Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing
Reexamination Certificate
2000-09-29
2001-11-06
Padmanabhan, Sreeni (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Amino nitrogen containing
C564S312000
Reexamination Certificate
active
06313349
ABSTRACT:
FIELD OF THE INVENTION
This invention relates to aminophenol compounds and a method for producing the same. More particularly, it relates to aminophenol compounds having a nitrogen-linking substituent at the 5-position which are intermediates in synthesizing benzoazole compounds useful as, for example, organic electroluminescence (EL) materials, and a method for producing the same.
DESCRIPTION OF THE RELATED ART
Tang et al. disclose that compounds having benzoazole skeleton are useful as electron transport compounds and luminous compounds in the electron injection and transport zones of internal junction organic EL devices or host substances doped with a luminous substance in, for example, JP-A-59-194,393 and JP-A-63-264,692 (the term “JP-A” as used herein means “unexamined published Japanese patent application”). Although the compounds having benzoazole skeleton disclosed in these documents are favorable in the capability of showing strong luminescence, these compounds are insufficient in the stability of vacuum evaporation films and electron transport properties. Therefore, devices with the use of these compounds show only extremely insufficient stability for practical use. Under these circumstances, the inventors have conducted intensive studies to find out a molecular structure ensuring improved stability of a luminescence device in compounds with benzoazole skeleton having favorable characteristics of showing strong luminescence.
As a result, they have found out that bisbenzoazole compounds having certain substituents (for example, alkoxy, dialkylamino or diarylamino) show an excellent performance in solving the problem as described above (JP-A-11-29556).
In these studies, it was also found that 2-amino-6-diarylaminophenols (i.e., intermediates in synthesizing bisbenzoazole compounds having a diarylamino group at the 6-position as a substituent) had never been reported and a method for synthesizing these compounds should be originally developed.
Thus, the inventors have studied on the synthesis method and thus tried to produce 2-amino-6-diarylaminophenols. Accordingly, the invention aims at providing a method for producing 2-amino-6-diarylaminophenols and analogs thereof, intermediates in the synthesis thereof, and novel aminophenol compounds which can be produced by the production method.
SUMMARY OF THE INVENTION
As the results of extensive studies, the inventors have found out that the desired compounds can be obtained by reducing compounds obtained by a nucleophilic substitution reaction of certain substituted nitrobenzene compounds. The invention has been completed based on this finding.
Accordingly, the invention provides:
(1) a method for producing an aminophenol compound represented by the following formula (I) via a compound represented by the following formula (II):
wherein Y
1
represents an N-alkyl-N-arylamino group, a diarylamino group, or a five-membered nitrogen-containing aromatic heterocyclic group having an endocyclic nitrogen atom bonded to the benzene ring, provided that when Y
1
is a substituted diphenylamino group, it is a diphenylamino group having at least one substituent selected from among alkyl, aryl, alkoxy, aryloxy, dialkylamino, N-alkyl-N-arylamino and diarylamino groups; R
2
, R
2
and R
3
represent each a hydrogen atom or a substituent; X
1
represents an acid group of an inorganic or organic acid; and m is from 0 to 2; and
wherein Y
1
, R
1
, R
2
and R
3
are each as defined above; and R
4
represents an alkyl group;
(2) an aminophenol compound represented by the following formula (III):
wherein Y
2
represents an N-alkyl-N-arylamino group, a diarylamino group, or a five-membered nitrogen-containing aromatic heterocyclic group having an endocyclic nitrogen atom bonded to the benzene ring, provided that when Y
2
is a substituted diphenylamino group, it is a diphenylamino group having at least one substituent selected from among alkyl, aryl, alkoxy, aryloxy, dialkylamino, N-alkyl-N-arylamino and diarylamino groups but not an N-(3-methylphenyl)-N-phenylamino group; R
5
, R
6
and R
7
represent each a hydrogen atom, a halogen atom, an alkyl group, an aryl group, an alkoxy group or an aryloxy group; X
2
represents an acid group of an inorganic or organic acid; and n is from 0 to 2; and
(3) a nitrobenzene compound represented by the following formula (IV):
wherein Y
3
represents an N-alkyl-N-arylamino group, a diarylamino group, or a five-membered nitrogen-containing aromatic heterocyclic group having an endocyclic nitrogen atom bonded to the benzene ring, provided that when Y
3
is a substituted diphenylamino group, it is a diphenylamino group having at least one substituent selected from among alkyl, aryl, alkoxy, aryloxy, dialkylamino, N-alkyl-N-arylamino and diarylamino groups; R
8
, R
9
and R
10
represent each a hydrogen atom, a halogen atom, an alkyl group, an aryl group, an alkoxy group or an aryloxy group; and R
11
represents a hydrogen atom or an alkyl group.
DETAILED DESCRIPTION OF THE INVENTION
Now, the compounds represented by the formulae (I), (II), (III) and (IV) in the invention will be described in detail.
In the formulae (I) and (II), Y
1
represents an N-alkyl-N-arylamino group, a diarylamino group, or a five-membered nitrogen-containing aromatic heterocyclic group having an endocyclic nitrogen atom bonded to the benzene ring. When the diarylamino group is a substituted diphenylamino group, it is a diphenylamino group having at least one substituent selected from among alkyl, aryl, alkoxy, aryloxy, dialkylamino, N-alkyl-N-arylamino and diarylamino groups. More particularly speaking, Y
1
represents an optionally substituted N-alkyl-N-arylamino group having from 7 to 40 carbon atoms, an optionally substituted diarylamino group having from 12 to 40 carbon atoms, or an optionally substituted five-membered nitrogen-containing aromatic heterocyclic group having from 4 to 40 carbon atoms and having an endocyclic nitrogen atom bonded to the benzene ring. In the former two groups, substituents on the nitrogen atom may be directly or indirectly bonded to each other to form a five- to seven-membered ring.
The five-membered nitrogen-containing aromatic heterocyclic group may be further condensed with a benzene ring, etc.
Examples of the fundamental structure of Y
1
are as follows:
N-Alkyl-N-arylamino groups:
Diarylamino groups:
Five-membered nitrogen containing aromatic heterocyclic groups:
It is preferable that Y
1
is a diarylamino group and particularly preferably a diarylamino group forming a five-or seven-membered ring by directly or indirectly bonding the two aryls on the nitrogen atoms.
When Y
1
is a group other than a diphenylamino group, it may have the same substituents as the substituents which may be carried by R
1
to R
3
as will be described hereinafter. Preferable examples of the substituents which may be carried by Y
1
other than a diphenylamino group are alkyl, aryl, alkoxy, dialkylamino and diarylamino groups.
When Y
1
is a diphenylamino group, it may have substituents such as alkyl, aryl, alkoxy, aryloxy, dialkylamino, N-alkyl-N-arylamino and diarylamino groups. Preferable examples of the substituents are alkyl, aryl and alkyloxy groups and alkyl and aryl groups are still preferable. Particularly preferable examples of the substituents are methyl and phenyl groups.
In the formula (III), Y
2
represents an N-alkyl-N-arylamino group, a diarylamino group, or a five-membered nitrogen-containing aromatic heterocyclic group having an endocyclic nitrogen atom bonded to the benzene ring. When Y
2
is a substituted diphenylamino group, it is a diphenylamino group having at least one substituent selected from among alkyl, aryl, alkoxy, aryloxy, dialkylamino, N-alkyl-N-arylamino and diarylamino groups but not an N-(3-methylphenyl)-N-phenylamino group. More particularly, Y
2
is exemplified by the same groups as defined in Y
1
except for not being an N-(3-methylphenyl)-N-phenylamino group. Preferable examples of Y
2
include diarylamino groups, still preferably diarylamino groups forming a five- or seven-memb
Fuji Photo Film Co. , Ltd.
Padmanabhan Sreeni
Sughrue Mion Zinn Macpeak & Seas, PLLC
Witherspoon Sikarl A.
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