JPS60228448A - squarylium compound - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to a novel squarylium compound. Specifically, it has absorption in the region up to around 1gQQnln, and is used in laser-written liquid crystal displays and electrophotographic photosensitive materials for electrophotographic printers using lasers as light sources, and recording materials for original discs that can be written and read by lasers. The present invention relates to a novel squarylium compound that is expected to be useful in fields such as infrared cut filters.

[Conventional technology]

It is known that the SQUA compound exhibits photoconductivity and is used, for example, as a charge generating agent in electrophotographic photoreceptors.
).

However, conventional squarylium compounds generally have an absorption of around bsorxm at most in solution, and in recent years, their application has been actively studied for use as a light source for laser sources. were not necessarily sufficient and improvements were desired.

[Purpose of the invention]

The inventors of the present invention, as a result of careful studies with these points in mind, have found that a specific SQUA IJ compound can achieve the intended purpose, and have completed the present invention.

That is, 1 gist of the present invention is the general formula m [wherein R1 and R2 are an alkyl group which may have a substituent or a tetrahydrofurfuryl group,
Further, R1 and R2 may be connected to each other to form a nitrogen-containing ring. X represents an alkyl group or alkoxy group which may have a substituent, or a Page 7 atom.
1 represents -R3 or 100, -R4 (R3 and R4 represent an optionally substituted alkyl group or phenyl group, or a hydrogen atom). ] It exists in the squarylium compound represented by

[Structure of the invention]

To explain the present invention, the squarylium compound of the present invention is represented by the general formula [11].

In the formula, Bl and ax represent an alkyl group such as a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, and a heptyl group, which may have a substituent, or a tetrahydrofurfuryl group. As a group, hydroxy group; cyano group; halogen atom such as fluorine atom, chlorine atom, bromine atom; methoxy group,
Alkoxy groups such as propoxy, butoxy, octoxy groups; alkoxyalkoxy groups such as methoxyethoxy, butoxyethoxy, ethoxymethoxy, hydroxybutoxy, dichlorohexyl, propylcyclohexyl, butylcyclohexyl, pentylcyclohexyl, etc. cycloalkyl group; acylamino group such as acetylamino group, pentanoylamino group, octanoylamino group; acyloxy group such as acetyloxy group, zolopanoyloxy group, hexanoyloxy group: phenyl group,
Propylphenyl group, butylphenyl group.

Aryl groups such as heptyl phenyl group, butoxyphenyl group, pentyloxyphenyl group, hexyloxyphenyl group, heptyloxyphenyl group, butoxymethylphenyl group; phenoxy group, butylphenoxy group, hexylphenoxy group, butoxyphenoxy group, ethoxymethylphenoxy Aryloxy groups such as groups; alkoxycarbonyl groups such as propoxycarbonyl group, butoxycarbonyl group, heptyloxycarbonyl group, and the like.

Also, R1 and the apex are connected to each other to form a morpholino group.

A nitrogen-containing ring such as a hyherazino group may be formed.

X is a methyl group which may have a substituent.

Ethyl group, propyl group, butyl group, pentyl group.

It represents an alkyl group such as a hexyl group or a heptyl group, an alkoxy group such as a methoxy group, an ethoxy group, a propoxy group, or a butoxy group, or a halogen atom such as a fluorine atom, a bromine atom, or a chlorine atom.

Here, as substituents for the alkyl group, alkoxy groups such as methoxy group, ethoxy group, butoxy group, hexyloxy group: N, N-dimethylamino group, N-methyl-N-ethylamino group, N-methyl-N Examples include alkylamino groups such as -butylamino group. Further, as a substituent for an alkoxy group, an alkoxy group such as a methoxy group, an ethoxy group, a butoxy group; a methoxyethoxy group;

Examples include alkoxyalkoxy groups such as ethoxybutoxy group and butoxyethoxy group.

Y indicates A-R31kt-80zR4Y. Rs Oyohi R4 is a methyl group, ethyl group, propyl group, butyl group, or hexyl group that may have a substituent.

Alkyl groups such as octyl groups or phenyl groups.

Or ask for a hydrogen atom.

Examples of substituents for the alkyl group include alkoxy groups such as methoxy, ethoxy, and butoxy groups; and 7-rogen atoms such as fluorine, bromine, and chlorine atoms. , alkyl groups such as methyl group, ethyl group, propyl group, butyl group; methoxy group,
Examples include alkoxy groups such as methoxy groups and butoxy groups.

The compound represented by the general formula [I] is, for example, a compound represented by the following structural formula CIII (wherein, R1, R2,
It is produced by reacting terdihydroxy-3-cyclobutene-1 with cordion in a t-solvent.

〔Effect of the invention〕

The squarylium compound of the present invention has maximum absorption near 0θnm from boo, as shown in the Examples below.

Therefore, various information materials that use laser light as a light source, such as laser-written liquid crystal displays and laser! It is expected to be useful in fields such as electrophotographic photosensitive materials for electrophotographic printers that use light sources, recording materials for optical disks that can be written and read by laser, and infrared cut filters.

〔Example〕

Next, the present invention will be explained in more detail with reference to Examples.

Example 1 3, l-dihydroxy-3-cyclobutene-7, cordion 0. ．． jgjiKn-butyl alcohol trmlz
Add and heat to 700°C to dissolve. Comethoxy 3-acetylamino-N,N-diethylaniline t, bsg)-o-dichlorobenzene A;rdyg was added to this solution and allowed to react for 30 minutes under reflux while removing the resulting water. The reaction solution was cooled to room temperature and purified by column chromatography to obtain a compound represented by the following structural formula. This compound is co-Oa, O
It has a melting point of ~2041.1°C and the maximum absorption wavelength of the visible absorption spectrum in a chloroform solution is 7 dajnlfl.
Met.

Example Instead of 2-methoxy-3-acetylamino-N,N-diethylaniline used in Example 1, λ-methoxy-3-formamino-N,N-diethylanilino 1.11. A compound represented by the following structural formula was obtained in the same manner as in Example except for the above. This compound is 0.0 to 0
O. It shows the melting point of S°C and the maximum absorption wavelength of the visible absorption spectrum in chloroform solution.

It was IIOnm.

Example 3 Examples of squarylium compounds of the present invention synthesized according to Examples 1 and 2 are shown in Table 1 along with their maximum absorption wavelengths in chloroform solutions.

Table 1 1- − Continuation of page 1

Claims (1)

[Claims] (1) General formula [■] [In the formula, R1 and R represent an alkyl group that may have a substituent or a tetrahydrofurfuryl group,
Further, R1 and Blz may be linked to each other to form a nitrogen-containing ring. Even if X has a substituent, it represents an alkyl group, an alkoxy group, or a halogen atom. Y is -3-R3'f- or -80, -R4 digits and 1
゛1 indicates an alkyl group or phenyl group which may have a substituent, or 1 L atom of water. ) is shown. ] A squarylium compound represented by