Polyselenophenes, the preparation thereof and the use thereof

Details Polyselenophenes, the preparation thereof and the use thereof Polyselenophenes, the preparation thereof and the use thereof

1998-09-09

2001-03-06

Truong, Duc (Department: 1711)

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

From heterocyclic reactant containing as ring atoms oxygen,...

C540S001000, C548S120000, C427S407100

Reexamination Certificate

active

06197922

ABSTRACT:

The present invention relates to novel polyselenophenes; it relates further to processes and monomers for preparing polyselenophenes, to the use thereof in various industrial sectors, and to an electrically conducting material which comprises at least one polyselenophene according to the invention.
Polythiophenes are known inter alia as conjugated polymers with high electrical conductivity and nonlinear optical properties. They can be used as materials for semiconductors (see, inter alia, EP-B-0 332 704 and P. N. Prasad, D. J. Williams “Introduction to NLO effects in molecules and polymers”, John Wiley and Sons, Inc. (1991)). The polythiophenes furthermore have electrochromic and antistatic properties (see N. Arsalani and K. E. Geckeler “Conducting isopolymers: preparation, properties, and applications”, J. Prakt. Chem. 337 (1995) 1-11).
Further details of polythiophenes which can be used particularly well are to be found in PCT/EP97/01140 and the literature quoted therein.
Previously disclosed electrically conducting materials have not always been able to meet the increasing demands on these materials such as comparatively high electrical conductivity with, at the same time, good mechanical properties. These considerations show by way of example the need to develop novel, previously unknown doped and undoped poly- and oligomers.
It is an object of the present invention to provide novel polyselenophenes which can be used in various industrial areas in an advantageous manner as outlined above.
We have found that this object is achieved by the polyselenophenes according to the invention which are described in detail below.
The present invention thus relates to a polyselenophene comprising one or more structural units of the formulae (I) or (II) or (I) and (II)
where
X and Y can be identical or different and, independently of one another, are hydrogen with the proviso that only one of X and Y is hydrogen; a linear or branched C
1
-C
22
-alkyl group; a linear or branched C
1
-C
22
-alkoxy group; a linear or branched C
1
-C
22
-alkyloxyalkyl group; a linear or branched C
1
-C
22
-acyl group; a linear or branched C
1
-C
22
-thioacyl group; a linear or branched C
1
-C
22
-acyloxy group; a linear or branched C
1
-C
22
-thioacyloxy group; a C
5
-C
8
-cycloalkyl group, a C
6
-C
18
-aryl group or a C
5
-C
8
-heterocyclic group, each of which in turn can be substituted by one or more linear or branched C
1
-C
22
-alkyl group(s), one or more linear or branched C
1
-C
22
-alkoxy group(s), one or more linear or branched C
1
-C
22
-alkyloxyalkyl group(s), one or more linear or branched C
1
-C
22
-acyl group(s) or one or more linear or branched C
1
-C
22
-thioacyl group(s); NO
2
; or NHR
1
where R
1
can be identical or different and is in each case hydrogen, a linear or branched C
1
-C
22
-alkyl group, a linear or branched C
1
-C
22
-alkoxy group, a linear or branched C
1
-C
22
-alkyloxyalkyl group, a linear or branched C
1
-C
22
-acyl group or a linear or branched C
1
-C
22
-thioacyl group, or X and Y form, together with the atoms to which they are bonded, a carbon-containing ring system which, besides carbon, has nitrogen (N), oxygen (O), sulfur (S) or phosphorus (P) hetero atoms or mixtures of two or more of these hetero atoms,
where this ring system can in turn be substituted on the carbon atom(s), the nitrogen atom(s) or the phosphorus atom(s) in each case by a group Z where Z is in each case, independently of one another, a group as defined above for X and Y, or
two adjacent groups Z together form a radical depicted by the following formulae (III) to (VI)
where A is carbon (C), nitrogen (N), phosphorus (P) or mixtures of two or more of these atoms,
and in the case where A is carbon, each of these A either carries a hydrogen atom or can in turn be substituted as defined above for X and Y.
In another embodiment, the polyselenophene according to the invention comprises one or more thiophene structural units of the formulae (XII) or (XIII) or (XII) and (XIII)
where
X and Y can be identical or different and, independently of one another, are defined as above for the polyselenophene units.
Preferred embodiments of the above thiophene units, and the preparation and properties of the corresponding compounds underlying these units, are to be found in the application PCT/EP97/01140 mentioned at the outset, which is in this regard incorporated in its entirety into the context of the present application.
The term “polyselenophene” as used in the present application comprises all poly- and oligomers which comprise one or more units of the formulae (I) and/or (II). This embraces both the presence of one or more identical units (I) and/or (II), and the presence of a plurality of different units (II), each of which can then in turn be present at least once in the polyselenophene according to the invention. The polyselenophenes according to the invention preferably comprise one or more units of the formulae (I) and (II). Also embraced are all poly- and oligomers which comprise one or more units of the formulae (I) and/or (II) together with one or more thiophene units of the formulae (XII) and/or (XIII).
Also embraced in addition are combinations of units of the formulae (I) and/or (II) with other conjugated organic structural units such as phenylene, biphenylene, terphenylene, naphthalene, anthracene, furan units, it being possible for these in turn to be mono- or polysubstituted as defined above for X and Y.
The structural unit (I) present in the polyselenophenes according to the invention is derived from selenophene.
In the structural unit (II), in which X and Y, if they do not form a carbon-containing ring system together with the atoms to which they are bonded, can in each case be the groups mentioned at the outset, it is preferred for X and Y to be identical. If X and Y are each the group NHR
1
, the two R
1
radicals are preferably likewise identical. Among the alkyl, alkoxy, alkyloxyalkyl, acyl and thioacyl groups with 1 to 22 carbon atoms listed above, those with 1 to 20 are preferred, those with 6 to 20 carbon atoms are further preferred, and those with 10 to 16 carbon atoms are particularly preferred.
Particularly preferred substituents X and Y are the above-defined acyl groups, thioacyl groups and NHR
1
.
The term “thioacyl group” means for the purpose of the present invention a group of the formula —C(S)—R where R is alkyl. The term “heterocyclic group” as mentioned at the outset means alicyclic saturated, alicyclic unsaturated and aromatic heterocyclic groups.
It is also possible for X and Y to form, together with the atoms to which they are bonded, a carbon-containing ring system which, besides carbon, has nitrogen (N), oxygen (O), sulfur (S) or phosphorus (P) hetero atoms or mixtures of two or more of these hetero atoms. In this case, X and Y preferably form a divalent radical which has two to eight atoms, furthermore preferably three to six atoms, and forms, together with the two atoms to which it is bonded, a ring system with four to ten or five to eight atoms. The number of the above-defined hetero atoms which may be present in this ring system is preferably up to three, furthermore preferably up to two. Among the above-defined hetero atoms, nitrogen (N) is preferred. The ring system described above is preferably a system having at least one, furthermore preferably two or more, double bonds. In particularly preferred embodiments of the present invention, the double bonds in the above ring system are conjugated with the double bonds in the selenophene fragment to which the ring system is bonded, and, where appropriate, with the double bonds in other radicals of the formulae (III) to (VI), as defined above which are bonded to the ring system described above.
This ring system may in turn be substituted on the carbon, nitrogen or phosphorus atoms in each case by one group Z where Z is in each case, independently of one another, a group as defined above for X and Y, and the substituents indicated as preferred for X and Y are in turn to be regarded as preferred here too.
Two adjacent gr

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