| 1,6-substituted 3,8-dihalogenopyrene and process for producing the same -> Monitor Keywords |
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  1,6-substituted 3,8-dihalogenopyrene and process for producing the sameUSPTO Application #: 20080015399Title: 1,6-substituted 3,8-dihalogenopyrene and process for producing the same Abstract: 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.
A 3,8-dihalogeno-1,6-substituted pyrene represented by a following general formula (2): (end of abstract)
Agent: Oblon, Spivak, Mcclelland Maier & Neustadt, P.C. - Alexandria, VA, US Inventor: Masakazu Funahashi USPTO Applicaton #: 20080015399 - Class: 570183000 (USPTO) Related Patent Categories: Organic Compounds -- Part Of The Class 532-570 Series, Azo Compounds Containing Formaldehyde Reaction Product As The Coupling Component, Amino Nitrogen Containing (e.g., Urea, Sulfonamides, Nitrosamines, Oxyamines, Etc., And Salts Thereof), Product, Benzene Ring Containing, Polycyclo Ring System The Patent Description & Claims data below is from USPTO Patent Application 20080015399. Brief Patent Description - Full Patent Description - Patent Application Claims
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, Number 22, discloses a compound having a following structure: [0004] It is generally known that a mixture of 1,6-substituted dibromopyrene and 1,8-substituted dibromopyrene is obtained by di-brominating pyrene [Journal of Chemical Society Perkin, Number 1, page 1622 (1972), etc.)]. 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. [0005] An object of the present invention is to provide a novel 3,8-dihalogeno-1,6-substituted pyrene having utility as an intermediate for dyes or so, and to provide an efficient process for producing the same. DISCLOSURE OF THE INVENTION [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. [0007] Namely, the present invention provides [0008] 1. A 3,8-dihalogeno-1,6-substituted pyrene represented by a following general formula (2): wherein R.sub.1 and R.sub.2 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, a substituted or 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; [0009] 2. The 3,8-dihalogeno-1,6-substituted pyrene according to the above term 1, wherein R.sub.1 and R.sub.2 each independently represents at least one selected from a group consisting of 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, and a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms. [0010] 3. The 3,8-dihalogeno- 1,6-substituted pyrene according to the above term 1, wherein X is a bromine atom. [0011] 4. A process for producing a 3,8-dihalogeno-1,6-substituted pyrene which comprises steps of: [0012] halogenating a 1,6-substituted pyrene represented by a following general formula (1): wherein R.sub.1 and R.sub.2 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, a substituted or unsubstituted aryloxy group having 5 to 50 carbon atoms, a halogen atom, a cyano group, or a silyl group; and [0013] forming the 3,8-dihalogeno-1,6-substituted pyrene represented by a following general formula (2): wherein R.sub.1 and R.sub.2 each independently represents the same as the above description; and X represents a halogen atom; [0014] 5. The process for producing a 3,8-dihalogeno-1,6-substituted pyrene according to the is above term 4, wherein R.sub.1 and R.sub.2 each independently represents at least one selected from a group consisting of 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, and a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms; and [0015] 6. The process for producing a 3,8-dihalogeno-1,6-substituted pyrene according to the above term 4, wherein a halogenating agent is N-bromosuccinimide. BRIEF DESCRIPTION OF THE DRAWINGS [0016] FIG. 1 is a chart showing .sup.1H-Nuclear Magnetic Resonance (NMR) spectrum of the compound obtained in Example 1; [0017] FIG. 2 is a chart showing .sup.1H-NMR spectrum of the compound obtained in Example 2; [0018] FIG. 3 is a chart showing .sup.1H-NMR spectrum of the compound obtained in Example 3; [0019] FIG. 4 is a chart showing .sup.1H-NMR spectrum of the compound obtained in Example 4; [0020] FIG. 5 is a chart showing .sup.1H-NMR spectrum of the compound obtained in Example 5; and [0021] FIG. 6 is a chart showing .sup.1H-NMR spectrum of the compound obtained in Reference Example. PREFERRED EMBODIMENTS TO CARRY OUT THE INVENTION [0022] The present invention provides a process for producing a 3,8-dihalogeno-1,6-substituted pyrene represented by a following general formula (2) by halogenating 1,6-substituted pyrene represented by a following general formula (1): wherein R.sub.1 and R.sub.2 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, a substituted or 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. [0023] Examples of a halogen atom employed for halogenating, namely, the halogen atom represented by X in the general formula (2) include fluorine atom, chlorine atom, bromine atom, iodine atom and so on, bromine (Br) atom and iodine (I) atom being preferable. [0024] Examples of the alkyl group represented by the above R.sub.1 and R.sub.2 include methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 2-hydroxyisobutyl group, 1,2-dihydroxyethyl group, 1,3-dihydroxy-isopropyl group, 2,3-dihydroxy-t-butyl group, 1,2,3-trihydroxypropyl group, chloromethyl group, 1-chloroethyl group, 2-chloroethyl group, 2-chloroisobutyl group, 1,2-dichloroethyl group, 1,3-dichloroisopropyl group, 2,3-dichloro-t-butyl group, 1,2,3-trichloropropyl group, bromomethyl group, 1-bromoethyl group, 2-bromoethyl group, 2-bromoisobutyl group, 1,2-dibromoethyl group, 1,3-dibromoisopropyl group, 2,3-dibromo-t-butyl group, 1,2,3-tribromopropyl group, iodomethyl group, 1-iodoethyl group, 2-iodoethyl group, 2-iodoisobutyl group, 1,2-diiodoethyl group, 1,3-diiodoisopropyl group, 2,3-diiodo-t-butyl group, 1,2,3-triiodopropyl group, aminomethyl group, 1-aminoethyl group, 2-aminoethyl group, 2-aminoisobutyl group, 1,2-diaminoethyl group, 1,3-diaminoisopropyl group, 2,3-diamino-t-butyl group, 1,2,3-triaminopropyl group, cyanomethyl group, 1-cyanoethyl group, 2-cyanoethyl group, 2-cyanoisobutyl group, 1,2-dicyanoethyl group, 1,3-dicyanoisopropyl group, 2,3-dicyano-t-butyl group, 1,2,3-tricyanopropyl group, nitromethyl group, 1-nitroethyl group, 2-nitroethyl group, 2-nitroisobutyl group, 1,2-dinitroethyl group, 1,3-dinitroisopropyl group, 2,3-dinitro-t-butyl group, 1,2,3-trinitropropyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, 4-methylcyclohexyl group, 1-adamantyl group, 2-adamantyl group, 1-norbornyl group, 2-norbornyl group, substituted or unsubstituted perfluoroalkyl group having 1 to 10 carbon atoms, etc. [0025] Examples of the aryl group represented by the above R.sub.1 and R.sub.2 include phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthryl group, 9-anthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-tolyl group, m-tolyl group, p-tolyl group, p-t-butylphenyl group, p-(2-phenylpropyl)phenyl group, 3-methyl-2-naphthyl group, 4-methyl-1-naphthyl group, 4-methyl-1-anthryl group, 4'-methylbiphenylyl group and 4''-t-butyl-p-terphenyl-4-yl group, etc. [0026] Examples of the aralkyl group represented by the above R.sub.1 and R.sub.2 include benzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, phenyl-t-butyl group, .alpha.-naphthylmethyl group, 1-.alpha.-naphthylethyl group, 2-.alpha.-naphthylethyl group, 1-.alpha.-naphthylisopropyl group, 2-.alpha.-naphthylisopropyl group, .beta.-naphthylmethyl group, 1-.beta.-naphthylethyl group, 2-.beta.-naphthylethyl group, 1-.beta.-naphthylisopropyl group, 2-.beta.-naphthylisopropyl group, 1-pyrrolylmethyl group, 2-(1-pyrrolyl)ethyl group, p-methylbenzyl group, m-methylbenzyl group, o-methylbenzyl group, p-chlorobenzyl group, m-chlorobenzyl group, o-chlorobenzyl group, p-bromobenzyl group, m-bromobenzyl group, o-bromobenzyl group, p-iodobenzyl group, m-iodobenzyl group, o-iodobenzyl group, p-hydroxybenzyl group, m-hydroxybenzyl group, o-hydroxybenzyl group, p-aminobenzyl group, m-aminobenzyl group, o-aminobenzyl group, p-nitrobenzyl group, m-nitrobenzyl group, o-nitrobenzyl group, p-cyanobenzyl group, m-cyanobenzyl group, o-cyanobenzyl group, 1-hydroxy-2-phenylisopropyl group, 1-chloro-2-phenylisopropyl group, etc. [0027] Examples of the cycloalkyl group represented by the above R.sub.1 and R.sub.2 include cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, etc. Continue reading... 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