Electroluminescent arrangements

Details Electroluminescent arrangements Electroluminescent arrangements

1998-12-21

2002-04-23

Yamnitzky, Marie (Department: 1774)

Stock material or miscellaneous articles

Composite

Of inorganic material

C428S704000, C428S917000, C313S504000, C313S506000, C257S103000

Reexamination Certificate

active

06376105

ABSTRACT:

The invention relates to electroluminescing arrangements (devices) that contain conducting polymers as hole-injecting and/or electron-injecting layer.
An electroluminescing (EL) arrangement is characterised by the fact that it emits light when an electrical voltage is applied with flow of current. Such arrangements have been known for a long time in industry and technology under the description “light-emitting diodes” (LEDs). Light is emitted on account of the fact that positive charges (holes) and negative charges (electrons) combine with the emission of light.
All LEDs commonly used in industry and technology consist largely of inorganic semiconductor materials. However, for some years EL arrangements have been known whose basic constituents are organic materials.
These organic EL arrangements as a rule contain one or more layers of organic charge transport compounds.
The layer structure is in principle as follows. The numbers 1 to 10 denote the following:
1. Carrier, substrate
2. Base electrode
3. Hole-injecting layer
4. Hole-transporting layer
5. Emitter layer
6. Electron-transporting layer
7. Electron-injecting layer
8. Top electrode
9. Contacts
10. Covering, encapsulation.
This structure represents the most general case and can be simplified by omitting individual layers, so that one layer performs several tasks. In the simplest case an EL arrangement consists of two electrodes between which an organic layer is arranged, which fulfils all functions, including emission of light. Such systems are described for example in Application WO 9013148 based on poly-[p-phenylene vinylene].
In the production of large-surface, electroluminescing display elements at least one of the current-carrying electrodes
2
or
8
must consist of a transparent and conducting material.
Suitable as substrate
1
are transparent carriers such as glass or plastics films (for example polyesters such as polyethylene terephthalate or polyethylene naphthalate, polycarbonate, polyacrylate, polysulphone, polyimide foil).
The following are suitable as transparent and conducting materials:
a) metal oxide, for example indium-tin oxide (ITO), tin oxide (NESA), etc.
b) semi-transparent metal films, for example Au, Pt, Ag, Cu, etc.
In the applications according to the invention low molecular weight or oligomeric as well as polymeric materials may be used as emitter layer
5
. The substances are characterised by the fact that they are photoluminescing. Accordingly, suitable substances are for example fluorescent dyes or fluorescing molecules and their reaction products forming oligomers or their incorporation into polymers.
Examples of such materials are coumarins, perylenes, anthracenes, phenanthrenes, stilbenes, distyryls, methines or metal complexes such as Alq
3
, etc. Suitable polymers include optionally substituted phenylenes, phenylene vinylenes or polymers with fluorescing segments in the polymer side chain or in the polymer backbone. A detailed list is given in EP-A 532 798.
It has been found however in practice that in order to increase the luminance, electron-injecting or hole-injecting layers (
3
,
4
and/or
6
,
7
) must be incorporated into the electroluminescing assemblies.
A large number of organic compounds that transport charges (holes and/or electrons) are described in the literature. Mainly low molecular weight substances are used, which are for example vacuum evaporated in a high vacuum. A comprehensive survey of the classes of substances and their use is given for example in the following publications: EP-A 387 715, U.S. Pat. Nos. 4 539 507, 4,720,432 and 4,769,292.
A disadvantage is the deposition of the substances by high-vacuum evaporation. In order to simplify the production process of ELP displays it would be advantageous if the layers
3
,
4
and
6
,
7
could be produced by deposition from solution.
From EP-A 686 662 it is known to use special mixtures of conducting organic polymeric conductors such as 3,4-polyethylene dioxythiophene and polyhydroxy compounds or lactams as electrode
1
in ELP assemblies.
In Synthetic Metals 76 (1996) 141-143 poly-(3,4-ethylenedioxythiophene) is described also as an electrode in LEDs, reference being made to the fact that poly-(3,4-ethylenedioxythiopene) electrodes produce lower luminance values than indium-tin oxide (ITO) electrodes.
It has now surprisingly been found that pure polymeric organic conductors such as 3,4-polyethylenedioxythiopene as charge-injecting intermediate layer on transparent metal electrodes such as ITO produce luminance values in LEDs that are significantly superior to the LEDs with pure metal electrodes or pure conducting polymer electrodes. These layers can be prepared from solution or by direct polymerisation of the monomers corresponding to the polymeric organic conductors.
Suitable polymeric organic conductors are for example polyfurans, polypyrroles, polyanilines, polythiophenes or polypyridines. These are described for example in EP-A 257 573 (polyalkoxythiophenes), WO 90/04256 (polyanilines), EP-A 589 529 (pyrrole), DE-A 2 262 743 (oligoanilines).
Particularly suitable are neutral or cationic thiophenes of the formula (I)
wherein
R
1
and R
2
denote, independently of one another, hydrogen, optionally substituted C
1
-C
20
-alkyl, CH
2
OH or C
6
-C
14
-aryl, or
R
1
and R
2
together denote —(CH
2
)
m
—CH
2
— with m=0 to 12, preferably 1 to 5, or C
6
-C
14
-aryls, and
n is an integer from 5 to 100.
R
1
and R
2
preferably denote —(CH
2
)
1
—CH
2
— where l=1 to 4.
The polythiophenes with the repeating structural unit of the formula (I) are known (cf. EP-A 440 957 and 339 340). The preparation of the dispersions or solutions according to the invention is described in EP-A 440 957 and DE-OS 4 211 459.
The polythiophenes are used in dispersion or solution, preferably in cationic form, obtained for example by treating neutral thiophenes with oxidising agents. Conventional oxidising agents such as potassium peroxodisulphate are used for the oxidation. Through the oxidation the polythiophenes receive positive charges, which are not shown in the formulae since their number and position cannot be specified with certainty. According to the information given in EP-A 339 340 they can be produced directly on carriers.
The polyanions are anions of polymeric carboxylic acids, such as polyacrylic acids, polymethacrylic acids or polymaleic acids, and polymeric sulfonic acids, such as polystyrene sulfonic acids and polyvinyl sulfonic acids. These polycarboxylic and polysulfonic acids may also be copolymers of vinyl carboxylic and vinyl sulfonic acids with other polymerizable monomers, such as acrylates and styrene.
The molecular weight of the polyacids supplying the polyanions is preferably in the range from 1,000 to 2,000,000 and more preferably in the range from 2,000 to 500,000. The polyacids or their alkali salts are commercially available, for example polystyrene sulfonic acids and polyacrylic acids, or may be produced by known methods (cf. for example Houben-Weyl, Methoden der organischen Chemie, Vol. E20, Makromolekulare Stoffe, Teil 2, (1987), pp. 1141 et seq.).
Instead of the free polyacids required for the formation of the dispersions of polythiophenes and polyanions according to the invention, it is also possible to use mixtures of alkali salts of the polyacids and corresponding quantities of mono-acids.
The polythiophene dispersions in the presence of polyanions according to the invention are obtained by oxidative polymerization of 3,4-dialkoxythiophenes corresponding to the following formula
in which
R
1
and R
2
are as defined for formula (I),
with oxidizing agents typically used for the oxidative, polymerization of pyrrole and/or oxygen or air in the presence of the polyacids, preferably in aqueous medium, at temperatures of 0 to 100° C.
The polythiophenes get positive changes by the oxidative polymerization, which are not shown in the formula, because their number and position cannot be determined without doubt.
For polymerization, the thiophenes corresponding to formula (II), polyacid and o

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