JPS61246258A - Green dye - Google Patents

Abstract

NEW MATERIAL:Compounds of formula I, wherein R<1> and R<2> are each (un) substituted (cyclo)alkyl, (un)substituted aryl. EXAMPLE:Compound of formula II. USE:Green dyes for color filters and coloring the surfaces of thermoplastic resins. PREPARATION:A compd. of formula III is reacted with NaCN or KCN at 40-100 deg.C in dimethyl sulfoxide or N,N-dimethylformamide.

Description

[Detailed Description of the Invention] Wataru 1”! The present invention is based on the general formula (I) [In formula (I), R1 and R2 represent an optionally substituted alkyl group, a cycloalkyl group, or an optionally substituted aryl group. ] The present invention relates to a novel green pigment shown in the following and a method for producing the same.

The compound of formula (I) is particularly useful as a green color chip for color filters and as a vivid pigment for coloring the surface of thermoplastic resins such as polyester resins and ABS resins, and molded products thereof.

Conventional technology and attempts to solve. Compounds conventionally known as green pigments include C,I Pig
ment Green L 4, C,I Pigment Green 7. Metal-containing compounds such as 8゜lO・12,36, C,I.

Most of them were benzene-based polycyclic compounds such as Pigment Green 47.

Furthermore, color filters have conventionally been used in image pickup devices for color television cameras, laser-based devices, and the like.

However, as described in Japanese Patent Application Laid-Open No. 59-155412, conventional filters used a base material made of a thin gelatin film, and therefore had insufficient durability. Therefore, in recent years,
A transparent base material with a porous layer created by applying an inorganic material such as alumina gel or silica gel to a transparent plate such as glass and firing it as a base material, or a transparent base material coated with a durable resin or a durable resin film. A filter using

However, the above dyes have poor sublimation and oil solubility, and are unsuitable for coloring glass substrates coated with alumina gel and fired as color filter substrates, resin coating substrates, resin thin film substrates, etc. there were.

Furthermore, to date, there has been no dye with a low molecular weight and spectral characteristics necessary as a green dye for filters.

In view of the above-mentioned problems, the present inventors have found that the dye represented by the following general formula (I) has excellent sublimation properties and compatibility with resins, etc., and can be used as a dye for green color filters, for example. It was discovered that the present invention has excellent spectral properties when the compound is a compound of the general formula (I) [In the formula (I), R1 and R2 are an optionally substituted alkyl group, a cycloalkyl group, or represents an optionally substituted aryl group. ] A novel green pigment of the compound represented by the above and a method for producing the same are provided.

The alkyl group in the above formula (Il) according to the present invention represents a linear or branched alkyl group having 1 to 10 carbon atoms, and the cycloalkyl group represents a cyclohexyl group, a cyclopentyl group, or a cyclohebutyl group, and the substituted Examples of alkyl groups include alkoxyalkyl groups such as ethoxymethyl group, methoxyethyl group, ethoxyethyl group, 1sO-propoxyethyl group, n-butoxyethyl group, hexyloxyethyl group, and-methoxypropyl group, and 3-methoxybutyl group. , 2-hydroxyethyl group, halogenated alkyl group such as chloroethyl group, benzyl group, phenylethyl group, and substituted or unsubstituted aryl group such as phenyl group, 4-methylphenyl group, 3-methylphenyl group, 2- C1-C6 alkyl group substituted phenyl group such as methylphenyl group, 3,4-dimethylphenyl group, 4-
Examples include phenyl groups substituted with alkoxy groups having 1 to 6 carbon atoms such as methoxyphenyl group, 4-ethoxyphenyl group, and 2-methoxyphenyl group, trifluoromethylphenyl group, halogenated phenyl group, and nitrophenyl group.

The dye of the present invention is prepared by adding 1 to 20 times the weight of 1,4-disubstituted anthraquinone as a starting material to dimethyl sulfoxide or N
After dissolving or suspending in N-dimethylformamide, 1 to 10 molar ratio of ammonium bicarbonate and 2 to 10 molar ratio of sodium cyanide or potassium cyanide are added, and the mixture is heated at 40 to 100°C to react.

Subsequently, the reaction solution is discharged to a volume 5 to 100 times that of water or alcohol, subjected to oxidation treatment, and then filtered, washed with water, and dried.

A method for manufacturing a color filter using the dye of the present invention includes, for example, a transparent base material made by coating and baking alumina gel on glass, a transparent base material coated with resin, or polyester, polyvinyl chloride, polystyrene,
Using a transparent film base material such as polyacrylonitrile,
Methods include sublimating the dye under reduced pressure to color the substrate, applying a dye solution or dispersion to the substrate and coloring it by heating, or immersing the substrate in the dye solution or dispersion to color it. be.

[Example 1] A green color filter was obtained by sublimating and coloring a base material made by firing glass coated with alumina gel under reduced pressure with the dye of [Example 1].

This filter had good spectral characteristics of transmitted light and good durability as a filter.

The compound of the above formula was synthesized as follows.

25.7 parts of 1,4-ditoluidinoanthraquinone, 10 parts of ammonium bicarbonate, 14.8 parts of sodium cyanide, and 100 parts of dimethyl sulfoxide were mixed and reacted at 90 to 95°C for 6 hours. Then, the mixture was poured into 500 parts of water, filtered and dried to obtain the above-mentioned compound.

(Yield: 5 oaIb) For the filter, a dye purified by column chromatography was used. This color is 6 at 545nm.
4qb, 620 parts m was 20 inches, and 700 parts m was 2 inches.

[Example-2] A green color filter was obtained by sublimating and coloring a resin-coated glass substrate with the dye of Example 2 under reduced pressure. This filter has good spectral characteristics of transmitted light and durability as a filter.

The compound of the above formula was synthesized in the same manner as in Example-1. Input max (in chloroform) = 660 nm [Example 3] A green film was obtained by hot immersing a transparent polyester film in a solution in which a dye of the following formula C) was dissolved in ethylene glycol. This film had good spectral properties as a television filter. Moreover, the durability was also good.

The compound of the above formula C) is prepared by mixing 9.7 parts of 1,4-diisopropylaminoanthraquinone, 4.8 parts of ammonium bicarbonate, 7.4 parts of sodium cyanide, and 100 parts of dimethyl sulfoxide at 90 to 95°C for 5 hours. After the reaction, the reaction mixture was poured into 500 parts of water, filtered and dried to obtain 9 parts. A m a x
(in chloroform) = 715 nm.

[Examples 4 to 15]

Claims (1)

[Claims] 1 General formula (I) ▲There are numerical formulas, chemical formulas, tables, etc.▼(I) [In formula (I), R^1 and R^2 are optionally substituted alkyl groups, cycloalkyl group, or an optionally substituted aryl group. ] A green pigment indicated by . 2 General formula (II) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (II) [In formula (II), R^1 and R^2 are optionally substituted alkyl groups, cycloalkyl groups, or substituted represents a good aryl group. ] General formula (I) characterized by reacting the compound represented by sodium cyanide or potassium cyanide in dimethyl sulfoxide or N,N-dimethylformamide ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [Formula ( I) R^1 and R^2 are R^1 and R of formula (II)
It has the same meaning as ^2. ] A method for producing a green pigment shown in