JPS61145143A - Squarylium compound - Google Patents

Abstract

NEW MATERIAL:The squarylium compound of formula I (R<1> is H or 1-13C alkyl; R<2> and R<3> are H, 1-13C alkyl or 1-13C alkoxy; R<2> and R<3> are substituted to the 5-. 6- or 8-position). EXAMPLE:The compound of formula II. USE:It exhibits an absorption peak at 700-800nm which is close to the oscillation wavelength of a semiconductor laser, and has excellent solubility and stability to liquid crystal. Accoringly a composition containing the liquid crystal is useful as a laser-writing liquid crystal display element to record and display with laser beam. It is useful also as a photo-sensitive material for electrophotography in the electrophotographic printer using a laser as the light source, a recording material of optical disk writable and readable with laser, and an infrared-cutting filter, etc. PREPARATION:The compound of formula I can be prepared by reacting the compound of formula III with a squaric acid in a solvent.

Description

DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a novel squarylium compound.

[Conventional technology]

Squarylium compound exhibits photoconductivity, Example-10jj
J Otsu).

However, conventional squarylium compounds generally have an absorption of around gj Onm at most in a solution, and there is a possibility that only highly active solvents can use laserable light as a light source.
im @ It was not necessarily sufficient to use it as a material.

[Problem that the invention seeks to solve]

The present invention is based on the oscillation wavelength of semiconductor lasers near 700-? 0
The object of the present invention is to provide a novel squarylium compound exhibiting 0nrnK polar dog absorption.

[Means for solving problems]

The present invention relates to the general formula [1] (wherein R1 represents a hydrogen atom or an alkyl group having a carbon number of /~/3, and R2 and R8 represent a hydrogen atom and a carbon number of /~/3).
3 alkyl group or an alkoxy group having /~/3 carbon atoms. However, R2 and RJ are located at the 1st position, tit or 1st position. ) is the squarylium compound represented by.

Specific examples of the substituent represented by R1 include a hydrogen atom;
Number of carbon atoms in methyl, ethyl, propyl, butyl, pentyl, hexyl, octyl, decyl, etc.
The alkyl group of ~/3 is reduced, and specific examples of R2 and RA include a hydrogen atom; a methyl group, an ethyl group, a propyl group, a methyl group, a pentyl group, a hexyl group, and a he7'? Alkyl groups having 1 to 3 carbon atoms, such as 1 to 3 carbon atoms, such as 1 to 3 carbon atoms; methoxy group, ethoxy group, p-boxy group, butoxy group, pentyloxy group, hexyl group, octyl group, decyloxy group Examples include alkoxy groups such as.

The squarylium compound represented by the above general formula [1] of the present invention can be produced, for example, as follows. That is, the following general formula CI) (wherein, R1, moiety and H
s represents the meaning of general formula [I] and Oka-. ) and squaric acid in a solvent.

〔effect〕

The squarylium compound represented by the general formula m of the present invention has an oscillation wavelength of a semiconductor laser 6-, and the liquid crystal composition containing the squarylium compound and liquid crystal is a laser writing liquid crystal display that records and displays by applying laser light. It can be used as an element.

As the liquid crystal used in combination with the squarylium compound of the present invention, the following smectic liquid crystals or cholesteric liquid crystals can be used.

Smectic liquid crystals include biphenyl liquid crystal, terphenyl liquid crystal, cyclohexylcyclohexane i-crystal,
Biphenylcyclohexane type i crystal, cyclohexylpiphenylcyclohexane type liquid crystal, phenylcyclohexylcarboxylate type liquid crystal, cyclohexylcyclohexylbenzoate type liquid crystal, cyclohexyl phenylcyclohexylcarboxylate type [&, cyclohexylcyclohexylcyclohexylcarboxylate type liquid crystal] , pyrimidine liquid crystal, etc. can be used alone or in combination.

Examples of cholesteric liquid crystals include cyclohexylcyclohexane liquid crystals, phenylcyclohexane liquid crystals,
Biphenyl liquid crystal, terphenyl [&, phenylcyclohexylcarboxylate liquid crystal, phenylbenzony) f I can do it.

The above-mentioned optically active substance includes a chi2 renematic compound,
For example, co-methylbutyl group, J-methylbutoxy group, 3
-Compounds in which optically active groups such as methylpentyl, 3-methylpentoxy, goomethylhexyl, and goomethylhexyl groups are introduced into nematic liquid crystals are included. Also, J-menthol shown in No. 4 of JP-A-Shoj/-4tjj4,
Alcohol derivatives such as alcohol such as d-borneol, derivatives such as d-camphor, 3-methylcyclohexane, etc., carboxylic acid such as d-citronellaic acid, 1-camphoric acid, etc. Examples include optically active substances such as Ik derivatives, aldehyde derivatives such as d-citronellal, alkene derivatives such as d-linonene, and other amine, amide, and nitrile derivatives. Furthermore, when forming a liquid crystal composition in the present invention, additives such as known dichroic dyes or reducing agents can be used in combination.

In addition, the squarylium compound of the present invention can be used in fields such as electrophotographic photosensitive materials for electrophotographic printers that use a laser as a light source, recording materials for original discs that can be written and read by a laser, and extraneous ray cut filters. can do.

EXAMPLES Hereinafter, the present invention will be explained in detail with reference to examples, but the present invention is not limited to these examples.

〔Example〕

Example 1 3.4t-dihydroxy-3-cyclobutene-/.

--Zion 0. //fKn-butyl alcohol/jyd
was added and heated to about 700°C to dissolve.

This solution K/-n-propyl-! - Add inglovir azulene o, 4t4 and benzene IQ-, and add 5
The mixture was stirred for about 7 hours while distilling off the water produced at ~101°C. After cooling, n-hexane was added, and the precipitated crystals were purified by column chromatography to obtain the squarylium compound of the present invention represented by the following structural formula. This compound showed 80 to 24 tJ of 24, a melting point of 0°C, and the maximum absorption wavelength of the visible absorption spectrum in a chloroform solution was 7.24 nm.

The obtained compound was converted into cyanooctylbiphenyl (biphenyl liquid crystal having a smectic phase) K O1! jj
Add at the rate of l amount percent,! The mixture was heated and stirred to a temperature of θ° C. or higher, and dissolved in an isotropic liquid state. In this state, the absorption spectrum was measured at 73 nm.
It showed a K maximum peak.

The liquid (liquid crystal composition) prepared in this manner is vertically aligned with a vertical alignment treatment agent (octadecyldimethyl[,?-()rimetosacisilyl)furobil]ammonium chloride) on the surface that has a transparent electrode and is in contact with the liquid crystal. An element consisting of a single top and bottom treated glass substrate (gap between substrates: 9
μm) K was enclosed. This element K 7 J' Onm is irradiated with a GaAlAs semiconductor laser having an oscillation wavelength,
Recording was made with a 70 μm spot. The temperature of this spot area increased, and the regularly vertically aligned liquid crystal area changed to an isotropic liquid state. Stop irradiating the laser light,
After cooling, a halogen lamp light is transmitted through this element to project a 10 times enlarged projected image onto a screen, which is recorded by laser light, and areas where the alignment of liquid crystal molecules is disordered are projected black on the screen, increasing the contrast. A good display was obtained.

Example - 〇 (○H3), ○HHO (O50゜) The squarylium compound of the present invention represented by the above structural formula CI[] was produced according to the method described in Example/. 2t exhibits a melting point of 7,0°C, and when the absorption spectrum is measured in chloroform, it is 732
It showed a maximum ΩmVC peak. This compound is added to a mixture of cyanooctylbiphenyl and cyanononylbiphenyl in an amount of 1% by weight, and! The mixture was heated to θ°C or higher to become an isotropic liquid and stirred well to dissolve it. The absorption spectrum in this state is 7gθnm
It showed a K maximum peak.

When displaying was performed using the obtained isotropic liquid in the same manner as in Example, results with good contrast were obtained.

Example 3 Using the squarylium compound of the present invention shown in Table 1 according to the method described in Example 1, an isotropic liquid was produced in the same manner as in Example 2, and its λmaX is shown in Table 1.

Claims (1)

[Claims] (1) General formula [I] ▲Mathematical formulas, chemical formulas, tables, etc.▼......[I] (In the formula, R^1 represents a hydrogen atom or an alkyl group having 1 to 13 carbon atoms, and R^2 and R^3 represents a hydrogen atom, an alkyl group having 1 to 13 carbon atoms, or an alkoxy group having 1 to 13 carbon atoms. However, R^2 and R^3 are located at the 5th, 6th, or 8th position.) A squarylium compound represented by