JPH03232856A - 4,4',4'-tricarbazolyl triphenylamine - Google Patents

Abstract

NEW MATERIAL:4,4',4'-tricarbazolyl triphenylamine expressed by the formula. USE:Used as an organic semiconductive material keeping in either state of amorphous or crystalline and stable in an amorphous state, namely glassy state capable of readily forming a film by itself. An application of said compound for photocell or a photosensor is possible and also useful as an optical memory, etc. PREPARATION:4,4',4'-triiodotriphenylamine is made to react with carbazole in a solvent such as decalin in the presence of a base such as OH and copper powder to afford the objective compound expressed by the formula.

Description

[Detailed Description of the Invention] The present invention can maintain an amorphous state at room temperature, and thus can be made into a thin film by itself, and can be used for photoelectric conversion elements, thermochromic elements, optical The present invention relates to 4,4',4''-tricarbazolyltriphenylamine, which is a new compound useful as memory devices and the like.

Traditionally, low molecular weight organic compounds that have so-called photo-electronic functions that generate conductivity and charge generation when irradiated with light do not have the ability to form thin films by themselves, so they are used to form thin films. In order to do this, it is necessary to disperse it in a binder resin (therefore in a diluted state) and apply it onto a substrate to form a thin film.

(i) The present invention differs from such conventional low molecular weight organic compounds having optical and electronic functions, in that it is in an amorphous state at room temperature, that is,
The object of the present invention is to provide a low molecular weight organic compound having novel optical and electronic functions that can maintain a glass state and, therefore, can be formed into a thin film by itself without using a binder resin.

According to the present invention, a novel compound 4,4',4''-tricarbazolyltriphenylamine is provided.

This compound has the following formula It has the structure represented by .

Such a compound according to the invention can be obtained by reacting 4,4',4''-triiodotriphenylamine and carbazole in a solvent in the presence of a base and copper powder.

The fact that the compounds according to the invention are in an amorphous state with no crystalline anisotropy is evidenced, for example, by the fact that they do not exhibit clear peaks in powder X-ray diffraction with a glass transition temperature.

(2) Fruit The present invention provides a novel compound, 4,4',4''-tricarbazolyltriphenylamine.

This compound can maintain both an amorphous state and a crystalline state at room temperature.

The amorphous state, that is, the glass state, is stable,
By utilizing this amorphous state, it can easily be made into a thin film by itself.

Therefore, the above compound according to the present invention can be applied as an organic semiconductor material to, for example, a photovoltaic cell or a photosensor, and if its unique morphology is utilized, it can be used as an optical memory.

Tip base 4.4',4''-triiodotriphenylamine 7.4
6 g, carbazole 9.97 g, potassium hydroxide 6.
25 g of copper powder, and 18.6 ml of decalin at a temperature of 170°C under a nitrogen atmosphere.
The reaction was allowed to proceed for 0 hours. Thereafter, the obtained reaction mixture was added to benzene, the solid content was filtered off, and the obtained benzene solution was subjected to alumina column chromatography to separate a white reaction product. This white solid was recrystallized from benzene/ethanol to obtain 0.93 g of 4.4',4''-1-ricarbazolyltriphenylamine. Yield: 10.
5%.

Melting point: 270.0'C and 302.9°C Elemental analysis: HN Calculated value 87.54 4.90 7.56 Measured value
87.63 4.83 7.57 Mass spectrometry: M” (m/e): 740 Infrared absorption spectrum: Shown in FIG.

Differential scanning calorimetry (DSC)? The DSC diagram is shown in Figure 2. At the first temperature increase, 27
Endothermic peaks appear at 0°C and 303°C, and an exothermic peak appears at 281°C. The endothermic peak indicates melting of the crystal;
Exothermic peaks indicate crystallization. In the second temperature increase,
The glass transition point is shown at 151°C, and 246°C
A broad exothermic peak appears in the vicinity. This broad exothermic peak indicates that the compound has changed from an amorphous state to a crystalline state, and furthermore, an endothermic peak indicating melting appears at 270°C.

Therefore, a stable amorphous state can be obtained by heating the compound according to the present invention to its melting point and cooling it to a temperature below the glass transition temperature. On the other hand, crystals can be obtained by heating the compound to the temperature of the exothermic peak shown by DSC (crystallization temperature) of 246°C and holding the compound at that temperature for a while.

Application Example 4. Pellets were prepared using each of the crystalline and amorphous states of 4',4''-tricarbazolyltriphenylamine, and the reflection spectra of their surfaces were measured. The peak at 282 nm is shown in Figure 4. The strength is different between the crystalline state and the amorphous state. Therefore, if the above compound according to the present invention is thermally changed in state by laser light or the like, it exhibits thermochromism and can be applied to optical memory.

[Brief explanation of drawings]

1 shows the infrared absorption spectrum of 4,4',4''-tricarbazolyltriphenylamine according to the present invention, FIG. 2 shows the DSC diagram, and FIG. 3 shows the crystalline and amorphous states. The reflection spectra of each surface are shown.

Claims (1)

[Claims] (1) 4,4',4''-tricarbazolyltriphenylamine.