JP3455747B2 - 4,4 ', 4 "-tri (N-phenoxazinyl) triphenylamine - Google Patents

Description

Detailed Description of the Invention

[0001]

INDUSTRIAL APPLICABILITY The present invention is capable of maintaining an amorphous state at room temperature and thus can be made into a thin film by itself, and is useful as a photoelectric conversion element, a thermochromic element, an optical memory element, etc. And a novel compound useful as an organic compound for forming a hole transport layer in an electroluminescence device 4,4 ′,
It relates to 4 "-tri (N-phenoxazinyl) triphenylamine.

[0002]

2. Description of the Related Art Conventionally, a low molecular weight organic compound having a so-called photo-electronic function which causes conductivity and charge generation by irradiating light has not been capable of forming a thin film by itself. In order to form the above, it is dispersed in a binder resin (hence, in a diluted state) and applied on a substrate,
It is necessary to make it thin.

[0003]

The present invention, unlike the conventional low molecular weight organic compound having an optical / electronic function,
A novel optoelectronic function that can maintain an amorphous state, that is, a glass state at room temperature, and thus can be thinned into a large area by itself by a vacuum deposition method without using a binder resin. It aims at providing the low molecular weight organic compound which has.

[0004]

According to the invention, the formula (I)

[0005]

[Chemical 1]

There is provided 4,4 ', 4 "-tri (N-phenoxazinyl) triphenylamine represented by: 4,4', 4" -tri (N-phenoxazinyl) triphenylamine according to the present invention It can be obtained by the Ullmann reaction of 4,4 ', 4 "-triiodotriphenylamine with phenoxazine. That is, 4,4', 4" -triiodotriphenylamine and phenoxazine are combined with a base and The reaction may be carried out by heating in a solvent in the presence of copper powder.

Alkali metal hydroxides such as potassium hydroxide and sodium hydroxide are preferably used as the base, and hydrocarbons such as decalin are preferably used as the solvent, but the solvent is not limited thereto. is not. After completion of the reaction, the obtained reaction mixture was cooled to room temperature, extracted with a hot solvent (preferably hot aromatic hydrocarbon), the solvent was distilled off, and the residue was subjected to silica gel chromatography and recrystallization method. If purified, the desired 4,4 ', 4 "
-Tri (N-phenoxazinyl) triphenylamine can be obtained.

The fact that the compound according to the present invention is in an amorphous and non-anisotropic amorphous state means, for example, that it has a glass transition temperature and does not show a clear peak in powder X-ray diffraction. It is proved.

[0009]

According to the present invention, the novel compound 4,
4 ', 4 "-tri (N-phenoxazinyl) triphenylamine is provided. Since this compound forms a stable amorphous film by a vacuum deposition method, it can be thinned into a large area by itself. In addition, the compound according to the present invention has a rigid structure and a glass transition point of 145.
Since the temperature is ℃ and the crystallization temperature is 176 ° C., the amorphous film has excellent heat resistance, is stable up to 176 ° C., and does not crystallize.

Thus, the compound according to the present invention can be formed into a thin film by itself at room temperature, and is useful as a photoelectric conversion element, a thermochromic element, an optical memory element, etc., and an electroluminescent element. It is also useful as an organic compound or the like for forming the hole transporting layer.

[0011]

【Example】

(Synthesis of 4,4 ', 4 "-tri (N-phenoxazinyl) triphenylamine) 4,4', 4" -triiodotriphenylamine 6.0 g, phenoxazine 8.2 g, potassium hydroxide 5.
0 g and 3.0 g of copper powder were placed in a four-necked flask together with 5 ml of decalin, and reacted at 170 ° C. for 6 hours under a nitrogen atmosphere.

After the reaction was completed, the resulting reaction mixture was cooled to room temperature and extracted with hot toluene. Toluene was distilled off from this extract and concentrated, and the residue was purified by silica gel chromatography and recrystallization to give 4,4 ', 4 "-tri (N-phenoxazinyl) tri as crystals having a melting point of 341 ° C. Phenylamine was obtained (yield 20%).

[0013] Mass spectrum M / Z = 752 Infrared absorption spectrum Shown in FIG. Differential Scanning Calorimetry (DSC) The DSC thermogram is shown in Figure 2 (heating rate 5 ° C / min). In the figure, (a) is a DSC thermogram obtained by recrystallization from benzene, and (b) is a DSC thermogram obtained by cooling and solidifying the melt.

When 4,4 ', 4 "-tri (N-phenoxazinyl) triphenylamine according to the present invention is melted and then cooled to be a solid, the solid is (b) in the figure.
As shown in (1), the glass transitioned to a glass state at room temperature, had a glass transition point at 145 ° C, crystallized at 176 ° C, and melted at 341 ° C. Therefore, the glass state is stably maintained up to 176 ° C.

[Brief description of drawings]

1 shows 4,4 ', 4 "-tri (N-phenoxazinyl)
The infrared absorption spectrum of triphenylamine is shown.

FIG. 2 shows 4,4 ′, 4 ″ -tri (N-phenoxazinyl)
3 shows a DSC thermogram of triphenylamine.

Continuation of front page (56) References Japanese Patent Laid-Open No. 4-288065 (JP, A) Shoji Higuchi et al., “Amorphous Molecular Materials: Synthesis and Properties of Novel Starburst Molecules Having Phenoxazine Skeleton in the Molecule”, Proceedings of the 65th Annual Meeting of the Chemical Society of Japan I. (1993), Japan Chemical Society, March 15, 1993, p. 124, 3C236 (58) Fields investigated (Int.Cl. ⁷ , DB name) C07D 265/38 CA (STN) REGISTRY (STN)

Claims (2)

(57) [Claims] 1. A 4,4 ′, 4 ″ -tri (N-phenoxazinyl).
Triphenylamine. 2. A 4,4 ′, 4 ″ -tri (N-phenoxazinyl).
A glassy solid consisting of triphenylamine.