CN105473666A - Novel compound and composition containing novel compound - Google Patents

Novel compound and composition containing novel compound Download PDF

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Publication number
CN105473666A
CN105473666A CN201480040982.5A CN201480040982A CN105473666A CN 105473666 A CN105473666 A CN 105473666A CN 201480040982 A CN201480040982 A CN 201480040982A CN 105473666 A CN105473666 A CN 105473666A
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carbonatoms
alkyl
group
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represent
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CN105473666B (en
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冈田光裕
松本健
金原有希子
松井依纯
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Adeka Corp
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Asahi Denka Kogyo KK
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
    • C07C255/34—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring with cyano groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by unsaturated carbon chains
    • 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
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/14—Styryl dyes
    • C09B23/143—Styryl dyes the ethylene chain carrying a COOH or a functionally modified derivative, e.g.-CN, -COR, -COOR, -CON=, C6H5-CH=C-CN
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
    • C07C255/37—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by etherified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
    • C07C255/38—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by esterified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
    • C07C255/42—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being further bound to other hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/30—Only oxygen atoms
    • C07D251/32—Cyanuric acid; Isocyanuric acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • 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
    • C09B57/00—Other synthetic dyes of known constitution
    • C09B57/008—Triarylamine dyes containing no other chromophores
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/22—Absorbing filters
    • G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Optical Filters (AREA)
  • Materials For Photolithography (AREA)
  • Epoxy Compounds (AREA)
  • Polymerisation Methods In General (AREA)

Abstract

The present invention provides: a novel compound suitable as a dye of a colored photosensitive composition having excellent thermal resistance and lightfastness; and a colored photosensitive composition using said novel compound. Specifically, the present invention provides a colored photosensitive composition containing a compound represented by general formula (1) and a dye (A) containing said compound, a polymerizable compound (B) having an ethylenically unsaturated bond with an acid value, a photo-radical initiator (C), and a monomer (D) having an ethylenically unsaturated bond. The specific content of general formula (1) is as described in the description of the present application.

Description

Novel cpd and the composition containing this compound
Technical field
The present invention relates to the form and aspect that are designed to expect and the dye well that improve thermotolerance is suitable for the novel compound of this dyestuff.In addition, the invention still further relates to the polymerisable coloring photosensitive combination under energy line effect employing this dyestuff and the colour filter employing this coloring photosensitive combination.
Background technology
The compound having a large absorption of intensity to specific light is used as the optical parameter of the image display device such as recording layer, liquid crystal indicator (LCD), plasma display (PDP), display of organic electroluminescence (ELD), cathode tube display unit (CRT), fluorescent display tube, field emission type display of the optical record mediums such as CD-R, DVD-R, DVD+R, BD-R.
In the spectral filter of the device used for image display such as liquid crystal indicator (LCD), plasma display (PDP), display of organic electroluminescence (ELD), cathode tube display unit (CRT), fluorescent display tube, field emission type display, the various compounds absorbing the light of the wavelength of 300 ~ 1100nm are used as light absorber.
Require the photoabsorption of these light absorbers half-width that is precipitous especially, i.e. λ max little and light or heat etc. effect under can not loss of function.
Colour filter is had in the spectral filter being mainly used in liquid crystal indicator (LCD).In colour filter, usually use this 3 primary colors of RGB, but be difficult to independent tinting material the form and aspect making it have pure RGB, carry out using multiple tinting material with the effort of the form and aspect close to pure RGB always.Therefore, not only need RGB, also need the tinting materials such as yellow, orange, purple.
The light absorber used in colour filter uses organic and/or mineral dye due to thermotolerance height always, owing to being pigment, thus there is the problem that the brightness as display unit is reduced, solves this problem by the brightness improving light source.But along with the trend of power reducing, the exploitation employing the colour filter of dyestuff is prosperous gradually.
In addition, in recent years, in the colour filter used in solid-state imager, from the view point of raising picture quality, requiring the filming of colored pattern, in order to carry out filming, from the angle improving depth of shade, needing to improve dye strength.In addition, when the molar absorbance backscatter extinction logarithmic ratio of dyestuff is low, also need to add a large amount of dyestuffs.
But, when improving dye strength, when implementing heat treated (curing afterwards) after film forming, being easy between the levels between neighbor or in stepped construction colour mixture occurs, therefore requiring that there is thermotolerance.
In addition, also there is the problem being easy to deterioration under the effect of exterior light in the light absorber used in colour filter, also requires to have photostabilization.
The colour filter colored resin composition of the organic pigment containing ad hoc structure is disclosed in patent documentation 1 ~ 3.
But the compound used in the color composition for color filter recorded in these documents is from taking into account thermotolerance and sunproof angle still can not be satisfactory.
Prior art document
Patent documentation
Patent documentation 1:WO2012/039286
Patent documentation 2:WO2012/101946
Patent documentation 3:WO2012/111400
Summary of the invention
Invent problem to be solved
Therefore, the object of the present invention is to provide can solve the problem employ the coloured compositions such as the coloring photosensitive combination of novel cpd.In addition, the spectral filter employing above-mentioned coloring photosensitive combination, the colour filter particularly not reducing brightness, be suitable for the image display devices such as display panels are provided provide.
For solving the means of problem
The result that present inventor carries out furtheing investigate repeatedly recognizes thermotolerance and the excellent in light-resistance of the compound with ad hoc structure, also recognize in addition, above-mentioned coloring photosensitive combination does not reduce the brightness of spectral filter (particularly colour filter), be suitable for the device used for image display colour filters such as display panels, thus complete the present invention.
The present invention completes based on above-mentioned cognition, and it provides the compound shown in following general formula (1).
(in formula, A represents phenyl ring, naphthalene nucleus or anthracene nucleus, and alkyl, alkoxyl group, haloalkyl or halogenated alkoxy that these rings can be 1 ~ 12 by halogen atom, cyano group, hydroxyl, nitro, carbonatoms replace,
Y represents cyano group or-COOR 4,
R 1represent hydrogen atom, phenyl, cyano group, nitro, alkoxyl group that alkyl that halogen atom, carbonatoms are 1 ~ 12, carbonatoms are 1 ~ 12, carbonatoms be 1 ~ 12 haloalkyl or carbonatoms be the halogenated alkoxy of 1 ~ 12,
R 2and R 3represent independently of one another hydrogen atom, carbonatoms be 1 ~ 12 alkyl, carbonatoms be 6 ~ 20 aryl or carbonatoms be the aralkyl of 7 ~ 20,
R 2and R 3the alkyl represented, aryl and aralkyl can be replaced by halogen atom or nitro,
R 2and R 3represent alkyl and aralkyl in methylene radical can be replaced by-COO-,-O-,-OCO-,-NHCO-,-NH-or-CONH,
R 4represent alkyl that hydrogen atom, carbonatoms are 1 ~ 12, aryl that carbonatoms is 6 ~ 20, carbonatoms be 7 ~ 20 aralkyl or carbonatoms be the heterocyclic radical of 2 ~ 35,
R 4represent alkyl and aralkyl in methylene radical can be replaced by-COO-,-O-,-OCO-,-NHCO-,-NH-or-CONH,
X represents singly-bound, nitrogen-atoms ,-NR 5-, Sauerstoffatom, sulphur atom ,-SO 2-,-SO-, phosphorus atom ,-PR 6-or meet the organic group of arbitrary condition in following <1> ~ <5>,
R 5and R 6represent independently of one another hydrogen atom, carbonatoms be 1 ~ 12 alkyl, carbonatoms be 6 ~ 20 aryl or carbonatoms be the aralkyl of 7 ~ 20,
The integer of m=2 ~ 6.)
<1>m=2, X are as shown in following formula (2).
*-Z 1-X 1-Z 2-*(2)
(in formula, X 1expression-NR 13-, the carbonatoms of divalence is the aliphatic alkyl of 1 ~ 35, the carbonatoms of divalence is the ester ring type alkyl of 3 ~ 35, the carbonatoms of divalence is 6 ~ 35 the carbonatoms containing aromatic nucleus alkyl, divalence be 2 ~ 35 the group represented containing any one in heterocyclic group or following (2-1) ~ (2-3)
X 1alkyl, alkoxyl group, haloalkyl or halogenated alkoxy that the aliphatic alkyl represented can be 1 ~ 8 by halogen atom, cyano group, hydroxyl, nitro, carbonatoms replace,
X 1methylene radical in the aliphatic alkyl represented can by-O-,-S-,-CO-,-CO-O-,-O-CO-,-SO 2-,-NH-or their groups of combining replace,
Z 1and Z 2represent Direct Bonding ,-O-,-S-,-SO independently of one another 2-,-SO-,-NR 13-or-PR 14-,
R 13and R 14represent independently of one another hydrogen atom, carbonatoms be 1 ~ 8 alkyl, carbonatoms be 6 ~ 20 aryl or carbonatoms be the aralkyl of 7 ~ 20,
R 13and R 14the alkyl represented, aryl and aralkyl can be replaced by halogen atom, hydroxyl or nitro,
R 13and R 14represent alkyl and aralkyl in methylene radical can be replaced by-COO-,-O-,-OCO-,-NHCO-,-NH-or-CONH-.
Wherein, the carbonatoms of group that represents of above-mentioned general formula (2) is in the scope of 1 ~ 35.)
(in formula, R 21represent hydrogen atom, can by carbonatoms be 1 ~ 10 alkyl or alkoxyl group replace phenyl or carbonatoms be the cycloalkyl of 3 ~ 10,
R 22represent that carbonatoms is alkyl, the carbonatoms alkoxyl group that is 1 ~ 10, carbonatoms be 2 ~ 10 alkenyl or the halogen atom of 1 ~ 10,
R 21and R 22the alkyl represented, alkoxyl group and alkenyl can be replaced by halogen atom or not replace,
D is the integer of 0 ~ 5.)
(in formula, R 23and R 24represent independently of one another carbonatoms be 1 ~ 10 alkyl, the carbonatoms aryl that is 6 ~ 20, the carbonatoms aryloxy that is 6 ~ 20, the carbonatoms arylthio that is 6 ~ 20, the carbonatoms aromatic yl alkenyl that is 8 ~ 20, carbonatoms be 7 ~ 20 aralkyl, carbonatoms be 2 ~ 20 containing heterocyclic group or halogen atom
R 23and R 24the alkyl represented, aryl, aryloxy, arylthio, aromatic yl alkenyl, aralkyl and can be replaced by halogen atom or not replace containing heterocyclic group,
R 23and R 24represent alkyl and aralkyl in methylene radical can be replaced by unsaturated link(age) ,-O-or-S,
R 23can at adjacent R 23between form ring,
E represents the number of 0 ~ 4,
F represents the number of 0 ~ 8,
G represents the number of 0 ~ 4,
H represents the number of 0 ~ 4,
Several sums of g and h are 2 ~ 4.)
<2>m=3, X are as shown in following formula (3).
(in formula, X 2represent by R 25the carbonatoms containing aromatic nucleus alkyl or trivalent that the carbon atom that instead of, the carbonatoms of trivalent are the aliphatic alkyl of 1 ~ 35, the carbonatoms of trivalent is the ester ring type alkyl of 3 ~ 35, the carbonatoms of trivalent is 6 ~ 35 be 2 ~ 35 containing heterocyclic group,
R 25represent hydrogen atom, carbonatoms be 1 ~ 8 alkyl, carbonatoms be 6 ~ 20 aryl or carbonatoms be the aralkyl of 7 ~ 20,
X 2alkyl, alkoxyl group, haloalkyl or halogenated alkoxy that the aliphatic alkyl represented can be 1 ~ 8 by halogen atom, cyano group, hydroxyl, nitro, carbonatoms replace,
X 2methylene radical in the aliphatic alkyl represented can by-O-,-S-,-CO-,-CO-O-,-O-CO-,-SO 2-,-NH-or their groups of combining replace,
Z 1~ Z 3independently of one another with the Z in above-mentioned general formula (2) 1and Z 2the group represented is identical.
Wherein, the carbonatoms of group that represents of above-mentioned general formula (3) is in the scope of 1 ~ 35.)
<3>m=4, X are as shown in following formula (4).
(in formula, X 3represent carbon atom, the carbonatoms of tetravalence be the aliphatic alkyl of 1 ~ 35, the carbonatoms of tetravalence is the ester ring type alkyl of 3 ~ 35, the carbonatoms of tetravalence be 6 ~ 35 the carbonatoms containing aromatic nucleus alkyl or tetravalence be 2 ~ 35 containing heterocyclic group,
X 3alkyl, alkoxyl group, haloalkyl or halogenated alkoxy that the aliphatic alkyl represented can be 1 ~ 8 by halogen atom, cyano group, hydroxyl, nitro, carbonatoms replace,
X 3methylene radical in the aliphatic alkyl represented can by-O-,-S-,-CO-,-CO-O-,-O-CO-,-SO 2-,-NH-or their groups of combining replace,
Z 1~ Z 4independently of one another with the Z in above-mentioned general formula (2) 1and Z 2the group represented is identical.
Wherein, the carbonatoms of group that represents of above-mentioned general formula (4) is in the scope of 1 ~ 35.)
<4>m=5, X are as shown in following formula (5).
(in formula, X 4represent that the carbonatoms of pentavalent is the aliphatic alkyl of 2 ~ 35, the carbonatoms of pentavalent is the ester ring type alkyl of 3 ~ 35, the carbonatoms of pentavalent be 6 ~ 35 the carbonatoms containing aromatic nucleus alkyl or pentavalent be 2 ~ 35 containing heterocyclic group,
X 4alkyl, alkoxyl group, haloalkyl or halogenated alkoxy that the aliphatic alkyl represented can be 1 ~ 8 by halogen atom, cyano group, hydroxyl, nitro, carbonatoms replace,
X 4methylene radical in the aliphatic alkyl represented can by-O-,-S-,-CO-,-CO-O-,-O-CO-,-SO 2-,-NH-or their groups of combining replace,
Z 1~ Z 5independently of one another with the Z in above-mentioned general formula (2) 1and Z 2the group represented is identical.
Wherein, the carbonatoms of group that represents of above-mentioned general formula (5) is in the scope of 2 ~ 50.)
<5>m=6, X are as shown in following formula (6).
(in formula, X 5represent that the carbonatoms of sexavalence is the aliphatic alkyl of 2 ~ 35, the carbonatoms of sexavalence is the ester ring type alkyl of 3 ~ 35, the carbonatoms of sexavalence be 6 ~ 35 the carbonatoms containing aromatic nucleus alkyl or sexavalence be 2 ~ 35 containing heterocyclic group,
X 5alkyl, alkoxyl group, haloalkyl or halogenated alkoxy that the aliphatic alkyl represented can be 1 ~ 8 by halogen atom, cyano group, hydroxyl, nitro, carbonatoms replace,
X 5methylene radical in the aliphatic alkyl represented can by-O-,-S-,-CO-,-CO-O-,-O-CO-,-SO 2-,-NH-or their groups of combining replace,
Z 1~ Z 6independently of one another with the Z in above-mentioned general formula (2) 1and Z 2the group represented is identical.
Wherein, the carbonatoms of group that represents of above-mentioned general formula (6) is in the scope of 2 ~ 50.)
In addition, the invention provides the coloured composition containing the compound shown in above-mentioned general formula (1).
In addition, the invention provides a kind of coloring photosensitive combination, it contains: the dyestuff (A) containing the compound shown in the above-mentioned general formula of at least one (1), the polymerizable compound (B) with ethylenic unsaturated link(age) with acid number, optical free radical polymerization starter (C) and have the monomer (D) of ethylenic unsaturated link(age).
In addition, the present invention also provides the cured article of above-mentioned coloring photosensitive combination and uses the display equipment colour filter of this cured article.
Invention effect
Containing the thermotolerance of coloring photosensitive combination of the present invention (painted alkali-developable photosensitive composition) of compound and the excellent in light-resistance with ad hoc structure.In addition, its cured article is suitable for display equipment colour filter,
Embodiment
Below, based on preferred embodiment the present invention will be described.
In compound shown in above-mentioned general formula (1), m group mutually can identical also can be different.The value of m is 2 ~ 6, from the angle of synthesis easiness, is preferably 2 ~ 3.
As halogen atom, the R of the A that can replace in above-mentioned general formula (1) 1shown halogen atom, maybe R can be replaced 2and R 3the halogen atom of the alkyl represented, aryl, aralkyl, can list fluorine, chlorine, bromine, iodine,
As alkyl or R that the carbonatoms that can replace A is 1 ~ 12 1~ R 6the carbonatoms represented is the alkyl of 1 ~ 12, methyl, ethyl, propyl group, sec.-propyl, butyl, sec-butyl, the tertiary butyl, isobutyl-, amyl group, isopentyl, tert-pentyl, cyclopentyl, hexyl, 2-hexyl, 3-hexyl, cyclohexyl, 4-methylcyclohexyl, heptyl, 2-heptyl, 3-heptyl, different heptyl, tertiary heptyl, 1-octyl group, iso-octyl, tertiary octyl group, adamantyl etc. can be listed
As alkoxyl group or R that the carbonatoms that can replace A is 1 ~ 12 1the carbonatoms represented is the alkoxyl group of 1 ~ 12, methoxyl group, oxyethyl group, propoxy-, isopropoxy, butoxy, sec-butoxy, tert.-butoxy, isobutoxy, pentyloxy, isopentyloxy, tertiary pentyloxy, hexyloxy, cyclohexyloxy, cyclohexyl methoxy, tetrahydrofuran base oxygen base, THP trtrahydropyranyl oxygen base etc. can be listed
As haloalkyl or R that the carbonatoms that can replace A is 1 ~ 12 1the carbonatoms represented is the haloalkyl of 1 ~ 12, can list above-mentioned carbonatoms is the group that at least 1 hydrogen atom of the alkyl of 1 ~ 12 is substituted by above-mentioned halogen atom, such as chloromethyl, dichloromethyl, trichloromethyl, methyl fluoride, difluoromethyl, trifluoromethyl, nine fluorine butyl etc.
As halogenated alkoxy or R that the carbonatoms that can replace A is 1 ~ 12 1the carbonatoms represented is the halogenated alkoxy of 1 ~ 12, can list above-mentioned carbonatoms is the group that at least 1 hydrogen atom of the alkoxyl group of 1 ~ 12 is substituted by above-mentioned halogen atom, such as chlorine methoxyl group, dichloro methoxyl group, trichloromethoxy, fluorine methoxyl group, difluoro-methoxy, trifluoromethoxy, nine fluorine butoxy etc.
As R 2~ R 6the carbonatoms represented is the aryl of 6 ~ 20, phenyl can be listed, naphthyl, anthryl, 2-aminomethyl phenyl, 3-aminomethyl phenyl, 4-aminomethyl phenyl, 4-ethenylphenyl, 3-isopropyl phenyl, 4-isopropyl phenyl, 4-butyl phenyl, 4-isobutyl phenenyl, 4-tert-butyl-phenyl, 4-hexyl phenyl, 4-cyclohexyl phenyl, 4-octyl phenyl, 4-(2-ethylhexyl) phenyl, 4-stearyl phenyl, 2, 3-3,5-dimethylphenyl, 2, 4-3,5-dimethylphenyl, 2, 5-3,5-dimethylphenyl, 2, 6-3,5-dimethylphenyl, 3, 4-3,5-dimethylphenyl, 3, 5-3,5-dimethylphenyl, 2, 4-bis--tert-butyl-phenyl, 2, 5-bis--tert-butyl-phenyl, 2, 6-bis--tert-butyl-phenyl, 2, 4-bis--tert-pentyl phenyl, 2, 5-bis--tert-pentyl phenyl, 2, 5-bis--tertiary octyl phenyl, 2, 4-dicumylphenyl, 4-cyclohexyl phenyl, (1, 1 '-xenyl)-4-base, 2, 4, 5-trimethylphenyl, ferrocenyl etc.,
As R 2~ R 6the carbonatoms represented is the aralkyl of 7 ~ 20, can list benzyl, fluorenyl, indenyl, 9-fluorenyl methyl, 2-phenyl-propane-2-base, diphenyl methyl, trityl group, styryl, cinnamyl etc.,
As R 4the carbonatoms represented is the heterocyclic radical of 3 ~ 25, pyridyl can be listed, pyrimidyl, pyridazinyl, piperidyl, pyranyl, pyrazolyl, triazinyl, pyrryl, quinolyl, isoquinolyl, imidazolyl, benzimidazolyl-, triazolyl, furyl (furyl), furyl (furanyl), benzofuryl (benzofuranyl), thienyl, sulfur phenenyl, benzimidazole thiophanate phenyl, thiadiazolyl group, thiazolyl, benzothiazolyl, oxazolyl, benzoxazolyl, isothiazolyl, isoxazolyl, indyl, 2-Pyrrolidone-1-base, 2-piperidone-1-base, 2, 4-dioxy base imidazolidine-3-base, 2, 4-bis-Yang Ji oxazolidine-3-base etc.
As the halogen atom recorded in above-mentioned general formula (2) ~ (6) and formula (2-1) ~ (2-3), alkyl, alkoxyl group, haloalkyl, halogenated alkoxy, aryl and aralkyl example separately, the group same with the group enumerated hereinbefore as alkyl, alkoxyl group, haloalkyl, halogenated alkoxy, aryl and aralkyl example separately in this part can be listed.In addition, in these groups, about the group that carbonatoms is different from the group enumerated in this part, the group of the carbonatoms meeting regulation in the group enumerated in this part can be listed.
About-the NR in A 2r 3base and-C (R 1the position of substitution of)=C (CN) Y base, when A is phenyl ring, is generally contraposition; When A is naphthalene nucleus, be generally 1,4 or 1,5; When A is anthracene nucleus, be generally 1,4,1,5,1,10 or 9,10.
As the X in above-mentioned general formula (2) 1the carbonatoms of the divalence represented is the aliphatic alkyl of 1 ~ 35, the groups such as methane, ethane, propane, isopropyl alkane, butane, secondary butane, tertiary butane, Trimethylmethane, hexane, 2-methyl hexane, 3-methyl hexane, heptane, 2-methylheptane, 3-methylheptane, isoheptane, tertiary heptane, 1-methyloctane, octane-iso, tertiary octane, cyclopropane, tetramethylene, pentamethylene, hexanaphthene, suberane, 2,4-dimethylcyclobutane, 4-methylcyclohexane can be listed by Z 1and Z 2the group of the divalence replaced, the methylene radical in these groups can by-O-,-S-,-CO-,-COO-,-OCO-,-SO 2-,-NH-or their groups of combining replace, the group that they combine represents such as-COO-O-,-COO-S-,-O-OCO-,-S-OCO-,-CO-NH-,-NH-CO-etc., wherein, preferably by the group of-COO-,-O-,-OCO-,-NHCO-,-NH-,-CONH-,-O-CONH-,-NHCO-O-replacement
Carbonatoms as divalence is the ester ring type alkyl of 3 ~ 35, can list cyclopentyl, cyclohexyl, suberyl, ring octyl group, ring decyl, 1-adamantyl, 2-adamantyl, noradamantyl, 2-methyl adamantane base, norcamphyl, different norcamphyl, hydronaphthyl, perhydro-anthryl, dicyclo [1.1.0] butyl, dicyclo [1.1.1] amyl group, dicyclo [2.1.0] amyl group, dicyclo [3.1.0] hexyl, dicyclo [2.1.1] hexyl, dicyclo [2.2.0] hexyl, dicyclo [4.1.0] heptyl, dicyclo [3.2.0] heptyl, dicyclo [3.1.1] heptyl, dicyclo [2.2.1] heptyl, dicyclo [5.1.0] octyl group, dicyclo [4.2.0] octyl group, dicyclo [4.1.1] octyl group, dicyclo [3.3.0] octyl group, dicyclo [3.2.1] octyl group, dicyclo [2.2.2] octyl group, spiral shell (4,4) nonyl, spiral shell (4,5) decyl, naphthane, three ring decyls, tetracyclododecyl group, cypress camphor, the groups such as cyclo-dodecyl are by Z 1and Z 2the group etc. of the divalence replaced,
Carbonatoms as divalence be 6 ~ 35 containing aromatic nucleus alkyl, the groups such as phenylene, naphthylidene, xenyl can be listed by Z 1and Z 2the group etc. of the divalence replaced,
Carbonatoms as divalence be 2 ~ 35 containing heterocyclic group, the groups such as pyridine, pyrazine, piperidines, piperazine, pyrimidine, pyridazine, triazine, Hexahydrotriazine, furans, tetrahydrofuran (THF), chroman, xanthene, thiophene, tetramethylene sulfide can be listed by Z 1and Z 2the group of the divalence replaced.
The alkoxyl group that these groups can also be 1 ~ 8 by halogen atom, cyano group, nitro or carbonatoms further replaces.
In above-mentioned formula (2-1), as R 21the carbonatoms represented is the cycloalkyl of 3 ~ 10, can list cyclopropyl, cyclobutyl, cyclopentyl, suberyl, ring octyl group etc. and these groups by carbonatoms be 1 ~ 10 alkyl or carbonatoms be 1 ~ 10 the group etc. that replaces of alkoxyl group,
Be the alkenyl of 2 ~ 10 as carbonatoms, vinyl, allyl group, 1-propenyl, pseudoallyl, crotyl, 1,3-butadiene base, pentenyl, 2-octenyl etc. can be listed,
Above-mentioned R 22in alkyl, alkoxyl group and alkenyl can be replaced by halogen atom, its position of substitution does not limit.
In above-mentioned formula (2-3), as R 23and R 24the carbonatoms represented is the aryloxy of 6 ~ 20, phenoxy group can be listed, naphthyloxy, 2-methylphenoxy, 3-methylphenoxy, 4-methylphenoxy, 4-ethenylphenyl dioxy base, 3-sec.-propyl phenoxy group, 4-sec.-propyl phenoxy group, 4-butyl phenoxy, 4-tertiary butyl phenoxy group, 4-hexyl phenoxy group, 4-cyclohexyl phenoxy group, 4-Octylphenoxy, 4-(2-ethylhexyl) phenoxy group, 2, 3-dimethyl phenoxy, 2, 4-dimethyl phenoxy, 2, 5-dimethyl phenoxy, 2, 6-dimethyl phenoxy, 3, 4-dimethyl phenoxy, 3, 5-dimethyl phenoxy, 2, 4-bis--tertiary butyl phenoxy group, 2, 5-bis--tertiary butyl phenoxy group, 2, 6-bis--tertiary butyl phenoxy group, 2, 4-bis--tert-pentyl phenoxy group, 2, 5-tert-pentyl phenoxy group, 4-cyclohexyl phenoxy group, 2, 4, 5-trimethylammonium phenoxy group, the group that the groups such as ferrocenyl oxygen base and these groups are replaced by halogen atom,
Be the arylthio of 6 ~ 20 as carbonatoms, can list the above-mentioned carbonatoms that can be replaced by halogen atom is the group etc. that the Sauerstoffatom of the aryloxy of 6 ~ 20 is substituted by sulphur atom,
Be the aromatic yl alkenyl of 8 ~ 20 as carbonatoms, the Sauerstoffatom that can to list the above-mentioned carbonatoms that can be replaced by halogen atom be the aryloxy of 6-20 is substituted by vinyl, allyl group, 1-propenyl, pseudoallyl, crotyl, 1, the group etc. of the alkenyls such as 3-butadienyl, pentenyl, 2-octenyl
As carbonatoms be 2 ~ 20 containing heterocyclic group, the group etc. that the groups such as pyridine, pyrazine, piperidines, piperazine, pyrimidine, pyridazine, triazine, Hexahydrotriazine, furans, tetrahydrofuran (THF), chroman, xanthene, thiophene, thio-furan and these groups are replaced by halogen atom can be listed.
As the X in above-mentioned general formula (3) 2the carbonatoms of the trivalent represented is the aliphatic alkyl of 3 ~ 35, can list the X in above-mentioned general formula (2) 1explanation in illustrative aliphatic alkyl by Z 1, Z 2and Z 3the group of the trivalent replaced, the methylene radical in these groups can by-O-,-S-,-CO-,-CO-O-,-O-CO-,-SO 2-,-NH-or their groups of combining replace, the group that they combine can list such as-COO-O-,-COO-S-,-O-OCO-,-S-OCO-,-CO-NH-,-NH-CO-etc., wherein, preferably by the group of-COO-,-O-,-OCO-,-NHCO-,-NH-,-CONH-,-O-CONH-,-NHCO-O-replacement
Carbonatoms as trivalent is the ester ring type alkyl of 3 ~ 35, can list the X in above-mentioned general formula (2) 1explanation in illustrative ester ring type alkyl by Z 1, Z 2and Z 3the group of the trivalent replaced,
Carbonatoms as trivalent be 6 ~ 35 containing aromatic nucleus alkyl, the X in above-mentioned general formula (2) can be listed 1explanation in illustrative containing aromatic nucleus alkyl by Z 1, Z 2and Z 3the group of the trivalent replaced,
Carbonatoms as trivalent be 2 ~ 35 containing heterocyclic group, the X in above-mentioned general formula (2) can be listed 1explanation in illustrative containing heterocyclic group by Z 1, Z 2and Z 3the group of the trivalent replaced.
As the X in above-mentioned general formula (4) 3the carbonatoms of the tetravalence represented is the aliphatic alkyl of 1 ~ 35, can list the X in above-mentioned general formula (2) 1explanation in illustrative aliphatic alkyl by Z 1, Z 2, Z 3and Z 4the group of the tetravalence replaced, the methylene radical in these groups can by-O-,-S-,-CO-,-COO-,-OCO-,-SO 2-,-NH-or their groups of combining replace, the group that they combine represents such as-COO-O-,-COO-S-,-O-OCO-,-S-OCO-,-CO-NH-,-NH-CO-etc., wherein, preferably by the group of-COO-,-O-,-OCO-,-NHCO-,-NH-,-CONH-,-O-CONH-,-NHCO-O-replacement
Carbonatoms as tetravalence is the ester ring type alkyl of 3 ~ 35, can list the X in above-mentioned general formula (2) 1explanation in illustrative ester ring type alkyl by Z 1, Z 2, Z 3and Z 4the group of the tetravalence replaced,
Carbonatoms as tetravalence be 6 ~ 35 containing aromatic nucleus alkyl, the X in above-mentioned general formula (3) can be listed 1explanation in illustrative containing aromatic nucleus alkyl by Z 1, Z 2, Z 3and Z 4the group of the tetravalence replaced,
Carbonatoms as tetravalence be 2 ~ 35 containing heterocyclic group, the X in above-mentioned general formula (2) can be listed 1explanation in illustrative containing heterocyclic group by Z 1, Z 2, Z 3and Z 4the group of the tetravalence replaced,
As the X in above-mentioned general formula (5) 4the carbonatoms of the pentavalent represented is the aliphatic alkyl of 2 ~ 35, can list the X in above-mentioned general formula (2) 1explanation in illustrative aliphatic alkyl by Z 1, Z 2, Z 3, Z 4and Z 5the group of the pentavalent replaced, the methylene radical in these groups can by-O-,-S-,-CO-,-CO-O-,-O-CO-,-SO 2-,-NH-or their groups of combining replace, the group that they combine represents such as-COO-O-,-COO-S-,-O-OCO-,-S-OCO-,-CO-NH-,-NH-CO-etc., wherein, preferably by the group of-COO-,-O-,-OCO-,-NHCO-,-NH-,-CONH-,-O-CONH-,-NHCO-O-replacement
Carbonatoms as pentavalent is the ester ring type alkyl of 3 ~ 35, can list the X in above-mentioned general formula (2) 1explanation in illustrative ester ring type alkyl by Z 1, Z 2, Z 3, Z 4and Z 5the group of the pentavalent replaced,
Carbonatoms as pentavalent be 6 ~ 35 containing aromatic nucleus alkyl, the X in above-mentioned general formula (2) can be listed 1explanation in illustrative containing aromatic nucleus alkyl by Z 1, Z 2, Z 3, Z 4and Z 5the group of the pentavalent replaced,
Carbonatoms as pentavalent be 2 ~ 35 containing heterocyclic group, the X in above-mentioned general formula (2) can be listed 1explanation in illustrative containing heterocyclic group by Z 1, Z 2, Z 3, Z 4and Z 5the group of the pentavalent replaced.
As the X in above-mentioned general formula (6) 5the carbonatoms of the sexavalence represented is the aliphatic alkyl of 2 ~ 35, can list the X in above-mentioned general formula (2) 1explanation in illustrative aliphatic alkyl by Z 1, Z 2, Z 3, Z 4, Z 5and Z 6the group of the sexavalence replaced, the methylene radical in these groups can by-O-,-S-,-CO-,-COO-,-OCO-,-SO 2-,-NH-or their groups of combining replace, the group that they combine represents such as-COO-O-,-COO-S-,-O-OCO-,-S-OCO-,-CO-NH-,-NH-CO-etc., wherein, preferably by the group of-COO-,-O-,-OCO-,-NHCO-,-NH-,-CONH-,-O-CONH-,-NHCO-O-replacement
Carbonatoms as sexavalence is the ester ring type alkyl of 3 ~ 35, can list the X in above-mentioned general formula (2) 1explanation in illustrative ester ring type alkyl by Z 1, Z 2, Z 3, Z 4, Z 5and Z 6the group of the sexavalence replaced,
Carbonatoms as sexavalence be 6 ~ 35 containing aromatic nucleus alkyl, the X in above-mentioned general formula (2) can be listed 1explanation in illustrative containing aromatic nucleus alkyl by Z 1, Z 2, Z 3, Z 4, Z 5and Z 6the group of the sexavalence replaced,
Carbonatoms as sexavalence be 2 ~ 35 containing heterocyclic group, the X in above-mentioned general formula (3) can be listed 1explanation in illustrative containing heterocyclic group by Z 1, Z 2, Z 3, Z 4, Z 5and Z 6the group of the sexavalence replaced.
In the compound shown in above-mentioned general formula (1), A is the compound of phenyl ring; R 1for the compound of hydrogen atom; R 2and R 3it is the compound of the alkyl of 1 ~ 12 for carbonatoms; R 4it is the compound of the alkyl of 1 ~ 12 for carbonatoms; When m is 2, the X of X as Suo Shi general formula (2), in this formula (2) 1for being selected from the compound of the group in following group 1; When m is 3, the X of X as Suo Shi general formula (3), in this formula (3) 2for being selected from the compound of the group in following group 2; When m is 4, the X of X as Suo Shi general formula (4), in this formula (4) 3for being selected from the compound of the group in group 3; When m is 5, the X of X as Suo Shi general formula (5), in this formula (5) 4for being selected from the compound of the group in following group 4; When m is 6, the X of X as Suo Shi general formula (6), in this formula (6) 5for the compound that is selected from the group in following group 5 due to raw material acquisition and easy to manufacture, thermotolerance is high, therefore preferably.
< group 1>
(in formula, R 5for with the R in above-mentioned general formula (1) 5identical group, when having in group more than 2, can be the same or different, and p represents that integer, the q of 1 ~ 3 represent that integer, the r of 0 ~ 3 represent the integer of 1 ~ 19.)
< group 2>
< group 3>
< group 4>
< group 5>
As the object lesson of the compound shown in above-mentioned general formula (1), the compound shown in following [chemical formula 15] ~ [chemical formula 20B] can be listed, but the present invention is not limited to these compounds.
[chemical formula 15]
[chemical formula 15A]
[chemical formula 16]
[chemical formula 17]
[chemical formula 18]
[chemical formula 19]
[chemical formula 20]
[chemical formula 20A]
[chemical formula 20B]
The compound at least with structure shown in an above-mentioned general formula (1) of the present invention except using in the coloured compositions such as coloring photosensitive combination described below as dyestuff, also for use in indicating meter or optical lens spectral filter, silver salt photo sensitive materials, contaminate in thing, coating, ink, electrophotographic photoconductor, toning agent, thermal recording paper, transfer belt, optical recording pigment, solar cell, organic semiconductor, clinical examination reagent, laser therapy pigment, dyeing etc.
The manufacture method of the compound shown in above-mentioned general formula (1) is not particularly limited, and such as m=2, A are phenyl ring, Y is cyano group, X is as *-Z 1-X 1-Z 2time shown in-*, as shown in following reaction formula, react in the basic conditions by making aldehyde cpd and propane dinitrile and manufacture.During m=3 ~ 6, also can manufacture based on this.As alkali, Piperazine anhydrous etc. also can be used to replace following shown triethylamine.
(in formula, R 1, R 2and R 3identical with above-mentioned general formula (1), Z 1, Z 2and X 1identical with above-mentioned general formula (2).)
Dyestuff of the present invention (A) can contain the compound shown in the above-mentioned general formula of at least one (1), can be used alone or is used by multiple combination.In addition, except the compound shown in above-mentioned general formula (1), also known dyestuff can be used.As known dyestuff, the dyestuffs etc. such as such as azoic dyestuff, anthraquinone dye, indigoid colouring matters, triarylmethane dye, xanthene dye, alizarine dyestuff, acridine dye stilbene dye, thiazole dye, naphthol dye, quinoline dye, nitro-dye, phenylene blue dyestuff, oxazine dye, phthalocyanine pigment, cyanine dyes can be listed, can use after multiple for these dyestuffs mixing.
Here, " dyestuff " uses after being dissolved in organic solvent, when using after disperseing with dispersion resin etc., is called " pigment " described later.
In dyestuff of the present invention (A), the content of the compound shown in above-mentioned general formula (1) is preferably 50 ~ 100 quality %, is more preferably 70 ~ 100 quality %.When the content of the compound shown in above-mentioned general formula (1) is less than 50 quality %, solvability in a solvent reduces sometimes, thermotolerance reduces.
Then, coloured composition of the present invention is described.Coloured composition of the present invention contains the compound shown in above-mentioned general formula (1).In this coloured composition, being the composition of composition to be coloring photosensitive combination of the present invention containing the above-mentioned dyestuff (A) of this compound, the polymerizable compound (B) with ethylenic unsaturated link(age) with acid number, optical free radical polymerization starter (C) and the monomer (D) with ethylenic unsaturated link(age) except above-mentioned (B) composition.Below coloring photosensitive combination of the present invention is described.
In above-mentioned coloring photosensitive combination, the content of above-mentioned dyestuff (A) is preferably 0.1 ~ 20 quality %, is more preferably 0.5 ~ 15 quality %.When the content of dyestuff (A) is less than 0.1 quality %, tint permanence is insufficient, and when for 20 quality %, in coloring photosensitive combination, dyestuff (A) likely can be separated out.
As the above-mentioned polymerizable compound with ethylenic unsaturated link(age) with acid number, (methyl) vinylformic acid can be listed, α-chloroacrylic acid, methylene-succinic acid, toxilic acid, citraconic acid, fumaric acid, Na Dike acid (himicacid), β-crotonic acid, iso-crotonic acid, vinyl-acetic ester, allyl acetate, styracin, Sorbic Acid, methylfumaric acid, mono succinate [2-(methyl) acryloyl-oxyethyl] ester, phthalic acid list [2-(methyl) acryloyl-oxyethyl] ester, two ends such as ω-carboxy-polycaprolactone list (methyl) acrylate have list (methyl) acrylate of the polymkeric substance of carboxyl and hydroxyl, (methyl) vinylformic acid oxysuccinic acid hydroxy methacrylate, (methyl) vinylformic acid oxysuccinic acid hydroxy propyl ester, the unsaturated polyprotonic acid such as Dicyclopentadiene (DCPD) malate or multifunctional (methyl) acrylate with 1 carboxyl and more than 2 (methyl) acryls, phenol and/or cresol novolak epoxy resin, xenyl skeleton, there is the novolak epoxy resins of naphthalene skeleton, bisphenol A novolac type epoxy compound, the novolac type epoxy compounds such as Dicyclopentadiene (DCPD) novolac type epoxy compound, there is the polyphenylene methane type epoxy resin of multi-functional epoxy's base, unsaturated monoprotic acid is made to act on the epoxy group(ing) of the epoxy resin such as the epoxy compounds shown in following general formula (7), and then the resin making multi-anhydride effect and obtain, as pentaerythritol triacrylate, the polyfunctional acrylic ester of the hydroxyls such as Dipentaerythritol Pentaacrylate and succinyl oxide, Tetra hydro Phthalic anhydride, the polymkeric substance with the polyfunctional acrylic ester of acid number etc. of the reactant of the dibasic acid anhydrides such as Tetra Hydro Phthalic Anhydride.
(in formula, X 41the ester ring type alkyl that the alkylidene that expression Direct Bonding, methylene radical, carbonatoms are 1 ~ 4, carbonatoms are 3 ~ 20 ,-O-,-S-,-SO 2-, the group that represents of-SS-,-SO-,-CO-,-OCO-or above-mentioned formula (2-1) ~ (2-3), this alkylidene can be replaced by halogen atom, R 41, R 42, R 43and R 44represent that hydrogen atom, carbonatoms are alkyl, the carbonatoms alkoxyl group that is 1 ~ 8, carbonatoms be 2 ~ 5 alkenyl or the halogen atom of 1 ~ 5 independently of one another, abovementioned alkyl, alkoxyl group and alkenyl can be replaced by halogen atom, s is the integer of 0 ~ 10.)
These polymerizable compounds can be used alone or two or more is used in combination, in addition, can also combinationally use with the polymerizable compound with ethylenic unsaturated link(age) without acid number.When two or more is used in combination, their copolymerization in advance can be used with multipolymer form.
As the above-mentioned polymerizable compound with ethylenic unsaturated link(age) without acid number, (methyl) 2-Hydroxy ethyl acrylate can be listed such as, (methyl) 2-hydroxypropyl acrylate, (methyl) glycidyl acrylate, following compound N o.A1 ~ No.A4, (methyl) methyl acrylate, (methyl) butyl acrylate, (methyl) isobutyl acrylate, (methyl) vinylformic acid-tert-butyl ester, (methyl) cyclohexyl acrylate, (methyl) n-octyl, (methyl) Isooctyl acrylate monomer, (methyl) vinylformic acid ester in the different ninth of the ten Heavenly Stems, (methyl) stearyl acrylate ester, (methyl) lauryl acrylate, (methyl) methoxyethyl acrylate, (methyl) acrylate methyl esters, (methyl) acrylate, (methyl) acrylic-amino propyl ester, (methyl) acrylate propyl ester, (methyl) ethoxyethyl acrylate, (methyl) vinylformic acid gathers (oxyethyl group) ethyl ester, (methyl) acrylate, butoxy ethoxy ethyl ester, (methyl) EHA, (methyl) acrylate, (methyl) vinylformic acid tetrahydrofuran ester, (methyl) vinyl acrylate, (methyl) allyl acrylate, (methyl) benzyl acrylate, ethylene glycol bisthioglycolate (methyl) acrylate, Diethylene Glycol two (methyl) acrylate, triethylene glycol two (methyl) acrylate, polyoxyethylene glycol two (methyl) acrylate, propylene glycol two (methyl) acrylate, BDO two (methyl) acrylate, 1,6-hexylene glycol two (methyl) acrylate, trimethylolethane trimethacrylate (methyl) acrylate, trimethylolpropane tris (methyl) acrylate, Dipentaerythritol five (methyl) acrylate, Dipentaerythritol six (methyl) acrylate, tetramethylolmethane four (methyl) acrylate, tetramethylolmethane three (methyl) acrylate, tristane dihydroxymethyl two (methyl) acrylate, three [(methyl) acryloyl ethyl] chlorinated isocyanurates, the ester of the unsaturated monoprotic acid such as polyester (methyl) acrylate oligomer and polyvalent alcohol or polyphenol, the metal-salt of the unsaturated polyprotonic acids such as (methyl) zinc acrylate resin, (methyl) Magnesium Acrylate Prepared, maleic anhydride, itaconic anhydride, citraconic anhydride, methyl tetrahydrophthalic anhydride, Tetra Hydro Phthalic Anhydride, trialkyl Tetra Hydro Phthalic Anhydride, 5-(2,5-dioxotetrahydrol furyl) acid anhydrides of the unsaturated polyprotonic acid such as-3-methyl-3-tetrahydrobenzene-1,2-dicarboxylic anhydride, trialkyl Tetra Hydro Phthalic Anhydride-maleic anhydride adduct, dodecenyl succinic anhydride, methylnadic anhydride, the acid amides of the unsaturated monoprotic acid such as (methyl) acrylamide, methylene-bis-(methyl) acrylamide, diethylenetriamine three (methyl) acrylamide, phenylenedimethylidyne two (methyl) acrylamide, α-chloroacrylamide, N-2-hydroxyethyl (methyl) acrylamides and polyamine, the unsaturated aldehydes such as propenal, the unsaturated nitriles such as (methyl) vinyl cyanide, α-chloro-acrylonitrile, vinylidene dicyanide, allyl cyanide, the unsaturated aromatics such as vinylbenzene, 4-vinyl toluene, 4-ethyl styrene, 4-methoxy styrene, 4-Vinyl phenol, 4-chloro-styrene, Vinylstyrene, Vinyl toluene, vinyl benzoic acid, vinylphenol, vinyl sulfonic acid, 4-vinylbenzenesulfonic acid, vinyl benzyl methyl ether, vinylbenzyl glycidyl ether, the beta-unsaturated ketones such as ethylene methacrylic ketone, the unsaturated amine compounds such as vinyl amine, allyl amine, NVP, vinylpiperidine, the vinyl ether such as methoxy ethylene, ethyl vinyl ether, n-butyl vinyl ether, IVE, glycidyl allyl ether, the unsaturated acid imides such as maleimide, N-phenylmaleimide, N-N-cyclohexylmaleimide, the indenes classes such as indenes, 1-methyl indenes, the aliphatic conjugated diene classes such as 1,3-butadiene, isoprene, chlorine pentadiene, at the end of polystyrene, poly-(methyl) methyl acrylate, poly-polymer molecular chain such as (methyl) n-butyl acrylate, polysiloxane etc., there is the macromonomer class of list (methyl) acryl, (methyl) vinyl cyanide, ethene, propylene, butylene, vinylchlorid, other vinyl compounds such as vinyl-acetic ester, and polymethylmethacrylate macromonomer, the macromonomer classes such as Group-capped Polystyrene Macromer, the monomethacrylates of tricyclodecane skeleton, N-phenylmaleimide, methacryloxymethyl-3-Ethyloxetane etc., (methyl) acrylic acid multipolymer and make they and Showa electrician (strain) Inc. KarenzMOI, the isocyanate compound reaction that AOI etc. have unsaturated link(age) obtains (methyl) acrylic acid multipolymer, vinylchlorid, vinylidene chloride, divinyl succinate, diallyl phthalate, triallyl phosphoric acid ester, triallyl isocyanurate, vinyl sulfide, vinyl imidazole, Yi Xi oxazolin, vinylcarbazole, vinyl pyrrolidone, vinyl pyridine, the vinyl monomer of hydroxyl and the vinyl carbamate compound of polyisocyanate compounds, the vinyl monomer of hydroxyl and the vinyloxirane of polyepoxides, pentaerythritol triacrylate, the polyfunctional acrylic ester of the hydroxyls such as Dipentaerythritol Pentaacrylate and first phenylene diisocyanate, the reactant etc. of the polyfunctional isocyanates such as hexamethylene diisocyanate.
Compound N o.A1
Compound N o.A2
Compound N o.A3
Compound N o.A4
In order to adjust acid number to improve the developability of above-mentioned photosensitive composite, simple function or multi-functional epoxy compound can be used further together with the above-mentioned polymerizable compound with ethylenic unsaturated link(age) with acid number.The above-mentioned acid number with the solids component of the polymerizable compound of ethylenic unsaturated link(age) with acid number is preferably the scope of 5 ~ 120mgKOH/g, and the consumption of simple function or multi-functional epoxy compound is preferably selected according to the mode meeting above-mentioned acid number.
As above-mentioned monofunctional epoxy compound, glycidyl methacrylate can be listed, methyl glycidyl ether, ethyl ether, propyl glycidyl ether, isopropyl glycidyl ether, butylglycidyl ether, isobutyl glycidyl ether, tertiary butyl glycidyl ether, amyl group glycidyl ether, hexyl glycidyl ether, heptyl glycidyl ether, octyl glycidyl ether, nonyl glycidyl ether, decyl glycidyl ether, undecyl glycidyl ether, lauryl diglycidyl ether, tridecyl glycidyl ether, tetradecyl glycidyl ether, pentadecyl glycidyl ether, cetyl glycidyl ether, 2-hexyl glycidyl ether, glycidyl allyl ether, propargyl glycidyl ether, to methoxy ethyl glycidyl ether, phenyl glycidyl ether, to methoxyl group glycidyl ether, p-butylphenol glycidyl ether, cresyl glycidyl ether, 2-methacresol base glycidyl ether, 4-nonyl phenyl glycidyl glyceryl ether, benzyl glycidyl ether, to cumyl phenyl glycidyl ether, trityl glycidyl ether, methacrylic acid 2,3-epoxy group(ing) propyl ester, epoxidised soybean oil, epoxidized linseed, Glycidyl butyrate, single ethylene oxide butylcyclohexane, 1,2-epoxy-4-vinyl cyclohexane, Styrene oxide 98min., pinene oxide, oxidation methyl vinylbenzene, cyclohexene oxide, propylene oxide etc.
As above-mentioned multi-functional epoxy compound, when use be selected from the group be made up of biphenol type epoxy compound and Racemic glycidol ethers more than one time, due to can the better painted alkali-developable photosensitive composition of acquired character, therefore preferably.As this biphenol type epoxy compound, except can using the epoxy compounds shown in above-mentioned general formula (7), also can list the biphenol type epoxy compounds such as such as A Hydrogenated Bisphenol A type epoxy compounds.As this Racemic glycidol ethers, ethylene glycol diglycidylether can be listed, propylene glycol diglycidylether, 1, 4-butanediol diglycidyl ether, 1, 6-hexanediol diglycidyl ether, 1, 8-ethohexadiol diglycidylether, 1, 10-decanediol diglycidylether, 2, 2-dimethyl-1, ammediol diglycidylether, diethylene glycol diglycidyl glyceryl ether, Triethylene Glycol Diglycidyl Ether, TEG diglycidylether, six ethylene glycol diglycidylethers, 1, 4-cyclohexanedimethanodiglycidyl diglycidyl ether, 1, 1, 1-tri-(glycidyl oxy methyl) propane, 1, 1, 1-tri-(glycidyl oxy methyl) ethane, 1, 1, 1-tri-(glycidyl oxy methyl) methane, 1, 1, 1, 1-tetra-(glycidyl oxy methyl) methane.
In addition, the novolac type epoxy compounds such as phenol novolak resin type epoxy compounds, xenyl novolac type epoxy compound, cresol novolak type epoxy compounds, bisphenol A novolac type epoxy compound, Dicyclopentadiene (DCPD) novolac type epoxy compound can also be used; The cycloaliphatic epoxy of 3,4-epoxy-6-methylcyclohexylmethyl-3,4-epoxy-6-methylcyclohexanecarboxylic acid ester, 3,4-epoxycyclohexyl-methyl-3,4-epoxycyclohexane carboxylate, 1-epoxy ethyl-3,4-epoxy cyclohexane etc.; The glycidyl ester classes such as o-phthalic acid diglycidyl ester, tetrahydrophthalic acid 2-glycidyl ester, dimer acid glycidyl ester ester; The glycidyl amines such as four glycidyl group diaminodiphenyl-methane, triglycidyl group-p-aminophenol, N, N-diglycidylaniline; The hetero ring type epoxy compoundss such as 1,3-diglycidyl-5,5-T10, triglycidyl group chlorinated isocyanurates; The dioxide compound such as dicyclopentadiene; Naphthalene type epoxy compounds, triphenylmethane type epoxy compound, dicyclopentadiene type epoxy compound etc.
In above-mentioned coloring photosensitive combination, the above-mentioned content with the polymerizable compound (B) with ethylenic unsaturated link(age) of acid number is preferably 0.1 ~ 90 quality %, is more preferably 1 ~ 80 quality % in coloring photosensitive combination.When the content of above-mentioned polymerizable compound (B) is less than 0.1%, developing property likely becomes insufficient, and when more than 90%, solidification film strength likely can become insufficient.
As long as above-mentioned optical free radical polymerization starter can cause the compound of radical polymerization by being subject to rayed, such as, can exemplify ketone based compound, the oxime compounds etc. such as methyl phenyl ketone based compound, benzyl based compound, benzophenone based compound, thioxanthone based compound as preferred initiator.
As methyl phenyl ketone based compound, such as diethoxy acetophenone can be listed, 2-hydroxy-2-methyl-1-phenyl-propane-1-ketone, 4'-sec.-propyl-2-hydroxy-2-methyl methyl phenyl ketone, 2-hydroxymethyl-2-methyl acetophenone, 2, 2-dimethoxy-1, 2-diphenylethane-1-ketone, to dimethylamino benzoylformaldoxime, to tertiary butyl dichloroacetophenone, to tertiary butyl Trichloroacetophenon, to nitrine benzylidene acetophenone, 1-hydroxycyclohexylphenylketone, 2-methyl isophthalic acid-[4-(methylsulfany) phenyl]-2-morpholinopropanone-1, 2-benzyl-2-dimethylamino-1-(4-morpholino phenyl)-butanone-1, bitter almond oil camphor, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, bitter almond oil camphor n-butyl ether, benzoin isobutyl ether, 1-[4-(2-hydroxyl-oxethyl)-phenyl]-2-hydroxy-2-methyl-1-propane-1-ketone etc.
As benzyl based compound, benzyl, methoxyphenyl etc. can be listed.
As benzophenone based compound, such as benzophenone, o-benzoyl yl benzoic acid methyl esters, Michler's keton, 4,4'-two diethylamino benzophenone, 4,4'-dichloro benzophenones, 4-benzoyl-4'-methyldiphenyl sulfide etc. can be listed.
As oxime compound, can 1 be listed, 2-acetyl caproyl, 1-[4-(phenylsulfartyl)-, 2-(O-benzoyl oximes)], ethyl ketone, 1-[9-ethyl-6-(2-methyl benzoyl)-9H-carbazole-3-base]-, 1-(O-ethanoyl oxime), ketone, (2-aminomethyl phenyl) [6-nitro-9-[3-(TMS) propyl group]-9H-carbazole-3-base]-, 1-O-ethanoyl oxime), ketone, (9-ethyl-6-nitro-9H-carbazole-3-base) (2-aminomethyl phenyl), O-ethanoyl oxime, ketone, (9-ethyl-6-nitro-9H-carbazole-3-base) [2-methyl-4-(4-morpholinyl) phenyl), O-ethanoyl oxime, ketone, (3, 5-dinitrophenyl) (9-ethyl-6-nitro-9H-carbazole-3-base) (2-aminomethyl phenyl), O-ethanoyl oxime, ketone, (9-ethyl-6-nitro-9H-carbazole-3-base) (3-nitrophenyl), O-ethanoyl oxime, 1, 3, 5-triazine-2, 4, 6 (1H, 3H, 5H)-triketone, 1, 3, 5-tri-[2-(ethanoyl oxygen base)-3-[3-[(1E)-1-[(ethanoyl oxygen base) Iminoethyl]-6-nitro-9H-carbazole-9-base] propyl group]-, 1, 2-butanedione, 1-[4-(phenylsulfartyl) phenyl]-, 2-(O-ethanoyl oxime), 1, 2-butanedione, 1-[4-[[4-(2-hydroxyl-oxethyl) phenyl] sulfenyl] phenyl]-, 2-(O-ethanoyl oxime), 1, 2-butanedione, 1, 1 '-(sulfenyl two-4, 1-phenylene) two-, 2, 2-two (O-ethanoyl oxime), 1, 2-acetyl caproyl, 1-[4-(phenylsulfartyl) phenyl]-, 2-[O-(4-methyl benzoyl) oxime] etc.
As thioxanthone based compound, thioxanthone, 2-methyl thioxanthone, 2-ethyl thioxanthone, CTX, ITX, 2,4-diethyl thioxanthones etc. can be listed.
As other optical free radical polymerization starter, TMDPO, two (cyclopentadienyl)-bis-[the fluoro-3-of 2,6-bis-(pyrroles-1-base)] titanium etc. can be listed.
These optical free radical polymerization starters can according to the performance expected with the use of one kind or two or more.
In above-mentioned coloring photosensitive combination, the content of above-mentioned optical free radical polymerization starter (C) is preferably 0.1 ~ 30 quality %, is particularly preferably 0.5 ~ 10 quality % in coloring photosensitive combination.When the content of above-mentioned Photoepolymerizationinitiater initiater (C) is less than 0.1 quality %, expose the solidification caused and may become insufficient, when being greater than 30 quality %, in resin combination, initiator (C) may be separated out.
In coloring photosensitive combination of the present invention, as the monomer (D) with ethylenic unsaturated link(age), the polymerizable compound with ethylenic unsaturated link(age) without above-mentioned acid number can be used.The content with the monomer (D) of ethylenic unsaturated link(age) is preferably 10 ~ 1000 quality % relative to the polymerizable compound 100 quality % with ethylenic unsaturated link(age) with acid number, is more preferably 20 ~ 800 quality %.
Mineral dye or pigment dyestuff can also be added further in above-mentioned coloring photosensitive combination, such as nitroso compound can be used, nitro-compound, azo-compound, two azo-compounds, xanthene compound, quinoline compound, anthraquinone compounds, coumarin compound, phthalocyanine compound, isoindolinone compound, isoindoline compounds, quinoline Azone compound, two and anthrone compound, purple cyclic ketone compound, perylene compound, diketopyrrolo-pyrrole compound, thioindigo compound, dioxazine compound, triphenylmethane compounds, quinophthalone compound, naphthalene tetracarboxylic acid, the metal complex compounds of azoic dyestuff, cyanine dyes, pigment lake, the carbon blacks such as the carbon black obtained by oven process, channel process, pyrolysis method or Shawinigan black, section's qin graphitized carbon black or lamp black method carbon black, with epoxy resin adjustment, coating above-mentioned carbon black and obtain pigment, in advance by above-mentioned carbon black in a solvent with resin carry out dispersion treatment, make its resin adsorbing 20 ~ 200mg/g and obtain pigment, above-mentioned carbon black carried out acidity or basic surface process and the pigment, the median size that obtain are more than 8nm and DBP oil number be below 90ml/100g pigment, by CO, the CO in the volatile component at 950 DEG C 2the total oxygen demand calculated is every 100m of carbon black 2surface-area is the pigment of more than 9mg, graphite, graphitized carbon black, gac, carbon fiber, carbon nanotube, micro-coiled carbon fibers, carbon nanohorn, carbon aerogels, soccerballene, nigrosine, Pigment black 7, titanium are black, mineral dye or the pigment dyestuff such as hydrophobic resin, chromoxide green, milori blue, cobalt green, cobalt blue, manganese system, yellow prussiate, phosphoric acid salt ultramarine, Prussian blue, ultramarine, cerulean blue, chrome green, emerald green, lead sulfate, yellow lead, zinc yellow, red iron oxide (red iron oxide (III)), cadmium red, synthesis iron oxide black, umber.These pigment can separately or by multiple used in combination.
As above-mentioned mineral dye or pigment dyestuff, also can use commercially available pigment, such as Pigment red 1,2,3,9,10,14,17,22,23,31,38,41,48,49,88,90,97,112,119,122,123,144,149,166,168,169,170,171,177,179,180,184,185,192,200,202,209,215,216,217,220,223,224,226,227,228,240,254 can be listed; Pigment Orange 13,31,34,36,38,43,46,48,49,51,52,55,59,60,61,62,64,65,71; Pigment Yellow 73 1,3,12,13,14,16,17,20,24,55,60,73,81,83,86,93,95,97,98,100,109,110,113,114,117,120,125,126,127,129,137,138,139,147,148,150,151,152,153,154,166,168,175,180,185; Pigment Green 7,10,36; Pigment Blue 15,15:1,15:2,15:3,15:4,15:5,15:6,22,24,56,60,61,62,64; Pigment violet 1,19,23,27,29,30,32,37,40,50 etc.
Above-mentioned coloring photosensitive combination can be made as required to dissolve or be distributed in organic solvent, the masking liquid spin coater obtained, roller coating machine, bar coater, mould painting machine, curtain coater, various printing, the known means of impregnating are applied in the support substrate such as soda glass, silica glass, semiconductor substrate, metal, paper, plastics, carry out rayed and make it solidify.
As above-mentioned organic solvent, the solvent that usually can dissolve or disperse above-mentioned each composition as required can be listed, the ketones such as such as methylethylketone, methyl amylketone, diethyl ketone, acetone, Methyl isobutyl ketone, mibk, pimelinketone, 2-heptanone; The ether series solvents such as ether, diox, tetrahydrofuran (THF), 1,2-glycol dimethyl ether, 1,2-diethoxyethane, dimethyl ether; The ester series solvents such as methyl acetate, ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, hexalin acetate, ethyl lactate, Succinic acid dimethylester, alcohol ester; The cellosolve such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether series solvent; The alcohol series solvents such as methyl alcohol, ethanol, XOR n-propyl alcohol, XOR propyl carbinol, amylalcohol; The ether-ether series solvents such as ethylene glycol monomethyl acetic ester, ethylene glycol list ethylhexoate, propylene glycol-1-monomethyl ether-2-acetic ester (PGMEA), dipropylene glycol monomethyl ether acetic ester, 3-methoxybutyl acetic ester, ethoxy ethyl propionate; The BTX series solvents such as benzene,toluene,xylene; The aliphatic hydrocarbon series solvent of hexane, heptane, octane, hexanaphthene etc.; The terpenic series hydrocarbon ils such as turps, D-limonene, firpene; The paraffin series solvents such as mineral turpentine, Swasol#310 (Cosmo Guia Hill oil (Co., Ltd.)), Solvesso#100 (Exxon chemistry (Co., Ltd.)); The halogenated aliphatic hydrocarbon system solvents such as tetracol phenixin, chloroform, trieline, vinylchlorid, 1,2-ethylene dichloride; Chlorobenzenes etc. are containing halo aromatic nucleus hydrocarbon system solvent; Trivalin SF series solvent, aniline, triethylamine, pyridine, acetic acid, acetonitrile, dithiocarbonic anhydride, N, dinethylformamide, N, N-N,N-DIMETHYLACETAMIDE, N-Methyl pyrrolidone, dimethyl sulfoxide (DMSO), water etc., these solvents can a kind use or use with mixed solvent form of more than two kinds.Wherein, ketone, ether-ether series solvent etc., particularly propylene glycol-1-monomethyl ether-2-acetic ester, pimelinketone etc. due in photosensitive composite the consistency of resist and Photoepolymerizationinitiater initiater good, therefore preferably.
Mineral compound can also be contained further in above-mentioned coloring photosensitive combination.As this mineral compound, the metal oxides such as such as nickel oxide, ferric oxide, iridium oxide, titanium oxide, zinc oxide, magnesium oxide, calcium oxide, potassium oxide, silicon-dioxide, aluminum oxide can be listed; Layered clay mineral, milori blue, calcium carbonate, magnesiumcarbonate, cobalt system, manganese system, glass powder, mica, talcum, kaolin, yellow prussiate, various metal sulfate, sulfide, selenide, pure aluminium silicate, Calucium Silicate powder, aluminium hydroxide, platinum, gold and silver, copper etc.
In above-mentioned coloring photosensitive combination, when using pigment and/or mineral compound, dispersion agent can be added.As this dispersion agent, as long as dispersion agent then any dispersion agent of the dispersion of tinting material, mineral compound, stabilization can be made, commercially available dispersion agent, such as BYK Inc., BYK series etc. can be used, preferably use formed by the polyester with basic functionality, polyethers, urethane macromolecule dispersing agent, have nitrogen-atoms as basic functionality and the functional group with nitrogen-atoms be amine and/or its quaternary salt, amine value is the dispersion agent of 1 ~ 100mgKOH/g.
In addition, can also add as required thermal polymerization inhibitors such as methyl-phenoxide, Resorcinol, pyrocatechol, tert-butyl catechol, thiodiphenylamine in above-mentioned coloring photosensitive combination; Softening agent; Adhesion promoters; Weighting agent; Defoamer; Flow agent; Surface conditioner; The antioxidants such as phenol system antioxidant, phosphorous acid ester system antioxidant, thioether system antioxidant; UV light absorber; Dispersing auxiliary; Anticoalescent; Catalyzer; Effect promotor; Linking agent; The additive that thickening material etc. are conventional.
In addition, by using other organic polymers together with the above-mentioned polymerizable compound with ethylenic unsaturated link(age) with acid number, the characteristic of the cured article of above-mentioned coloring photosensitive combination can be improved.As above-mentioned organic polymer, such as polystyrene can be listed, polymethylmethacrylate, Eudragit NE30D, poly-(methyl) vinylformic acid, vinylbenzene-(methyl) acrylic copolymer, (methyl) acryl acid-methyl methacrylate copolymer, ethylene-vinyl chloride copolymer, ethylene-vinyl base co-polymer, polyvinyl chloride (PVC) RESINS, ABS resin, nylon 6, nylon66 fiber, nylon 12, urethane resin, polycarbonate polyvinyl butyral acetal, cellulose ester, polyacrylamide, saturated polyester, resol, phenoxy resin, polyamide-imide resin, polyamic acid resin, epoxy resin etc., wherein, preferred polystyrene, (methyl) acryl acid-methyl methacrylate copolymer, epoxy resin.
Can also also with hot radical polymerization starter, chain-transfer agent, sensitizing agent, tensio-active agent, silane coupling agent, melamine etc. in above-mentioned coloring photosensitive combination.
As above-mentioned hot radical polymerization starter, can 2 be listed, 2 '-Diisopropyl azodicarboxylate, 2,2 '-azo two (methyl isobutyrate), 2,2 '-azo two-2,4-methyl pentane nitrile, 1, the azo series initiators such as 1 '-azo two (1-acetoxyl group-1-diphenylphosphino ethane); The persulphates etc. such as superoxide series initiators, ammonium persulphate, Sodium Persulfate, Potassium Persulphate such as benzoyl peroxide, di-tertiarybutyl benzoyl, t-butylperoxy pivarate, two (4-tert-butylcyclohexyl) peroxy dicarbonate.They can a kind of use or more than two kinds used in combination.
As above-mentioned chain-transfer agent, sensitizing agent, the compound of usual sulfur atom-containing can be used.Such as Thiovanic acid, dimercaptosuccinic acid, sulfydryl Whitfield's ointment, 2 mercaptopropionic acid, 3-thiohydracrylic acid, 3-mercaptobutyric acid, N-(2-mercapto radical propionyl group) glycine, 2-sulfydryl nicotinic acid, 3-[N-(2-mercaptoethyl) formamyl] propionic acid, 3-[N-(2-mercaptoethyl) is amino] propionic acid, N-(3-mercapto radical propionyl group) L-Ala, 2-mercapto ethane sulfonic acid, 3-mercaptopropanesulfonic acid, 4-sulfydryl butane sulfonic acid, dodecyl (4-methylsulfany) phenylate, 2 mercapto ethanol, 3-Mercapto-1，2-propanediol, 1-sulfydryl-2-propyl alcohol, 3-sulfydryl-2-butanols, mercapto-phenol, 2-MEA, 2-mercaptoimidazole, 2-mercaptobenzimidazole, 2-sulfydryl-3-pyridol, 2-mercaptobenzothiazole, Thiovanic acid, trimethylolpropane tris (3-mercaptopropionic acid ester), the sulfhydryl compounds such as tetramethylolmethane four (3-mercaptopropionic acid ester), the di-sulphide compounds that the oxidation of this sulfhydryl compound is obtained, iodoacetic acid, iodopropionic acid, ethylene iodohydrin, 2-iodoethane sulfonic acid, the iodine alkylates such as 3-iodopropane sulfonic acid, trimethylolpropane tris (3-mercaptoisobutanoic acid esters), butyleneglycol two (3-mercaptoisobutanoic acid esters), hexanedithiol, decanedithiol, Isosorbide-5-Nitrae-dimethyl sulfydryl benzene, butyleneglycol disulfide group propionic ester, butyleneglycol disulfide group acetic ester, ethylene glycol bis ethyl thioglycollic acid ester, trimethylolpropane tris ethyl thioglycollic acid ester, butyleneglycol disulfide group propionic ester, trimethylolpropane tris thiohydracrylic acid ester, trimethylolpropane tris ethyl thioglycollic acid ester, tetramethylolmethane four thiohydracrylic acid ester, tetramethylolmethane four ethyl thioglycollic acid ester, trihydroxy-ethyl three sulfenyl propionic ester, following compound N o.C1, the aliphatics multi-functional thiol compounds such as tri-thiol propionic acid three (2-hydroxyethyl) chlorinated isocyanurates, Showa electrician Inc. KarenzMTBD1, PE1, NR1 etc.
As above-mentioned tensio-active agent, can use the tensio-active agents such as nonionogenic tenside, amphoterics, silicone based surfactants such as positively charged ion system tensio-active agent, polyethylene glycol alkyl ether, cithrol, sorbitan fatty acid esters, glycerine monofatty ester such as negatively charged ion system tensio-active agent, higher amines halate, quaternary ammonium salt such as the fluorine surfactant such as perfluoralkyl phosphate, perfluoroalkyl carboxylate, higher fatty acid basic salt, alkylsulfonate, alkyl-sulphate, they can also combinationally use.
As above-mentioned silane coupling agent, such as chemical company of SHIN-ETSU HANTOTAI silane coupling agent can be used, wherein preferably use KBE-9007, KBM-502, KBE-403 etc. to have the silane coupling agent of isocyanate group, methacryloyl, epoxy group(ing).
As above-mentioned melamine compounds, the active methylol (CH in the nitrogen compounds such as (gathering) methylol melamine, (gathering) methylol glycoluril, (gathering) methylol benzo guanamine, (gathering) methylolurea can be listed 2oH yl) all or part of (at least 2) by alkyl etherified and compound that is that obtain.Here, as the alkyl forming alkyl oxide, methyl, ethyl or butyl can be listed, mutually can be the same or different.In addition, can oneself condensation in a molecule by alkyl etherified methylol, also can two intermolecular condensations, its result forms oligomer composition.Specifically, hexa methoxy methyl melamine, six butoxymethyl melamines, tetramethoxymethylglycoluril, four butoxymethyl glycolurils etc. can be used.Wherein, preferred hexa methoxy methyl melamine, six butoxymethyl melamines etc. are through alkyl etherified melamine.
In above-mentioned coloring photosensitive combination, except dyestuff (A), the polymerizable compound (B) with ethylenic unsaturated link(age) with acid number, optical free radical polymerization starter (C) and there is ethylenic unsaturated link(age) monomer (D) except the content of any composition (wherein not comprising organic solvent) suitably can limit according to its application target, but preferably add up to below 500 mass parts relative to polymerizable compound (B) 100 mass parts with ethylenic unsaturated link(age) with acid number.
In addition, as the light source of the active light used when making above-mentioned coloring photosensitive combination solidify, the light source of the light sending wavelength 300 ~ 450nm can be used, such as ultrahigh pressure mercury lamp, Mercury arc lamp, carbon arc lamp, xenon electric arc lamp etc.
In addition, by using laser as exposure light source, do not use mask and the direct picture of laser directly forming image from computer digital information is also not only useful from productivity but also from the angle of the raising seeking sharpness, positional precision etc., as this laser, preferably can use the light of the wavelength of 340 ~ 430nm, argon laser, He-Ne Lasers, YAG laser and semiconductor laser etc. also can be used to send the laser of the light from visible ray to region of ultra-red.When using these laser, adding and having absorption from visible ray to the sensitizing coloring matter in this infrared region.
Above-mentioned coloring photosensitive combination (or its cured article) can be used for light solidified coating or varnish, Photocurable adhesive agent, printed base plate, or color TV, PC watch-dog, portable data assistance, colour filter in the display panels of the colour such as digital camera display, the colour filter of ccd image sensor, the electrode materials of plasma display, powder coated, printing-ink, press plate, caking agent, dental composition, light appearance resin, jelly paint, the photo-resist of electronics engineering, resistance to platedresist, etch-resistant coating, both liquid and desciccator diaphragms, soldering resist, for the manufacture of the colour filter of various display purposes or at plasma display, electric luminous display unit, and for the formation of the resist of structure in the manufacturing process of LCD, for enclosing electrically and the composition of electronic unit, soldering-resistance layer, magnetic recording material, milli machine parts, waveguide, photoswitch, plating mask, etching mask, color test system, glass fiber cable coatings, screen painting template, for being manufactured the material of three-dimensional body by stereolithography, holographic recording material, image recording material, fine circuits, decoloring material, for the decoloring material of image recording material, use the decoloring material of the image recording material of microcapsule, printing distributing board photo anti-corrosion agent material, the photo anti-corrosion agent material of UV and visible laser through image system, for tellite successively stacked in the photo anti-corrosion agent material that formed of dielectric layer or the various uses such as protective membrane, its purposes is not particularly limited.
Above-mentioned coloring photosensitive combination can use to form the pixel of colour filter, and the photosensitive composite particularly as the display equipment colour filter for the formation of device used for image display such as display panels is useful.
Above-mentioned display equipment colour filter is formed preferably by following operation: the operation that (1) forms the operation of the film of above-mentioned coloring photosensitive combination on substrate, (2) irradiate the operation of active light via the mask with predetermined pattern shape to this film, the tunicle developing solution after exposure develops by (3) operation, (4) are heated this tunicle after development.In addition, above-mentioned coloring photosensitive combination is also useful as the coloring photosensitive combination of the ink-jetting style of Nonvisualization operation.
Embodiment
Below enumerate embodiment etc. to be described in detail further to the present invention, but the present invention is not limited to these embodiments etc.
O.1 and the synthesis of No.2 [embodiment 1-1 and 1-2] compound N
In reaction vessel, add aldehyde cpd (4mmol), propane dinitrile (8mmol), Piperazine anhydrous (0.03g) and N,N-DIMETHYLACETAMIDE (5g), make them dissolve, stir 5 hours at 80 DEG C.Drip ethanol 7g and make its partial crystallization, by the solid filtering obtained, concentrated after carrying out washing with alcohol, refined by silica gel column chromatography (developping solution: toluene), dry, obtain yellow solid respectively.With 1h-NMR, IR confirm that the yellow solid obtained is target compound.In addition, absorbing wavelength characteristic is measured.Show the result in [table 1] and [table 2].
O.3 and the synthesis of No.4 [embodiment 1-3 and 1-4] compound N
In reaction vessel, add aldehyde cpd (4mmol), ethyl cyanacetate (8mmol), Piperazine anhydrous (0.03g) and N,N-DIMETHYLACETAMIDE (5g), make it dissolve, stir 5 hours at 50 DEG C.Drip ethanol 7g and make its partial crystallization, by the solid filtering, the washing with alcohol that obtain, obtain yellow solid respectively.With 1h-NMR, IR confirm that the yellow solid obtained is target compound.In addition, absorbing wavelength characteristic is measured.Show the result in [table 1] and [table 2].
The synthesis o.5 of [embodiment 1-5] compound N
In reaction vessel, add aldehyde cpd (4mmol), propane dinitrile (12mmol), Piperazine anhydrous (0.04g) and N,N-DIMETHYLACETAMIDE (5g), make it dissolve, stir 3 hours at 50 DEG C.Drip ethanol 7g and make its partial crystallization, by the solid filtering, the washing with alcohol that obtain, obtain yellow solid.With 1h-NMR, IR confirm that the yellow solid obtained is target compound.In addition, absorbing wavelength characteristic is measured.Show the result in [table 1] and [table 2].
[table 1]
1h-NMR (solvent: CDCl 3)
[table 2]
[evaluation Example 1-1 ~ 1-5] absorbing wavelength evaluating characteristics
Use CHCl 3solution evaluate compound N obtained above o.1 ~ the absorbing wavelength characteristic of No.5 and above-mentioned comparative compound No.1 and 2.Show the result in [table 3].
[table 3]
λmax/nm ε
Compound N o.1 448 1.22×10 5
Compound N o.2 449 1.32×10 5
Compound N o.3 426 9.5×10 4
Compound N o.4 420 9.72×10 4
Compound N o.5 442 3.30×10 5
Comparative compound No.1 437 1.20×10 5
Comparative compound No.2 438 1.63×10 5
From the result of above-mentioned [table 3], the dyestuff of the present invention (A) containing the compound shown in above-mentioned general formula (1) has suitable absorbing wavelength.
The preparation of [embodiment 2-1 ~ 2-5] coloring photosensitive combination No.1 ~ No.5
The preparation of < step 1> photosensitive composite No.1
To mix as the SPC-1000 of (B) composition (Showa electrician Inc.) 39.7g and A-9300-1-CL (chemical industrial company of the Xin Zhong village system) 9.2g as (D) composition, IrgacureOXE-01 (BASF AG's system) 0.8g, the PGMEA28.0g as solvent and the FZ2122 as other compositions (TorayDowCorning Inc.) 2.31g as (C) composition, stir until insolubles disappears, obtain photosensitive composite No.1.
The preparation of < step 2> dye solution No.1 ~ No.5
Respectively to the compound N obtained above as (A) composition o.1 ~ each 0.10g of No.5 in add N,N-DIMETHYLACETAMIDE 1.90g, stir make it dissolve.
The preparation of < step 3> coloring photosensitive combination No.1 ~ No.5
The 5.0g of the photosensitive composite No.1 obtained in step 1 is mixed with each 1.0g of dye solution No.1 ~ No.5 obtained in step 2, obtains coloring photosensitive combination No.1 ~ No.5 of the present invention respectively.
[comparative example 2-1 and 2-2] compares the preparation of tint permanence photosensitive composite No.1 and No.2
Except o.1 changing to except comparative compound No.1 and No.2 by the compound N of (A) composition in the step 2 of embodiment 2-1, adopting the gimmick same with embodiment 2-1, obtaining comparing coloring photosensitive combination No.1 and No.2.
[evaluation Example 2-1 ~ 2-5 and comparative evaluation example 2-1 and 2-2] is by burning till the Evaluation of Heat Tolerance carried out
By coloring photosensitive combination No.1 ~ No.5 obtained above and compare coloring photosensitive combination No.1 and No.2 and be applied on glass substrate under the condition of 410rpm × 7 second respectively, make its drying (90 DEG C, 90 seconds) with hot-plate.With ultrahigh pressure mercury lamp, (150mJ/cm is exposed to the film obtained 2).Film after exposure is burnt till under the condition of 230 DEG C × 30 minutes.The absorbancy of the absorbancy of the film of (after exposure) and the film after burning till before measuring the burning till of the maximum absorption wavelength (λ max) of compound (dyestuff) used, the ratio of the absorbancy of the film after the burning till when absorbancy of the film of (exposure is rear) is designated as 100 before burning till is evaluated as relative intensity.Wherein, close to 100, the absorbancy of the film after burning till more represents that thermotolerance is higher.Show the result in [table 4].
[table 4]
Known by the above results, the thermotolerance of coloring photosensitive combination of the present invention is high.
[evaluation Example 3-1 ~ 3-5 and comparative evaluation example 3-1 and 3-2] Investigation on Photodegradation
By coloring photosensitive combination No.1 ~ No.5 obtained above and compare coloring photosensitive combination No.1 and No.2 and be applied to respectively on glass substrate under the condition of 410rpm × 7 second, make its drying (90 DEG C, 90 seconds) with hot-plate.With ultrahigh pressure mercury lamp, (150mJ/cm is exposed to the film obtained 2).Film Suga test system xenon light fastness test machine tableSanXT-1500L after exposure is implemented 12 hours light fastness tests.Measure the absorbancy of the film after the absorbancy of the film before the light fastness test in the maximum absorption wavelength (λ max) of compound (dyestuff) used and light fastness test, the ratio of the absorbancy of the film after light fastness test during the absorbancy of the film before light fastness test to be designated as 100 is evaluated for relative intensity.Wherein, close to 100, the absorbancy of the film after light fastness test more represents that photostabilization is higher.Evaluation shows the result in [table 5].
[table 5]
Compound (dyestuff) Relative intensity
Evaluation Example 2-1 Compound N o.1 94
Evaluation Example 2-2 Compound N o.2 94
Evaluation Example 2-3 Compound N o.3 92
Evaluation Example 2-4 Compound N o.4 92
Evaluation Example 2-5 Compound N o.5 94
Comparative evaluation example 2-1 Comparative compound No.1 90
Comparative evaluation example 2-2 Comparative compound No.2 79
Known by the above results, the photostabilization of coloring photosensitive combination of the present invention is high.
Known by above result, the dyestuff employing novel cpd of the present invention has absorption in suitable wavelength region may, employs the photosensitive composite of this dyestuff and the thermotolerance of cured article and photostabilization thereof high.Therefore, novel cpd of the present invention and coloring photosensitive combination are for display equipment colour filter and use the display panels of this colour filter to be useful.

Claims (5)

1. the compound shown in following general formula (1),
In general formula (1), A represents phenyl ring, naphthalene nucleus or anthracene nucleus, and alkyl, alkoxyl group, haloalkyl or halogenated alkoxy that these rings can be 1 ~ 12 by halogen atom, cyano group, hydroxyl, nitro, carbonatoms replace,
Y represents cyano group or-COOR 4,
R 1represent hydrogen atom, phenyl, cyano group, nitro, alkoxyl group that alkyl that halogen atom, carbonatoms are 1 ~ 12, carbonatoms are 1 ~ 12, carbonatoms be 1 ~ 12 haloalkyl or carbonatoms be the halogenated alkoxy of 1 ~ 12,
R 2and R 3represent independently of one another hydrogen atom, carbonatoms be 1 ~ 12 alkyl, carbonatoms be 6 ~ 20 aryl or carbonatoms be the aralkyl of 7 ~ 20,
R 2and R 3the alkyl represented, aryl and aralkyl can be replaced by halogen atom or nitro,
R 2and R 3represent alkyl and aralkyl in methylene radical can be replaced by-COO-,-O-,-OCO-,-NHCO-,-NH-or-CONH,
R 4represent alkyl that hydrogen atom, carbonatoms are 1 ~ 12, aryl that carbonatoms is 6 ~ 20, carbonatoms be 7 ~ 20 aralkyl or carbonatoms be the heterocyclic radical of 2 ~ 35,
R 4represent alkyl and aralkyl in methylene radical can be replaced by-COO-,-O-,-OCO-,-NHCO-,-NH-or-CONH,
X represents singly-bound, nitrogen-atoms ,-NR 5-, Sauerstoffatom, sulphur atom ,-SO 2-,-SO-, phosphorus atom ,-PR 6-or meet the organic group of arbitrary condition in following <1> ~ <5>,
R 5and R 6represent independently of one another hydrogen atom, carbonatoms be 1 ~ 12 alkyl, carbonatoms be 6 ~ 20 aryl or carbonatoms be the aralkyl of 7 ~ 20,
The integer of m=2 ~ 6;
<1>m=2, X as shown in following formula (2),
＊-Z 1-X 1-Z 2-＊(2)
In formula (2), X 1expression-NR 13-, the carbonatoms of divalence is the aliphatic alkyl of 1 ~ 35, the carbonatoms of divalence is the ester ring type alkyl of 3 ~ 35, the carbonatoms of divalence is 6 ~ 35 the carbonatoms containing aromatic nucleus alkyl, divalence be 2 ~ 35 the group represented containing any one in heterocyclic group or following (2-1) ~ (2-3)
X 1alkyl, alkoxyl group, haloalkyl or halogenated alkoxy that the aliphatic alkyl represented can be 1 ~ 8 by halogen atom, cyano group, hydroxyl, nitro, carbonatoms replace,
X 1methylene radical in the aliphatic alkyl represented can by-O-,-S-,-CO-,-CO-O-,-O-CO-,-SO 2-,-NH-or their groups of combining replace,
Z 1and Z 2represent Direct Bonding ,-O-,-S-,-SO independently of one another 2-,-SO-,-NR 13-or-PR 14-,
R 13and R 14represent independently of one another hydrogen atom, carbonatoms be 1 ~ 8 alkyl, carbonatoms be 6 ~ 20 aryl or carbonatoms be the aralkyl of 7 ~ 20,
R 13and R 14the alkyl represented, aryl and aralkyl can be replaced by halogen atom, hydroxyl or nitro,
R 13and R 14represent alkyl and aralkyl in methylene radical can be replaced by-COO-,-O-,-OCO-,-NHCO-,-NH-or-CONH-,
Wherein, the carbonatoms of group that represents of above-mentioned general formula (2) is in the scope of 1 ~ 35;
In formula (2-1), R 21represent hydrogen atom, can by carbonatoms be 1 ~ 10 alkyl or alkoxyl group replace phenyl or carbonatoms be the cycloalkyl of 3 ~ 10,
R 22represent that carbonatoms is alkyl, the carbonatoms alkoxyl group that is 1 ~ 10, carbonatoms be 2 ~ 10 alkenyl or the halogen atom of 1 ~ 10,
R 21and R 22the alkyl represented, alkoxyl group and alkenyl can be replaced by halogen atom or not replace,
D is the integer of 0 ~ 5;
In formula (2-3), R 23and R 24represent independently of one another carbonatoms be 1 ~ 10 alkyl, the carbonatoms aryl that is 6 ~ 20, the carbonatoms aryloxy that is 6 ~ 20, the carbonatoms arylthio that is 6 ~ 20, the carbonatoms aromatic yl alkenyl that is 8 ~ 20, carbonatoms be 7 ~ 20 aralkyl, carbonatoms be 2 ~ 20 containing heterocyclic group or halogen atom
R 23and R 24the alkyl represented, aryl, aryloxy, arylthio, aromatic yl alkenyl, aralkyl and can be replaced by halogen atom or not replace containing heterocyclic group,
R 23and R 24represent alkyl and aralkyl in methylene radical can be replaced by unsaturated link(age) ,-O-or-S,
R 23can at adjacent R 23between form ring,
E represents the number of 0 ~ 4,
F represents the number of 0 ~ 8,
G represents the number of 0 ~ 4,
H represents the number of 0 ~ 4,
Several sums of g and h are 2 ~ 4;
<2>m=3, X as shown in following formula (3),
In formula (3), X 2represent by R 25the carbonatoms containing aromatic nucleus alkyl or trivalent that the carbon atom replaced, the carbonatoms of trivalent are the aliphatic alkyl of 1 ~ 35, the carbonatoms of trivalent is the ester ring type alkyl of 3 ~ 35, the carbonatoms of trivalent is 6 ~ 35 be 2 ~ 35 containing heterocyclic group,
R 25represent hydrogen atom, carbonatoms be 1 ~ 8 alkyl, carbonatoms be 6 ~ 20 aryl or carbonatoms be the aralkyl of 7 ~ 20,
X 2alkyl, alkoxyl group, haloalkyl or halogenated alkoxy that the aliphatic alkyl represented can be 1 ~ 8 by halogen atom, cyano group, hydroxyl, nitro, carbonatoms replace,
X 2methylene radical in the aliphatic alkyl represented can by-O-,-S-,-CO-,-CO-O-,-O-CO-,-SO 2-,-NH-or their groups of combining replace,
Z 1~ Z 3independently of one another with the Z in above-mentioned general formula (2) 1and Z 2the group represented is identical,
Wherein, the carbonatoms of group that represents of above-mentioned general formula (3) is in the scope of 1 ~ 35;
<3>m=4, X as shown in following formula (4),
In formula (4), X 3represent carbon atom, the carbonatoms of tetravalence be the aliphatic alkyl of 1 ~ 35, the carbonatoms of tetravalence is the ester ring type alkyl of 3 ~ 35, the carbonatoms of tetravalence be 6 ~ 35 the carbonatoms containing aromatic nucleus alkyl or tetravalence be 2 ~ 35 containing heterocyclic group,
X 3alkyl, alkoxyl group, haloalkyl or halogenated alkoxy that the aliphatic alkyl represented can be 1 ~ 8 by halogen atom, cyano group, hydroxyl, nitro, carbonatoms replace,
X 3methylene radical in the aliphatic alkyl represented can by-O-,-S-,-CO-,-CO-O-,-O-CO-,-SO 2-,-NH-or their groups of combining replace,
Z 1~ Z 4independently of one another with the Z in above-mentioned general formula (2) 1and Z 2the group represented is identical,
Wherein, the carbonatoms of group that represents of above-mentioned general formula (4) is in the scope of 1 ~ 35;
<4>m=5, X as shown in following formula (5),
In formula (5), X 4represent that the carbonatoms of pentavalent is the aliphatic alkyl of 2 ~ 35, the carbonatoms of pentavalent is the ester ring type alkyl of 3 ~ 35, the carbonatoms of pentavalent be 6 ~ 35 the carbonatoms containing aromatic nucleus alkyl or pentavalent be 2 ~ 35 containing heterocyclic group,
X 4alkyl, alkoxyl group, haloalkyl or halogenated alkoxy that the aliphatic alkyl represented can be 1 ~ 8 by halogen atom, cyano group, hydroxyl, nitro, carbonatoms replace,
X 4methylene radical in the aliphatic alkyl represented can by-O-,-S-,-CO-,-CO-O-,-O-CO-,-SO 2-,-NH-or their groups of combining replace,
Z 1~ Z 5independently of one another with the Z in above-mentioned general formula (2) 1and Z 2the group represented is identical,
Wherein, the carbonatoms of group that represents of above-mentioned general formula (5) is in the scope of 2 ~ 50;
<5>m=6, X as shown in following formula (6),
In formula (6), X 5represent that the carbonatoms of sexavalence is the aliphatic alkyl of 2 ~ 35, the carbonatoms of sexavalence is the ester ring type alkyl of 3 ~ 35, the carbonatoms of sexavalence be 6 ~ 35 the carbonatoms containing aromatic nucleus alkyl or sexavalence be 2 ~ 35 containing heterocyclic group,
X 5alkyl, alkoxyl group, haloalkyl or halogenated alkoxy that the aliphatic alkyl represented can be 1 ~ 8 by halogen atom, cyano group, hydroxyl, nitro, carbonatoms replace,
X 5methylene radical in the aliphatic alkyl represented can by-O-,-S-,-CO-,-CO-O-,-O-CO-,-SO 2-,-NH-or their groups of combining replace,
Z 1~ Z 6independently of one another with the Z in above-mentioned general formula (2) 1and Z 2the group represented is identical,
Wherein, the carbonatoms of group that represents of above-mentioned general formula (6) is in the scope of 2 ~ 50.
2. a coloured composition, it contains compound according to claim 1.
3. a coloring photosensitive combination, it contains: the dyestuff (A) containing at least one compound according to claim 1, the polymerizable compound (B) with ethylenic unsaturated link(age) with acid number, optical free radical polymerization starter (C) and have the monomer (D) of ethylenic unsaturated link(age).
4. the cured article of coloring photosensitive combination according to claim 3.
5. a display equipment colour filter, it uses cured article described in claim 4.
CN201480040982.5A 2013-12-05 2014-11-27 Compound and the composition containing the compound Active CN105473666B (en)

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CN111868027A (en) * 2018-04-19 2020-10-30 株式会社艾迪科 Compound, light absorbing agent, composition and optical filter

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JP7293119B2 (en) * 2017-10-05 2023-06-19 株式会社Adeka Compound, latent antioxidant, composition, cured product and method for producing cured product
KR102344202B1 (en) 2017-11-13 2021-12-27 주식회사 엘지화학 Polymer, coating composition comprising the same, organic light emitting device using the same and method of manufacturing the same

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