Organic compounds -- part of the class 532-570 series – Organic compounds – Unsubstituted hydrocarbyl chain between the ring and the -c-...
Reexamination Certificate
2000-09-29
2002-11-05
Coleman, Brenda (Department: 1624)
Organic compounds -- part of the class 532-570 series
Organic compounds
Unsubstituted hydrocarbyl chain between the ring and the -c-...
Reexamination Certificate
active
06476221
ABSTRACT:
FIELD OF THE INVENTION
This invention relates to a method for the production of tribenzazepine compounds which are useful as the synthesis material of electric charge transportation agents to be used, e.g., in photosensitive materials for electrophotography use and organic electroluminescence (EL) devices.
DESCRIPTION OF THE RELATED ART
In recent years, organic substances are mainly used as the photoconductive material of photosensitive materials to be used in the electrophotographic system. Their examples include a photosensitive material comprised of poly-N-vinylcarbazole and 2,4,7-trinitrofluoren-9-one (U.S. Pat. No. 3,484,237), a material in which poly-N-vinylcarbazole is sensitized with a pyrylium salt based pigment (JP-B-48-25658; the term “JP-B” as used herein means an “examined Japanese patent publication”), a photosensitive material which contains an organic pigment as the main component (JP-A-47-37543; the term “JP-A” as used herein means an “unexamined published Japanese patent application”), a photosensitive material which contains a euteric complex comprised of a dyestuff and a resin as the main component (JP-A-47-10735), a photosensitive material which contains a hydrazone based compound as the main component (JP-A-57-101844 and JP-A-54-150128), a photosensitive material which contains an aromatic tertiary amine based compound as the main component (JP-B-58-32372) and a photosensitive material which contains a stilbene based compound as the main component (JP-A-58-198043). These photosensitive materials seem to have high practical values because of their excellent characteristics, but when various requirements for photosensitive materials to be used in the electrophotographic system are taken into consideration, it is the actual circumstances that a material which fully satisfies these requirements is not available yet. Accordingly, studies are still being carried out actively on the photosensitive materials for electrophotography use in which organic substances, particularly organic electric charge transportation agents, are used.
VanSlyke and Tang et al. have revealed that, when an aromatic tertiary amine containing phenyl, phenylene or biphenylene group is used as an electric charge transportation agent in the positive hole injection/transportation region of an internally connected organic EL apparatus, stability of the optical output is improved and the operating life is thereby prolonged, as they have disclosed for example in U.S. Pat. Nos. 4,539,507 and 4,720,432 and JP-A-5-234,681. Thereafter, in order to obtain more stable optical output, attempts have been made by many researchers to improve aromatic tertiary amine based electric charge transportation agents to be used in the positive hole injection transportation region, and the results have been reported in a large number of patent applications and scientific papers. Examples of these reports include
Japanese Journal of Applied Physics,
27, L269 (1988), JP-A-59-194393,
Appl. Phys. Lett.,
66,2679 (1995), JP-A-5-234681, JP-A-7-331238, JP-A-8-48656 and WO 95/09147 regarding biphenyl based tertiary amines and
Appl. Phys. Lett.,
65, 807 (1994) and JP-B-7-110940 regarding star burst tertiary amines. However, since these amines are still insufficient for practical use, such studies are conducted more actively by a large number of researchers.
It has been disclosed recently that a compound having tribenzazepine structure in its molecule is useful as an electric charge transportation agent of electrophotography and organic EL device (JP-A-10-59943, JP-A-10-219241, JP-A-10-316875, JP-A-10-324680 and JP-A-10-330365). However, the tribenzazepine synthesis methods so far known were difficult to be applied to the industrial large scale synthesis because of the use of deoxidation reaction by a special reagent (
J. Org. Chem.,
56, 3906 (1991)).
SUMMARY OF THE INVENTION
In view of the above, it therefore becomes an object of the invention to provide a new method for the synthesis of tribenzazepine compounds which are useful as the synthesis material of electric charge transportation agents to be used, e.g., in photosensitive materials for electrophotography use and organic electric field generation devices.
As a result of intensive studies, the present inventors have found a tribenzazepine structure synthesizing method which does not use a special reagent and accomplished the invention based on this finding.
Accordingly, the invention provides (1) a method for the production of a tribenzazepine compound represented by formula (I), which comprises carrying out the process by way of a dehydration reaction of a compound represented by formula (II):
wherein Y represents a hydrogen atom or an alkyl, aryl, acyl, alkoxycarbonyl, aryloxycarbonyl, alkanesulfonyl or arenesulfonyl group, each of R
1
and R
2
represents a hydrogen or halogen atom or an alkyl, aryl, hydroxy, alkoxy, aryloxy, acyl, alkoxycarbonyl, aryloxycarbonyl, formyl, carboxyl, sulfo or amino group, each of R
3
, R
4
, R
5
and R
6
represents a hydrogen atom or an alkyl or aryl group, and each of m and n is an integer of from 1 to 4.
wherein Y, R
1
, R
2
, R
3
, R
4
, R
5
, R
6
, m and n are as defined in the above, (2) a method for the production of a compound represented by formula (I) described in the above item (1), wherein the compound represented by formula (II) is produced by reducing a compound. represented by formula (III):
wherein Y, R
1
, R
2
, R
3
, R
4
, R
5
, R
6
, m and n are as defined in the foregoing, and (3) a tribenzazepine compound represented by formula (IV):
wherein Y
1
represents a group having the same meaning of the Y, and each of R
7
, R
8
, R
9
, and R
10
represents a hydrogen atom or an alkyl group having 10 or less of carbon atoms, with the proviso that all of R
7
to R
10
are not hydrogen atoms at the same time and that Y
1
does not represent hydrogen atom or an aryl group when R
8
is methyl group and each of R
7
, R
9
and R
10
is hydrogen atom.
In this connection, according to the invention, it is intended that the respective groups represented by Y, R
1
, R
2
, R
3
, R
4
, R
5
and R
6
in the formulae (I) to (III) include not only unsubstituted groups but also those which are further substituted with substituent groups as is evident from the following descriptions.
Other objects and advantages of the invention will be made apparent as the description progresses.
DETAILED DESCRIPTION OF THE INVENTION
Firstly, Y, Y
1
, R
1
, R
2
, R
3
, R
4
, R
5
, R
6
, R
7
, R
8
, R
9
, R
10
, m and n in the formulae (I) to (IV) are described.
Each of Y and Y
1
represents a hydrogen atom or an alkyl, aryl, acyl, alkoxycarbonyl, aryloxycarbonyl, alkanesulfonyl or arenesulfonyl group, and more detailed examples of the groups excluding hydrogen atom, in the case of unsubstituted groups, are an alkyl group having from 1 to 20 carbon atoms, an aryl group having from 6 to 36 carbon atoms, an acyl group having from 2 to 20carbon atoms, an alkoxycarbonyl group having from 2 to 20 carbon atoms, an aryloxycarbonyl group having from 7 to 40 carbon atoms, an alkanesulfonyl group having from 1 to 20 carbon atoms and an arenesulfonyl group having from 6 to 40 carbon atoms.
Their illustrative examples include an alkyl group such as methyl, ethyl, isopropyl, n-butyl, t-butyl, n-dodecyl or cyclohexyl, an aryl group such as phenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, naphthacenyl, pentacenyl or pentaphenyl, an acyl group such as acetyl, propionyl or benzoyl, an alkoxycarbonyl group such as methoxycarbonyl, ethoxycarbonyl or octyloxycarbonyl, an aryloxycarbonyl group such as phenoxycarbonyl or 2-naphthyloxycarbonyl, an alkanesulfonyl group such as methanesulfonyl or ethanesulfonyl and an arenesulfonyl group such as benzenesulfonyl, p-toluenesulfonyl or 2-naphthalenesulfonyl.
Preferred among them is hydrogen atom, an alkyl, an aryl group, an acyl or alkoxycarbonyl group, and particularly preferred is hydrogen atom, an acyl group or an alkoxycarbonyl group.
Each of R
1
and R
2
represents a hydrogen or halogen atom, a substituted or
Motoki Masuji
Sato Tadahisa
Coleman Brenda
Fuji Photo Film Co. , Ltd.
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