Organic compounds -- part of the class 532-570 series – Organic compounds – Silicon containing
Reexamination Certificate
2001-01-09
2002-04-23
Shaver, Paul F. (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Silicon containing
C313S504000, C313S506000, C428S690000
Reexamination Certificate
active
06376694
ABSTRACT:
This application is 371 application PCT/JP99/03671 filed Jul. 7, 1999.
TECHNICAL FIELD
The present invention relates to a silole derivative which can be widely applied to electronically functional materials and optically functional materials, and an organic electroluminescent element containing the same.
BACKGROUND ART
Various institutions have tried to apply &pgr; electron base organic compounds to optically functional materials and electronically functional materials in various ways.
Among those compounds, a group of &pgr; electron base organic compounds having a hetero five-membered ring structure as a fundamental structure, for example, thiophene and pyrrole are known as one of typical &pgr; electron base organic compound groups. However, most of their hetero five-membered rings have an electron-donating property, which has limited an application of the compounds to the materials. Accordingly, &pgr; electron-accepting compounds have so far been required.
Recently, it has been reported that a silole ring shows an electron-accepting property, and an application thereof to various functional materials is expected. An application of the ring to conductive polymers has been reported in JP-A 6-100669 and JP-A 6-166746, for example.
An application of silole derivatives to organic EL elements making the best use of their electron-accepting property has been reported, for example, in JP-A 9-87616; JP-A 9-194487; Japan Chemical Society, 70 Annual Spring Meeting, Lecture Abstract II, pp. 700, 2D102; Japan Chemical Society, 70 Annual Spring Meeting, Lecture Abstract II, pp. 701, 2D103; Japan Chemical Society, 71 Annual Autumn Meeting, Lecture Abstract, pp. 32, 2P1&agr;21; and Japan Chemical Society, 71 Annual Autumn Meeting, Lecture Abstract, pp. 32, 2P1&agr;22. Among them, several compounds have a suitable electron-accepting property and electron-donating property and also an electroluminescent property, and are therefore applied to electroluminescent materials. However, the compounds described therein do not have a sufficiently high electroluminescent brightness for practical use.
An organic EL element comprises a structure in which an organic compound is interposed between electrodes, and the organic compound used includes a charge-transporting material and an electroluminescent material. In order to prepare an organic EL element having a low power consumption and a high efficacy, it is necessary to use an electroluminescent material having a high electroluminescent efficiency. However, there have been few reports on an electroluminescent characteristic of a silole derivative.
JP-A 7-179477 and JP-A 7-300489, for example, disclose syntheses of various silole derivatives by introducing reactive substituents into the 2- and 5-positions of a silole ring. However, their electroluminescent property is not described therein.
German Patent (DE4442050) discloses a spirosilole derivative applied to an organic EL element, but an electroluminescent characteristic of those compounds is not described at all. The structure thereof is restricted to a dibenzo derivative, and there is no description about a synthetic method or physical property values of a compound having an asymmetric skeleton.
Further, dithienosilole derivatives are described in Chemistry Letters, 1998, 1233, but they have been very poor in performance and low in practicability as an electroluminescent material for an organic EL element.
The present invention has been achieved in light of the problems involved in the conventional techniques described above. An object of the invention is to provide a novel silole derivative having a high electroluminescent efficiency and an organic EL element containing the said silole derivative.
DISCLOSURE OF THE INVENTION
The present inventors have intensively investigated a silole derivative which can solve the preceding problems involved in conventional organic EL elements, and which is applied to various functional materials. As a result, the inventors have found a specific silole derivative and further found that use of the silole derivative provides an organic EL element having a high electroluminescent efficiency, and thus completed the present invention.
More specifically, the present invention comprises structures shown in the following items (1), (2), (3), (4) and (5):
(1) A silole derivative represented by the following Formula (1):
wherein R
1
and R
2
each independently represent a substituted or unsubstituted alkyl, silyl, aryl, heterocyclic or alkenyl group and may be bonded with each other at the respective terminals; Ar
1
and Ar
2
each independently represent a substituted or unsubstituted aryl or heterocyclic group; and R
3
to R
10
each independently represent a substituted or unsubstituted alkyl, aryl or heterocyclic group and may be bonded with each other at the respective terminals.
(2) A silole derivative represented by the following Formula (2):
wherein R
11
to R
30
each independently represent a substituted or unsubstituted alkyl, aryl or heterocyclic group and may be bonded with each other at the respective terminals; and R
3
to R
10
each independently represent a substituted or unsubstiituted alkyl, aryl or heterocyclic group and may be bonded with each other at the respective terminals.
(3) A silole derivative represented by the following Formula (3):
wherein A
1
and A
2
are bonded with each other to form a 5- or 6-membered ring; B
1
and B
2
are bonded with each other to form a 5- or 6-membered ring; C
1
and C
2
are bonded with each other to form a 5- or 6-membered ring; and D
1
and D
2
are bonded with each other to form a 5- or 6-membered ring.
(4) A silole derivative represented by the following Formula (4):
wherein A
1
and A
2
are bonded with each other to form a 5- or 6-membered ring; B
1
and B
2
are bonded with each other to form a 5- or 6-membered ring; C
1
and C
2
are bonded with each other to form a 5- or 6-membered ring; E
1
and E
2
are bonded with each other to form a 5- or 6-membered ring; X represents oxygen, sulfur or NR; and R represents hydrogen, an alkyl group or an aryl group.
(5) An organic electroluminescent element containing the silole derivative as described in at least one of the items (1), (2), (3) and (4) for an electroluminescent layer.
BEST MODE FOR CARRYING OUT THE INVENTION
The present invention shall be explained below in details.
Specific examples of the silole derivative of the present invention represented by Formula (1) include compounds represented by the following Formulas (5) to (15):
The silole derivative of the present invention can be obtained, for example, by the production process, which comprises reacting a diene derivative represented by Formula (16)
wherein F
2
and G
2
each independently represent a substituted or unsubstituted alkyl, silyl, aryl, heterocyclic or alkenyl group and may be bonded with each other at the respective terminals; F
1
and G
1
each independently represent a substituted or unsubstituted aryl or heterocyclic group; F
1
and F
2
may be bonded with each other to form a 5- or 6-membered ring; G
1
and G
2
may be bonded with each other to form a 5- or 6-membered ring; and Y and Z each independently represent a halogen atom; with a base and subsequently reacting it with a silane derivative.
In the above production process, the base to be used includes, for example, organic lithium reagents such as n-butyllithium, tert-butyllithium and phenyllithium, and Grignard reagents such as magnesium and magnesium bromide. The solvent to be used shall not specifically be restricted as long as it is inactive to these bases, and usually used are ethers such as diethyl ether and tetrahydrofuran (hereinafter referred to as THF) and aromatics such as benzene and toluene.
The silole derivative of the present invention, particularly that represented by Formula (2) is also obtained by reacting an acetylene derivative represented by Formula (17)
wherein Ar
1
and Ar
2
each independently represent a substituted or unsubstituted aryl or heterocyclic group, with metall
Furukawa Kenji
Izumizawa Takenori
Koike Toshihiro
Uchida Manabu
Chisso Corporation
Shaver Paul F.
Wenderoth , Lind & Ponack, L.L.P.
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