A compound, a dye and use of the compound

Abstract

The present application belongs to the technical field of dye compounds, and provides a compound with a general formula (I): wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 each independently represents a hydrogen atom or a substituent; and the substituent is an arylamine group and derivatives thereof. The compound provided by the present application is used for dyes, colorants, colored curable resin compositions, optical filters, and display devices such as image sensors and liquid crystal displays. The present application adopts a closed ring fused ring π conjugated mother nucleus structure such as phenanthraquinone, and the closed ring and π conjugated characteristics can make the molecular skeleton have high chemical bond energy, so that the phenanthraquinone derivatives have good photochemical stability. The present application overcomes the problems of unstable photo-physical properties and thermal stability of traditional dyes, and the problems of poor solubility and compatibility in a color photoresist system.

Description

Technical Field

[0001] This invention belongs to the field of compound technology, and particularly relates to a compound, a dye, and the use of the compound. Background Technology

[0002] Dyes are used in fields such as liquid crystal displays, image sensors, fiber materials, and inkjet printing to display colors by using reflected or transmitted light.

[0003] With the rapid popularization of flat panel display products such as Liquid Crystal Display (LCD) and Organic Light Emitting Diode (OLED), people's requirements for display color display are constantly increasing. Color filters are key raw materials for color display in LCD panels, OLEDs, and other flat panel display products. There are many methods for preparing color filters, such as dyeing, pigment dispersion, and printing. Among them, the pigment dispersion method for preparing color filters involves coating a coloring photosensitive resin composition onto a colored glass substrate with a pre-prepared black matrix; after photolithography processes such as exposure and development, a color pattern of the color filter is formed; then, heating and other treatments are performed, and the above process is repeated to form a pattern of all colors of the color filter; finally, an indium tin oxide conductive layer is formed, and a color filter with multiple color patterns is obtained.

[0004] Currently, pigment dispersion methods using photolithography to form red-green-blue (RGB) patterned pixels are widely used to manufacture color filters because they can produce filters with excellent stability. While filters produced by this method have good thermal and photochemical stability, their particulate nature leads to light scattering, reducing brightness, contrast, and resolution. Furthermore, the aggregation behavior of molecules within the pigment and its impact on the pigment's optical properties are difficult to predict, making precise control of color purity challenging and hindering the achievement of high color purity and a wide color gamut. Dyes can be an attractive alternative to overcome this limitation because they dissolve in the medium and exist in molecular form, thus reducing light scattering. Moreover, dye molecules have well-defined structures, and their molecular structure has a clear structure-activity relationship with photophysical properties, giving them an advantage in achieving superior optical performance. Although dyes can generally be used to manufacture color filters with high transmittance and high contrast, their poor heat and light resistance can easily lead to colorimetric changes during the high-temperature heating process in color filter manufacturing. In addition, they should be highly soluble in industrial solvents and have strong absorption peaks to obtain excellent optical performance. Specifically:

[0005] (1) Dyes in a molecularly dispersed state are generally inferior in terms of lightfastness and heat resistance compared to pigments that form molecular aggregates. In particular, there is a problem that the optical properties are altered by high-temperature processes when forming indium tin oxide (ITO) films, which are widely used as electrodes for liquid crystal displays and the like.

[0006] (2) Dyes in a molecularly dispersed state typically have a lower solvent resistance variance compared to pigments that form molecular aggregates.

[0007] (3) Dyes tend to inhibit free radical polymerization, which makes it difficult to design colorable curable compositions for systems that use free radical polymerization as a curing method.

[0008] (4) Traditional dyes exhibit low solubility in alkaline aqueous solutions or organic solvents, making it difficult to obtain colorable curable compositions with the desired spectrum.

[0009] (5) Dyes often interact with other components in coloring curable compositions, making it difficult to control the solubility (developability) of the exposed and unexposed portions.

[0010] (6) When the molar absorptivity (ε) of the dye is low, a large amount of dye needs to be added. Therefore, the amount of other components in the coloring curable composition, such as polymerizable compounds (monomers), binders or photopolymerization initiators, must be relatively reduced, thereby reducing the curability, heat resistance after curing and developability of the composition.

[0011] As a solution to this problem, a polymeric dye method has been disclosed that imparts the dye to be developable by copolymerizing a monomer having a colorant group and a monomer having an alkali-soluble group (see, for example, JP-A Nos. 2007-139906 and 2007-138051, and Japanese Patent No. 3736221).

[0012] To improve the aforementioned problems, it is known to use dyes as colorants (see, for example, Patent Document 1 below). When dyes are used as colorants, the hue or brightness of the displayed image can be improved by the purity of the dye's color or the vividness of its hue, and the contrast is improved due to the disappearance of coarse particles, which is more useful in this respect.

[0013] Examples of dyes known include compounds with a wide variety of pigment precursors, such as phthalocyanine dye, dipyrromethene dye, pyrimidine azo dye, pyrazoleazo dye, and xanthene dye (see, for example, Patent Documents 2-6).

[0014] The patent documents mentioned above are as follows:

[0015] Patent Document 1: Japanese Patent Application Publication No. 6-75375;

[0016] Patent Document 2: Japanese Patent Application Publication No. 2008-292970;

[0017] Patent document 3: Japanese Patent Application Publication No. 2007-039478;

[0018] Patent document 4: Japanese Patent Application Publication No. 9-157536;

[0019] Patent document 5: Japanese Patent Application Publication No. 6-51115;

[0020] Patent document 6: Japanese Patent Application Publication No. 11-152415;

[0021] Patent document 7: Japanese Patent Application Publication No. 2012-32754;

[0022] Patent document 8: Japanese Patent Application Publication No. 2007-138051;

[0023] Patent document 9: Japanese Patent Application Publication No. 2000-162429;

[0024] Patent document 10: Japanese Patent Application Publication No. 2003-246935.

[0025] Among these problems related to dyes, dipyrromethene metal complexes have been studied as dyes that address the issues in the above entries (1) concerning the lightfastness and heat resistance of dyes and (6) concerning the molar absorptivity (ε) of dyes (e.g., see U.S. Patent Publication No. 2008 / 0076044).

[0026] In polymerizable compositions integrated with visible light, dipyrrole methylene metal complexes are used as functional compounds other than sensitizers for free radical polymerization initiators (e.g., see Japanese Patent Nos. 3279035 and 3324279, and JP-A Nos. 11-352685, 11-352686, 2000-19729, 2000-19738, and 2002-236360). Dipyrrole methylene metal complexes have reportedly exhibited excellent lightfastness and heat resistance, high molar absorptivity (ε), and excellent light absorption characteristics, considering color reproduction (e.g., see U.S. Patent Application Publication No. 2008 / 0076044).

[0027] To date, it has been difficult to use dyes to form color patterns for high-resolution color filters, which consist of fine thin films and possess excellent durability. Furthermore, for color filters used in solid-state image sensors, the coloring layer needs to be formed from a thin film with a thickness of less than 1 μm. Therefore, to achieve the desired absorption, a large amount of colorant needs to be added to the curable composition, thus leading to the aforementioned problems.

[0028] Furthermore, regarding dye-containing coloring curing compositions, it has been noted that color transfer is prone to occur between adjacent different colored patterns or between stacked and overlapping layers when heat treatment is applied after film formation. In addition to color transfer, pattern peeling is prone to occur in low exposure dose areas due to decreased sensitivity, and thermal relaxation caused by the reduction in the relative amount of photosensitive components that affect photolithography properties, elution during development, etc., prevent the attainment of the desired shape or color density.

[0029] Various methods have been conventionally proposed to address these problems, including selecting the type of initiator and increasing the amount of initiator added (e.g., see JP-A No. 2005-316012). Furthermore, methods for preparing color filters have been disclosed, in which a color pattern is formed, and then polymerization is performed at an elevated exposure temperature by irradiating the color pattern with light while heating the substrate, thereby increasing the curing of the system (e.g., see Japanese Patent No. 3309514). Additionally, methods for preparing color filters have been disclosed, in which light irradiation is performed between the development process and the heat treatment to prevent deformation of the color filter (e.g., see JP-A No. 2006-258916).

[0030] Traditional dyes suffer from the following drawbacks: when used to form colored images for applications such as liquid crystal displays (LCDs) and image sensors, it is typically required that the coloring photosensitive composition form an extremely thin layer, and that a high color density be maintained even at this thin thickness. Therefore, the optical properties of filters, such as contrast, need improvement. Furthermore, the lightfastness or heat resistance of color pixels may not be sufficient for practical applications, making it difficult to cope with the high brightness of recent backlighting issues. ITO (indium tin oxide), which is widely used as an electrode in FPDs (flat panel displays) such as LCDs, suffers from the aforementioned problems of altered photochemical and photophysical properties due to the high temperatures involved in film formation.

[0031] On the other hand, dyes need to be dispersed in organic solvents in a highly uniform and finely dispersed state. However, to date, no dye dispersion or composition thereof has been provided that meets these requirements and has excellent dispersibility, flowability, etc. Summary of the Invention

[0032] To solve at least one of the above problems, the present invention provides a compound having excellent properties for use as a dye.

[0033] According to a first aspect of the present invention, a compound is provided having the following general formula (Ⅰ):

[0034]

[0035] Among them, R 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 Each can independently represent a hydrogen atom or a substituent;

[0036] The substituents are arylamine groups and their derivatives.

[0037] According to one embodiment of the present invention, the aromatic amino group is selected from one or more of diphenylamino and its derivatives, triphenylamino and its derivatives.

[0038] According to one embodiment of the present invention, the substituent is one or more of phenyl-substituted or unsubstituted arylamino, phenyl-substituted or unsubstituted alkoxyarylamino, and arylcarbazole having phenyl-substituted or unsubstituted.

[0039] According to one embodiment of the present invention, R 1 R 2 R 3 R 4 R 5 R 6R 7 R 8 In, the substituent is located in R 2 and / or R 7 The rest are hydrogen atoms; or

[0040] R 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 In, the substituent is located in R 3 and / or R 6 The rest are hydrogen atoms.

[0041] According to one embodiment of the present invention, R 1 ~R 8 The structural formula is selected from one or more of the structures shown in the following formulas (A-1) to (A-46):

[0042]

[0043]

[0044]

[0045]

[0046] Wherein, the dashed line represents R in general formula (Ⅰ) 1 ~R 8 The connection key.

[0047] According to one embodiment of the present invention, any substituent R of formulas (A-1) to (A-46) is replaced by one or more identical or different groups, said groups being selected from one or more of hydrogen atoms, halogen groups, cyano groups, straight-chain alkyl / branched alkane / cyclic alkyl / alkoxy / alkathioyl groups with 1 to 10 carbon atoms, or aromatic rings with 6 to 30 ring atoms.

[0048] According to one embodiment of the present invention, any substituent R in formulas (A-1) to (A-46) is selected from one or more of hydrogen atom, isobutyl, methoxy, or formula (B-1):

[0049]

[0050] In formula (B-1), e represents an integer from 1 to 5. When e is greater than 1, the R on the phenoxy group... 9 Same or different, R 9 For equation (C-1)

[0051] And / or formula (C-2):

[0052]

[0053] In equations (C-1) and (C-2), R 10 For any one or more of the equations (D-1) to (D-22):

[0054]

[0055]

[0056] In this context, dashed lines represent the connecting bonds of functional groups;

[0057] r, n, m, p, q are zero or positive integers, and r+q+p+n+m≥10.

[0058] According to one embodiment of the present invention, the compound has a structural formula as shown in one of the following formulas (1) to (292):

[0059]

[0060]

[0061]

[0062]

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084] According to a second aspect of the invention, the invention also provides a dye having the chemical formulas (M-1) to (M-8) representing dye amine salts and sulfonamide derivatives:

[0085] D - (SO 3- ) m’ (C n’ H 2n’+1 N + H3) m’ (M-1)

[0086] D - (SO 3- ) m’ [(C n’ H 2n’+1 )2N + H2] m’ (M-2)

[0087] D - (SO 3- ) m’ [(C n’ H 2n’+1 )3N + H] m’ (M-3)

[0088] D - (SO 3- ) m’ [(C n’ H 2n’+1 )4N + ] m’ (M-4)

[0089] D- (SO 3- ) m’ (C e’ H 2'e’+1 OC f H 2f N + H3) m’ (M-5)

[0090] D - (SO 3- ) m’ (C n’ H 2n’+1 (PhCH2)2N + H) m’ (M-6)

[0091] D - (SO 3- ) m’ [(C n’ H 2n’+1 Py + )] m’ (M-7)

[0092] D - {[SO2NH(C e H 2e+1 OC f H 2f )] p}[(SO3L) q (M-8)

[0093] In formulas (M-1) to (M-8), D represents a dye matrix composed of one or more compounds of general formula (I) from any one of claims 1-9, m' represents an integer from 1 to 20, n' represents an integer from 1 to 20, e' and f each independently represent an integer from 1 to 10, Ph represents a phenyl group, and Py represents a group bonded to C via hydrogen atoms. n H 2n+1 The pyridine ring residue or methylpyridine ring residue, p' represents an integer from 1 to 8, q' represents an integer from 0 to 8, and L represents a hydrogen atom or a monovalent cation.

[0094] m' preferably represents an integer from 1 to 10, more preferably an integer from 1 to 8.

[0095] n' preferably represents an integer from 1 to 10, more preferably an integer from 1 to 8.

[0096] e' and f each preferably independently represent integers from 1 to 8, more preferably integers from 1 to 6.

[0097] Py preferably represents a methylpyridine ring residue.

[0098] p' preferably represents an integer from 1 to 6, more preferably an integer from 1 to 5.

[0099] q' preferably represents an integer from 0 to 6, more preferably an integer from 0 to 5.

[0100] Monovalent cations in L include lithium ions, sodium ions, potassium ions, and quaternary ammonium ions, such as (C2H5)3HN. + Sodium ions are preferred.

[0101] According to one embodiment of the present invention, the dye structure is shown in one of the following formulas (293) to (308):

[0102]

[0103]

[0104] According to a third aspect of the invention, the invention also provides the use of the compound as described above for the preparation of dyes, colorants, color-curing resin compositions, filters, image sensors, and display devices.

[0105] This invention employs a closed-ring fused-ring π-conjugated phenanthrenequinone acceptor with high photochemical stability. By modifying the periphery of the phenanthrenequinone with photochemically stable aromatic electron-donating groups, the charge transfer effect between the acceptor and donor is modulated, thereby achieving the control of the photochemical and photophysical properties of the dye and obtaining dyes with excellent color purity and stable photochemical and photophysical properties. Furthermore, modification with alkyl molecular chain groups not only reduces intermolecular interactions and enhances the thermal stability of the dye, but also improves the dye's solubility in solvents and its compatibility with other components of the color photoresist.

[0106] Of course, it is not necessary to achieve the above-mentioned technical effects simultaneously in any of the solutions of the present invention. Attached Figure Description

[0107] The present invention will be further described below with reference to the accompanying drawings and specific embodiments.

[0108] Figure 1 The wavelength-transmittance curves of dyes (99), (131), and Pigment Red 254 are shown. Detailed Implementation

[0109] The technical solutions in the embodiments of the present invention will be clearly and completely described below. Obviously, the described embodiments are only some embodiments of the present invention, and not all embodiments. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without creative effort are within the scope of protection of the present invention.

[0110] This invention provides a compound having the following general formula (Ⅰ):

[0111]

[0112] Among them, R 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 Each can independently represent a hydrogen atom or a substituent;

[0113] The substituents are arylamine groups and their derivatives.

[0114] In one embodiment, the aromatic amino group is selected from one or more of diphenylamino and its derivatives, triphenylamino and its derivatives.

[0115] In one embodiment, the substituent is one or more of a phenyl-substituted or unsubstituted arylamino group, a phenyl-substituted or unsubstituted alkoxyarylamino group, or an arylcarbazole having a phenyl-substituted or unsubstituted group.

[0116] In one embodiment, R 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 In, the substituent is located in R 2 and R 7 The remainder consists of hydrogen atoms; or the substituent is located in R. 2 Or R 7 The remainder consists of hydrogen atoms; or the substituent is located in R. 3 and R 6 The remainder consists of hydrogen atoms; or the substituent is located in R. 3 Or R 6 The rest are hydrogen atoms.

[0117] In one embodiment, R 1 ~R 8 The structural formula is selected from one or more of the structures shown in the following formulas (A-1) to (A-46):

[0118]

[0119]

[0120]

[0121] Wherein, the dashed line represents R in general formula (Ⅰ) 1~R 8 The connection key.

[0122] In one embodiment, any substituent R in formulas (A-1) to (A-46) is replaced by one or more identical or different groups selected from hydrogen atoms, halogen groups, cyano groups, straight-chain alkyl / branched alkane / cyclic alkyl / alkoxy / alkathioyl groups with 1 to 10 carbon atoms, or aromatic rings with 6 to 30 ring atoms.

[0123] In one embodiment, any substituent R in formulas (A-1) to (A-46) is selected from one or more of hydrogen atom, isobutyl, methoxy, or formula (B-1):

[0124]

[0125] In formula (B-1), e represents an integer from 1 to 5. When e is greater than 1, the R on the phenoxy group... 9 Same or different, R 9 For formula (C-1) and / or formula (C-2):

[0126]

[0127] In equations (C-1) and (C-2), R 10 For any one or more of the equations (D-1) to (D-22):

[0128]

[0129]

[0130] In this context, dashed lines represent the connecting bonds of functional groups;

[0131] r, n, m, p, q are zero or positive integers, and r+q+p+n+m≥10.

[0132] In one embodiment, the compound has a structural formula as shown in one of formulas (1) to (292):

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

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[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157] In another embodiment, the present invention also provides a dye having the chemical formulas (M-1) to (M-8) representing dye amine salts and sulfonamide derivatives:

[0158] D - (SO 3- ) m’ (C n’ H 2n’+1 N + H3) m’ (M-1)

[0159] D - (SO 3- ) m’ [(C n’ H 2n’+1 )2N +H2] m’ (M-2)

[0160] D - (SO 3- ) m’ [(C n’ H 2n’+1 )3N + H] m’ (M-3)

[0161] D - (SO 3- ) m’ [(C n’ H 2n’+1 )4N + ] m’ (M-4)

[0162] D - (SO 3- ) m’ (C e’ H 2'e’+1 OC f H 2f N + H3) m’ (M-5)

[0163] D - (SO 3- ) m’ (C n’ H 2n’+1 )(PhCH2)2N + H) m’ (M-6)

[0164] D - (SO 3- ) m’ [(C n’ H 2n’+1 )Py + )] m’ (M-7)

[0165] D - {[SO2NH(C e H 2e+1 OC f H 2f )] p }[(SO3L) q ] (M-8)

[0166] In formulas (M-1) to (M-8), D represents a dye matrix composed of one or more compounds of general formula (I) in any of the foregoing embodiments, m' represents an integer from 1 to 20, n' represents an integer from 1 to 20, e' and f each independently represent an integer from 1 to 10, Ph represents phenyl, and Py represents a compound bonded to C via hydrogen atoms. n H 2n+1 The pyridine ring residue or methylpyridine ring residue, p' represents an integer from 1 to 8, q' represents an integer from 0 to 8, and L represents a hydrogen atom or a monovalent cation.

[0167] m' preferably represents an integer from 1 to 10, more preferably an integer from 1 to 8.

[0168] n' preferably represents an integer from 1 to 10, more preferably an integer from 1 to 8.

[0169] e' and f each preferably independently represent integers from 1 to 8, more preferably integers from 1 to 6.

[0170] Py preferably represents a methylpyridine ring residue.

[0171] p' preferably represents an integer from 1 to 6, more preferably an integer from 1 to 5.

[0172] q' preferably represents an integer from 0 to 6, more preferably an integer from 0 to 5.

[0173] Monovalent cations in L include lithium ions, sodium ions, potassium ions, and quaternary ammonium ions, such as (C2H5)3HN. + Sodium ions are preferred.

[0174] In one embodiment, the dye structure is shown in one of the following formulas (293) to (308):

[0175]

[0176]

[0177] According to a third aspect of the invention, the invention also provides the use of the compound as described above for the preparation of dyes, colorants, color-curing resin compositions, filters, image sensors, and display devices.

[0178] The specific preparation method of the dye provided in this invention will be described in detail in the following embodiments. The related synthetic routes and preparation processes are all conventional steps and choices in the field of organic synthesis, and will not be repeated here.

[0179] Synthesis of intermediates

[0180] 1. Synthesis of Lithium Polystyrene A-1

[0181]

[0182] The amount of n-butyllithium was quantitatively calculated and added to a reaction flask containing sufficient purified THF at -78°C, with thorough stirring. Purified styrene monomer was then quantitatively added to the reaction flask at -78°C, and polymerization continued at -78°C until the monomer reaction was complete. The solution was then stored for later use. For testing and sampling: An appropriate amount of the reaction solution was taken using a vacuum syringe and added to purified anhydrous methanol to terminate the polymerization. After the solvent was evaporated, THF was added to dissolve the solution, and the molecular weight and molecular weight distribution were measured. W =1100, PDI=1.07.

[0183] 2. Synthesis of Lithium Polystyrene-b-polymethyl methacrylate B-1

[0184]

[0185] Purified methyl methacrylate monomer was added to a reaction flask containing lithium polystyrene A-1 at -78℃, and stirred thoroughly. Polymerization continued at -78℃ until the monomer reaction was complete, and then stored for later use. Testing and sampling: An appropriate amount of reaction solution was taken using a vacuum syringe and added to purified anhydrous methanol to terminate the polymerization. After the solvent was evaporated, THF was added to dissolve the solution, and the molecular weight and molecular weight distribution were tested. W =1900, PDI=1.12.

[0186] 3. Synthesis of Lithium Polystyrene-b-polymethyl methacrylate B-2

[0187]

[0188] Purified methyl acrylate monomer was added to a reaction flask containing lithium polystyrene A-1 at -78℃, stirred thoroughly, and polymerized continuously at -78℃ until the monomer reaction was complete. The polymer was then stored for later use. For testing and sampling: A suitable amount of the reaction solution was taken using a vacuum syringe and added to purified anhydrous methanol to terminate the polymerization. After the solvent was evaporated, THF was added to dissolve the solution. The molecular weight and molecular weight distribution were then tested. W =1800, PDI=1.11.

[0189] 4. Synthesis of polystyrene-b-polymethyl methacrylate boric acid C-1

[0190]

[0191] Maintaining the anionic polymerization system temperature at -78℃, trimethyl borate (trimethyl borate:Li = 1.5:1) was added dropwise to the reaction solution of B-1 using a syringe. After the addition was complete, the temperature was gradually raised to room temperature, and the reaction was allowed to proceed for 2 hours. Then, 3N dilute hydrochloric acid was added and stirred for 1 hour to stop the reaction. After the reaction was complete, the reaction solution was poured into a separatory funnel and extracted three times with ethyl acetate. The organic layers were combined and evaporated to dryness. The solution was purified by flash chromatography (PE:EA = 29:1), and the solvent was removed to constant weight to obtain a white powdery intermediate C-1 (0.6 eq).

[0192] The synthesis methods of polystyrene-b-polymethyl methacrylate boric acid C-2 and polystyrene-b-polymethyl methacrylate boric acid C-1 are similar.

[0193] Synthesis of 5,4-polystyrene-b-polymethyl methacrylate phenol D-1

[0194]

[0195] Under argon protection, polystyrene-b-polymethyl methacrylate boric acid C-1 (1 eq), (4-bromophenoxy) tert-butyldimethylsilane (1.3 eq), toluene, potassium phosphate trihydrate (2 eq), Pd2(dba)3 (0.01 eq), and S-phos (0.04 eq) were added to a three-necked flask equipped with a mechanical stirrer, thermometer, and condenser. The mixture was purged with argon three times, heated to reflux, and the reaction was stopped when no raw material remained on the TLC plate. The system temperature was lowered to room temperature, deionized water was added to the reaction system, and the mixture was stirred for half an hour. After standing, the mixture was separated. The aqueous phase was washed twice with ethyl acetate, and the organic phases were combined. The organic phases were washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated. The mixture was then dissolved in THF, and 1.0 M tetrabutylammonium fluoride-THF solution was added. The mixture was stirred at room temperature for 2 hours until the reactants had reacted completely. Deionized water was added and stirred thoroughly before being poured into a separatory funnel. The aqueous phase was washed twice with ethyl acetate, and the organic phases were combined. The organic phases were washed once with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated. The mixture was purified by flash chromatography (PE:EA = 15:1) to obtain 4-polystyrene-b-polymethyl methacrylate phenol D-1 (0.6 eq).

[0196] The synthetic routes of the compounds involved in this invention are as follows:

[0197]

[0198]

[0199] The following will provide further details with reference to specific embodiments.

[0200] Example 1: Synthesis of compound 2,7-bis(diphenylamino)phenanthrene-9,10-dione

[0201]

[0202] 2,7-Dibromophenanthrenequinone (3 mmol), diphenylamine (6.6 mmol), palladium acetate (0.3 mmol), 10% tri-tert-butyltetrafluoroborate (0.9 mmol), sodium tert-butoxide (6.6 mmol), and ultradry dioxane (30 mL) were added to a two-necked flask and heated under N2 protection at 120 °C for 24 h under reflux. After the reaction was stopped, the mixture was cooled to room temperature, and the ultradry dioxane was removed by rotary evaporation. The dioxane was then purified by separation on a silica gel column using petroleum ether:dichloromethane = 1:1 eluent. 1.77 g of a blue solid was given, with a yield of 84%.

[0203] After high-resolution mass spectrometry, ESI source, and positive ion mode detection, the molecular formula of compound 2,7-bis(diphenylamino)phenanthrene-9,10-dione is C 38 H 26 N₂O₂, detected value 542.20, theoretical value 542.64; elemental content (%): C, 84.21; H, 4.73; N, 5.06; O, 6.00. Theoretical elemental content (%): C, 84.11; H, 4.83; N, 5.16; O, 5.90. The above analytical results indicate that the obtained product is the expected product.

[0204] Example 2: Synthesis of compound 2,7-bis(4-(diphenylamino)phenyl)phenanthrene-9,10-dione

[0205]

[0206] 2,7-Dibromophenanthrenequinone (3 mmol), triphenylamine 4-borate (7.5 mmol), tetra-triphenylpalladium (0.3 mmol), potassium carbonate (9 mmol), and a mixture of toluene, water, and ethanol (total 30 mL) were added to a two-necked flask. The mixture was heated under nitrogen protection at 100 °C for 12 h under reflux. After the reaction was stopped, the mixture was cooled to room temperature, poured into a separatory funnel, and extracted with water and dichloromethane. The dichloromethane mixture was collected and dried over anhydrous sodium sulfate. The solid insolubles were filtered off, and dichloromethane was removed by rotary evaporation. The mixture was purified by separation on a silica gel column using petroleum ether:dichloromethane = 2:1 as the eluent. 2.36 g of a purple solid was obtained, with a yield of 76%.

[0207] After detection by high-resolution mass spectrometry, ESI source, and positive ion mode, the molecular formula of compound 2,7-bis(4-(diphenylamino)phenyl)phenanthrene-9,10-dione is C 50 H 34N₂O₂, detected value 694.26, theoretical value 694.83; detected elemental content (%): C, 86.33; H, 5.03; N, 4.13; O, 4.51. Theoretical elemental content (%): C, 86.43; H, 4.93; N, 4.03; O, 4.61. The above analytical results indicate that the obtained product is the expected product.

[0208] Example 3: Synthesis of compound 3,6-bis(diphenylamino)phenanthrene-9,10-dione

[0209]

[0210] 3,6-Dibromophenanthrenequinone (3 mmol), diphenylamine (6.6 mmol), palladium acetate (0.3 mmol), 10% tri-tert-butyltetrafluoroborate (0.9 mmol), sodium tert-butoxide (6.6 mmol), and ultradry dioxane (30 mL) were added to a two-necked flask and heated under N2 protection at 120 °C for 24 h under reflux. After the reaction was stopped, the mixture was cooled to room temperature, and the ultradry dioxane was removed by rotary evaporation. The dioxane was then purified by separation on a silica gel column using petroleum ether:dichloromethane = 2:1 as the eluent. 1.77 g of a red solid was given, with a yield of 84%.

[0211] After detection by high-resolution mass spectrometry, ESI source, and positive ion mode, the molecular formula of compound 3,6-bis(diphenylamino)phenanthrene-9,10-dione is C 38 H 26 N₂O₂, detected value 542.20, theoretical value 542.64; detected elemental content (%): C, 84.01; H, 4.93; N, 5.10; O, 5.96. Theoretical elemental content (%): C, 84.11; H, 4.83; N, 5.16; O, 5.90. The above analytical results indicate that the obtained product is the expected product.

[0212] Example 4: Synthesis of compound 3,6-bis(4-(diphenylamino)phenyl)phenanthrene-9,10-dione

[0213]

[0214] 3,6-Dibromophenanthrenequinone (3 mmol), triphenylamine 4-borate (7.5 mmol), tetra-triphenylpalladium (0.3 mmol), potassium carbonate (9 mmol), and a mixture of toluene, water, and ethanol (total 30 mL) were added to a two-necked flask. The mixture was heated under nitrogen protection at 100 °C for 12 h under reflux. After the reaction was stopped, the mixture was cooled to room temperature, poured into a separatory funnel, and extracted with water and dichloromethane. The dichloromethane mixture was collected and dried over anhydrous sodium sulfate. The solid insolubles were filtered off, and the dichloromethane was removed by rotary evaporation. The mixture was purified by separation on a silica gel column using petroleum ether:ethyl acetate = 2:1 as eluent. 2.65 g of a reddish-brown solid was obtained, with a yield of 81%.

[0215] After detection by high-resolution mass spectrometry, ESI source, and positive ion mode, the molecular formula of compound 3,6-bis(4-(diphenylamino)phenyl)phenanthrene-9,10-dione is C 50 H 34 N₂O₂, detected value 694.26, theoretical value 694.83; elemental content (%): C, 86.53; H, 5.03; N, 4.13; O, 4.51. Theoretical elemental content (%): C, 86.43; H, 4.93; N, 4.03; O, 4.61. The above analytical results indicate that the obtained product is the expected product.

[0216] Example 5: Synthesis of compound 3,6-bis(bis(4-methoxyphenyl)amino)phenanthrene-9,10-dione

[0217]

[0218] 3,6-Dibromophenanthrenequinone (3 mmol), bis(4-methoxyphenyl)amine (6.3 mmol), palladium acetate (0.3 mmol), 10% tri-tert-butyltetrafluoroborate (0.9 mmol), sodium tert-butoxide (6.6 mmol), and ultradry dioxane (30 mL) were added to a double-necked flask and heated under N2 protection at 120 °C for 24 h under reflux. After the reaction was stopped, the mixture was cooled to room temperature, and the ultradry dioxane was removed by rotary evaporation. The dioxane was then purified by separation on a silica gel column using petroleum ether:dichloromethane = 1:1 eluent. 1.98 g of a red solid was given, with a yield of 79%.

[0219] After detection by high-resolution mass spectrometry, ESI source, and positive ion mode, the molecular formula of compound 3,6-di(bis(4-methoxyphenyl)amino)phenanthrene-9,10-dione is C 42 H 34N₂O₆, detected value 662.24, theoretical value 662.74; elemental content (%): C, 76.02; H, 5.27; N, 4.13; O, 14.58. Theoretical elemental content (%): C, 76.12; H, 5.17; N, 4.23; O, 14.48. The above analytical results indicate that the obtained product is the expected product.

[0220] Example 6: Synthesis of compound 3-(4-(diphenylamino)phenyl)phenanthrene-9,10-dione

[0221]

[0222] 3-Phenylacetylbromide 9,10-dione (3 mmol), triphenylamine 4-borate (3.1 mmol), tetra-triphenylpalladium (0.3 mmol), potassium carbonate (9 mmol), and a mixture of toluene, water, and ethanol (total 30 mL) were added to a two-necked flask. The mixture was heated under nitrogen protection and refluxed at 100 °C for 12 h. After the reaction was stopped, the mixture was cooled to room temperature, poured into a separatory funnel, and extracted with an appropriate amount of water and dichloromethane. The dichloromethane mixture was collected and dried over anhydrous sodium sulfate. The solid insoluble matter was then filtered off, and dichloromethane was removed by rotary evaporation. The mixture was purified by separation on a silica gel column using petroleum ether:dichloromethane = 2:1 as the eluent. 1.15 g of an orange-yellow solid was obtained, with a yield of 72%.

[0223] After detection by high-resolution mass spectrometry, ESI source, and positive ion mode, the molecular formula of compound 3-(4-(diphenylamino)phenyl)phenanthrene-9,10-dione is C 32 H 21 NO2, detected value 451.16, theoretical value 451.53; elemental content (%): C, 85.22; H, 4.59; N, 3.19; O, 7.00. Theoretical elemental content (%): C, 85.12; H, 4.69; N, 3.10; O, 7.09. The above analytical results indicate that the obtained product is the expected product.

[0224] Example 7: Synthesis of compound 3,6-bis(4-(9H-carbazol-9-yl))phenyl)phenanthrene-9,10-dione

[0225]

[0226] 3,6-Dibromophenanthrenequinone (3 mmol), 4-(9H-carbazol-9-yl)phenyl)boronic acid (6.2 mmol), tetra-triphenylpalladium (0.3 mmol), potassium carbonate (9 mmol), and a mixture of toluene, water, and ethanol (total 30 mL) were added to a two-necked flask. The mixture was heated under N2 protection and refluxed at 100 °C for 12 h. After the reaction was stopped, the mixture was cooled to room temperature, poured into a separatory funnel, and extracted with an appropriate amount of water and dichloromethane. The dichloromethane mixture was collected and dried over anhydrous sodium sulfate. The solid insoluble matter was then filtered off, and the dichloromethane was removed by rotary evaporation. The mixture was purified by separation on a silica gel column using petroleum ether:ethyl acetate = 2:1 as eluent. 2.15 g of a yellow-green solid was obtained, with a yield of 82%.

[0227] After detection by high-resolution mass spectrometry, ESI source, and positive ion mode, the molecular formula of compound 3,6-di(4-(9H-carbazol-9-yl))phenyl)phenanthrene-9,10-dione is C 50 H 30 N₂O₂, detected value 690.23, theoretical value 690.80; elemental content (%): C, 86.84; H, 4.48; N, 4.00; O, 4.69. Theoretical elemental content (%): C, 86.94; H, 4.38; N, 4.06; O, 4.63. The above analytical results indicate that the obtained product is the expected product.

[0228] Example 8: Synthesis of the macromolecular formula (238) of the compound

[0229]

[0230] 3-Phenylacetylbromide 9,10-dione (3 mmol), 4-polystyrene-b-polymethyl methacrylate phenol (6.2 mmol), anhydrous potassium carbonate (4.5 mmol), and acetonitrile were added to a two-necked flask and heated under nitrogen protection at 110 °C for 18 h under reflux. After the reaction was stopped, the mixture was cooled to room temperature, poured into a separatory funnel, and extracted with an appropriate amount of water and dichloromethane. The dichloromethane mixture was collected and dried over anhydrous sodium sulfate. The solid insoluble matter was then filtered off, and the dichloromethane was removed by rotary evaporation. The mixture was purified by separation on a silica gel column using petroleum ether:ethyl acetate = 20:1 as eluent. 2.03 g of a red solid was given, with a yield of 79%.

[0231] After gel permeation chromatography, the molecular weight of compound (238) was determined to be 7800, and the PDI was 1.04. The above analytical results indicate that the obtained product is the expected product.

[0232] Since the preparation method (synthetic route) and principle of the general formula (Ⅰ) in the invention are the same as those of Examples 1 to 8 listed above, it is only necessary to replace the reactants with the reactants corresponding to the target product and adjust the amount of reactants according to the corresponding stoichiometric ratio to obtain the corresponding compound. Therefore, it will not be listed exhaustively here. The embodiments of the present invention refer to the preparation method of Examples 1 to 8 to complete the synthesis of compounds with structural formulas as shown in Formulas (7), (8), (17), (18), (28), (35), (36), (40), (42), (46), (65), (67), (87), (101), (103), (117), (135), (147), (171), (183), (293), (305), (306) in the invention. Their mass spectra, molecular formulas and yields are shown in Table 1.

[0233] Table 1

[0234]

[0235]

[0236] The molecular weights and PDI of the macromolecular dyes (230), (234), (238), (247), and (264) are shown in Table 2.

[0237] Table 2

[0238] Example Compound numbering molecular weight PDI 32 (230) 6700 1.01 33 (234) 6800 1.03 34 (238) 8400 1.02 35 (247) 8500 1.04 36 (264) 8600 1.07

[0239] It should be noted that the other compounds claimed in this application can be obtained by referring to the preparation methods of the examples listed above, so they will not be listed one by one here.

[0240] Example 1-1 Preparation of red photosensitive resin composition E1

[0241] Using the phenanthrenequinone dye formula (99) prepared in Example 6 above, a colored photosensitive resin composition E1 was formulated and subjected to photolithography development to compare the relevant properties of the photosensitive resin composition. Specifically, a lithography method well known to those skilled in the art was applied.

[0242] formula:

[0243] Take 200 parts by weight of colorant L1 (composed of 100 parts by weight of dye formula (99) and 100 parts by weight of solvent Q1), 50 parts by weight of multifunctional monomer M1, 50 parts by weight of multifunctional monomer M2, 100 parts by weight of alkali-soluble resin N, 0.2 parts by weight of additive 01, 0.3 parts by weight of additive 02, and 5 parts by weight of photoinitiator P. Add about 100 parts by weight of solvent Q1 and about 50 parts by weight of solvent Q2 to fully dissolve and mix, and control the solid content to about 20% to obtain a red photosensitive resin composition.

[0244] in,

[0245] Multifunctional monomer M1: dipentaerythritol hexaacrylate (analytical grade), purchased from Sartoma;

[0246] Multifunctional monomer M2: propionyl trimethylolpropane trimethacrylate (analytical grade), purchased from Double Bond Chemical Co., Ltd., Taiwan, China;

[0247] Alkali-soluble resin N: Trade name Sarbox SB400 (analytical grade), purchased from Sardoma;

[0248] Additive 01: F-556 (trade name, purchased from DIC Corporation);

[0249] Additive 02: KH570 (γ-methacryloyloxypropyltrimethoxysilane), purchased from Bailingwei;

[0250] Photoinitiator P: IRGACURE OXE 01 (trade name, purchased from BASF);

[0251] Solvent Q1: PGMEA (propylene glycol methyl ether acetate), purchased from Dow Chemical;

[0252] Solvent Q2: PM (propylene glycol methyl ether), purchased from Dow Chemical.

[0253] Example 1-2 Preparation of red photosensitive resin composition E2

[0254] Using the phenanthrenequinone dye formula (132) prepared in Example 7 above, a colored photosensitive resin composition E1 was formulated and subjected to photolithography development to compare the relevant properties of the photosensitive resin composition. Specifically, a lithography method well known to those skilled in the art was applied.

[0255] formula:

[0256] Take 200 parts by weight of colorant L2 (composed of 100 parts by weight of dye formula (131) and 100 parts by weight of solvent Q1), 50 parts by weight of multifunctional monomer M1, 50 parts by weight of multifunctional monomer M2, 100 parts by weight of alkali-soluble resin N, 0.2 parts by weight of additive 01, 0.3 parts by weight of additive 02, and 5 parts by weight of photoinitiator P, add about 100 parts by weight of solvent Q1 and about 50 parts by weight of solvent Q2 to fully dissolve and mix, and control the solid content to about 20% to obtain a red photosensitive resin composition.

[0257] Comparative Example 2-1 Preparation of Red Photosensitive Resin Composition R1

[0258] Take 200 parts by weight of colorant L3 (composed of 100 parts by weight of CI pigment red 254 and 100 parts by weight of solvent Q1), 50 parts by weight of multifunctional monomer M1, 50 parts by weight of multifunctional monomer M2, 100 parts by weight of alkali-soluble resin N, 0.2 parts by weight of additive 01, 0.3 parts by weight of additive 02, and 5 parts by weight of photoinitiator P. Add about 100 parts by weight of solvent Q1 and about 50 parts by weight of solvent Q2 and fully dissolve and mix them, controlling the solid content to be about 20%, to obtain a red photosensitive resin composition.

[0259] The performance testing of photosensitive resin compositions E1-E2 and R1 was performed using photolithography, including the following steps:

[0260] The glass slides were washed and dried, and then coated with a spin coater to obtain a uniform film layer of 1.5-2.0 μm. The film was pre-baked at 90℃ for 120 s, exposed to 365 nm ultraviolet light at an exposure dose of 40 mJ / cm², with a mask distance of 180 μm from the coating. Development was performed at 23℃ for 50 s, followed by post-baking at 230℃ for 20 min. Subsequent performance tests were conducted, and the results are shown in Table 1.

[0261] Performance testing and evaluation methods:

[0262] (1) Colorimetry: Detected using a Konica Minolta CM-5 spectrophotometer.

[0263] (2) System compatibility: The photosensitive resin composition was stored in the dark at 0-10℃, and its viscosity was tested (for at least six months). The composition was then photolithographically processed according to the process conditions, and the presence of particles on the color filter surface was examined under a 500x optical microscope (OM).

[0264] The evaluation criteria are as follows:

[0265] ○: Viscosity change < ±5% mPa·s and X500 surface free of particles;

[0266] △: Viscosity change < ±10% mPa·s and X500 surface free of particles;

[0267] ×: Viscosity change value > ±10% mPa.s or x500 indicates particles on the surface;

[0268] (3) Heat resistance test: The heat resistance of the photosensitive resin composition was verified by color difference. The sample was baked at 230℃ for 20 minutes and the baking was repeated twice. The film thickness was measured by XP-2 step meter. The color difference was the color difference value between the sample baked in the second baking and the sample baked in the first baking. It was measured by Minolta CM-5. If ΔEab < 3, it indicates that it has good heat resistance.

[0269] (4) Solvent resistance evaluation:

[0270] After drying, the sample was placed in isopropanol and immersed at room temperature for 5 minutes. Then, it was baked in an oven at 150°C for 30 minutes. The color difference before and after was measured. If ΔEab < 3, it indicates good solvent resistance.

[0271] (5) Evaluation of anti-migration performance:

[0272] Following the manufacturing process of color filters, red or blue pixel A is first prepared on TFT glass. Then, a sample is coated, and after development, the surface of the color filter is dried. The color difference before and after pixel A is measured. If ΔEab < 3, it indicates good resistance to staining migration.

[0273] (6) Line width, edge neatness, and development process tolerance:

[0274] The linewidth and edge neatness were tested at x500 OM, and the mask linewidth was 140μm.

[0275] When evaluating process margin, other process conditions are kept constant, and the edge neatness and edge residue or edge peeling of the image obtained with a development time between 40s and 100s are examined. The peeling property is determined by referring to the adhesion measurement method in this field.

[0276] The evaluation criteria for edge neatness are as follows:

[0277] ○: After 50 seconds of development, the edges are neat and there is no residue at the edges;

[0278] △: The image developed for 50 seconds has rough, uneven edges or residue at the edges;

[0279] ×: Image missing

[0280] The specific criteria for evaluating the development process margin are as follows:

[0281] ○: After developing for 40-100 seconds, the edges are neat and there is no residue or peeling at the edges;

[0282] △: After developing for 50-80 seconds, the edges are neat and there is no residue or peeling at the edges;

[0283] ×: The edges are uneven after 50-80 seconds of development, or there is residue at the edges, or there is peeling at the edges;

[0284] The alkaline developing solutions used above, such as aqueous solutions of alkaline compounds like sodium hydroxide, potassium hydroxide, sodium carbonate, sodium bicarbonate, calcium carbonate, ammonia, diethylamine, or tetramethylammonium hydroxide, have an [OH-] concentration of 0.2-1.0%, preferably 0.4-0.6%. Sodium hydroxide solution was used in all the embodiments described.

[0285] The evaluation results are shown in Table 3.

[0286] Table 3

[0287]

[0288] The experimental results show that the CI pigment red 254 of Comparative Example 2-1 is insoluble in PGMEA, while the dye formulas (99) and (131) in Examples 1-1 and 1-2 have good solubility in the color photoresist solvent PGMEA. Furthermore, the dye formulas (99) and (131) in Examples 1-1 and 1-2 exhibit higher red color purity in the color photoresist solvent PGMEA. Meanwhile, the photosensitive resin compositions E1 and E2 using these two dyes exhibit similar good processing properties to the photosensitive resin composition R1 of Comparative Example 2-1 using CI pigment red 254, such as system compatibility, edge neatness, and development process margin.

[0289] The preparation of the red photosensitive resin compositions E3-E36 in Examples 1-3 to 1-36 is based on Examples 1-1 and 1-2.

[0290] The evaluation results are shown in Table 4.

[0291] Table 4

[0292]

[0293]

[0294] This invention provides a high-performance compound suitable for use as a dye in filters for display and sensing devices such as liquid crystal displays and image sensors. The invention employs a closed-ring fused-ring π-conjugated core structure, such as phenanthrenequinone. The closed-ring and π-conjugated characteristics of phenanthrenequinone allow for high bond energies in the molecular skeleton, resulting in excellent photochemical stability of the phenanthrenequinone derivative. Based on the superior stability of the phenanthrenequinone core, the phenanthrenequinone derivative can be used as a dye in filters for display and sensing devices such as liquid crystal displays and image sensors.

[0295] This invention overcomes the problems of unstable photophysical properties and thermal stability of traditional dyes, as well as their poor solubility and compatibility in color photoresist systems.

[0296] In the description of this specification, the references to terms such as "an embodiment," "an example," "a specific implementation process," and "an example" indicate that a specific feature, structure, material, or characteristic described in connection with that embodiment or example is included in at least one embodiment or example of the present invention. In this specification, the illustrative expressions of the above terms do not necessarily refer to the same embodiment or example. Furthermore, the specific features, structures, materials, or characteristics described may be combined in any suitable manner in one or more embodiments or examples.

[0297] Finally, it should be noted that the above embodiments are only used to illustrate the technical solutions of the present invention, and not to limit them. Although the present invention has been described in detail with reference to the foregoing embodiments, those skilled in the art should understand that modifications can still be made to the technical solutions described in the foregoing embodiments, or equivalent substitutions can be made to some or all of the technical features therein. Such modifications or substitutions do not cause the essence of the corresponding technical solutions to deviate from the scope of the technical solutions of the embodiments of the present invention.

Claims

1. A compound, characterized in that, having the following general formula (I): wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 each independently represent a hydrogen atom or a substituent; the substituent is selected from one or more of the structures shown below: wherein the dotted line indicates the bond of R1 to R8 in the general formula (I); R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , the substituent is located at R 2 and / or R 7 , and the rest are hydrogen atoms; or R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , the substituent is located at R 3 and / or R 6 , and the rest are hydrogen atoms.

2. The compound of claim 1, wherein The compound is used for preparing dyes, dye amine salts and sulfonamide derivatives represented by formulas (M-1) to (M-8). D - (SO3 - ) m’ (C n’ H 2n’+1 N + H3) m’ (M-1) D - (SO3 - ) m’ [(C n’ H 2n’+1 )2N + H2] m’ (M-2) D - (SO3 - ) m’ [(C n’ H 2n’+1 )3N + H] m’ (M-3) D - (SO3 - ) m’ [(C n’ H 2n’+1 )4N + ] m’ (M-4) D - (SO3 - ) m’ (C e’ H 2e’+1 OC f H 2f N + H3) m’ (M-5) D - (SO3 - ) m’ (C n’ H 2n’+1 )(PhCH2)2N + H) m’ (M-6) D - (SO3 - ) m’ [(C n’ H 2n’+1 )Py + )] m’ (M-7) D - {[SO2NH(C e’ H 2e’+1 OC f H 2f )] p}[(SO3L) q ] (M-8) In formulae (M-1) to (M-8), D represents a dye base consisting of one or more compounds of the general formula (I) according to claim 1, m' represents an integer from 1 to 20, n' represents an integer from 1 to 20, e' and f each independently represent an integer from 1 to 10, Ph represents a phenyl group, Py represents a pyridine ring residue or a methylpyridine ring residue bonded to C n H 2n+1 via a hydrogen atom, p represents an integer from 1 to 8, q represents an integer from 0 to 8, L represents a hydrogen atom or a monovalent cation selected from the group consisting of lithium ion, sodium ion, potassium ion and (C2H5)3HN + .

3. Use of a compound as claimed in claim 1, characterized in that, for preparing dyes, colorants, colored curable resin compositions, optical filters, image sensors, and display devices.

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