Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
1999-12-29
2001-01-09
McKane, Joseph K. (Department: 1626)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C558S432000, C558S370000, C160S287000, C160S287000, C160S287000
Reexamination Certificate
active
06172240
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
This invention relates to metallically-lustered pyrrole derivatives, particularly 2-(2-thienyl)-5-(5-tricyanoethenyl-2-thienyl)pyrrole derivatives, which can be used for a coating material, organic metal plating material, organic semiconductor material or the like.
2. Description of Related Art
It has been known that a high-molecular weight compound having a conjugated &pgr;-electron system in the molecule thereof has a metallic luster. Because the metallic luster in such a compound is based on free electrons in the &pgr;-electron system, the compound is expected to have semiconductor-like properties. Poly(acetylene), poly(sulfur nitride) and the like are examples of such a compound.
SUMMARY OF THE INVENTION
Since they are unstable in doped and even undoped states, organic compounds having metallic luster which are stable even in air are demanded.
Further, since the high-molecular weight compound having a &pgr;-electron conjugated system generally has a low solubility in an organic solvent, it is difficult to form a film by dissolving the compound in the organic solvent to make a solution and then applying the resulting solution on an appropriate substrate.
An object of the invention is, therefore, to provide an organic compound which has metallic luster and is stable even in air.
Further, another object of the invention is to provide the organic compound which has a high solubility in the organic solvent and consequently is an excellent film-forming material.
There is, therefore, a provision of pyrrole derivatives, particularly 2-(2-thienyl)-5-(5-tricyanoethenyl-2-thienyl)pyrrole derivatives, having the following general formula:
(R represents hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aromatic group, formyl group, an acyl group, an alkoxycarbonyl group, or an alkenyl group.)
Moreover, there is a provision of a film-forming material composed of the above pyrrole derivative, and further provision of the present invention is a method of preparing the above derivatives.
As mentioned above, some high-molecular weight compounds have been known which have metallic luster. However, no organic low-molecular weight compound has been reported at all which clearly has metallic luster.
The inventor has found that the aforementioned low-molecular weight compound which has the specific structure, namely the &pgr;-electron conjugated system, in a molecule thereof has a stable metallic luster and good stability in air, and further has a high solubility in common organic solvents and hence is an excellent film-forming material, and then accomplished this invention.
The aforementioned compounds having the tricyanoethenyl group show a clear gold color, bronze color or the like in its crystal state or thin film state. Further, nevertheless the compounds can dissolve in the common organic solvents such as acetone, benzene, chloroform, or the like, they can easily precipitate therefrom after dissolving therein. For example, standing of the solution allows metallic colored crystals to precipitate therefrom.
Further, by developing, coating, and drying the solution containing the compound in the organic solvent on a surface of an appropriate substrate, a coating film can easily be formed thereon.
Since the compounds according to the present invention have a surprisingly high stability against beat, they can be used for formation of a evaporated film. Further, by heating the compound up to not less than its melting point to melt it and then cooling the melt, crystals can be formed. Moreover, the compounds according to the invention can have a stable melting state and also exhibit a relatively high electrical conductivity.
Besides, iodine or the like may dope into the compound according to the present invention, for the purpose of enhancing its electrical conductivity.
In the aforementioned general formula, R represents hydrogen, a substituted or unsubstituted alkyl or cycloalkyl group, a substituted or unsubstituted aromatic group, formyl group, an acyl group, an alkoxycarbonyl group, or an alkenyl group. Besides, the alkyl or cycloalkyl group constituting R preferably has 1-18 carbon(s) and more preferably 1-12 carbon(s). The substituent for the an alkyl or cycloalkyl group is preferably alkoxy group having 1-18 carbon(s); an aromatic group such as phenyl group, naphthyl group, benzothienyl group, indolyl group, pyridyl group, phenoxy group, naphthyloxy group; or a halogen atom such as bromine, iodine, chlorine, or fluorine.
The aromatic group constituting R is preferably phenyl group, naphthyl group, thienyl group, benzothienyl group, indolyl group, pyridyl group or the like. A substituent for the aromatic group is preferably alkyl group having 1-18 carbon(s), more preferable 1-12 carbon(s), alkoxy group having 1-18 carbon(s), more preferable 1-12 carbon(s), phenoxy group, naphthyloxy group, monoalkylamino group, dialkylamino group, thioalkyl group, bromine, iodine, chlorine, fluorine. An alkyl group constituting the monoalkylamino group, the dialkylamino group, or the thioalkyl group has preferably 1-18 carbon(s).
The acyl group, the alkoxycarbonyl group, or the alkenyl group constituting R preferably has 1-18 carbon(s), more preferable 1-12 carbon(s).
Particularly when R represents alkylphenyl or alkoxyphenyl group having 4-12 carbons of alkyl or alkoxy group, a thin film with metallic luster can be made by spin coating the compound according to the invention on the appropriate substrate.
The compound according to the invention can be manufactured by reacting a compound shown by the following general formula with tetracyanoethylene in an organic solvent.
Alternatively, an organic metal compound shown by the following general formula is produced by reacting the above compound with a base such as butyllithium, lithium diisopropylamide or the like.
Subsequently, the reaction of the resulting compound with tetracyanoethylene generates the compound according to the invention.
Besides, when R is t-butoxycarbonyl group, heating of the compound according to the invention can bring substitution of R by hydrogen.
REFERENCES:
Meeker et al., Macromolecules (1998), 31(9) pp. 2943-2946.*
Chiba University
McKane Joseph K.
Solola Taofiq A.
Sughrue Mion Zinn Macpeak & Seas, PLLC
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