-1-(4-phenyl sulfydryl phenyl) butane-1-ketone-2-imines, N-benzoyloxy-1-(4-phenyl sulfydryl phenyl) octane-1-ketone-2-imines, N-acetoxyl group-1-[9-ethyl-6-(2-methyl benzoyl)-9H-carbazole-3-yl] ethane-1-imines, N-acetoxyl group-1-[9-ethyl-6-{2-methyl-4-(3; 3-dimethyl-2,4-dioxa cyclopentyl-methyl oxygen base) benzoyl }-9H-carbazole-3-yl] ethane-1-imines etc.
In addition, as living radical, produce agent, also can use as 2,4,6-Three methyl Benzene formyl diphenyl phosphine oxide, 2,2 '-bis-(adjacent chlorophenyls)-4,4 ', 5,5 '-tetraphenyl-1,2 '-bis-imidazoles, 10-butyl-2-chloro dihydroketoacridine, 2-ethyl-anthraquinone, dibenzoyl, 9,10-phenanthrenequione, camphorquinone, phenyl glyoxalic acid methylester, two cyclopentadiene titanium compounds etc.
Described acid producing agent, has salt such as 4-hydroxy phenyl dimethyl sulfonium tosilate, 4-hydroxy phenyl dimethyl sulfonium hexafluoro antimonate, 4-acetoxyl group phenyl dimethyl sulfonium tosilate, 4-acetoxyl group phenyl methyl benzyl sulfonium hexafluoro antimonate, triphenylsulfonium tosilate, triphenylsulfonium hexafluoro antimonate, phenylbenzene iodine tosilate, phenylbenzene iodine hexafluoro antimonate etc., nitrobenzyl toluenesulphonic acids salt, st-yrax toluenesulphonic acids salt etc. for example.
Described polymerization starter, can also can be used in combination two or more separately.
The content of polymerization starter (D), total amount 100 mass parts with respect to resin (B) and polymerizable compound (C), are preferably 0.1～30 mass parts, more preferably 1～20 mass parts.The content of polymerization starter (D), when above-mentioned scope, shortens the time shutter, productivity improves, therefore preferably because of high-sensitivity.
As solvent (E), have for example such as: ethers, aromatic hydrocarbon based, ketone, alcohols, ester class, amides etc.
Described ethers, , for example have for example, tetrahydrofuran (THF), tetrahydropyrans, 1, 4-diox, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, diethylene glycol dimethyl ether, Diethylene Glycol (two) ether, Diethylene Glycol MEE, Diethylene Glycol dipropyl ether, dibutyl ethylene glycol ether, propylene glycol methyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetic ester, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetic ester, butyl carbitol acetate etc.
Described aromatic hydrocarbon based, have for example such as, benzene,toluene,xylene, mesitylene etc.
Described ketone, for example has for example, acetone, 2-butanone, 2-heptanone, 3-heptanone, dipropyl ketone, 4-methyl-2 pentanone, 4-hydroxy-4-methyl-2-pentanone, cyclopentanone, pimelinketone etc.
Described alcohols, for example has for example, methyl alcohol, ethanol, propyl alcohol, butanols, hexanol, hexalin, ethylene glycol, glycerol etc.
Described ester class, for example have for example, ethyl acetate, n-butyl acetate, isobutyl acetate, pentyl formate, isoamyl acetate, isobutyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, alkyl esters, methyl lactate, ethyl lactate, n-Butyl lactate, methoxy menthyl acetate, methoxyacetic acid ethyl ester, methoxyacetic acid butyl ester, ethoxy acetate, oxyethyl group vinyl acetic monomer, 3-methoxy methyl propionate, 3-methoxyl group-propionic acid ethyl ester, 3-ethoxy-propionic acid methyl esters, 3-ethoxyl ethyl propionate, 2-methoxy methyl propionate, 2-methoxy propyl acetoacetic ester, 2-methoxy propyl propyl propionate, 2-ethoxy-propionic acid methyl esters, 2-ethoxyl ethyl propionate, 2-methoxyl group-2-methyl-methyl propionate, 2-oxyethyl group-2-methyl-ethyl propionate, Pyruvic Acid Methyl ester, Pyruvic Acid Ethyl ester, Propyl pyruvate, methyl acetoacetate, methyl aceto acetate, 3-methoxyl group butylacetic acid ester, 3-methyl-3-methoxyl group butylacetic acid ester, gamma-butyrolactone etc.
Described amides, for example has for example, DMF, N,N-dimethylacetamide, N-Methyl pyrrolidone etc.
These solvents can be used alone, also two or more use capable of being combined.
The content of the solvent in coloured composition (E), with respect to coloured composition, is preferably 70～95 quality %, more preferably 75～90 quality %.
Photosensitive composition of the present invention, can contain the various additives of tensio-active agent, weighting agent, other macromolecular compounds, adhesion promotor, antioxidant, ultraviolet Line absorption agent, photostabilizer, chain-transfer agent etc. as required.
Salt of the present invention is useful as dyestuff.Because molar absorptivity is high and show high solvability in organic solvent, therefore the dyestuff especially using in the colour filter as display unit such as liquid crystal indicators is useful.
In addition, the coloured composition that contains salt of the present invention, can be in known manner for having in for example, the machine being associated with various rendered images as the display unit (, known liquid crystal indicator, organic El device etc.) of a part for its component parts, solid-state imager etc. of colour filter.
Embodiment
Below, by embodiment, describe further photosensitive composition of the present invention in detail." % " in example and " part ", as long as no special record, are exactly quality % and mass parts.
The synthesis example 1 of an alkali metal salt of the negatively charged ion that formula (1) represents
In 1.30 parts of lithium hydroxide monohydrates (with the pure pharmaceutical worker's industry of light (strain) system), add 13 parts of methyl alcohol, under 60 degree, stir.Be added in further in 67 parts of methyl alcohol, dissolved 1.92 parts of boric acid (with the pure pharmaceutical worker's industry of light (strain) system) with 11.55 part 2,2 ' solution of xenol (Tokyo changes into industry (strain) system) stirs 7 hours under 60 degree.This mixed solution is cooling until after room temperature, suction filtration obtains precipitate, with 70 parts of washing with acetones, obtain the compound of formula (BC-26-Li) expression of 5.62 parts.
The synthesis example 2 of an alkali metal salt of the negatively charged ion that formula (1) represents
In 2.00 parts of sodium hydroxide (with the pure pharmaceutical worker's industry of light (strain) system), add 100 parts of methyl alcohol, make its dissolving.Further, add 16.02 part 2,3-dihydroxy naphthlene (Tokyo changes into industry (strain) system) and 3.09 parts of boric acid (with the pure pharmaceutical worker's industry of light (strain) system), at room temperature stir two hours, further under 65 degree, stirs 8 hours.This mixed solution is cooled to after room temperature, and suction filtration obtains precipitate, with 268 parts of ion exchanged waters, 331 parts of methyl alcohol, 869 parts of acetonitrile washings, obtains the compound of formula (BC-25-Na) expression of 4.16 parts.
The synthesis example 3 of an alkali metal salt of the negatively charged ion that formula (1) represents
In 2.00 parts of sodium hydroxide (with the pure pharmaceutical worker's industry of light (strain) system), add 50 parts of methyl alcohol, make its dissolving.Further, add 18.82 parts of 3-hydroxy-2-naphthoic acids (Tokyo changes into industry (strain) system) are dissolved in to the solution forming in 50 parts of methyl alcohol, be warming up to 65 degree, stir 15 minutes.Further, add 3.09 parts of boric acid (with the pure pharmaceutical worker's industry of light (strain) system), under 65 degree, stir 6 hours.This mixed solution is cooling until after room temperature, suction filtration obtains precipitate, by 607 parts of ion exchanged waters, 95 parts of methanol wash, obtain the compound of formula (BC-27-Na) expression of 15.34 parts.
The synthesis example 4 of an alkali metal salt of the negatively charged ion that formula (1) represents
In 1.30 parts of lithium hydroxide monohydrates (with the pure pharmaceutical worker's industry of light (strain) system), add the water of 19 parts, at room temperature stir.Further, add 1.92 parts of boric acid (with the pure pharmaceutical worker's industry of light (strain) system) with 9.56 part 2,4-resorcylic acid (Tokyo changes into industry (strain) system) stirs 1 hour under 100 degree.This mixed solution is cooling until after room temperature, suction filtration obtains precipitate, with 50 parts of cold ion-exchange water washings, obtain the compound of formula (BC-3-Li) expression of 5.90 parts.
The synthesis example 5 of an alkali metal salt of the negatively charged ion that formula (1) represents
In 2.00 parts of sodium hydroxide (with the pure pharmaceutical worker's industry of light (strain) system), add 50 parts of methyl alcohol, make its dissolving.Further, add 15.41 parts of DHBs (Tokyo changes into industry (strain) system) and 3.09 parts of boric acid (with the pure pharmaceutical worker's industry of light (strain) system), at room temperature stir 3.5 hours, further under 65 degree, stir 5 hours.This mixed solution is cooled to after room temperature, and suction filtration obtains precipitate, by 15 parts of methanol wash, obtains the compound of formula (BC-2-Na) expression of 6.78 parts.
The synthesis example 6 of an alkali metal salt of the negatively charged ion that formula (1) represents
In 2.00 parts of sodium hydroxide (with the pure pharmaceutical worker's industry of light (strain) system), add 50 parts of methyl alcohol, make its dissolving.Further, add 15.41 parts of 2,6-DHBAs (Tokyo changes into industry (strain) system) and 3.09 parts of boric acid (with the pure pharmaceutical worker's industry of light (strain) system), under 65 degree, stir 8.5 hours.This mixed solution is cooled to after room temperature, and suction filtration obtains precipitate, with 237 parts of ion-exchange water washings, obtains the compound of formula (BC-1-Na) expression of 10.90 parts.
Embodiment 1
At the compound dissolution that 2.00 parts (h-1) represented, in the solution of 10 parts of N-Methyl pyrrolidone, under room temperature, be added on the solution that has dissolved the compound that the formula (BC-26-Li) of 1.26 parts represents in 19 parts of N-Methyl pyrrolidone, stir 8 hours.In this mixed solution, add 116 parts of ion exchanged waters, further stir 4 hours.Afterwards, suction filtration obtains precipitate, with 144 parts of ion-exchange water washings, obtains the salt of formula (I-83) expression of 2.07 parts.
Embodiment 2
In solution at the compound dissolution that 2.00 parts (h-1) represented in 10 parts of N-Methyl pyrrolidone, under room temperature, be added on the solution that has dissolved the compound of 1.15 parts of formulas (BC-25-Na) expressions in 5.7 parts of N-Methyl pyrrolidone, stir 6 hours.In this mixed solution, add 63 parts of ion exchanged waters, further stir 1 hour.Afterwards, suction filtration obtains precipitate, with 64 parts of ion-exchange water washings, obtains the salt of formula (I-63) expression of 2.65 parts.
Embodiment 3
In solution at the compound dissolution that 2.00 parts (h-1) represented in 10 parts of N-Methyl pyrrolidone, under room temperature, be added on the solution that has dissolved the compound of 1.33 parts of formulas (BC-3-Li) expressions in 6.7 parts of N-Methyl pyrrolidone, stir 7 hours.In this mixed solution, add 67 parts of ion exchanged waters, further stir 1 hour.Afterwards, suction filtration obtains precipitate, with 67 parts of ion-exchange water washings, obtains the salt of formula (I-82) expression of 2.76 parts.
Embodiment 4
In solution at the compound dissolution that 2.00 parts (h-1) represented in 10 parts of N-Methyl pyrrolidone, under room temperature, be added on the solution that has dissolved the compound of 1.05 parts of formulas (BC-2-Na) expressions in 5.3 parts of N-Methyl pyrrolidone, stir 7 hours.In this mixed solution, add 61 parts of ion exchanged waters, further stir 1 hour.Afterwards, suction filtration obtains precipitate, with 65 parts of ion-exchange water washings, obtains the salt of formula (I-48) expression of 2.44 parts.
Embodiment 5
In solution at the compound dissolution that 2.00 parts (h-1) represented in 10 parts of N-Methyl pyrrolidone, under room temperature, be added on the solution that has dissolved the compound of 1.11 parts of formulas (BC-1-Na) expressions in 5.5 parts of N-Methyl pyrrolidone, stir 7 hours.In this mixed solution, add 124 parts of ion exchanged waters, further stir 1 hour.Afterwards, suction filtration obtains precipitate, with 124 parts of ion-exchange water washings, obtains the salt that 1.02 parts of formulas (I-31) represent.
Embodiment 6
In solution at the compound dissolution that 2.00 parts (h-1) represented in 10 parts of N-Methyl pyrrolidone, under room temperature, be added on the solution that has dissolved the compound of 1.11 parts of formulas (BC-27-Na) expressions in 5.5 parts of N-Methyl pyrrolidone, stir 7 hours.In this mixed solution, add 62 parts of ion exchanged waters, further stir 1 hour.Afterwards, suction filtration obtains precipitate, with 42 parts of ion-exchange water washings, obtains the salt of formula (I-84) expression of 2.89 parts.
Embodiment 7
2.00 parts of C.I. alkali violet 11:1s (Aizen Cathilon Brilliant Pink CD-BH, hodogaya chemical industry (strain) system) are being dissolved in 10 parts of solution in N-Methyl pyrrolidone, under room temperature, be added on the solution that has dissolved the compound of 1.38 parts of formulas (BC-2-Na) expressions in 6.9 parts of N-Methyl pyrrolidone, stir 7 hours.In this mixed solution, add 68 parts of ion exchanged waters, further stir 1 hour.Afterwards, suction filtration obtains precipitate, with 145 parts of ion-exchange water washings, obtains the salt of formula (I-18) expression of 2.83 parts.
Embodiment 8
2.00 parts of C.I. alkali violet 11:1s (Aizen Cathilon Brilliant Pink CD-BH, hodogaya chemical industry (strain) system) are being dissolved in 10 parts of solution in N-Methyl pyrrolidone, under room temperature, be added on the solution that has dissolved the compound of 1.33 parts of formulas (BC-25-Na) expressions in 6.7 parts of N-Methyl pyrrolidone, stir 7 hours.In this mixed solution, add 67 parts of ion exchanged waters, further stir 1 hour.Afterwards, suction filtration obtains precipitate, with 50 parts of ion-exchange water washings, obtains the salt of formula (I-28) expression of 2.50 parts.
Embodiment 9
In the compound representing in 4.00 parts of formulas (XA-1), add 28 parts of N-Methyl pyrrolidone, under room temperature, stir.Further, add 6.85 parts of dibutylamines (Tokyo changes into industry (strain) system), be warming up to 65 degree, stir 1.5 hours.This mixed solution is cooling until after room temperature, limit remains on below 25 degree, and add in 10% hydrochloric acid of 388 parts on limit, further stirs 1 hour.Suction filtration obtains precipitate, with 388 parts of ion-exchange water washings, obtains the compound of formula (h-120) expression of 3.01 parts.
In solution at the compound dissolution that 1.00 parts (h-120) represented in 5 parts of N-Methyl pyrrolidone, under room temperature, add the compound that 0.57 part of formula (BC-1-Na) represents, be warming up to 60 degree, stir 9 hours.This mixed solution is cooled to after room temperature, adds the salt solution of 20 part 10%, further stir 1 hour.Afterwards, suction filtration obtains precipitate, with 19 parts of ion-exchange water washings, obtains the salt of formula (I-45) expression of 1.38 parts.
Embodiment 10
At room temperature mix compound, 40 parts of isopropyl alcohol (with the pure pharmaceutical worker's industry of light (strain) system) that 10.0 parts of formulas (XA-1) represent, to the mixture 7.2 parts of diethylamides (Tokyo change into industry (strain) system) that drip, be warming up to 65 ℃, stir 3 hours.Reaction solution is cooled to after room temperature, is fed in 0.5% salt solution of 280 parts.Get the residue of suction filtration as resulting precipitate, with dry after 200 parts of ion-exchange water washings, obtain the compound of formula (h-100) expression of 8.0 parts.Yield is 68%.
Determining of the compound that formula (h-100) represents
(mass analysis) ionization mode=ESI
+: m/z=[M+H]
+479.3
Accurate mass: 478.2
In solution at the compound dissolution that 1.00 parts (h-100) represented in 5 parts of N-Methyl pyrrolidone, under room temperature, add the compound that 0.71 part of formula (BC-1-Na) represents, be warming up to 60 degree, stir 9 hours.At this mixed solution, be cooled to room temperature, add 10% the salt solution of 20 parts, further stir 1 hour.Afterwards, suction filtration obtains precipitate, with 19 parts of ion-exchange water washings, obtains the salt that 1.30 parts of formulas (I-43) represent.
Embodiment 11
In solution at the compound dissolution that 4.07 parts (h-1) represented in 20 parts of N-Methyl pyrrolidone, under room temperature, add the compound that 3.54 parts of formulas (BC-18-Na) represent, stir 6 hours.In this mixed solution, add the salt solution of 20 part 10%, further stir 1 hour.Afterwards, suction filtration obtains precipitate, with 19 parts of ion-exchange water washings, obtains the salt of formula (I-88) expression of 6.29 parts.
Embodiment 12
3.94 parts of C.I. alkali violet 11:1s are being dissolved in 20 parts of solution in N-Methyl pyrrolidone, under room temperature, are adding the compound that 3.16 parts of formulas (BC-18-Na) represent, stirring 6 hours.10% the salt solution that adds 20 parts in this mixed solution, further stirs 1 hour.Afterwards, suction filtration obtains precipitate, with 19 parts of ion-exchange water washings, obtains the salt of formula (I-89) expression of 6.34 parts.
Embodiment 13
4.00 parts of C.I. alkali red 1:1s are dissolved in to 20 parts of solution in N-Methyl pyrrolidone and are warming up to 60 degree, be added in the solution that has dissolved 2.90 parts of C.I. solvent yellow 2s 1 in 14.5 parts of N-Methyl pyrrolidone, be warming up to 60 degree, stir 3 hours.
The compound that adds 2.44 parts of formulas (BC-18-Na) to represent in this mixed solution further stirs 8 hours under 60 degree.This mixed solution is cooled to room temperature, adds 138 parts of ion exchanged waters, further stir 1 hour.Afterwards, suction filtration is obtained precipitate, with 213 parts of ion-exchange water washings, the positively charged ion of C.I. alkali red 1:1 that obtains salt that 7.47 parts of formulas (I-90) represent, represents with formula (IA-1) and the mixing salt (below, being designated as mixing salt (I-90-IA-1)) of the salt of the negatively charged ion of C.I. solvent yellow 21.
(mensuration of absorbancy)
0.35g salt is dissolved in solvent, and making volume is 250cm
3, by 2cm wherein
3with solvent cut, be 100cm
3, be adjusted into the solution of concentration 0.028g/L.To this solution, use ultraviolet-visible pectrophotometer (V-650DS; Japan's light splitting (strain) system) (quartz colorimetric utensil, optical length; 1cm) be determined at maximum absorption wavelength (λ
max) and maximum absorption wavelength (λ
max) under absorbancy.Together with the solvent of result and use, be displayed in Table 4.DMF is the abbreviation of DMF.
[table 4]
(deliquescent evaluation)
The compound that the salt obtaining respectively in the embodiment of obtaining 1～12 as described below, formula (h-1), formula (h-120), formula (h-100) represent respectively and C.I. alkali violet 11:1 are (following at propylene glycol methyl ether acetate, referred to as PGMEA), propylene glycol monomethyl ether is (following, referred to as PGME), the solubleness in ethyl lactate (following, referred to as EL).
In addition, the mixing salt I-90-IA-1 obtaining in the embodiment of obtaining 13 as described below and the C.I. alkali red 1:1 solubleness in DMF (being designated hereinafter simply as DMF), diacetone alcohol (following, referred to as DAA).
In the sample hose of 50mL, with following ratio mixing cpd and above-mentioned solvent, afterwards, fill in tight sample hose, at 30 ℃, with ultra-sonic oscillation machine, vibrate 3 minutes.Then, at room temperature place after 30 minutes, filter its residue of visual observations.In the time of cannot confirming the insolubles as residue, be judged as favorable solubility, while confirming insolubles, be judged as solvability bad.In table 5, recorded the peak concentration that is judged as favorable solubility.Outcome record is in table 5 and table 6.* mean to be 1%, be judged to bad.
1% salt or compound 0.01g, solvent 1g
3% salt or compound 0.03g, solvent 1g
5% salt or compound 0.05g, solvent 1g
7% salt or compound 0.07g, solvent 1g
10% salt or compound 0.10g, solvent 1g
20% salt or compound 0.20g, solvent 1g
[table 5]
[table 6]
| ? | Salt or compound | DMF | DAA |
| Embodiment 13 | Mixing salt (I-90-IA-1) | 3％ | 1％ |
| Comparative example 5 | Alkali red 1:1 | × | × |
Embodiment 14
(preparation of coloured composition)
By (A) tinting material: salt (I-43): in embodiment 10, synthetic salt is 20 parts
(B-1) resin: methacrylic acid/methacrylic acid benzyl ester multipolymer (mol ratio; 30/70; Weight-average molecular weight 10700, acid number 70mgKOH/g) 70 parts
(C-1) polymerizable compound: six vinylformic acid dipentaerythritol ester (Japanese chemical drug society system)
30 parts
(D-1) Photoepolymerizationinitiater initiater: benzil dimethyl ketal (IRGACURE651; BASF Japan company system)
15 parts
(E-1) solvent: 680 parts of DMFs
After mixing, obtain coloured composition.
(making of colour filter)
With spin-coating method, coloured composition obtained above is coated on glassly, makes volatile component volatilization.After cooling, the figuratum silica glass of apparatus photomask processed and exposure machine carry out rayed.After rayed, with potassium hydroxide aqueous solution, developing, is 200 ℃ by baking oven for heating, obtains colour filter.
Embodiment 15
Except the synthetic compound (I-43) of embodiment 10 is replaced to the synthetic compound of embodiment 5 (I-31), other are the same with embodiment 11, obtain coloured composition and colour filter.
From the result of table 5 and table 6, the salt pair organic solvent of embodiment demonstrates high-dissolvability.In addition, the coloured composition that contains this salt, seldom produces foreign matter, can make and obtain high-quality colour filter.
The solvability of salt of the present invention in organic solvent is excellent.
Claims (7)
1. a salt, described salt is to form the cationic salt of the dyestuff of salt by the represented negatively charged ion of formula (1) with coming self energy and this negatively charged ion,
In formula (1), Z
1and Z
2represent to have independently respectively 2 substituent groups, these 2 substituting groups are discharged proton and form for proton substituting group by 1 valency.
2. salt according to claim 1, wherein, described positively charged ion is, from the positively charged ion of anthocyanin dye, from the positively charged ion of triarylmethane dye, from the positively charged ion of xanthene dye or from the positively charged ion of anthraquinone dye.
3. according to the salt described in claim 1 or 2, wherein, Z
1and Z
2represent independently respectively any of the group shown in following formula (a-1)～(a-10),
In formula, R
21and R
22represent independently respectively hydrogen atom, can substituted carbonatoms 1～6 alkyl, can substituted carbonatoms 3～7 cycloalkyl or can substituted phenyl, R
23～R
92represent independently respectively the alkyl of hydrogen atom, carbonatoms 1～4, haloalkyl, halogen atom, hydroxyl, amino or the nitro of the alkoxyl group of carbonatoms 1～4, carbonatoms 1～4.
4. salt according to claim 3, wherein, Z
1and Z
2for formula (a-1), formula (a-5), formula (a-6) or the represented group of formula (a-8).
5. according to the salt described in any one of claim 1～4, wherein, having 2 substituent groups that formed for proton substituting group discharges proton by 1 valency is for 2 these confession proton substituting groups of the substituent compound of proton, to discharge respectively the group of proton by having 21 valencys, having 21 valencys for the substituent compound of proton is, can there is substituent catechol, can have substituent 2, 3-dihydroxy naphthlene, can have substituent 2, 2 '-xenol, can there is substituent 3-hydroxy-2-naphthoic acid, can there is substituent 2-hydroxyl-1-naphthoic acid, can there is substituent 1-hydroxy-2-naphthoic acid, can there is substituent dinaphthol, can there is substituent Whitfield's ointment, can there is substituent benzilic acid or can there is substituent tussol.
6. a dyestuff, wherein, the salt described in any one that contains claim 1～5 is as effective constituent.
7. a coloured composition, wherein, contains dyestuff claimed in claim 6.
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| KR (1) | KR102104008B1 (en) |
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| CN105315708A (en) * | 2014-06-13 | 2016-02-10 | 东友精细化工有限公司 | Dye parent material manufacture method |
| CN107075270A (en) * | 2014-09-30 | 2017-08-18 | 富士胶片株式会社 | Coloured composition, ink for ink-jet recording and ink jet recording method |
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| JP6454273B2 (en) * | 2013-06-07 | 2019-01-16 | 東友ファインケム株式会社Ｄｏｎｇｗｏｏ Ｆｉｎｅ−Ｃｈｅｍ Ｃｏ．， Ｌｔｄ． | Colored curable resin composition |
| KR101653865B1 (en) * | 2013-06-18 | 2016-09-02 | 주식회사 엘지화학 | Dye and color filter comprising the same |
| EP3115420B1 (en) | 2014-03-07 | 2018-04-25 | Wako Pure Chemical Industries, Ltd. | Cyanine coloring composition |
| WO2018199316A1 (en) * | 2017-04-28 | 2018-11-01 | 富士フイルム株式会社 | Curable composition, planographic printing master plate, method for manufacturing planographic printing plate, and salt compound |
| JP7113907B2 (en) | 2018-09-18 | 2022-08-05 | 富士フイルム株式会社 | Composition, film, optical filter, solid-state imaging device, infrared sensor, method for manufacturing optical filter, camera module, compound, and dispersion composition |
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| IT1122748B (en) * | 1979-08-10 | 1986-04-23 | Acna | SALTS OF BASIC DYES, THEIR PREPARATION AND USE |
| JP2000044824A (en) * | 1998-07-28 | 2000-02-15 | Idemitsu Kosan Co Ltd | Color converting film and organic electroluminescent element |
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| CN105315708A (en) * | 2014-06-13 | 2016-02-10 | 东友精细化工有限公司 | Dye parent material manufacture method |
| CN105315708B (en) * | 2014-06-13 | 2018-05-18 | 东友精细化工有限公司 | The manufacturing method of dyestuff masterbatch |
| CN107075270A (en) * | 2014-09-30 | 2017-08-18 | 富士胶片株式会社 | Coloured composition, ink for ink-jet recording and ink jet recording method |
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| JP2014037530A (en) | 2014-02-27 |
| KR102104008B1 (en) | 2020-04-23 |
| TW201408736A (en) | 2014-03-01 |
| KR20140012592A (en) | 2014-02-03 |
| TWI582176B (en) | 2017-05-11 |
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