Classifications

• • 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]
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
  • C08K5/0041—Optical brightening agents, organic pigments
• • 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
  • 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
  • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
  • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
  • C09B67/0041—Blends of pigments; Mixtured crystals; Solid solutions mixtures containing one azo dye
• • 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
  • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
  • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
  • C09B67/0084—Dispersions of dyes
  • C09B67/0085—Non common dispersing agents
  • C09B67/0086—Non common dispersing agents anionic dispersing agents
• • 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
• • 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

Definitions

• the present invention relates to novel colorant compositions 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 located on the surface of a transparent substrate, usually made of glass, and are there 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. If light now passes through the arrangement, 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
• CONFIRMATION COPY human eye results in the plan view of the screen a corresponding R, G, B building, colored, moving or still image.
• Various ways of arranging liquid crystals, electronic controls and polarizers are known, such as twisted nematic (TN), super twisted nematic (STN), vertical alignment (VA) and in-plane switching (IPS).
• 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 generate from pixels of organic light emitting diodes (Organic Light Emitting Diodes) first a white light, which then under
• 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 is determined after irradiating a color filter on a transparent substrate, in which the substrate is located 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.
• pigmented coatings are commonly used today. For their preparation, pigments in the presence of
• Dispersing aids dispersed in an organic solvent Dispersing aids dispersed in an organic solvent
• UV-curable photoresist is formulated with the addition of suitable binders (acrylates, acrylic esters, polyimides, polyvinyl alcohols, epoxies, polyesters, melamines, gelatin, caseins) and other excipients to form a UV-curable photoresist.
• suitable binders acrylates, acrylic esters, polyimides, polyvinyl alcohols, epoxies, polyesters, melamines, gelatin, caseins
• photoresist is applied in a thin layer on the carrier substrate, hardened by applying UV light through masks in the form of a pattern (patterning) and finally developed and treated by heat.
• the color filter is generated in the form of a pixel pattern.
• dyes are also used in color filters to optimally match the contrast, brightness, hue and transmission to the required
• Acid dyes in the form of the free acid for color filters are disadvantageous from the work safety, to work with free acids.
• compositions with organic pigments the compounds of formula (I) improve the dispersibility of the pigments and permit one
• the invention provides colorant compositions comprising at least one compound of the formula (I) and at least one pigment, in which the compounds of the formula (I) have the general formula:
• R 1 is sulfo, carboxy, C 1 -C 4 -alkylene-sulfo, C 1 -C 4 -alkylene-carboxy, CONH 2 ,
• R 2 is d-Cis-alkyl, C 2 -C 8 -alkenyl, hydroxy-d-cis-alkyl, or - (dC 6 -alkylene-O-) m -R, where R is H, Ci-Ci6-alkyl or hydroxy-Ci-Ci6-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, C 1 -C 6 -alkyl or C 1 -C 6 -alkoxy
• R 5 is OH, OM, C 1 -C 6 -alkyl, unsubstituted C 6 -C 10 -aryl or by C 1 -C 6 -alkyl, halogen, e.g. B. F, Cl, Br, carboxy or sulfo substituted C 6 -C-io-aryl, wherein the compounds of formula (I) at least one anionic radical from the group sulfo and carboxy, preferably sulfo, with the
• 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 are examples of organic phosphonium cation.
• 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 dC 2 -alkyl, very particularly preferably methyl.
• Preferred radicals R 1 have the meaning Ci-C 2 -alkylene-sulfo, CONH (Ci-C 2 - alkyl) or CONH 2 , particularly preferably dd-alkylene-sulfo, CONH (CrC 2 ) alkyl or CONH 2 , very particularly preferred CH 2 sulfo or CONH 2 .
• R 2 have the meaning Ci-Cs-alkyl, hydroxy-Ci-Ca-alkyl or - (Ci-C 4 -alkylene-O-) m -R, wherein R has the meaning H or Ci-Ci 0 -alkyl and m is a number from 1 to 15, especially ethyl, hydroxyethyl
• 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 are H, C -C 4 -alkyl or C 1 -C -alkoxy, in particular H, methyl or methoxy, very particularly preferably H.
• Preferred radicals R 5 have the meaning OH, O "M ⁇ Ci-C alkyl, a Ci-C with 2 -. Substituted alkyl, halogen, such as 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, ⁇ " , methyl, tolyl or phenyl where M + is one
• Alkali metal cation a primary, secondary, tertiary or quaternary
• R 2 is d-Ce-alkyl, hydroxy-dC 8 -alkyl or - (dC 4 -alkylene-O-) m -R, wherein R has the meaning H or Ci-Cio-alkyl and m is a number from 1 to 15 .
• R 3 is H, sulfo ', C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy,
• R 4 is H, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy
• R 5 is OH, O " M + , C 1 -C 4 -alkyl, a phenyl or unsubstituted phenyl substituted by C 1 -C 2 -alkyl, halogen, for example F, Cl, Br or sulfo,
• R 1 is dC 2 -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 6 -alkyl and m is a number from 1 to 15,
• R 3 is H, methyl, methoxy or sulfo
• R 4 is H, methyl or methoxy
• R 5 OH, O " M ⁇ CC 2 alkyl, a substituted with dC 2 alkyl, chlorine or sulfo
• R ° is methyl
• 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 m is a number from 1 to 12,
• R 3 is H or methyl
• R 4 H, R 5 is OH, ⁇ , methyl, tolyl or phenyl
• Formulas (I) and (IIa) is the counter cation M + preferably an organic cation from the group of imidazolium cations, Alkylguanidiniumkationen,
• the imidazolium cations preferably have the general formula (C1):
• R 1 is d-alkyl, hydroxy-C 1 -C 6 -alkyl, C 2 -C 8 -alkenyl, - (C 1 -C 6 -alkylene-O-) m -R, where R is H, C 1 -C 6 -alkyl or hydroxy -CrCi alkyl has 6 and m is a number from 1 to 20, C 6 -C 0 aryl or C 6 -C 10 aryl which is substituted by 1, 2 or 3 dC 4 alkyl radicals,
• R 2 d-ds-alkyl, hydroxy-Cgs-alkyl, C 2 -C 18 -alkenyl, - (dC 6 -alkylene-O-) m -R, wherein R is H, Ci-Ci 6 alkyl or hydroxy -CrCi 6 alkyl and m is a number from 1 to 20, C 6 -C 10 aryl or C 6 -C 0 aryl, by 1, 2 or 3 CrC ⁇ alkyl radicals is substituted,
• R 1 and R 2 are identical or different and are C 6 -C 2 -alkyl, - (C 2 -C 3 alkylene-O-) m -R, wherein R is C 4 -C 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)
• R, R 2 , R 3 and R 4 are the same or different and are C 1 -C 4 -alkyl, preferably
• R 5 and R 6 are identical or different and Ci-Cia-alkyl, hydroxy-C
• Ci-Ci has the meaning H 6 alkyl or hydroxy Ci-Ci6-alkyl and m is a number from 1 to 20, preferably R 5 and R 6 is C 6 -C 2 -alkyl or phenyl.
• the phosphonium cations preferably have the general formula (C3): wherein
• R 1 is d-Ce-alkyl or hydroxy-d-Ce-alkyl
• R 3 is C 1 -C 20 -alkyl, C 2 -C 2 o-alkenyl, hydroxy-dC 20 -alkyl, C 6 -C 10 -aryl, - (C 1 -C 6 -alkylene-O-) m -R, where R is H, Ci-Ci6-alkyl or hydroxy-Ci
• Ci6-alkyl and m is a number from 1 to 20
• R 4 CC 20 alkyl, C 2 -C 2 -alkenyl, C 6 -C 10 aryl, hydroxy-Ci-C 20 alkyl, - (Ci-C 6 - alkylene-O-) m -R, wherein R is H, Ci-Ci 6 alkyl or hydroxy-Ci
• Ci is 6- alkyl and m is a number from 1 to 20;
• the organic ammonium cations are primary, secondary, tertiary or quaternary ammonium cations and preferably have the general formula (C4):
• R 1 , R 2 , R 3 and R 4 are the same or different and are hydrogen, (dC 3 o) -
• 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, Ci-C 4 alkyl, hydroxy-C 2 -C 4 alkyl,
• R 2 is H, -C 3 -alkyl, hydroxy-C 2 -C 4 alkyl, benzyl, C 4 -C 3 -alkenyl, phenyl or dd alkylene OCOR 5, wherein R 5 is C 8 -C 18 alkyl or C 8 -C 18 -alkenyl, R 3 is H, C 1 -C 30 -alkyl, C 3 -C 30 -alkenyl, benzyl, phenyl or C 1 -C 4 -alkylene-OCOR 5 , where R 5 is C 8 -C 18 - Alkyl or C 8 -C 18 -alkenyl,
• R 4 C -C 3 o-alkyl, C 4 -C 3 o-alkenyl, benzyl or phenyl, with the above
• R 1 is H, C 1 -C 6 -alkyl, hydroxyethyl,
• R2 is H, Ci-C2o-alkyl, hydroxyethyl, benzyl, phenyl or CH 2 -OCOR 5 wherein R 5
• R 3 is H, C 1 -C 20 -alkyl, C 6 -C 20 -alkenyl, benzyl, phenyl or CH 2 -OCOR 5 , where R 5 is C 8 -C 8 -alkyl or C 8 -C 18 -alkenyl,
• R 4 is C 6 -C 20 -alkyl, C 6 -C 20 -alkenyl, benzyl or phenyl, with the above
• Trioctylmethylammonium cocoalkyldimethylbenzylammonium, bis (N, N-hydroxyethyl) -dodecylmethylammonium, methyltrioctylammonium, N, N-bis-stearoylethyl-N, N-dimethyl-ammonium.
• the benzotriazolium cations preferably have the general formula (C5): wherein
• R 1 and R 2 are the same or different and Ci-Ci 2 alkyl, hydroxy
• the pyridinium cations preferably have the general formula (C6):
• R 1 and R 2 are identical or different and C 1 -C 6 -alkyl
• Ci-Ci alkyl has 6 -alkyl or hydroxy-CrC 16 is H and m is a number from 1 to 20 group, or C 6 -C 0 aryl, preferably C 4 -C 2 -alkyl, or phenyl.
• Suitable pigments are inorganic or organic pigments, preferably organic pigments.
• organic pigments can be used for the compositions according to the invention: anthraquinone pigments, laked or unpainted azo pigments, anthanthrone pigments, benzimidazolone pigments, Quinacridone pigments, quinophthalone pigments, diketopyrrolopyrrole pigments, dioxazine pigments, disazocondensation pigments, isoindolinone pigments,
• Isoindoline pigments metal complex pigments, perinone pigments, perylene pigments, phthalocyanine pigments and triarylcarbonium pigments.
• Preferred yellow pigments are C.I. Pigment Yellow 138, 139, 150, 151, 155, 180, 213 and 214. Particularly preferred are C.I. Pigment Yellow 138, 139 or 150.
• Preferred red pigments are C.I. Pigment Red 122, 149, 166, 168, 177, 242, 254, 264, particularly preferred are PR 254, PR 264, PR 242 or PR 177.
• Preferred green pigments are C.I. Pigment Green 7, 36 and 58.
• Pigment Blue 15: 6, 15: 3, 15: 2, 15: 1 and 15, Pigment Blue 80 and C.I. Pigment Violet 19 and 23 are preferred. Particularly preferred are Pigment Blue 15: 6 and Pigment Blue 80.
• organic pigment may in principle be from 1 to 99 to 99 to 1 parts by weight.
• the quantitative ratio between compound of formula (I) and pigment can vary within wide limits, for example from 5 to 95 to 95 to 5, preferably 10 to 90 to 90 to 10, particularly preferably from 20 to 80 80 to 20, most preferably 30 to 70 to 70 to 30, especially 40 to 60 to 60 to 40 parts by weight.
• the compound of the formula (I) is used primarily as
• Dispersing agent of the pigment can also be used smaller amounts, such as 1 to 20 wt .-%, preferably 2 to 10 wt .-%, of compound of formula (I), based on the total weight of the colorant composition, suffice.
• the compounds of formula (I) may be prepared by diazotization of amines of formula (A), preferably at a temperature of 0 to 10 ° C, and azo coupling with one equivalent of the pyridone coupling component of formula (P), preferably at a temperature of 0 up to 40 ° C,
• R ° to R 5 have the meanings given above, and
• Ex is a leaving group, e.g. H or carbamoyl
• 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 isolated from the reaction medium by salting out with an alkali metal salt, filtration and drying, 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 US5132423.
• 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
• Dyeing of high molecular weight organic materials of natural or synthetic origin for example, of plastics, resins, paints, especially metallic paints, paints, electrophotographic toners and developers, electret materials, as well as inks, inkjet inks, printing inks and seeds.
• Colorant compositions 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 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 colorant composition according to the invention. Based on the high molecular weight organic material to be colored, the colorant compositions 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.
• colorant for color filters is suitable for both additive and subtractive color production, such as
• electro-optical systems such as LCD (liquid crystal displays), OLED displays, charge coupled devices, plasma displays or electroluminescent displays, which in turn be active (twisted nematic) or passive (supertwisted nematic) ferroelectric displays or light-emitting diodes as well as colorants for electronic inks ("e-inks”) or "electronic paper” (“e-paper”).
• LCD liquid crystal displays
• OLED displays charge coupled devices
• plasma displays electroluminescent displays
• electroluminescent displays which in turn be active (twisted nematic) or passive (supertwisted nematic) ferroelectric displays or light-emitting diodes as well as colorants for electronic inks ("e-inks”) or “electronic paper” (“e-paper”).
• Dyestuffs of the formula (I) can also be present as Mill Base or as a binder-containing colorant dispersion (photoresist).
• the present invention therefore also provides a mill base containing from 0.01 to 45% by weight, preferably from 2 to 20% by weight, in particular from 7 to
• Suitable 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,
• 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.
• 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.
• Colorant compositions are combined with conventional auxiliaries or additives to a colorant composition, such as
• Surfactants for example the binders of the system in which the inventive
• composition should be used. If available, the
• Auxiliaries and additives preferably in an amount of 0.01 to 15 wt .-%, in particular 0.5 to 10 wt .-%, based on the total weight of
• Colorant composition used.
• Colorant composition for example, still contain surfactants, dispersants, resins and waxes.
• the mill base according to the invention may in particular contain dispersing aids.
• dispersing agents it is possible to use generally known compounds, for example polymeric dispersants. Common are polymers or copolymers based on polyesters, polyacrylates, polyurethanes and polyamides. Furthermore, wetting agents, e.g. As anionic or nonionic wetting agents can be used. The wetting and dispersing agents mentioned can be used individually or in combination. you will be
• Colorant composition subjected to dispersion with conventional dispersing can be used.
• the colorant composition of the invention in the form of a
• dispersed colorant used in a milliliter base it is advantageous to previously set a small primary particle size for the pigment in a suitable manner.
• Particularly suitable are primary particle sizes of less than 60 nm, preferably less than 40 nm in d 5 o value.
• the particle size distribution after comminution is preferably approximated to a Gaussian distribution in which the standard deviation sigma is preferably less than 30 nm, more preferably less than 20 nm.
• the standard deviations are between 5 and 30 nm, preferably between 6 and 25 nm, in particular between 7 and 20 nm.
• the standard deviation sigma ( ⁇ ) corresponds to the positive square root of the variance.
• the variance v is the sum of the squared deviations from
• the dgs value of the comminuted particles is less than or equal to 70 nm.
• the length-to-width ratio of the comminuted particles is preferably between 2: 1 and 1: 1.
• salt kneading with a crystalline inorganic salt in the presence of an organic solvent is used for the fine dispersion.
• a crystalline inorganic salt for example
• organic solvents are, for example, ketones, esters, amides, sulfones,
• Particularly preferred are water-miscible high-boiling organic solvents based on monomeric, oligomeric and polymeric C 2 -C 3 alkylene glycols, such as. B. diethylene glycol, diethylene glycol monomethyl and ethyl ether, triethylene glycol, triethylene glycol monomethyl and ethyl ether,
• the weight ratio between the inorganic salt and the pigment or colorant composition used is preferably (2 to 10) to 1, especially (3 to 7) to 1.
• the weight ratio between the organic solvent and the inorganic salt is preferably (1 ml: 10 g) to (2 ml: 7 g).
• Colorant composition or the pigment used is preferably (1 ml: 2 g) to (1 ml: 10 g).
• the temperature during kneading can be between 40 and 140 ° C,
• the kneading time is expediently 4 hours to 32 hours, preferably 8 hours to 20 hours.
• the inorganic salt and the organic solvent are expediently removed by washing with water and the crushed colorants thus obtained are dried by conventional methods.
• the material obtained after the fine distribution may be subjected to a solvent treatment (finish treatment) as a suspension, filter cake or dry material, if necessary, in order to obtain a more homogeneous particle shape without appreciably increasing the particle size.
• a solvent treatment finish treatment
• the material obtained after the fine distribution may be subjected to a solvent treatment (finish treatment) as a suspension, filter cake or dry material, if necessary, in order to obtain a more homogeneous particle shape without appreciably increasing the particle size.
• finish treatment as a suspension, filter cake or dry material
• steam-volatile solvents such as alcohols and aromatic solvents, particularly preferably branched or unbranched C 1 -C 6 -alcohols, toluene, xylene, chlorobenzene, dichlorobenzene, nitrotoluene or Nitrobenzene usually at elevated temperature, for example up to 200 ° C, and optionally under elevated pressure.
• the invention further relates to a binder-containing
• Colorant dispersion containing 0.01 to 40 wt .-%, preferably 0.1 to 30 wt .-%, in particular 1 to 20 wt .-%, of the inventive
• Colorant composition dispersed in at least one organic solvent, at least one polymeric binder and optionally further auxiliaries.
• the binder-containing colorant dispersion is advantageously prepared by mixing the colorant dispersion (Mill Base) described above with the other components mentioned above.
• Suitable polymeric binders are, for example, acrylates, acrylic esters, polyimides, polyvinyl alcohols, epoxides, 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 nonvolatile constituents of the colorant dispersion.
• Non-volatile constituents are understood as meaning the compounds of the formula (I), the pigments, 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 dispersion, included. In the case that other auxiliaries are used, a lower limit of 0.01 wt .-%, preferably 0.1 wt .-%, is appropriate, based on the
• Suitable organic solvents are the solvents mentioned above for the Mill Base. They are useful in an amount of 10 to
• 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 present invention also provides a process for the preparation of the colorant compositions according to the invention from compounds of the formula (I) and pigment, which comprises combining the compounds of the formula (I) and the organic pigments with one another.
• Primary particle size combined in a dispersion step or by mixing a solution or dispersion of compounds of formula (I) with a dispersion of the pigment.
• Granule or powder form or in moist form, such as. B. as press cake, are used.
• the combination is during a reduction of
• the reduction of the primary particle size can be done by a wet or
• Dry grinding but preferably by salt kneading with a crystalline inorganic salt in the presence of an organic solvent, as described above.
• the invention further relates to the use of
• Colorant compositions and in the form of the described Mill Base or binder-containing colorant dispersion in color filters.
• the use concentration of the colorant composition 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 colorant composition 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 dyes were obtained in Table 1.
• an equivalent amount of 4-aminophenyl p-tolylsulfone is used instead of 4-aminophenyl methylsulfone.
• an equivalent amount of 4-aminophenylsulfonic acid is used for the dye anions of examples I m to 1 p.
• Example Z1 (Composition Z1)
• compositions Z2 to Z6 according to the invention are obtained.
• Example Z3 The procedure is as in Example Z3, but instead of the C.I. Pigment Yellow 138 the C.I. Pigment Green 36 and receives the inventive
• Composition Z7 as a yellowish green solid.
• Example Z1 The procedure is as in Example Z1, but using the compound (I n) instead of the compound (I a) and instead of the C.I. Pigment Yellow 138 the C.I. Pigment Green 58 and receives the inventive composition Z8 as a yellowish green solid.
• Example Z3 The procedure is as in Example Z3, but instead of the C.I. Pigment Yellow 138 the C.I. Pigment Red 254 and receives the inventive
• Composition Z9 as a red solid.
• 10.0 g of the composition according to Example Z1 are in a Paint Shaker beaker with 72.5 g of methoxypropyl acetate (PGMEA), 5.0 g n-butanol and 12.5 g of Disperbyk ® 2001 (BYK-Chemie, polymeric Dispergierangesstoff- Solution) with stirring. After addition of 250 g zirconium oxide beads (0.3 mm) is dispersed for three hours in a dispersing the company Lau (Dispermat). The Millbase obtained is separated from the beads by filtration. The viscosity of the Mill Base is measured (Haake RheoStress 1 rotational viscometer,
• the layer thickness is in each case about 1 to 2 micrometers.
• the glass plates are allowed to flash and then dried for 10 min at 80 ° C. in a circulating air drying cabinet (Binder).
• Binder circulating air drying cabinet
• Tables 5a and 5b show the results of the examples according to the invention and the comparative examples in the postbake.
• the relative contrast ratio KV refers to the color dispersion of the respective comparative example (100%).
• 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.
• the composition according to the invention was compared with the associated base pigment.
• the contrast value of the base pigment of the comparative example was set to 100%.
• the difference between each other was formed in each case. If this value is> 0, then the brightness of the sample according to the invention is greater than that of the comparative example.
• the Mill bases of the compositions according to the invention have reduced viscosities compared to those of the untreated pigments.
• Brightness Y and improved contrast They have steeper ones
• a salt kneading is carried out in which 20.0 g of commercial C.I. Pigment Yellow 138 with 120 g of sodium chloride and 25 ml of diethylene glycol are kneaded at a temperature of 80 ° C for 18 h.
• the kneading dough is stirred in 0.9 l of water for two hours and the composition is then filtered off.
• the filter cake is again treated for 1 h while stirring with 0.9 l of deionized water. After filtration, the pigment is washed with water and dried in vacuo.
• Example K1 The procedure is as in Example K1, but uses dye (I d) instead of (I b) and receives the micronized colorant composition K2 (greenish yellow).
• Example K1 The procedure is as in Example K1, but uses dye (I r) instead of (I b) and receives the micronized colorant composition K3 (greenish yellow).
• micronized compositions are analogously to
• micronized compositions K1-K3 according to the invention have higher contrast value and higher brightness Y than the respective analog salt-kneaded pure pigment.

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