WO2015135633A1 - Neue pyridon-farbmittel - Google Patents
Neue pyridon-farbmittel Download PDFInfo
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- WO2015135633A1 WO2015135633A1 PCT/EP2015/000490 EP2015000490W WO2015135633A1 WO 2015135633 A1 WO2015135633 A1 WO 2015135633A1 EP 2015000490 W EP2015000490 W EP 2015000490W WO 2015135633 A1 WO2015135633 A1 WO 2015135633A1
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- Prior art keywords
- alkyl
- sulfo
- compounds
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- formula
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- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
- C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
- C09B29/3617—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom
- C09B29/3621—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring
- C09B29/3626—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring from a pyridine ring containing one or more hydroxyl groups (or = O)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/76—Nitrogen atoms to which a second hetero atom is attached
- C07D213/77—Hydrazine radicals
-
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
- C09B29/0029—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing only nitrogen as heteroatom
- C09B29/0048—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing only nitrogen as heteroatom containing a six-membered heterocyclic ring with one nitrogen atom
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- 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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- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
- G02F1/133509—Filters, e.g. light shielding masks
- G02F1/133514—Colour filters
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
- H10K59/30—Devices specially adapted for multicolour light emission
- H10K59/38—Devices specially adapted for multicolour light emission comprising colour filters or colour changing media [CCM]
Definitions
- the present invention relates to novel colorants used, for example, in color filters for liquid crystal displays or in OLED displays.
- Liquid crystal displays are widely used in e.g.
- LCDs liquid crystal displays
- color filters are additionally introduced into the arrangement between the polarizers.
- These color filters are usually on the surface of a
- the transparent substrate usually made of glass, and there are in the form of numerous regularly arranged pixels of primary colors, eg. B. red, green, blue (R, G, B) applied.
- the single pixel has a size of a few micrometers to 100 micrometers.
- a liquid crystal display also has numerous other functional components such as thin-film transistors (TFT), alignment layers and others involved in the control of the liquid crystals and thus ultimately the imaging.
- TFT thin-film transistors
- the liquid crystals can be set separately for each pixel by electronic control to "light” or “dark” (or to any intermediate stage). Accordingly, the respective associated color filter pixels are supplied with light and for the
- TN twisted nematic
- STN super twisted nematic
- VA vertical alignment
- IPS in-plane switching
- the color filter pixels may be arranged in different defined patterns for each base color.
- the basic colors are present as separate color points next to each other and result from backlit a full color image.
- an additional color for example yellow, for expanding the color space or the use of cyan, magenta and yellow as primary colors is also known.
- W-OLED displays also use color filters. These displays first generate a white light from pixels of organic light emitting diodes (Organic Light Emitting Diodes), which is then split using color filters in individual colors, for example red, green and blue.
- organic light emitting diodes Organic Light Emitting Diodes
- the color filters in the manufacture of the liquid crystal displays, elevated process temperatures of typically 230 ° C are used during the application of the liquid crystal control transparent electrode and the orientation layer. Accordingly, the color filters used must have high heat stability.
- a high contrast ratio affects the quality of the image positively.
- the light intensity becomes after irradiation a color filter on a transparent substrate, where the substrate is between two polarizers.
- the contrast ratio also known as the contrast value, indicates the ratio of the light intensities in parallel and perpendicular polarizers.
- a high transmission and resulting brightness of the color filter is desirable because it requires less light to be radiated into the display to produce the same image brightness than a less bright color filter, allowing for overall energy savings.
- Formula (I) are well suited for use in color filters. They usually have a good solubility in the solvents typically used.
- the invention relates to compounds of the formula (I), their preparation and use, in particular for dyeing transparent systems.
- the compounds of the formula (I) have the following general formula:
- R 1 is sulfo, carboxy, C 4 -C 4 -alkylene-sulfo, C 1 -C 4 -alkylene-carboxy, CONH 2 ,
- R 2 is C 1 -C 6 -alkyl or - (C 1 -C 6 -alkylene-O-) m -R, where R is H or C 1 -C 6 -alkyl and m is a number from 1 to 20,
- R 3 is H, sulfo, carboxy, C 1 -C 6 -alkyl or C 1 -C 6 -alkoxy,
- R 4 is H, d-Ce-alkyl or CC 6 -alkoxy
- R 5 is OH, OM, Ci-Ce-alkyl, unsubstituted or by d-Ce-alkyl, halogen, z.
- Counter cation M + wherein M + is an alkali metal cation, such as Li +, Na + or K +, or preferably an organic cation, in particular an organic ammonium cation or an organic phosphonium cation means. It is also possible that the counter cation M + is a mixture of the aforementioned cations.
- alkylene groups and the alkyl groups in the alkyl and alkoxy radicals are branched or linear.
- alkyl groups are methyl, ethyl, propyl, iso-propyl, butyl, preferably n-butyl and iso-butyl, pentyl, preferably n-pentyl and iso-pentyl, hexyl, octyl, ethylhexyl.
- the C 1 -C 6 -alkylene-O groups in the radical - (C 1 -C 6 -alkylene-O-) m -R may be the same or different when m is greater than 1.
- Preferred radicals R ° have the meaning CC 2 alkyl, very particularly preferably methyl.
- Preferred radicals R 1 have the meaning dC 2 -alkylene-sulfo, CONH (C 1 -C 2 -alkyl) or CONH 2 , particularly preferably C 1 -C 2 -alkylene-sulfo, CONHid-C 1 -C 4 -alkyl or CONH 2 , very particularly preferably CH 2 sulfo or CONH 2 .
- R 2 have the meaning Ci-C 8- alkyl, hydroxy-CiC 8 -alkyl or - (CiX-alkylene-O-Jm-R, wherein R has the meaning H or Ci-Ci 0 -alkyl and m is a number from 1 to 15, in particular ethyl, hydroxyethyl or - (C 1 -C 3 -alkylene-O-) m -R, where R is H or C 1 -C 8 -alkyl and m is a number from 1 to 15, completely particularly preferably ethyl or - (C 2 -C 3 -alkylene-O-) m -R, where R is H or methyl and m is a number from 1 to 12.
- Preferred radicals R 3 have the meaning H, sulfo, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy, in particular H, methyl, methoxy or sulfo, very particularly preferably H or methyl.
- Preferred radicals R 4 have the meaning H, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy, in particular H, methyl or methoxy, very particularly preferably H.
- R 5 are OH, O " M + , C 1 -C 4 -alkyl, a phenyl which is substituted by C 1 -C 2 -alkyl, halogen, for example F, Cl, Br or sulfo, or
- unsubstituted phenyl in particular OH, O " M + , C 1 -C 2 -alkyl, a C 1 -C 2 -alkyl, chlorine or sulfo-substituted phenyl or an unsubstituted phenyl, very particularly preferably OH, O " M + , methyl, tolyl or phenyl, where M + is one
- Alkali metal cation a primary, secondary, tertiary or quaternary
- R 1 is CC-alkylene-sulfo, CONH (C 1 -C 2 -alkyl) or CONH 2 , in particular C 1 -C 2 -alkylene-sulfo, CONH (C 1 -C 2 -alkyl) or CONH 2 ,
- R 2 is d-Cs-alkyl, hydroxy-dC 8 -alkyl or - (C 1 -C 4 -alkylene-O-) m -R, where R is the
- n 1 to 15
- R 3 is H, sulfo, C 1 -C 4 -alkyl or C -C -alkoxy,
- R 4 is H, CC 4 -alkyl or C 1 -C 4 -alkoxy
- R 5 OH, O ⁇ M ⁇ CC 4 alkyl, one with Ci-C 2 alkyl, halogen, eg F, Cl, Br, or
- R 1 is d-Ca-alkylene-sulfo, CONH (dC 2 -alkyl) or CONH 2 ,
- R 2 is ethyl, hydroxyethyl or - (dC 3 -alkylene-O-) m -R, where R is H or C 1 -C 8 -alkyl and
- n 1 to 15
- R 3 is H, methyl, methoxy or sulfo
- R 4 is H, methyl or methoxy
- R 5 is OH, O " M + , C 1 -C 2 -alkyl, a phenyl or unsubstituted phenyl substituted by C 1 -C 2 -alkyl, chlorine or sulfo,
- R 1 is CH 2 -sulfo or CONH 2
- R 2 is ethyl or - (C 2 -C 3 -alkylene-O-) m -R, where R is H or methyl and
- n is a number from 1 to 12
- R 3 is H or methyl
- R 5 is OH, ⁇ , methyl, tolyl or phenyl
- Example of a particularly preferred compound is (IIa)
- the counter cation M + is preferably an organic cation from the group of imidazolium cations, alkylguanidinium cations,
- the imidazolium cations preferably have the general formula (C1):
- R 1 is d-Cis-alkyl, hydroxy-C 1 -C 8 -alkyl, C 2 -C 18 -alkenyl,
- R has the meaning H, Ci-Ci 6 -alkyl or hydroxy-Ci-C 16- alkyl and m is a number from 1 to 20, C 6 -C 0 aryl, or C 6 -Cio-aryl substituted by
- R 2 is C 1 -C 18 -alkyl, hydroxy-C 1 -C 8 -alkyl, C 2 -d 8 -alkenyl, - (C 1 -C 6 -alkylene-O-) m -R, where R is H, C 1 -C 6 -alkyl or hydroxy-Ci-Ci 6 alkyl and m is a number from 1 to 20, C 6 -C 10 aryl or C 6 -C 10 aryl, by
- R 3 is H or methyl.
- imidazolium cations of the formula (C1) in which R 1 and R 2 are identical or different and C 6 -C 12 -alkyl, - (C 2 -C 3 -alkylene-O-) m R, where R is C -C -alkyl 2 alkyl and m is the number 1; or phenyl or di (isopropyl) phenyl, and R 3 is hydrogen or methyl.
- the alkylguanidinium cations preferably have the general formula (C2):
- D R2, n R3, and n R4 are the same or different and Ci-C 4 alkyl, preferably
- R 5 and R 6 are identical or different and C 1 -C 8 -alkyl, hydroxy-d-
- C 18 -alkyl C 2 -Ci8-alkenyl, - (dC 6 -alkylene-O-) m -R, or C 6 -C 0 -aryl, preferably C 6 -C 2 -alkyl or phenyl wherein R is H, C 1 -C 6 -alkyl or hydroxy-C 1 -C 6 -alkyl and
- m is a number from 1 to 20.
- the phosphonium cations preferably have the general formula (C3):
- R 1 is C 1 -C 6 -alkyl or hydroxy-C 1 -C 6 -alkyl
- R 2 is C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, hydroxy-d-Ce-alkyl or C 6 -C 10 -aryl,
- R 3 Ci-C 2 -alkyl, C 2 -C 2 o-alkenyl, hydroxy-dC 20 alkyl, C 6 -C 10 aryl, - (dC 6 - alkylene-O-) m -R,
- R is H, C 1 -C 6 -alkyl or hydroxy-C 1 -C 6 -alkyl
- n is a number from 1 to 20
- R 4 dC 20 alkyl, C 2 -C 20 alkenyl, hydroxy-Ci-C2o-alkyl, C 6 -C 0 -aryl, - (dC 6 - alkylene-0-) m -R,
- R 1 , R 2 and R 3 are the same or different and are C 1 -C 4 -alkyl or phenyl, and
- the organic ammonium cations are primary, secondary, tertiary or quaternary ammonium cations and preferably have the general formula (C4):
- R, R 2 , R 3 and R 4 are the same or different and are hydrogen, (dC 30 ) -
- Hydroxy-Ci-d6-alkyl and m is a number from 1 to 20,
- the sum of the carbon atoms in the radicals R 1 to R 4 is at least 6, preferably at least 8, in particular at least 12, particularly preferably at least 16.
- R 1 is H, CC 4 -alkyl, hydroxy-C 2 -C 4 -alkyl,
- R 2 is H, C 1 -C 30 -alkyl, hydroxy-C 2 -C 4 -alkyl, benzyl, C 4 -C 30 -alkenyl, phenyl or C 1 -C 4 -alkylene-OCOR 5 , where R 5 is C 8 -C 8 - Alkyl or C 8 -C 18 alkenyl, R 3 is H, C 1 -C 30 -alkyl, C 4 -C 30 -alkenyl, benzyl, phenyl or C 4 -alkylene-OCOR 5 , wherein R 5 is C 8 -C 8 -alkyl or C 8 -C 8 -alkenyl,
- R 4 is C 4 -C 30 -alkyl, C 4 -C 30 -alkenyl, benzyl or phenyl, with the above
- R 1 is H, C 1 -C 6 -alkyl, hydroxyethyl,
- R 2 is H, dC 2 o-alkyl, hydroxyethyl, benzyl, phenyl or CH 2 -OCOR 5 , where R 5 is C 8 -C 8 -alkyl or C 8 -C 8 -alkenyl,
- R 3 is H, C 1 -C 20 -alkyl, C 6 -C 2 o-alkenyl, benzyl, phenyl or CH 2 -OCOR 5 , wherein R 5
- R 4 is C 6 -C 2 o-alkyl, C6-C 20 alkenyl, benzyl or phenyl, with the above
- Trioctylmethylammonium cocoalkyldimethylbenzylammonium, bis (N, N-hydroxyethyl) -dodecylmethylammonium, methyltrioctylammonium, N, N-bis-stearoylethyl-N, N-dimethylammonium.
- the benzotriazolium cations preferably have the general formula (C5):
- R 1 and R 2 are the same or different and Ci-C-
- R is H, C 1 -C 6 -alkyl or hydroxy-C 1 -C 6 -alkyl and m is a number from 1 to 20.
- R and R 2 are C 2 -C 8 alkyl or phenyl.
- the pyridinium cations preferably have the general formula (C6):
- R 1 and R 2 are identical or different and C 1 -C 6 -alkyl
- R is H, Ci-Ci 6 -alkyl or hydroxy-Ci-C 16 -alkyl and m is a number from 1 to 20, or C 6 -Cio-aryl, preferably
- the invention also relates to a process for preparing the compounds of the formula (I) according to the invention by diazotization of amines of the formula (A), preferably at a temperature of 0 to 10 ° C, and azo coupling with one equivalent of the pyridone coupling component of the formula (P ), preferably at a temperature of 0 to 40 ° C,
- R ° to R 5 have the meanings given above, and
- the amine in question is advantageously cooled to 0 to 10 ° C, preferably to 0 to 5 ° C and by adding nitrosylsulfuric acid or sodium nitrite in an acidic medium, eg. B. between pH 0 and 5, diazotized.
- an acidic medium eg. B. between pH 0 and 5, diazotized.
- the diazotized amine is allowed to react with the coupling component P, preferably in aqueous solution.
- the coupling component P preferably in aqueous solution.
- Coupling reaction carried out at temperatures from 0 to 40 ° C.
- the pH is usually between 4 and 9. It can also be adjusted to the desired range by using a suitable buffer.
- the resulting dyes can be removed from the reaction medium
- Salination with an alkali metal salt, filtration and drying are isolated, if necessary under reduced pressure and at elevated temperature.
- the dyes of formula (I) can be obtained as a free acid, as a salt or as a mixed salt containing, for example, one or more cations from the
- the dye salts of formula (I) may be further purified, for example by diafiltration through a semipermeable membrane or recrystallization, thereby avoiding undesirable
- the salts with the organic counterions M + can be obtained for example by reacting an aqueous solution of Farbstoffalkalimetallsalzes at elevated temperature, for. B. 40 to 95 ° C, mixed with an aqueous solution of the counterion halide salt and the newly formed dye salt in a preferably non- or slightly water-soluble organic solvent such. As methoxypropyl acetate, extracted. From the organic phase, the dye salts of the formula (I) with the organic counterions M + after removal of the solvent, if necessary in conjunction with a
- imidazolium halides (C1) which are used as ionic liquids as well as phase transfer catalysts can be prepared according to US 5,132,423.
- Benzotriazolium halides (C5) may e.g. As described by Kuhn et al., Chem. Ber. 1940, 1109-1113. Pyridinium halides (C6) may be known to one skilled in the art
- the compounds of the formula (I) according to the invention can be used for coloring high molecular weight organic materials of natural or synthetic origin, for example plastics, resins, lacquers,
- Compounds can be colored, for example
- Cellulose compounds such as cellulose ethers and esters, such as
- Ethylcellulose nitrocellulose, cellulose acetates or cellulose butyrates, natural binders such as fatty acids, fatty oils, resins and theirs
- Conversion products, or synthetic resins such as polycondensates, polyadducts, polymers and copolymers, such as aminoplasts, in particular urea and melamine-formaldehyde resins, alkyd resins, acrylic resins, phenolic resins and phenolic resins, such as novolaks or resols, urea resins, polyvinyls, such as polyvinyl alcohols, polyvinyl acetals, polyvinyl acetates or polyvinyl ethers,
- Polycarbonates such as polystyrene, polyvinyl chloride, polyethylene or polypropylene, styrene-butadiene copolymers, poly (meth) acrylates and their
- Copolymers such as polyacrylic acid esters, styrene acrylates, or polyacrylonitriles, polyamides, polyesters, polyurethanes, polysulfones, coumarone indene and
- Synthetic resins polymers, acrylates
- waxes aldehyde and ketone resins
- rubber rubber and its derivatives and latices
- casein silicones and silicone resins
- the invention likewise provides a high molecular weight organic medium containing a dyeing effective amount of a compound of the formula (I) according to the invention.
- the compounds according to the invention are usually used in an amount of from 0.01 to 45% by weight, preferably from 0.1 to 40% by weight. Preference is given to the use of compounds of the formula (I) for color filters and the mass coloration of polymers.
- colorant for color filters is suitable for both additive and subtractive color production, such as
- LCD liquid crystal displays
- OLED displays charge coupled devices, plasma displays or electroluminescent displays, which in turn may be active (twisted nematic) or passive (supertwisted nematic) ferroelectric displays or light-emitting diodes, as well as colorants for electronic inks ("electronic inks").
- E-inks electronic inks
- e-paper electronic paper
- the colorants of the formula (I) need not be subjected to dispersion in suitable solvents. It is thus possible to dissolve them in appropriate solvents mentioned below, and so in
- the compounds of the formula (I) according to the invention can also be present as a solution or as a binder-containing colorant solution (photoresist).
- the present invention therefore also provides a solution containing from 0.01 to 45% by weight, preferably from 1 to 20% by weight, in particular from 2 to
- organic solvent 17% by weight of the compounds of the formula (I) according to the invention, dissolved in an organic solvent.
- organic solvents are, for example:
- Ethylene glycol monoisopropyl ether ethylene glycol monoethyl ether, ethylene glycol monoethyl ether acetate, ethylene glycol mono-tert-butyl ether,
- Cyclohexanone dipropylene glycol methyl ether, dipropylene glycol methyl ether acetate, dipropylene glycol monoethyl ether, dipropylene glycol monobutyl ether,
- Diacetone alcohol triacetylglycerol, tripropyleneglycol monobutyl ether,
- Particularly advantageous are ethyl lactate, propylene glycol monomethyl ether acetate (methoxypropyl acetate), propylene glycol monoethyl ether acetate,
- Ethylene glycol monomethyl ether acetate ketones such as cyclohexanone or alcohols such as n-butanol or benzyl alcohol.
- the organic solvents can be used alone or in mixtures with one another.
- the compounds according to the invention may be combined with customary auxiliaries or additives to give a colorant composition, for example surfactants, dispersants, rheology control additives, fillers, control agents, resins, waxes, defoamers, anti-dust agents, extenders, antistatic agents, charge control agents,
- a colorant composition for example surfactants, dispersants, rheology control additives, fillers, control agents, resins, waxes, defoamers, anti-dust agents, extenders, antistatic agents, charge control agents,
- Preservatives for example, the binders of the system in which the composition according to the invention is to be used. If available, the aids and additives
- Colorant composition for example, still contain surfactants, dispersants, resins and waxes.
- the invention likewise provides a binder-containing colorant solution containing 0.01 to 40% by weight, preferably 0.1 to 30% by weight, in particular 1 to 20% by weight, of the colorant of the formula (I) according to the invention in at least one organic solvent, at least one polymeric binder and optionally further auxiliaries.
- the binder-containing colorant solution is conveniently prepared by mixing the colorant solution described above with the other components mentioned.
- polymeric binders are, for example, acrylates, acrylic esters, polyimides, polyvinyl alcohols, epoxies, polyesters, melamines, gelatin, caseins and
- polymerizable ethylenically unsaturated monomers and oligomers preferably those which crosslink either thermally or under the influence of UV light and radical initiators.
- the polymeric binders are useful in an amount of 5 to 90 wt .-%, preferably from 20 to 70 wt .-%, based on the total amount of all non-volatile constituents of the colorant solution.
- Non-volatile constituents are understood as meaning the compounds of the formula (I), the polymeric binders and the other auxiliaries.
- volatile components is meant the organic solvents which are volatile under the applied baking temperatures.
- Crosslinking agents and radical initiators, leveling agents, defoamers and deaerators may be considered as further auxiliaries. They are useful in an amount of 0 to 10 wt .-%, preferably from 0 to 5 wt .-%, based on the total amount of the colorant solution.
- Colorant compositions are particularly well suited to the Color Filter Red-Green-Blue (R, G, B) color set. These three colors are present as separate color points next to each other, and result from backlit one
- the invention further provides the use of the above
- the use concentration of the colorants according to the invention in the applied color filter film can be between 5 and 95% by weight, preferably between 10 and 70% by weight, very particularly preferably between 15 and 50% by weight, based on the total weight of the Color filter film.
- the invention also provides a color filter comprising a dyeing effective amount of the colorants of the invention.
- a color filter comprising a dyeing effective amount of the colorants of the invention.
- Water phase is decanted off.
- the oily organic phase is taken up in 350 ml of methoxypropyl acetate, dried with magnesium sulfate and stored at 4 ° C. for one night. After filtering off the precipitated solid, the solvent is removed in vacuo and the residue obtained is dried to constant weight.
- the obtained binder-containing colorant solution is applied with the aid of a spin coater (POLOS Wafer Spinner) on glass plates (SCHOTT, laser-cut, 10 ⁇ 10 cm) in a layer thickness which, when using a light source C, the color coordinates y mentioned in Table 2 as Set reference values.
- a spin coater POLOS Wafer Spinner
- the layer thickness is in each case about 1 to 2 micrometers.
- the glass plates are allowed to flash off and then dried for 10 min at 80 ° C. in a circulating air drying cabinet (Binder).
- Binder a circulating air drying cabinet
- Table 2 shows the results of the examples according to the invention in the postbake.
- the values x, y and Y denote the measured color coordinates in the CIE-Yxy standard color space, where Y is a measure of the brightness.
- coated glass plates (color filter) of the invention are coated glass plates (color filter) of the invention.
- Compositions each have transparent, greenish-yellow colorations.
- the colorations in each case show high contrast values and brightness values Y. Likewise, they exhibit steep transmission curves.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Nonlinear Science (AREA)
- Mathematical Physics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Optical Filters (AREA)
- Plural Heterocyclic Compounds (AREA)
- Electroluminescent Light Sources (AREA)
- Pyridine Compounds (AREA)
Abstract
Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP15710105.6A EP3116856A1 (de) | 2014-03-08 | 2015-03-05 | Neue pyridon-farbmittel |
JP2016555649A JP2017513966A (ja) | 2014-03-08 | 2015-03-05 | 新規ピリドン着色剤 |
KR1020167027689A KR20160130826A (ko) | 2014-03-08 | 2015-03-05 | 신규한 피리돈 염료 |
CN201580012660.4A CN106458906A (zh) | 2014-03-08 | 2015-03-05 | 新型吡啶酮着色剂 |
US15/124,609 US20170015829A1 (en) | 2014-03-08 | 2015-03-05 | Novel Pyridone Dyes |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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DE102014003307.4 | 2014-03-08 | ||
DE102014003307.4A DE102014003307A1 (de) | 2014-03-08 | 2014-03-08 | Neue Pyridon-Farbmittel |
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WO2015135633A1 true WO2015135633A1 (de) | 2015-09-17 |
Family
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Family Applications (1)
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PCT/EP2015/000490 WO2015135633A1 (de) | 2014-03-08 | 2015-03-05 | Neue pyridon-farbmittel |
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US (1) | US20170015829A1 (de) |
EP (1) | EP3116856A1 (de) |
JP (1) | JP2017513966A (de) |
KR (1) | KR20160130826A (de) |
CN (1) | CN106458906A (de) |
DE (1) | DE102014003307A1 (de) |
TW (1) | TW201602082A (de) |
WO (1) | WO2015135633A1 (de) |
Families Citing this family (1)
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JP7310724B2 (ja) * | 2020-06-04 | 2023-07-19 | 信越化学工業株式会社 | オニウム塩、化学増幅ネガ型レジスト組成物及びレジストパターン形成方法 |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2162858A1 (de) | 1970-12-22 | 1972-07-13 | Ciba-Geigy Ag, Basel (Schweiz) | 3-Sulfoalkyl-6-hydroxy-pyridone-(2), deren Herstellung und Verwendung |
US4359418A (en) * | 1979-03-12 | 1982-11-16 | Ciba-Geigy Corporation | Amine salts of azo dyestuffs of the pyridone series |
US4668774A (en) * | 1984-05-03 | 1987-05-26 | Basf Aktiengesellschaft | 2-ethylhexylamine salts of anionic monoazo dyes |
US5132423A (en) | 1990-02-05 | 1992-07-21 | General Electric Company | Method for conducting organic reactions using guanidinium salt as phase transfer catalyst |
JP2701387B2 (ja) * | 1988-12-06 | 1998-01-21 | 三菱化学株式会社 | 記録液 |
US20070277701A1 (en) * | 2006-05-19 | 2007-12-06 | Canon Kabushiki Kaisha | Novel dye, dye production method and ink containing dye |
-
2014
- 2014-03-08 DE DE102014003307.4A patent/DE102014003307A1/de not_active Withdrawn
-
2015
- 2015-03-05 EP EP15710105.6A patent/EP3116856A1/de not_active Withdrawn
- 2015-03-05 KR KR1020167027689A patent/KR20160130826A/ko unknown
- 2015-03-05 CN CN201580012660.4A patent/CN106458906A/zh active Pending
- 2015-03-05 US US15/124,609 patent/US20170015829A1/en not_active Abandoned
- 2015-03-05 JP JP2016555649A patent/JP2017513966A/ja active Pending
- 2015-03-05 WO PCT/EP2015/000490 patent/WO2015135633A1/de active Application Filing
- 2015-03-06 TW TW104107207A patent/TW201602082A/zh unknown
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2162858A1 (de) | 1970-12-22 | 1972-07-13 | Ciba-Geigy Ag, Basel (Schweiz) | 3-Sulfoalkyl-6-hydroxy-pyridone-(2), deren Herstellung und Verwendung |
US4359418A (en) * | 1979-03-12 | 1982-11-16 | Ciba-Geigy Corporation | Amine salts of azo dyestuffs of the pyridone series |
US4668774A (en) * | 1984-05-03 | 1987-05-26 | Basf Aktiengesellschaft | 2-ethylhexylamine salts of anionic monoazo dyes |
JP2701387B2 (ja) * | 1988-12-06 | 1998-01-21 | 三菱化学株式会社 | 記録液 |
US5132423A (en) | 1990-02-05 | 1992-07-21 | General Electric Company | Method for conducting organic reactions using guanidinium salt as phase transfer catalyst |
US20070277701A1 (en) * | 2006-05-19 | 2007-12-06 | Canon Kabushiki Kaisha | Novel dye, dye production method and ink containing dye |
Non-Patent Citations (1)
Title |
---|
QINJI PENG ET AL: "HYDRAZONE-AZO TAUTOMERISM OF PYRIDONE AZO DYES: \PART 1-NMR SPECTRA OF TAUTOMERS", DYES AND PIGMENTS, ELSEVIER APPLIED SCIENCE PUBLISHERS. BARKING, GB, vol. 14, no. 2, 1 January 1990 (1990-01-01), pages 89 - 99, XP000141186, ISSN: 0143-7208, DOI: 10.1016/0143-7208(90)87009-R * |
Also Published As
Publication number | Publication date |
---|---|
EP3116856A1 (de) | 2017-01-18 |
JP2017513966A (ja) | 2017-06-01 |
KR20160130826A (ko) | 2016-11-14 |
DE102014003307A1 (de) | 2015-09-10 |
US20170015829A1 (en) | 2017-01-19 |
TW201602082A (zh) | 2016-01-16 |
CN106458906A (zh) | 2017-02-22 |
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