EP3116955A1

EP3116955A1 - Pyridone dye composition

Info

Publication number: EP3116955A1
Application number: EP15712521.2A
Authority: EP
Inventors: Gerald Engel; Yvonne KAHLE
Original assignee: Clariant International Ltd
Current assignee: Clariant International Ltd
Priority date: 2014-03-08
Filing date: 2015-03-05
Publication date: 2017-01-18
Also published as: JP2017512240A; DE102014003312A1; US20170018599A1; CN106414616A; TW201546194A; KR20160129086A; WO2015135634A1

Abstract

The invention relates to a dye composition containing at least one compound of the formula (I) and at least one pigment. The compounds of the formula (I) have the following general formula, in which R⁰ represents C₁-C₆ alkyl or CF₃; R¹ represents sulfo, carboxy, C₁-C₄ alkylene sulfo, C₁-C₄ alkylene carboxy, CONH₂, CONH(C₁-C₄ alkyl), or CN; R² represents C₁-C₁₈ alkyl, C₂-C₁₈ alkenyl, hydroxy C₁-C₁₈ alkyl, or (C₁-C₆ alkylene-O-)_m-R, wherein R represents H, C₁-C₆ alkyl, or hydroxy C₁-C₁₆ alkyl, and m represents a number from 1 to 20; R³ represents H, sulfo, carboxy, C₁-C₆ alkyl, or C₁-C₆ alkoxy; R⁴ represents H, C₁-C₆ alkyl, or C₁-C₆ alkoxy; R⁵ represents OH, OM, C₁-C₆ alkyl, unsubstituted C₆-C₁₀ aryl, or C₆-C₁₀ aryl substituted with C₁-C₆ alkyl, halogen, for example F, Cl, Br, carboxy, or sulfo. The compounds of formula (I) contain at least one anionic group from the group of sulfo and carboxy with the counter-cation M⁺, M⁺ representing and alkali metal cation or an organic cation. The dye compositions are suitable for use in color filters in particular.

Description

Pyridone dye composition

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.

Televisions, PC monitors, mobile phones and tablet computers. The function of liquid crystal displays (LCDs) is based on the following principle: light shines through first a polarizer, then a liquid crystal layer and then a second polarizer. By

suitable electronic control and alignment of the liquid crystals by means of thin-film transistors, these change the direction of rotation of the polarized light, whereby the brightness of the light emerging from the second polarizer and thus out of the device can be controlled.

In the case of colored LCD 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. In addition to the components mentioned above, 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). Furthermore, 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. In addition to the use of the three primary colors red, green and blue, the use of 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.

In the case of OLED displays, so-called 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

Use of color filters in single colors, such as red, green and blue, split.

Certain requirements are placed on 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.

Further important requirements are, for example, a high contrast ratio, a high brightness of the color filter and the best possible color tone. A high contrast ratio affects the quality of the image positively. For the measurement of the contrast ratio, 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.

Light intensity (parallel)

Light intensity (perpendicular)

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.

In color filters, pigmented coatings are commonly used today. For their preparation, pigments in the presence of

Dispersing aids dispersed in an organic solvent and

then 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. This so-called 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. By

Repeated repetition of these steps for the individual primary colors, the color filter is generated in the form of a pixel pattern.

Increasingly, dyes are also used in color filters to optimally match the contrast, brightness, hue and transmission to the required

Purpose to adapt. However, commercially available dyes usually have insufficient fastness properties, in particular insufficient temperature stability and insufficient coloristic properties. The patent JP S62-180302 (1986) describes the use of various

Acid dyes in the form of the free acid for color filters. However, the azo compounds listed therein show insufficient heat stability. It is also disadvantageous from the work safety, to work with free acids.

US2012 / 205599A1 describes green color filters which, in addition to a green or cyan pigment, also contain a yellow dye as coloring component. The dye may also be, inter alia, pyridone dyes, but free of acid groups. The requirements for the colorants used in the color filters are constantly increasing. Even the commercially available commercial products do not always meet all the requirements of technology. In particular, there is one

Need for improvement in terms of heat stability, contrast levels and

Brightness of the colorant used without negative influence on chroma and hue. In the case of dyes, it is desirable to have good solubility of the colorants in the application system. It was a further object to provide greenish yellow colorants with good heat stability for color filter applications. Surprisingly, it has now been found that novel colorant compositions of dyes of the general formula (I) and pigments are well suited for use in color filters.

In compositions with organic pigments, the compounds of formula (I) improve the dispersibility of the pigments and permit one

Farbtonadjustierung. They thereby lead to advantageous performance properties such as reduced viscosity in dispersions and increased brilliance and higher contrast in the color filter. 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:

wherein

R ° d-Ce-alkyl or CF ₃ ;

R ^{1 is} sulfo, carboxy, C 1 -C ₄ -alkylene-sulfo, C 1 -C ₄ -alkylene-carboxy, CONH ₂ ,

CONH (dC ₄ -alkyl) or CN,

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

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.

It is also possible that the counter cation M ^{+ is} a mixture of the aforementioned cations.

The alkylene groups and the alkyl groups in the alkyl and alkoxy radicals are branched or linear. Examples of 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 .

Preferred radicals 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

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, very 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 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, ΟΊν ^" , methyl, tolyl or phenyl where M ^{+ is} one

Alkali metal cation, a primary, secondary, tertiary or quaternary

Ammonium ion or a phosphonium ion means. In preferred compounds of the general formula (I)

R ° C ₁ -C ₂ -alkyl, in particular methyl,

R ¹ dC ₄ alkylene sulfo, CONH (dC ₂ alkyl) or CONH ₂ , in particular

CC ₂ -alkylene-sulfo, CONH (C ₁ -C ₂ -alkyl) or CONH _2,

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,

where the compounds of the formula (I) have at least one sulfo group,

preferably 1 or 2 sulfo groups, and the counter cation M ^{+ is} as defined above. In more preferred compounds of the general formula (I)

R ° methyl,

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

Phenyl or unsubstituted phenyl,

wherein the compounds of formula (I) contain 1 or 2 sulfo groups and the counter cation M ^{+ is} as defined above.

In particularly preferred compounds of the general formula (I), 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, ΟΊνΤ, methyl, tolyl or phenyl,

wherein the compounds of the formula (I) contain 1 or 2 sulfo groups, in particular 1 sulfo group, and the counter cation M ^{+ is} as defined above.

An example of a particularly preferred compound is (IIa):

In all compounds of the invention described above

Formulas (I) and (IIa) is the counter cation M ⁺ preferably an organic cation from the group of imidazolium cations, Alkylguanidiniumkationen,

Phosphonium cations, primary, secondary, tertiary or quaternary

Ammonium ions, benzotriazolyl cations and pyridinium cations.

The imidazolium cations preferably have the general formula (C1):

wherein

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,

Mean H or methyl.

Particular preference is given to imidazolium cations of the formula (C1) in which R ¹ and R ^{2 are} identical or different and C ₄ -C- _2- alkyl, - (Ci-C ₃ -alkylene-O-) _m -R, where R is H, Ci-Ci ₂ -alkyl or hydroxy-Ci-Ci ₂ -alkyl and m is a number from 1 to 3 means phenyl or di (isopropyl) phenyl, and R ^{3 is} hydrogen or methyl. Are very particularly preferred imidazolium cations of the formula (C1), wherein 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)

wherein

R, R ² , R ³ and R ^{4 are the} same or different and are C 1 -C ₄ -alkyl, preferably

Methyl or ethyl, and

R ⁵ and R ^{6 are} identical or different and Ci-Cia-alkyl, hydroxy-C

C ₁₈ -alkyl, C ₂ -C ₈ alkenyl, C ₆ -C ₁₀ aryl, - (d-Ce-alkylene-O-) ™ -

R, where R, 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 ² ₆ -alkyl, C ₂ -C ₆ -alkenyl, hydroxy-dC ₆ alkyl or C ₆ -C ₀ aryl,

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;

mean.

Particular preference is given to phosphonium cations of the formula (C3) in which R ¹ , R ² and R ^{3 are} identical or different and denote C ₄ -alkyl or phenyl, and R ⁴ denotes C ₆ -C 18 -alkyl or phenyl.

The organic ammonium cations are primary, secondary, tertiary or quaternary ammonium cations and preferably have the general formula (C4):

wherein

R ¹ , R ² , R ³ and R ^{4 are the} same or different and are hydrogen, (dC ₃ o) -

Alkyl, (C ₂ -C ₃₀ ) -alkenyl, hydroxy (C ₁ -C ₃₀ ) -alkyl, C ₁ -C ₄ -alkylenephenyl, (C ₆ -C ₁₀ ) -aryl, CC ₆ -alkylene-OCOR ⁵ , wherein R ⁵ is C ₆ - C ₂₀ means alkyl or C ₆ -C ₂₀ alkenyl; - (dC ₆ -alkylene-O-) _m -R, where R is H, Ci-Ci6-alkyl or hydroxy- Ci-C ₁₆ alkyl and m is a number from 1 to 20;

with the proviso that 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.

In more preferred compounds of the general formula (C4)

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

defined proviso. In particularly preferred compounds of the general formula (C4), 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

C ₈ -C ₈ -alkyl or C ₈ -C ₈ -alkenyl,

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

defined proviso.

Examples of ammonium cations of the formula (C4) are:

Stearylammonium, Oleylammonium, ethylhexylammonium, Cocosfettammonium, 3-lsotridecylether-propylammonium, Didecylammonium, Diisotridecylammonium, Dimethyldecylammonium, Jeffamine ^® M600 ammonium, triethylammonium, didecyldimethylammonium, distearyl dimethyl ammonium,

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

(Ci-Ci ₂ ) alkyl, - (dC ₆ -alkylene-O-) _m -R, wherein R is H, Ci-Ci6-alkyl or hydroxy-Ci-Cie-alkyl and m is a number from 1 to 20 means, or Ce-C-io-aryl, preferably C ₂ -C 8 -alkyl or phenyl.

The pyridinium cations preferably have the general formula (C6):

wherein

R ¹ and R ^{2 are} identical or different and C ¹ -C 6 -alkyl,

Hydroxy (CIC | ₈₎ alkyl, - (Ci-Ce-alkylene-O-Jm-R, wherein R, 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. For example, the following 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.

Preference is further given to C.I. Pigment Orange 34, 36, 38, 43, 62, 64, 68, 71, 72, 73, 74, and 81. Preferred green pigments are C.I. Pigment Green 7, 36 and 58.

In the blue and violet area C.l. 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.

The mixing ratios of compound of formula (I) to pigment,

preferably organic pigment, may in principle be from 1 to 99 to 99 to 1 parts by weight. In order to achieve certain coloristic properties, 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. In the case that 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,

wherein

R ° to R ^{5 have} the meanings given above, and

Ex is a leaving group, e.g. H or carbamoyl,

and optionally subsequent exchange of the resulting in the synthesis

Cations, eg H ⁺ or Na ⁺ , are prepared against the cation M ⁺ .

The compounds of the formulas (A) and (P) are known to the person skilled in the art from the literature.

In the diazotization, 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.

Subsequently, the diazotized amine is allowed to react with the coupling component P, preferably in aqueous solution. In general, the

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. Depending on the reaction and work-up conditions, 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

Alkali metal cations, for example sodium ion, or the ammonium ions or phosphonium ions. If desired, the dye salts of formula (I) may be further purified, for example by diafiltration through a semipermeable membrane or recrystallization, thereby avoiding undesirable

By-products and inorganic salts are separated from the crude product.

From the Farbstoffalkalimetallsalzen 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

Purification step, isolate.

The compounds of the formulas (C1) to (C6) are the

Skilled in the art. For example, 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

Procedure from pyridine and chloroacetic acid methyl ester as well

subsequent reaction with the corresponding amine can be obtained. The colorant compositions according to the invention can be used for

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.

High molecular weight organic materials with the inventive

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, polyolefins, 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

Hydrocarbon resins, Epoxy resins, Phenolic epoxy resins, Unsaturated

Synthetic resins (polyesters, acrylates) with the different hardening mechanisms, waxes, aldehyde and ketone resins, rubber, rubber and its derivatives and latices, casein, silicones and silicone resins; individually or in mixtures. It does not matter if the mentioned high molecular weight organic

Compounds as plastic masses, melts or in the form of

Spinning solutions, dispersions, paints, paints or printing inks are present. 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.

Preferred is the use of the colorant compositions for color filters and the mass coloration of polymers.

Particularly preferably, the use as colorant for color filters is suitable for both additive and subtractive color production, such as

For example, in 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").

The colorant compositions according to the invention of pigment and

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

17% by weight of the colorant composition of compounds of formula (I) and pigment dispersed in an organic solvent. Suitable organic solvents are, for example:

Ethyl lactate, benzyl alcohol, 1, 2,3-trichloropropane, 1, 3-butanediol,

1, 3-butylene glycol, 1,3-butylene glycol diacetate, 1,4-dioxane, 2-heptanone, 2-methyl-1,3-propanediol, 3,5,5-trimethyl-2-cyclohexen-1-one, 3,3,5-trimethyl-cyclohexanone, 3-ethoxyethyl propionate, 3-methyl, 3-butanediol, 3-methoxy-3-methyl-1-butanol,

3-methoxy-3-methylbutyl acetate, 3-methoxybutano-1, 3-methoxybutyl acetate,

4-heptanone, m-xylene, m-diethylbenzene, m-dichlorobenzene, N, N-dimethylacetamide, N, N-dimethylformamide, n-butyl alcohol, n-butylbenzene, n-propyl acetate, o-xylene, o-chlorotoluene, o-diethylbenzene, o-dichlorobenzene, p-chlorotoluene, p-diethylbenzene, sec-butylbenzene, tert-butylbenzene, gamma-butyrolactone, isobutyl alcohol,

Isophorone, ethylene glycol diethyl ether, ethylene glycol dibutyl ether,

Ethylene glycol monoisopropyl ether, ethylene glycol monoethyl ether, ethylene glycol monoethyl ether acetate, ethylene glycol mono-tert-butyl ether,

Ethylene glycol monobutyl ether, ethylene glycol monobutyl ether acetate,

Ethylene glycol monopropyl ether, ethylene glycol monohexyl ether,

Ethylene glycol monomethyl ether, ethylene glycol monomethyl ether acetate,

Diisobutyl ketone, diethylene glycol diethyl ether, diethylene glycol dimethyl ether,

Diethylene glycol monoisopropyl ether, diethylene glycol monoethyl ether acetate,

Diethylene glycol monobutyl ether, diethylene glycol monobutyl ether acetate,

Diethylene glycol monomethyl ether, cyclohexanol, cyclohexanol acetate,

Cyclohexanone, dipropylene glycol methyl ether, dipropylene glycol methyl ether acetate, dipropylene glycol monoethyl ether, dipropylene glycol monobutyl ether,

Dipropylene glycol monopropyl ether, dipropylene glycol monomethyl ether,

Diacetone alcohol, triacetylglycerol, tripropyleneglycol monobutyl ether,

Tripropylene glycol monomethyl ether, propylene glycol diacetate, propylene glycol phenyl ether, propylene glycol monoethyl ether, propylene glycol monoethyl ether acetate, propylene glycol monobutyl ether, propylene glycol monopropyl ether,

Propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate,

Propylene glycol monomethyl ether propionate, benzyl alcohol, methyl isobutyl ketone, methyl cyclohexanol, n-amyl acetate, n-butyl acetate, isoamyl acetate, isobutyl acetate, propyl acetate, dibasic ester (DBE).

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.

Depending on the application, the inventive

Colorant compositions are combined with conventional auxiliaries or additives to a colorant composition, such as

Surfactants, dispersants, rheology control additives, fillers, modifiers, resins, waxes, defoamers, anti-dusting agents, extenders, antistatic agents, charge control agents, preservatives, drying retardants, wetting agents, antioxidants, UV absorbers, light stabilizers, and binders, 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.

In particular for color filters, the inventive

Colorant composition, for example, still contain surfactants, dispersants, resins and waxes.

The mill base according to the invention may in particular contain dispersing aids.

As 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

expediently in an amount of from 2 to 90% by weight, preferably from 10 to

50 wt .-%, based on the total weight of the colorant composition used. For the preparation of the Mill bases, the inventive

Colorant composition subjected to dispersion, with conventional dispersing can be used. Is 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. Likewise, it is an advantage, a close

Adjust particle size distribution.

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. As a rule, 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 (σ) corresponds to the positive square root of the variance. The variance v is the sum of the squared deviations from

Mean value divided by the number of samples minus 1. It is also advantageous if 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. As a possibility, salt kneading with a crystalline inorganic salt in the presence of an organic solvent is used for the fine dispersion. As a crystalline inorganic salt, for example

Aluminum sulfate, sodium sulfate, calcium chloride, potassium chloride or sodium chloride, preferably sodium sulfate, sodium chloride and potassium chloride. As organic solvents are, for example, ketones, esters, amides, sulfones,

Sulfoxides, nitro compounds, mono-, bis- or tris-hydroxy-C ₂ -C 12 alkanes, which may be substituted by C is Cs-alkyl and one or more hydroxy groups, into consideration. 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,

Dipropylene glycol, dipropylene glycol monomethyl and ethyl ether,

Propylene glycol monomethyl and ethyl ether and liquid polyethylene and

Polypropylene glycols, N-methylpyrrolidone and also triacetin,

Dimethylformamide, dimethylacetamide, ethyl-methyl-ketone, cyclohexanone,

Diacetone alcohol, butyl acetate, nitromethane, dimethylsulfoxide and sulfolane. 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). The weight ratio between the organic solvent and the sum of inorganic salt and the invention

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,

preferably 60 to 120 ° C, amount. The kneading time is expediently 4 hours to 32 hours, preferably 8 hours to 20 hours.

After the salt kneading, 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. Preferably, the

Use of 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. By 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

Total amount of colorant dispersion. Suitable organic solvents are the solvents mentioned above for the Mill Base. They are useful in an amount of 10 to

90 wt .-%, preferably from 20 to 80 wt .-%, based on the total amount of the colorant dispersion. The yellow shades of the compounds of the invention and

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

Full color image. In addition, there are color filter systems that work with four primary colors red-green-blue and yellow (R, G, B, Y), for which the colorants of the invention are also well suited.

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.

Appropriately, optionally after reduction of

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.

The respective components in dry form, such as. In

Granule or powder form, or in moist form, such as. B. as press cake, are used.

Preferably, the combination is during a reduction of

Primary. This serves to smaller particle sizes, closer

Particle size distributions and the resulting further optimization of the to achieve application properties, especially for color filters. 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.

In the following examples, percentages are percentages by weight and parts by weight unless otherwise stated.

Examples:

Preparation of the acid azo dye (I a):

A suspension consisting of 17.1 g of 4-amino-phenyl-methylsulfone (0.10 mol) in 100 ml of water and 22 ml of conc. Hydrochloric acid (37% strength by weight) is diazotized at 0 ° -5 ° C. with 17.3 g sodium nitrite solution (40% strength by weight, 0.1 mole NaNO ₃ ). The resulting diazonium salt is added in portions at 0 to 5 ° C to a suspension consisting of 24.6 g (0.1 mol) of the compound of the following formula

in 9 ml of 30% sodium hydroxide solution and 50 ml of water. By adding

15 wt .-% sodium carbonate solution, the pH is maintained at 7 to 9. The volume of the dye suspension is made up with water to about 700 ml, then heated to 90 ° C for 30 min. After cooling, the product is filtered off with suction, washed with water and dried in vacuo. 40.2 g of a yellow dye powder of the formula (Ia) are obtained.

Preparation of hexaalkylguanidinium chloride (C2a):

To a solution of 15.5 ml (0.13 mol) of tetramethylurea in 60 ml of toluene 13 ml (0.13 mol) of phosphoryl chloride are added dropwise at 60 - 65 ° C. After two hours of stirring is cooled and added dropwise at 0 - 5 ° C, a mixture of 18 ml of triethylamine and 40 ml (0.14 mol) of bis (2-ethylhexyl) amine in 30 ml of toluene. Subsequently, the temperature is allowed to rise to about 20 ° C and stirs overnight. Then, the pale yellow mixture is added with cooling with 54 ml of NaOH (30 wt .-%). The mixture is stirred with 150 ml of NaCl solution. The toluene phase is separated off, dried with magnesium sulfate and the solvent is removed in vacuo. This gives 47 g of a light beige,

waxy solid.

Preparation of hexaalkylguanidinium dye salt (I b):

27.5 g (66 mmol) of Hexaalkylguanidiniumchlorids (C2a) are dissolved at 90 ° C in 500 ml of water with stirring (solution A).

29.2 g (64 mmol) of the yellow acid azo dye of the formula (I a) are introduced into 500 ml of water and heated to 60 to 65 ° C after the addition of five drops of 15 wt .-% sodium carbonate solution. This suspension is added in portions at about 90 ° C to solution A. After one hour reaction time at this temperature, an emulsion is obtained from which after cooling the

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.

By analogous procedure, the dyes were obtained in Table 1. For the dye anion of Example II, an equivalent amount of 4-aminophenyl p-tolylsulfone is used instead of 4-aminophenyl methylsulfone. For the dye anions of examples I m to 1 p, instead of 4-aminophenyl methylsulfone, an equivalent amount of 4-aminophenylsulfonic acid is used.

Table 1 (prepared dye salts)

These are yellow substances with decomposition points> 200 ° C.

Further dye anions were prepared starting from the following nitrilopyridones:

They are made of methyl cyanoacetate, methyl acetoacetate and the corresponding amine - available - methoxypropylamine or Jeffamine ^® M600. The nitrile group can be removed by heating with dilute sulfuric acid. The 3.5 unsubstituted pyridones obtained are reacted with formaldehyde and sodium bisulfite according to a known procedure (analogous to DE 2162858), the following pyridone couplers being obtained.

R = methyl.

From this, the dyes I q and I s were obtained. The reaction of the named Na dye salts with the respective quaternary ammonium compounds analogously to the preparation of I b gave the dye salts I r and 1 1.

Examples of the Preparation of the Compositions According to the Invention Containing Dyes I and Organic Pigments: Example Z1: (Composition Z1)

2.0 g of the compound (I a) are mixed with 18.0 g of C.I. Grinding Pigment Yellow 138 in an IKA laboratory powder mill. After discharge from the mill, 19.4 g of the composition Z1 according to the invention are obtained in the form of a greenish-yellow powder.

Examples Z2 to Z6:

Analogously to Example Z1 instead of the compound I a in the

used in Table 1 below. Each of the compositions Z2 to Z6 according to the invention is obtained.

Table 3

Example dye pigment

Z1 I a C.I. Pigment Yellow 138

Z2 I d C.I. Pigment Yellow 138

Z3 I b C.I. Pigment Yellow 138

Z4 Cl Clg Pigment Yellow 138 Z5 1 1 Cl Pigment Yellow 138

Z6 1 o C.I. Pigment Yellow 138

Example Z7:

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 Z8:

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 Z9:

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.

Table 4

Application Example 10

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 Dispergierhilfsmittel- 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,

Measuring geometry plate-cone, 23 ° C, linear increase of the shear rate D to 250 1 / s, value determination at 250 1 / s.).

20.0 g of the Millbase obtained are mixed with 20.5 g of a 10 wt .-% solution of Joncryl ^® 611 (styrene-acrylate resin, BASF AG) in PGMEA by shaking 10 minutes without beads. Subsequently, the dispersion is filtered. The resulting binder-containing colorant dispersion is using a

Spin Coaters (POLOS Wafer Spinner) coated on glass plates (SCHOTT, laser cut, 10 x 10 cm) in a layer thickness, which makes it possible, when using a light source C, the color coordinates y mentioned in Table 5a or the color coordinates x mentioned in Table 5b as reference values put.

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). The so-called prebake values of the color coordinates (x, y, Y, and CIELAB,

Spectrophotometer Datacolor 650, illuminant C, 2 ° observer),

Measure transmission curves (ditto) and contrast values (Contrast Tester Tsubosaka CT-1). The glass plates are then subjected to a heat treatment at 230 ° C for 1 h in a convection oven and re-measured, from which one receives the postbake values.

Comparative Examples: V1 - V4:

The Mill bases and color dispersions are analogous as in the case of

Application Example 10 produced. However, none are used

Pigment compositions according to the invention, but the

underlying base pigments. 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. In each case, the composition according to the invention was compared with the associated base pigment. For each contrast value, the contrast value of the base pigment of the comparative example was set to 100%. For the comparison of the brightnesses Y, 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.

For the comparison of the viscosities in each case the viscosity of the

Comparative example set to 100%.

Table 5a: (relative to y values).

Example Description Relative y (Ref.) = X = Relative KV

Viscosity Y value

the Millbase [%] [%]

10 Z1 83 0.500 0.428 +2.7 185

11 Z2 83 0.500 0.428 +2.7 185

12 Z3 40 0.500 0.429 + 4.5 253

13 Z4 53 0.500 0.430 +3.1 177

14 Z5 38 0.500 0.427 +4.6 267

15 Z6 95 0.500 0.431 + 1, 3 117 V1 Cl Pigment 100 0.500 0.435 0 (Ref.) 100 Yellow 138

16 Z7 20 0.420 0.255 +0.9 103

V2 C.I. Pigment 100 0.420 0.248 0 (Ref.) 100

Green 36

17 Z8 85 0.500 0.283 + 2.0 107

V3 C.I. Pigment 100 0.500 0.260 0 (Ref.) 100

Green 58

Table 5b: (reference to x-values).

The Mill bases of the compositions according to the invention have reduced viscosities compared to those of the untreated pigments. The

Examples according to the invention show increased in the color filter application

Brightness Y and improved contrast. They have steeper ones

Transmittance curves exemplified for the preparation of a micronized dye composition by addition during salt kneading:

Example K1:

In a laboratory kneader (Werner & Pfleiderer, 300 ml) 2.0 g of compound (I b) with 18.0 g of commercial C.I. Pigment Yellow 138 with the addition of

120 g of sodium chloride and 25 ml of diethylene glycol at a temperature of 80 ° C for Kneaded for 18 hours. 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 colorant composition is washed with water and dried in vacuo.

A finely divided greenish-yellow pigment composition K1 is obtained. Comparative Example KV1:

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 K2

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 K3

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). Application test of examples K1-3 and KV1:

The micronized compositions are analogously to

Application Example 10 checked. However, instead of the

Composition Z1 given in Table 6 below

Used compositions. Table 6: (reference to y values).

The micronized compositions K1-K3 according to the invention have higher contrast value and higher brightness Y than the respective analog salt-kneaded pure pigment.

Claims

claims:

A colorant composition comprising at least one compound of the formula (I) and at least one pigment, in which the compounds of the formula (I) d have the general formula:

wherein

R ° d-Ce-alkyl or CF ₃ ;

CONH (dC ₄ -alkyl) or CN,

R ² Ci-Cie-alkyl, C ₂ -C ₈ alkenyl, hydroxy-Ci-C ₈ alkyl, or - (dC ₆ alkylene- O-) _m -R, wherein R is H the meaning -C ₁₆ alkyl or hydroxy-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 d-Ce-alkoxy,

R ^{5 is} OH, OM, Ci-Ce-alkyl, unsubstituted C ₆ -C ₀ -aryl or by C ₆ alkyl, halogen, carboxy or sulfo-substituted C ₆ -do-aryl

in which the compounds of the formula (I) contain at least one anionic radical from the group consisting of sulfo and carboxy with the counter cation M ⁺ , where M ⁺ denotes an alkali metal cation or an organic cation.

2. Colorant composition according to claim 1, characterized in that the compounds of formula (I) contain at least one sulfo group with the counter cation M ⁺ .

3. Colorant composition according to claim 1 or 2, characterized in that the counter cation M ^{+ is} an organic ammonium cation or an organic phosphonium cation.

4. Colorant composition according to claim 3, characterized in that the organic ammonium cation is a primary, secondary, tertiary or quaternary ammonium cation.

5. colorant composition according to claim 3 or 4, characterized

in that the organic ammonium cation is an imidazolium cation, alkylguanidinium cation, benzotriazolyl cation or pyridinium cation.

6. colorant composition according to one or more of claims 1 to 5, characterized in that the pigment is an organic pigment.

7. colorant composition according to one or more of claims 1 to 6, characterized in that the organic pigment from the group of Anthrachinonpigmente, 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 triaryl carbonium pigments is selected.

8. colorant composition according to one or more of claims 1 to 7, characterized in that the mixing ratio of compound of formula (I) to pigment of 1 to 99 to 99 to 1 parts by weight.

9. Colorant composition according to one or more of claims 1 to 8, characterized in that the compound of formula (I) in an amount of 1 to 20 wt .-%, based on the total weight of

Colorant composition is included.

10. Mill base containing 0.01 to 45 wt .-% of the colorant composition according to one or more of claims 1 to 9, dispersed in at least one organic solvent.

11. Binder-containing colorant dispersion containing 0.01 to 40 wt .-% of the colorant composition according to one or more of claims 1 to 9, dispersed in at least one organic solvent, at least one polymeric binder and optionally further auxiliaries.

12. A process for the preparation of the colorant composition according to

at least one of claims 1 to 9, characterized in that one combines the compounds of formula (I) and the pigments together.

13. Use of colorant compositions according to one or more of claims 1 to 11 for coloring high molecular weight

organic materials of natural or synthetic origin

14. Use according to claim 13 for dyeing for color filters, in

Liquid crystal displays or in OLED displays or for Polymermassefärbung.