JPH01268669A - Novel triphenylamine derivative - Google Patents

Abstract

NEW MATERIAL:A compound shown by formula I (R1 is -NR4R5; R2-R5 are H or lower alkyl which may be substituted). USE:A nonlinear optical material, photo-recording material (light absorbing dye stuff), etc. PREPARATION:A triphenylaminaldehyde derivative shown by formula II and malononitrile shown by formula III are dissolved in a solvent such as alcohol and reacted to give a compound shown by formula I. The reaction is usually advanced at room temperature in the absence of a solvent and may be carried out optionally under heating or in the presence of a catalyst such as pyridine.

Description

DETAILED DESCRIPTION OF THE INVENTION [Technical Field] The present invention relates to a novel triphenylamine derivative, and more particularly to a novel triphenylamine derivative that is expected to be useful as information and electronic materials.

[Prior art]

In recent years, research has been actively conducted to put organic compounds into practical use as information and electronic materials. One of them is organic nonlinear optical materials, and the second-order nonlinear optical effect of this material,
In particular, various materials have been proposed that contribute to second harmonic generation. As a guideline for the design of these materials, it is known that an aromatic nucleus having π electrons is combined with an electron-withdrawing group and an electron-donating group [for example, Optronis (1986
) 80 pages].

Another example is a recording medium used for optical recording, and examples of materials that can be used for this include 1, for example, JP-A-60-898
43, 5-amino-2,3-dicyano-8-
Intramolecular charge transfer complexes such as (3°5-dimethylanilino)-1,4-naphthoquinone dyes have been disclosed.

As a result of research on intramolecular charge transfer complexes, the present inventors discovered a novel triphenylamine derivative and completed the present invention.

〔the purpose〕

That is, an object of the present invention is to provide a novel triphenylamine derivative that is expected to be useful as an information electronic material.

〔composition〕

According to the present invention, there is provided a novel triphenylamine derivative represented by the general formula (1), each of which represents an optional lower alkyl group.

The triphenylamine derivative represented by the general formula (1) of the present invention is a new substance, and this product is made by combining, for example, the triphenylamine aldehyde derivative represented by the general formula (n) below and malononitrile in a solvent such as alcohol. It can be synthesized by dissolving it in and reacting it.

The reaction usually proceeds easily at room temperature without a catalyst, but
If necessary, the reaction may be carried out by heating or by adding a catalyst such as pyridine.

Specific examples of the triphenylamine derivative represented by the general formula (1) of the present invention include those shown in Table 1, but are not limited thereto.

Table 1 [Effects] The triphenylamine derivative of the present invention is a compound having a strong electron-donating group and a strong electron-withdrawing group in the same molecule, that is, an intramolecular charge transfer complex. Like complexes, they are expected to be useful as non-glandular optical materials or optical recording materials (light-absorbing dyes).

〔Example〕

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

Example 1 Synthesis of Compound Specific Example Na (1) 4-diethylamino-4'-formyltriphenylamine [In general formula (n), I+1=)l, R,==
1.72 g of R, = C, H, compound) and 0.40 g of malononitrile were dissolved in 20 d of ethanol and reacted at room temperature for 2 hours. - After leaving it for the night, filter out the formed crystals,
When recrystallized from ethanol, 1.04 g of orange plate crystals were obtained (yield 53%).

The melting point of the obtained compound was 149.5 to 151.0°C, and the elemental analysis values (%) were as follows.

In addition, the infrared absorption spectrum of this compound (KBrBr
(method), cyano group absorption was observed at 2210 cm-1.

Example 2 Synthesis of Compound Specific Example Nα(8) 4.4′-bis(dibutylamino)-4″-formyltriphenylamine [In general formula (n), R□=N
-+n-Cn-C4H.

0.35 g of a compound (R2=R3=n-C4H) and 0.10 g of malononitrile were dissolved in ethanol LM, and reacted at room temperature for one day. The resulting reaction solution was concentrated using a rotary evaporator and recrystallized from ethanol to obtain 0.26 g of dark red needle-like crystals (yield: 6
8%).

The melting point of the obtained compound was 113.0 to 114.0°C, and the elemental analysis values (%) were as follows.

*: Calculated as specific compound example Nα(8).

The infrared absorption spectrum (KBr tablet method) of this compound is shown in FIG.

Example 3 Synthesis of Compound Specific Example NQ (6) As a compound represented by general formula (II), 4.4'-
Bis(diethylamino)-4''-formyltriphenylamine [in general formula (Il), R1=N-+CJs
)z, R, = R3 = C2H,] The reaction, concentration, and purification were carried out in the same manner as in Example 2, and red plate-like crystals were obtained.

The obtained compound decomposed at 203° C., and its infrared absorption spectrum (KBrBr method) showed absorption of cyano group at 2210 cm −1 .

[Brief explanation of the drawing]

FIG. 1 shows the infrared absorption spectrum of the compound obtained in Example 2 of the present invention.

Claims (1)

[Claims] (1) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (However, in the formula, R_1 is a hydrogen atom or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, and R_2, R_3, R_4 and R_5 are hydrogen atoms or A novel triphenylamine derivative represented by (representing an optionally substituted lower alkyl group).