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Imidazopyridine derivatives and organic electroluminescent elements containing same

A technology of imidazopyridine derivatives, which is applied in the field of imidazopyridine derivatives and organic electroluminescence elements containing them, can solve the problem that the properties of the benzofluoranthene skeleton do not have any mention, and achieve the effect of reducing the driving voltage

Inactive Publication Date: 2012-05-23
IDEMITSU KOSAN CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, although Patent Document 1 discloses a plurality of anthracene skeletons, for example, there is no mention of the properties of the benzofluoranthene skeleton.

Method used

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  • Imidazopyridine derivatives and organic electroluminescent elements containing same
  • Imidazopyridine derivatives and organic electroluminescent elements containing same
  • Imidazopyridine derivatives and organic electroluminescent elements containing same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0197] [Synthesis of intermediates]

Synthetic example 1

[0199] (a) Synthesis of 7,12-diphenylbenzo[k]fluoranthene-3-boronic acid

[0200] According to the following scheme, 7,12-diphenylbenzo[k]fluoranthene-3-boronic acid was synthesized.

[0201]

[0202] (a-1) Synthesis of 5-bromoacenaphthylene

[0203] To 25.4g (107.3mmol) of 5-bromoacenaphthylene and 500ml of dehydrated benzene, add 29.2g (128.7mmol) of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ). It was stirred under reflux for 6 hours. 6.0 g (26.4 mmol) of DDQ was added to the reaction mixture, followed by stirring for 4 hours. After natural cooling, the precipitate was filtered out and washed with chloroform. The combined filtrates were washed with 10% aqueous sodium hydroxide solution and water. After liquid separation, the organic phase was dried over anhydrous sodium sulfate, and the solvent was distilled off. The residue was dried under reduced pressure to obtain 13.0 g of 5-bromoacenaphthylene as a brown solid (51.6% yield).

[0204] (a-2) Synthesis of 3-br...

Synthetic example 2

[0209] (b) Synthesis of 4-(7,12-diphenylbenzo[k]fluoranthene-3-yl)phenylboronic acid

[0210] According to the following scheme, 4-(7,12-diphenylbenzo[k]fluoranthene-3-yl)phenylboronic acid was synthesized.

[0211]

[0212] (b-1) Synthesis of 3-(4-bromophenyl)-7,12-diphenylbenzo[k]fluoranthene

[0213] Under an argon atmosphere, 1.79 g (4 mmol) of 7,12-diphenylbenzo[k]fluoranthene-3-boronic acid, 1.25 g (4.4 mmol) of 4-bromoiodobenzene, tetrakis(triphenylphosphine) A mixture of 0.14 g (0.12 mmol) of palladium (0), 12 ml of toluene and 6 ml of a 2M aqueous sodium carbonate solution was stirred under reflux for 7 hours. The reaction solution was cooled to room temperature, extracted with toluene, and the organic layer was washed with saturated brine. After the obtained organic layer was dried over anhydrous sodium sulfate, the solvent was distilled off, and the resulting residue was purified by silica gel chromatography to obtain 3-(4-bromophenyl)-7,12-diphenylbenzo[k]fluo...

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Abstract

Imidazopyridine derivatives represented by formula (1).

Description

technical field [0001] The present invention relates to imidazopyridine derivatives and organic electroluminescent elements containing them. Background technique [0002] An organic electroluminescence (EL) device using an organic substance is expected to be used as a solid-state light-emitting type inexpensive large-area full-color display device, and many developments are currently underway. [0003] In general, an organic EL element is composed of a light emitting layer and a pair of opposing electrodes sandwiching it. Light emission is a phenomenon in which, when an electric field is applied between the two electrodes, electrons are injected from the cathode side and holes are injected from the anode side, and the electrons recombine with the holes in the light-emitting layer to generate an excited state and return to the ground state in the excited state energy is emitted as light. [0004] It is difficult to increase the performance of an organic EL device that exhib...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04H01L51/50H10K99/00
CPCH01L51/0072H01L51/5076H01L51/5072C07D471/04H01L51/0055H01L51/0058H10K85/623H10K85/626H10K85/6572H10K50/165H10K50/16C07C2603/52
Inventor 伊藤裕胜河村昌宏河村祐一郎水木由美子齐藤博之
Owner IDEMITSU KOSAN CO LTD