Organic electronic component and method for producing an organic electronic component

Abstract

The invention relates to an organic electronic component comprising a cathode, an anode, at least one light-emitting layer which is arranged between the anode and the cathode, a first layer, which comprises a first matrix material and a dopant, a second layer, which comprises a second matrix material, wherein the first layer is arranged between the second layer and the anode, wherein the second layer is arranged between the anode and the at least one light-emitting layer, wherein the dopant is a fluorinated sulfonimide metal salt of the following formula 1: ##STR00001##

Claims

1. An organic electronic component comprising a cathode, an anode, at least one light-emitting layer which is arranged between the anode and the cathode, a first layer, which comprises a dopant and a first matrix material comprising organic small non-polymeric molecules, and a second layer, which comprises a second matrix material comprising organic small non-polymeric molecules, wherein the first layer is arranged between the second layer and the anode, wherein the second layer is arranged between the anode and the at least one light-emitting layer, wherein the dopant is a fluorinated sulfonimide metal salt of the following formula 1: ##STR00007## wherein M is either a divalent or higher-valent metal having an atomic mass of greater than 26 g/mol or a monovalent metal having an atomic mass of greater than or equal to 6 g/mol, wherein 1n7, wherein R.sub.1, R.sub.2 are selected independently of one another and from a group consisting of a fluorine-substituted aryl radical, a fluorine-substituted alkyl radical and a fluorine-substituted arylalkyl radical.

2. The organic electronic component according to claim 1, where M=copper and n=2.

3. The organic electronic component according to claim 1, wherein the first layer is formed as a hole injection layer and directly adjoins the anode, wherein the second layer is directly adjacent to the first layer and is formed as a hole-transport layer.

4. The organic electronic component according to claim 1, wherein the first matrix material and the second matrix material are identical, wherein the second layer is free of the dopant.

5. The organic electronic component according to claim 1, wherein the dopant is a p-type dopant and contains a proportion between and including 1% by volume and 30% by volume in the first matrix material.

6. The organic electronic component according to claim 1, wherein the first layer has a layer thickness of less than 50 nm and/or wherein the second layer has a layer thickness of 50 nm to 300 nm.

7. The organic electronic component according to claim 1, wherein the first and the second matrix material are the same, wherein the second layer is free of the dopant, wherein the dopant in the first layer has a proportion in the first matrix material between 1% by volume and 30% by volume, inclusive, wherein the first layer has a layer thickness of less than 50 nm, and wherein the second layer has a layer thickness of 50 nm to 300 nm.

8. The organic electronic component according to claim 1, wherein the first layer is hole injecting, wherein the fluorinated sulfonimide metal salt is a p-type dopant, which acts as an electron acceptor in relation to the first matrix material.

9. The organic electronic component according to claim 1, wherein M is copper, zinc, aluminium, bismuth, potassium, rubidium, cesium or tin.

10. The organic electronic component according to claim 1, wherein R.sub.1, R.sub.2 are selected independently of one another and from a group consisting of a linear or branched, at least partially fluorine-substituted alkyl radical having 1 to 10 carbon atoms, an at least partially fluorine-substituted aryl radical having 1 to 20 carbon atoms and an at least partially fluorine-substituted arylalkyl radical having 1 to 20 carbon atoms.

11. The organic electronic component according to claim 1, wherein R.sub.1 and R.sub.2 are the same substituents and are selected from the following group: ##STR00008##

12. The organic electronic component according to claim 1, which is an organic light-emitting diode.

13. The organic electronic component according to claim 1, which is a solar cell, a photodetector or an organic field-effect transistor.

14. The organic electronic component according to claim 1, wherein the first layer is produced by co-deposition of the matrix material and of the dopant via physical vapour deposition.

15. The organic electronic component according to claim 1, wherein the first layer is produced by means of a wet-chemical method.

16. The organic electronic component according to claim 1, wherein the first and/or second matrix material are selected independently of one another from a group consisting of HTM014, HTM081, HTM163, HTM222, NHT5, NHT49, NHT51, EL-301, EL-22T, HTM226, HTM355, HTM133, HTM334 and HTM604.

17. The method for producing an organic electronic component according to claim 1 comprising the steps of: A) provision of the anode, B) applying the first layer to the anode, which acts in a hole injecting manner, wherein the dopant has a proportion between 1 vol. % (inclusive) and 30% vol. % (inclusive) in the first matrix material, C) applying the second layer, which acts in a hole-transporting manner, to the first layer, D) applying the at least one light-emitting layer to the second layer, and E) applying the cathode to the at least one light-emitting layer.

18. An organic electronic component comprising a cathode, an anode, at least one light-emitting layer which is arranged between the anode and the cathode, a hole injecting and/or hole transporting layer, which comprises a matrix material and a dopant, wherein the hole injecting and/or hole transporting layer is arranged between the anode and the at least one light-emitting layer, wherein the hole injecting and/or hole transporting layer comprises an interface doping with the dopant on the anode side, wherein the interface doping comprises a doping of only at least one interface of the hole injecting and/or hole transporting layer while the majority of the hole injecting and/or hole transporting layer remains undoped, wherein the dopant is a fluorinated sulfonimide metal salt of the following formula 1: ##STR00009## wherein M is either a divalent or higher-valent metal having an atomic mass of greater than 26 g/mol or a monovalent metal having an atomic mass of greater than or equal to 6 g/mol, wherein 1n7, and wherein R.sub.1, R.sub.2 are selected independently of one another and from a group consisting of a fluorine-substituted aryl radical, a fluorine-substituted alkyl radical and a fluorine-substituted arylalkyl radical.

Description

(1) Further advantages, advantageous embodiments and developments will become apparent from the exemplary embodiments described below in conjunction with the figures.

(2) FIG. 1A shows a schematic side view of a comparative example of an organic electronic component,

(3) FIG. 1B shows a schematic side view of an exemplary embodiment of an organic electronic component described here,

(4) FIG. 2 shows measurement data of physical properties according to a plurality of exemplary embodiments of an organic electronic component described here,

(5) FIG. 3 shows the normalized luminance as a function of the time of comparative examples and exemplary embodiments.

(6) In the exemplary embodiments and figures, identical or identically acting elements can in each case be provided with the same reference symbols. The elements illustrated and their size relationships among one another are not to be regarded as true to scale. Rather, individual elements such as, for example, layers, components and regions can be represented with an exaggerated size for better representability and/or for a better understanding.

(7) FIGS. 1A and 1B each show a schematic side view of an organic electronic component, in this case of an organic light-emitting diode 100 according to a comparison example (FIG. 1A) and an embodiment (FIG. 1B).

(8) The organic electronic component 100 of FIG. 1B has an anode 2. The anode is preferably applied to a substrate 1, for example made of glass. In particular, the substrate 1 and the anode 2 form a common layer. The anode 2 can be formed, for example, from indium tin oxide (ITO) or another transparent conductive oxide. The first layer is applied above the anode, in particular in direct mechanical contact. The first layer 3 has a first matrix material 31 and at least one dopant 32. The dopant 32 can be homogeneously distributed in the first layer. NHT51, for example, can be used as the first matrix material 31. The layer thickness of the first layer 3 can be, for example, between 5 nm or 10 nm and 20 nm inclusive. The first layer 3 can have a hole injecting effect. The second layer 4 can be arranged in direct mechanical contact over the first layer 3. The second layer 4 preferably has the same matrix material 41 as the first layer 3. The second matrix material 41 can alternatively also be different from the first matrix material 31. The layer thickness of the second layer 4 can preferably be between 50 nm and 300 nm. An electron-blocking layer 11, at least one light-emitting layer 5, a hole-blocking layer 6, an electron-injecting layer 8 and a cathode 9 can be arranged above the second layer 4. The cathode 9, for example, can be reflective. For example, the cathode is formed from aluminium.

(9) In comparison thereto, FIG. 1A shows an organic electronic component according to a comparative example. The component 100 of FIG. 1A differs from the component 100 of FIG. 1B in that the undoped second layer 4 is absent. For this purpose, however, the first layer 3 of the component of FIG. 1 is in particular provided with a larger layer thickness, that is to say with a layer thickness of between 50 nm and 300 nm inclusive. The component of FIG. 1A therefore has a full doping with a p-dopant for hole injection and/or hole transport in the first layer 3. In comparison thereto, the component of FIG. 1B has a so-called interface doping with a p-type dopant (first layer 3), wherein subsequently an undoped hole transport layer (second layer 4) is arranged, which is formed only from a second matrix material, that is to say without a dopant.

(10) FIG. 2 shows measurement data of physical properties of a component according to an embodiment and of comparative examples. As an example the dopant Cu(TFSI).sub.2 (abbreviated to Cu-TFSI) is used. In principle, however, other dopants disclosed here are also possible. A p-type dopant having 3% by volume is shown as the reference R. In this case, V means that a component of FIG. 1A has been used in which the dopant content in the first layer 3 is 1% by volume, 3% by volume and 5% by volume, respectively. The last three rows of the table show a component according to an embodiment, for example according to FIG. 1B, with a different proportion of the dopant of 1% by volume to 5% by volume in the first layer 3. L, Peff, Ieff, EQE and U mean luminance (L), power efficiency (Peff), current efficiency (Ieff), external quantum efficiency (EQE) and voltage (U).

(11) It is to be observed that a component according to the invention which has, for example, 1 vol. % Cu-TFSI can reach comparable values as a boundary surface doping as a conventional OLED having a proportion of cu-TFSI of 1 to 5% by volume and the reference of a p-type dopant having a proportion of 3% by volume.

(12) FIG. 3 shows the normalized luminescence L/L0 as a function of the time tin hours h.

(13) The curves 31 show a component, for example according to the embodiment of FIG. 1B, with a dopant, for example Cu(TFSI).sub.2 with a proportion of 1, 3 and 5% by volume. Curve 3-2 shows the reference of the p-type dopant with one in the proportion of 3% and the curves 3-3 show a component according to FIG. 1A, in which Cu(TFSI).sub.2 with a proportion of 1% by volume, 3% by volume or 5% by volume is used. The arrow in the curves 3-3 shows that the concentration of the dopant increases in the direction of the arrow.

(14) It can be seen from the graphic that a clear improvement in the service life of components, in particular for OLEDs, with the dopant, for example Cu(TFSI).sub.2, can be achieved according to the embodiment. Furthermore, it can be seen from the figure that the service life is independent of the proportion of the dopant, in particular the proportion of Cu(TFSI).sub.2.

(15) Preparation of Fluorinated Sulfonimide Metal Salts

(16) 1. Purification of Zinc Bis (Trifluoromethanesulfonimide), Zn(TFSI).sub.2

(17) Zn(TFSI).sub.2 (CAS: 1616106-25-0) is commercially available from Sigma-Aldrich. The solid was sublimed in a high vacuum. The input weight is 800 mg, and the output weight is 156 mg. The temperature is 174 to 178 C. at a pressure of approximately 5.Math.10.sup.6 mbar. The product was obtained as a white amorphous solid.

(18) 2. Purification of Copper Bis (Trifluoromethanesulfonimide), Cu(TFSI).sub.2

(19) Cu(TFSI).sub.2.xH2O (CAS: 1334406-76-6) is commercially available from Sigma-Aldrich. The solid was sublimated twice in a high vacuum. The first sublimation took place at an input weight of 580 mg and an output weight of 331 mg at a temperature of 115 to 145 C. The product was obtained as a white amorphous solid. The second sublimation took place at an input weight of 331 mg and an output weight of 266 mg at a temperature of 115 to 145 C. The product was obtained as a white amorphous solid.

(20) 3. Purification of Lithium Trifluoromethanesulfonimide, Li(TFSI)

(21) Li(TFSI) (CAS: 9076-65-6) is commercially available from Sigma-Aldrich. The solid was distilled twice under high vacuum. The first distillation took place at an input weight of 1.2 g and an output weight of 0.92 g. The white Li(TFSI) is liquid at 225 to 230 C. and distilled at 250 to 270 C. as a white amorphous solid. The second distillation took place at an input weight of 0.92 g and an output weight of 0.40 g and a temperature of 250 to 270 C. The product is obtained as a white amorphous solid.

(22) 4. Purification of Sodium Trifluoromethanesulfonimide, Na(TFSI)

(23) Na(TFSI) (CAS: 91742-21-1) is commercially available from Sigma-Aldrich. The solid was distilled twice under high vacuum. The first distillation took place at an input weight of 505 mg and an output weight of 410 mg. The white Na(TFSI) is liquid at 265 C. and distilled at 270 to 295 C. as a white partially crystalline solid. The second distillation took place at an input weight of 410 mg and an output weight of 270 mg and a temperature of 270 to 275 C. The product is obtained as a white solid.

(24) 5. Purification of Potassium-Trifluoromethanesulfonimide, K(TFSI)

(25) K(TFSI) (CAS: 9076-67-8) is commercially available from Sigma-Aldrich. The solid was distilled twice in a high vacuum in the ball tube. The first distillation took place at an initial weight of 482 mg and a balance of 366 mg. The white K(TFSI) is liquid at 205 C. and distilled at 270 to 290 C. The second distillation took place at an input weight of 366 mg and an output weight of 241 mg at a temperature of 270 to 285 C.

(26) The exemplary embodiments described in conjunction with the figures and the features thereof can also be combined with one another in accordance with further exemplary embodiments, even if such combinations are not explicitly shown in the figures. Furthermore, the exemplary embodiments described in conjunction with the figures can have additional or alternative features according to the description in the general part.

(27) The invention is not restricted by the description on the basis of the exemplary embodiments. Rather, the invention encompasses any new feature and also any combination of features, which includes in particular any combination of features in the patent claims, even if this feature or this combination itself is not explicitly specified in the patent claims or exemplary embodiments.

(28) This patent application claims the priority of German patent application 10 2017 111 425.4, the disclosure content of which is hereby incorporated by reference.

LIST OF REFERENCE NUMERALS

(29) 1 substrate 2 anode 3 first layer 4 second layer 5 light-emitting layer 6 hole-blocking layer 7 electron-transporting layer 8 electron-injecting layer 9 cathode 10 organic electronic component 11 electron-blocking layer 100 organic light-emitting diode 31 first matrix material 32 dopant 41 second matrix material