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1,6-Substituted 3,8-Dihalogenopyrene And Process For Producing The Same

a technology of dihalogenopyrene and pyrene, which is applied in the field of producing the 1,6-substituted 3,8-dihalogenopyrene and the process of producing the same, can solve the problem of not being able to easily improve the purity of the (1,8) articl

Inactive Publication Date: 2008-01-17
IDEMITSU KOSAN CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0006] As a result of intensive researches and studies to achieve the above object by the present inventors, it was found that an employment of 1,6-substituted pyrene as a starting material and a halogenating its 3,8-position enable to efficiently produce 3,8-dihalogeno-1,6-substituted pyrene resultantly completing the present invention.

Problems solved by technology

However, considering about an effect of re-crystallization, despite the easiness in getting high purity product of the (1,6-) article owing to its high crystallinity, it is impossible to easily improve purity of the (1,8-) article because of its low crystallinity.

Method used

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  • 1,6-Substituted 3,8-Dihalogenopyrene And Process For Producing The Same
  • 1,6-Substituted 3,8-Dihalogenopyrene And Process For Producing The Same
  • 1,6-Substituted 3,8-Dihalogenopyrene And Process For Producing The Same

Examples

Experimental program
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Effect test

example 1

Synthesis of (1,6-diisopropyl-3,8-dibromopyrene)

[0051] Under an atmospheric argon gas flow, 1,6-dibromopyrene in an amount of 20 g (55.6 millimole), isopropylmagnesiumbromide in an amount of 117 milliliter [117 millimole, 1 mole / litter (THF: tetrahydrofuran)], (diphenylphosphinoferrocene)palladium(II)dichloride in an amount of 2.27 g (5% by mole) and dried dioxane in an amount of 130 milliliter were placed into a three-neck flask equipped with a cooling pipe and having a capacity of 500 milliliter, and the resultant solution was stirred with heating at a temperature of 90° C. for 8 hours.

[0052] After the completion of the reaction, adding 100 milliliter of dilute hydrochloric acid, an organic layer was separated and concentrated under a reduced pressure. Then, the organic layer was passed through a silicagel short column, and after concentrating under the reduced pressure again, a precipitated crystal was separated by filtration and as a result, 7.4 g of 1,6-diisopropyl pyrene (pa...

example 2

Synthesis of (1,6-dicyclohexyl-3,8-dibromopyrene)

[0056] Under an atmospheric argon gas flow, 1,6-dibromopyrene in an amount of 20 g (55.6 millimole), cyclohexylmagnesiumbromide in an amount of 117 milliliter (117 millimole, 1 mole / litter (THF)), (diphenylphosphinoferrocene)palladium(II)dichloride in an amount of 2.27 g (5% by mole) and dried dioxane in an amount of 80 milliliter were placed into a three-neck flask equipped with a cooling pipe and having a capacity of 500 milliliter, and the resultant solution was stirred with heating at a temperature of 90° C. for 8 hours.

[0057] After the completion of the reaction, adding 100 milliliter of dilute hydrochloric acid, an organic layer was separated and concentrated under a reduced pressure. Then, the organic layer was passed through a silicagel short column, and after concentrating under the reduced pressure again, a precipitated crystal was separated by filtration and as a result, 7.0 g of 1,6-dicyclohexylpyrene (pale yellow powder...

example 3

Synthesis of 1,6-di(2-naphthyl)-3,8-dibromopyrene]

[0061] Under an atmospheric argon gas flow, 1,6-dibromopyrene in an amount of 10.3 g (28.6 millimole), 2-naphthylboronic acid in an amount of 11.8 g (68.7 millimole), tetrakis(triphenylphosphine)palladium(0) in an amount of 0.66 g (2% by mole), sodium carbonate aqueous solution in an amount of 43 milliliter (59.4 millimole, 2M), dimethoxyethane (DME) in an amount of 100 milliliter and dried THF in an amount of 70 milliliter were placed into a three-neck flask equipped with a cooling pipe and having a capacity of 200 milliliter, and the resultant solution was stirred with heating at a temperature of 90° C. for 8 hours.

[0062] After the completion of the reaction, adding 50 milliliter of water, precipitated crystal was separated by filtration and washed with the use of 50 milliliter of water and 100 milliliter of ethanol, and as a result. 13.2 g of pale yellow powder was obtained (the yield: 99%).

[0063] Subsequently, under an atmosphe...

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Abstract

A 3,8-dihalogeno-1,6-substituted pyrene represented by a following general formula (2): wherein R1 and R2 each independently represents a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted alkoxyl group having 1 to 50 carbon atoms, unsubstituted aryloxy group having 5 to 50 carbon atoms, a halogen atom, a cyano group, or a silyl group; and X represents a halogen atom. It is useful as an intermediate for dyes or so, as intermediates for a charge transporting material of particularly an electronic photographic photosensitive article, for a material for an organic electroluminescence device and for a hole transporting material or a light emitting material for an organic electroluminescence device.

Description

TECHNICAL FIELD [0001] The present invention relates to a 3,8-dihalogeno-1,6-substituted pyrene and a process for producing the 3,8-dihalogeno-1,6-substituted pyrene. BACKGROUND ART [0002] Making a halogeno group as a reaction point, various pyrene compounds substituted at 4 positions are deliverable from the 3,8-dihalogeno-1,6-substituted pyrene. It is a compound having utility as an intermediate for dyes or so, and especially as an intermediate for a charge transporting material of electronic photographic photosensitive article, for a material of organic electroluminescence (“electroluminescence” will be occasionally referred to as “EL”, hereinafter) device, for a hole transporting material or a light emitting material of an organic electroluminescence device. [0003] Regarding with the 3,8-dibromo-1,6-substituted pyrenes, Journal of Materials Chemistry, 2000,10, pp 315-319 discloses a compound whose substituent is 3,5-di-t-butylbenzene. Further, Math. -fys. Medd (1941), Volume 18,...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C07C25/18C07B61/00C07C17/12C07C25/22C07C209/10C07C211/61C07C253/30C07C255/51C09K11/06G03G5/06H05B33/14
CPCC07C25/22C07C211/61C07C255/51C07C2103/50C07C2102/08C07C2102/10C07C2103/18C07C2101/14C07C2601/14C07C2602/08C07C2602/10C07C2603/18C07C2603/50H10K85/631H10K85/657
Inventor FUNAHASHI, MASAKAZU
Owner IDEMITSU KOSAN CO LTD
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