JPH09241255A - Imidazole derivative - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain an imidazole derivative which is represented by a specific formula, has chromatically interesting color tone, tinting strength and fluorescence and is useful as a display element such as EL. SOLUTION: This derivative is represented by formula I [R<1> -R<6> are each H, a (substituted) alkyl, a (substituted) alkenyl, a (substituted) alkynyl]. The derivative is prepared, for example, by heating 2quinolinecarboxaldehyde derivative of formula II or 2-quinoline carboxylic acid derivative of formula III and diaminomaleonitrile in an organic solvent in the presence of a catalytic amount of an acid. The derivative product is allowed to coordinate with a metal ion such as strontium ion to form a chelate complex.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to (1) a novel imidazole derivative and (2) a metal chelate complex thereof. The compound of the present invention can be easily synthesized, and the chelate complex is expected to be used as a display device and a wavelength conversion material because it becomes a phosphor.

[0002]

DISCLOSURE OF THE INVENTION It is an object of the present invention to provide a novel imidazole derivative having a color tone, tinting strength and fluorescence of color interest and a metal chelate complex thereof.

The present invention provides (1) general formula [I]

[0003]

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[Wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R
⁶ is the same or different from each other, hydrogen, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, a halogen group, a phenyl group, a benzyl group, a pyridyl group, a hydroxyl group, A nitro group, a ketone group, an amide group, a group represented by the formula — (CH ₂ ) _n OH (n represents an integer of 1 to 22), a carboxyl group, a saturated or unsaturated alkoxycarbonyl having 1 to 22 carbon atoms Group or an aryloxycarbonyl group. ]
And a chelate complex represented by the general formula [II-a] or [II-b] using the imidazole derivative represented by the general formula [I] as a ligand.

[0005]

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(Wherein M is a metal atom, n is an integer of 2 to 3, and R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ have the same meanings as described above).

The imidazole derivative [I] of the present invention comprises, for example, a 2-quinolinecarboxaldehyde derivative [III] or a 2-quinolinecarboxylic acid derivative [IV] and diaminomaleonitrile (abbreviated as DAMN) in an organic solvent in a catalytic amount. It can be easily produced by heating with the acid.

[0008]

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Further, a chelate complex of the formula [II] is formed by coordinating the imidazole derivative [I] with a divalent to trivalent metal ion. The metal ions are strontium ions,
Magnesium ion, calcium ion, aluminum ion, gallium ion, copper ion, nickel ion,
Examples thereof include cobalt ion and titanium ion.

[0010]

EXAMPLES The present invention will be further described with reference to examples.
The structure of the compound of the present invention was confirmed by elemental analysis. In the following examples, unless otherwise indicated, parts means parts by weight,
Percentages are stated in weight percent. Example 1

[0011]

[Chemical 6]

1.43 g (10 mm) of 2-methylquinoline
ol) and 1.11 g (10 mmol) of SeO ₂ are added to 20 ml of dioxane, and the mixture is heated under reflux in the presence of 0.2 ml of water for 4.5 hours. After the reaction, hot filtration is performed, and DAMN is added to the filtrate.
Add 1.08 g (10 mmol), catalytic amount of acetic acid and
Heat to reflux for hours. After cooling, the solvent was distilled off and recrystallization was performed using an ethanol / acetonitrile mixed solvent to obtain 1.55 g of white crystals. Yield 63.2%, m.p. p is 250 to 251 ° C., and elemental analysis values are measured values (%): C, 68.56, H, 2.88, N, 2
8.56 Calculated value (%): C, 68.52, H, 3.15, N, 2
It was 8.30.

Example 2 0.49 g (2) of the imidazole derivative synthesized in Example 1
mmol) and MX ₂ or MX ₃ (X is halogen, OH,
Alkoxy, OAc, NO ₃ , 1/2 (SO ₄ ) and the like. 1 to 1/3 mmol of the above is added to 10 ml of ethanol and refluxed for 2.5 hours. The reaction product was hot filtered, washed with ethanol, water, and acetone, and dried. Yield of the obtained chelate complex, λmax, m.p. p (° C) is shown in Table 1.

[0014]

[Table 1]

Reference Example 1 The chloroform solution of the chelate complex (2-e) prepared in Example 2 had a fluorescent property and was excited by light having a wavelength of UV to 500 nm to exhibit strong fluorescence at 590 nm.

[0016]

INDUSTRIAL APPLICABILITY The novel imidazole derivative of the present invention and its metal chelate complex can be easily produced. Since the chelate complex is made into a phosphor, it is expected to be applied to a display element such as an EL and a wavelength conversion material.

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Claims (2)

[Claims] 1. A compound of the general formula [I] [Wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ are the same or different and are hydrogen or an optionally substituted alkyl group,
Optionally substituted alkenyl group, optionally substituted alkynyl group, halogen group, phenyl group, benzyl group, pyridyl group, hydroxyl group, nitro group, ketone group, amide group, formula-(CH ₂ ) _n OH Group represented (n is 1 to 2
2), carboxyl group, carbon number 1 to 22
Is a saturated or unsaturated alkoxycarbonyl group or aryloxycarbonyl group. ] The imidazole derivative represented by these. 2. A general formula [II-a] or [II-b] having an imidazole derivative represented by the general formula [I] as a ligand.
A chelate complex represented by [Wherein M is a metal atom, n is an integer of 2 to 3, R ¹ and R
² , R ³ , R ⁴ , R ⁵ , and R ⁶ are the same or different and each is hydrogen, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, or a halogen group. , Phenyl group, benzyl group, pyridyl group, hydroxyl group, nitro group, ketone group, amide group, formula- (C
H ₂ ) _n OH (n represents an integer of 1 to 22), a carboxyl group, a saturated or unsaturated alkoxycarbonyl group having 1 to 22 carbon atoms, or an aryloxycarbonyl group. ]