Organic Electronic Device Comprising a Compound of Formula (I), Display Device Comprising the Organic Electronic Device as Well as Compounds of Formula (I) for Use in Organic Electronic Devices

Abstract

The present invention relates to an organic electronic device comprising a compound of formula (I) and a display device comprising the organic electronic device. The invention further relates to novel compounds of formula (I) which can be of use in organic electronic devices.

Claims

1. An organic electronic device comprising an anode layer, a cathode layer and a charge generation layer, wherein the charge generation layer comprises a p-type charge generation layer and a n-type charge generation layer, wherein the p-type charge generation layer comprises a compound of formula (I) ##STR00538## whereby A.sup.1 is selected from formula (II) ##STR00539## X.sup.1 is selected from CR.sup.1 or N; X.sup.2 is selected from CR.sup.2 or N; X.sup.3 is selected from CR.sup.3 or N; X.sup.4 is selected from CR.sup.4 or N; X.sup.5 is selected from CR.sup.5 or N; whereby when any of R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 is present, then the corresponding X.sup.1, X.sup.2, X.sup.3, X.sup.4 and X.sup.5 is not N; wherein “*” denotes the binding position; with the proviso that R.sup.1 (if present) is selected from D or H; and at least one of R.sup.2, R.sup.3, R.sup.4 is present and for each of the R.sup.2, R.sup.3, R.sup.4 that are present, the corresponding σ.sup.x is >0.33, with σ.sup.x being the Hammett constant of R.sup.x; A.sup.2 and A.sup.3 are independently selected from formula (III) ##STR00540## wherein Ar is independently selected from substituted or unsubstituted C.sub.6 to C.sub.18 aryl and substituted or unsubstituted C.sub.2 to C.sub.18 heteroaryl, wherein the substituents on Ar are independently selected from CN, partially or perfluorinated C.sub.1 to C.sub.6 alkyl, halogen, Cl, F, D; and R′ is selected from Ar, substituted or unsubstituted C.sub.6 to C.sub.18 aryl or C.sub.3 to C.sub.18 heteroaryl, partially fluorinated or perfluorinated C.sub.1 to C.sub.8 alkyl, halogen, F or CN.

2. The device of claim 1, whereby the p-type charge generation layer comprises a compound of formula (IV) ##STR00541## whereby B.sup.1 is selected from formula (V) ##STR00542## B.sup.3 and B.sup.5 are Ar and B.sup.2, B.sup.4 and B.sup.6 are R′.

3. The device of claim 1, whereby σ.sup.total>0.5, with σ.sup.total=σ.sup.2+σ.sup.3+σ.sup.4 and σ.sup.x being the Hammett constant of R.sup.x (if present).

4. The device of claim 1, whereby the compound of formula (I) comprises less than nine cyano moieties.

5. The device of claim 1, whereby the LUMO of the compound of formula (I) is ≤−5.05 eV.

6. The device of claim 1, whereby R.sup.5 (if present) is selected from D or H.

7. The device of claim 1, whereby σ.sup.total is >0.6.

8. The organic electronic device of claim 1, whereby the p-type charge generation layer comprises a composition comprising a compound of formula (IV) and at least one compound of formula (IVa) to (IVd) ##STR00543##

9. The organic electronic device of claim 1, wherein the p-type charge generation layer further comprises a substantially covalent matrix compound.

10. The organic electronic device of claim 1, further comprising a hole injection layer, wherein the hole injection layer is arranged between the anode layer and the charge generation layer and whereby the hole injection layer comprises a compound of formula (I) or (IV).

11. The organic electronic device of claim 1, whereby the p-type charge generation layer and the hole injection layer comprise an identical compound of formula (I) or (IV).

12. The organic electronic device of claim 1, whereby the p-type charge generation layer and the hole injection layer comprise an identical substantially covalent matrix compound.

13. The organic electronic device of claim 1, whereby the electronic organic device is an electroluminescent device.

14. A display device comprising an organic electronic device according to claim 1.

15. A compound of formula (I) of claim 1 having less than nine cyano moieties and a LUMO of ≤−5.05 eV.

Description

DESCRIPTION OF THE DRAWINGS

[0223] The aforementioned components, as well as the claimed components and the components to be used in accordance with the invention in the described embodiments, are not subject to any special exceptions with respect to their size, shape, material selection and technical concept such that the selection criteria known in the pertinent field can be applied without limitations.

[0224] Additional details, characteristics and advantages of the object of the invention are disclosed in the dependent claims and the following description of the respective figures which in an exemplary fashion show preferred embodiments according to the invention. Any embodiment does not necessarily represent the full scope of the invention, however, and reference is made therefore to the claims and herein for interpreting the scope of the invention. It is to be understood that both the foregoing general description and the following detailed description are exemplary and explanatory only and are intended to provide further explanation of the present invention as claimed.

[0225] FIG. 1 is a schematic sectional view of an OLED comprising a charge generation layer, according to an exemplary embodiment of the present invention.

[0226] FIG. 2 is a schematic sectional view of a stacked OLED comprising a charge generation layer, according to an exemplary embodiment of the present invention.

[0227] Hereinafter, the figures are illustrated in more detail with reference to examples. However, the present disclosure is not limited to the following figures.

[0228] Herein, when a first element is referred to as being formed or disposed “on” or “onto” a second element, the first element can be disposed directly on the second element, or one or more other elements may be disposed there between. When a first element is referred to as being formed or disposed “directly on” or “directly onto” a second element, no other elements are disposed there between.

[0229] FIG. 1 is a schematic sectional view of an OLED 100, according to one exemplary embodiment of the present invention.

[0230] Referring to FIG. 1 the OLED 100 includes a substrate 110, an anode layer 120, a hole injection layer (HIL) 130, a first hole transport layer (HTL1) 140, an electron blocking layer (EBL) 145, an emission layer (EML) 150, a hole blocking layer (HBL) 155, an electron transport layer (ETL) 160, an n-type charge generation layer (n-CGL) 185, a p-type charge generation layer (p-GCL) 135 which may comprise a compound of Formula (I), a second hole transport layer (HTL2) 141, and electron injection layer (EIL) 180 and a cathode layer 190. The HIL may comprise a compound of Formula (I).

[0231] FIG. 2 is a schematic sectional view of a stacked OLED 100, according to another exemplary embodiment of the present invention. FIG. 2 differs from FIG. 1 in that the OLED 100 of FIG. 1 further comprises a second emission layer.

[0232] Referring to FIG. 2 the OLED 100 includes a substrate 110, an anode layer 120, a hole injection layer (HIL) 130, a first hole transport layer (HTL) 140, a first electron blocking layer (EBL) 145, a first emission layer (EML) 150, an optional first hole blocking layer (HBL) 155, a first electron transport layer (ETL) 160, an n-type charge generation layer (n-CGL) 185, a p-type charge generation layer (p-GCL) 135 which may comprise compound of Formula (I), a second hole transport layer (HTL) 141, a second electron blocking layer (EBL) 146, a second emission layer (EML) 151, an optional second hole blocking layer (HBL) 156, a second electron transport layer (ETL) 161, an electron injection layer (EIL) 181 and a cathode layer 190. The HIL may comprise a compound of Formula (I).

[0233] In the description above the method of manufacture an OLED 100 of the present invention is started with a substrate 110 onto which an anode layer 120 is formed, on the anode layer 120, a hole injection layer 130, a first hole transport layer 140, optional a first electron blocking layer 145, a first emission layer 150, optional a first hole blocking layer 155, optional at least one first electron transport layer 160, an n-CGL 185, a p-CGL 135, a second hole transport layer 141, optional a second electron blocking layer 146, a second emission layer 151, an optional second hole blocking layer 156, an optional at least one second electron transport layer 161, an optional electron injection layer 180 and a cathode layer 190 are formed, in that order or the other way around.

[0234] While not shown in FIGS. 1 and 2, a capping and/or a sealing layer may further be formed on the cathode layer 190, in order to seal the organic electronic device 100. In addition, various other modifications may be applied thereto.

[0235] Hereinafter, one or more exemplary embodiments of the present invention will be described in detail with, reference to the following examples. However, these examples are not intended to limit the purpose and scope of the one or more exemplary embodiments of the present invention.

DETAILED DESCRIPTION

[0236] The invention is furthermore illustrated by the following examples which are illustrative only and non-binding.

[0237] Compounds of formula (I) may be prepared as described in EP2180029A1 and WO2016097017A1.

HOMO and LUMO

[0238] The HOMO and LUMO are calculated with the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany). The optimized geometries and the HOMO and LUMO energy levels of the molecular structures are determined by applying the hybrid functional B3LYP with a 6-31G* basis set in the gas phase. If more than one conformation is viable, the conformation with the lowest total energy is selected.

Thermogravimetric Analysis

[0239] The term “TGA5%” denotes the temperature at which 5% weight loss occurs during thermogravimetric analysis and is measured in ° C.

[0240] The TGA5% value may be determined by by heating a 9-11 mg sample in a thermogravimetric analyser at a heating rate of 10 K/min in an open 100 μL aluminium pan, under a stream of nitrogen at a flow rate of 20 mL/min in the balance area and of 30 mL/min in the oven area.

[0241] The TGA5% value may provide an indirect measure of the volatility and/or decomposition temperature of a compound. In first approximation, the higher the TGA5% value the lower is the volatility of a compound and/or the higher the decomposition temperature.

[0242] According to one embodiment, the TGA5% value of compound of formula (I) is selected in the range of ≥270° C. and ≤450° C.; preferably of ≥280° C. and ≤440° C., also preferred of ≥295° C. and ≤43° C.

Glass Transition Temperature The glass transition temperature, also named Tg, is measured in ° C. and determined by Differential Scanning Calorimetry (DSC).

[0243] The glass transition temperature is measured under nitrogen and using a heating rate of 10 K per min in a Mettler Toledo DSC 822e differential scanning calorimeter as described in DIN EN ISO 11357, published in March 2010.

General Procedure for Fabrication of OLEDs with a Transparent Anode Layer (Bottom Emission Device)

[0244] For OLEDs, see Table 5, a 152/cm.sup.2 glass substrate with 90 nm ITO (available from Corning Co.) was cut to a size of 50 mm×50 mm×0.7 mm, ultrasonically washed with isopropyl alcohol for 5 minutes and then with pure water for 5 minutes, and washed again with UV ozone for 30 minutes, to prepare the anode.

[0245] Then a substantially covalent matrix compound and a compound of formula (1) or a comparative compound was vacuum co-deposited on the anode, to form a HIL having a thickness of 10 nm. The composition of the HIL can be seen in Table 5.

[0246] Then the same substantially covalent matrix compound was vacuum deposited on the HIL, to form a first HTL having a thickness of 128 nm.

[0247] Then N,N-di([1,1′-biphenyl]-4-yl)-3′-(9H-carbazol-9-yl)-[1,1′-biphenyl]-4-amine was vacuum deposited on the first HTL, to form a first electron blocking layer (EBL1) having a thickness of 5 nm.

[0248] Then 97 vol.-% H09 (Sun Fine Chemicals, Korea) as EML host and 3 vol.-% BD200 (Sun Fine Chemicals, Korea) as fluorescent blue dopant were deposited on the EBL, to form a first emission layer (EML1) with a thickness of 20 nm.

[0249] Then a first electron transport layer (ETL1) is formed on the first emission layer by depositing 2,4-diphenyl-6-(3′-(triphenylen-2-yl)-[1,1′-biphenyl]-3-yl)-1,3,5-triazine having a thickness of 25 nm.

[0250] Then, the n-CGL having a thickness of 10 nm is formed on the ETL by co-depositing 99 vol.-% 2,2′-(1,3-Phenylene)bis[9-phenyl-1,10-phenanthroline] and 3 vol.-% Li.

[0251] Then, the p-CGL having a thickness of 10 nm is formed on the n-CGL by co-depositing a substantially covalent matrix compound and a compound of formula (I). The composition of the p-CGL can be seen in Table 5.

[0252] Then, a second hole transport layer (HTL2) having a thickness of 25 nm is formed on the p-CGL by depositing a substantially covalent matrix compound as in the first hole transport layer. The composition of the second hole transport layer is the same as of the first hole transport layer.

[0253] Then N,N-di([1,1′-biphenyl]-4-yl)-3′-(9H-carbazol-9-yl)-[1,1′-biphenyl]-4-amine was vacuum deposited on the second HTL, to form a second electron blocking layer (EBL2) having a thickness of 5 nm.

[0254] Then 97 vol.-% H09 (Sun Fine Chemicals, Korea) as EML host and 3 vol.-% BD200 (Sun Fine Chemicals, Korea) as fluorescent blue dopant were deposited on the EBL, to form a second emission layer (EML2) with a thickness of 20 nm.

[0255] Then a second electron transport layer (ETL2) is formed on the second emission layer by depositing 2,4-diphenyl-6-(3′-(triphenylen-2-yl)-[1,1′-biphenyl]-3-yl)-1,3,5-triazine having a thickness of 26 nm.

[0256] Then, the electron injection layer having a thickness of 10 nm is formed on the second electron transport layer by co-depositing 99 vol.-% 2,2′-(1,3-Phenylene)bis[9-phenyl-1,10-phenanthroline] and 3 vol.-% Li.

[0257] Then Al is vacuum deposited on the electron injection layer at a rate of 0.01 to 1 Å/s at 10-7 mbar to form a cathode layer with a thickness of 100 nm.

[0258] The OLED stack is protected from ambient conditions by encapsulation of the device with a glass slide. Thereby, a cavity is formed, which includes a getter material for further protection.

[0259] General Procedure for Fabrication of OLEDs with a Transparent Cathode Layer (Top Emission Device)

[0260] For OLEDs comprising a CGL, see Table 6, a glass substrate was cut to a size of 50 mm×50 mm×0.7 mm, ultrasonically washed with isopropyl alcohol for 5 minutes and then with pure water for 5 minutes, and washed again with UV ozone for 30 minutes, to prepare the substrate.

[0261] Then, the anode layer having a thickness of 100 nm is formed on the substrate by vacuum depositing Ag at a rate of 0.01 to 1 Å/s at 10.sup.−7 mbar.

[0262] Then, a hole injection layer (HIL) having a thickness of 10 nm is formed on the anode layer by co-depositing a substantially covalent matrix compound and a compound of formula (I) or a comparative compound. The composition of the HIL can be seen in Table 6.

[0263] Then, a first hole transport layer (HTL1) having a thickness of 34 nm is formed on the HIL by depositing the substantially covalent matrix compound. The substantially covalent matrix compound is the same as in the HIL.

[0264] Then, an electron blocking layer (EBL) having a thickness of 5 nm is formed on the HTL1 by depositing N-([1,1′-biphenyl]-4-yl)-9,9-diphenyl-N-(4-(triphenylsilyl)phenyl)-9H-fluoren-2-amine.

[0265] Then, a first emission layer (EML1) having a thickness of 20 nm is formed on the EBL by co-depositing 97 vol.-% H09 (Sun Fine Chemicals, Korea) as EMVL host and 3 vol.-% BD200 (Sun Fine Chemicals, Korea) as fluorescent blue dopant.

[0266] Then, a hole blocking layer (HBL) is formed with a thickness of 5 nm is formed on the first emission layer by depositing 2-(3′-(9,9-dimethyl-9H-fluoren-2-yl)-[1,1′-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine.

[0267] Then, an electron transporting layer (ETL) having a thickness of 20 nm is formed on the hole blocking layer by co-depositing 50 wt.-% 2-([1,1′-biphenyl]-4-yl)-4-(9,9-diphenyl-9H-fluoren-4-yl)-6-phenyl-1,3,5-triazine and 50 wt.-% LiQ.

[0268] Then, the n-CGL having a thickness of 10 nm is formed on the ETL by co-depositing 99 vol.-% 2,2′-(1,3-Phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 vol.-% Li.

[0269] Then, the p-CGL is formed on the n-CGL by co-depositing a substantially covalent matrix compound and a compound of formula (I) having a thickness of 10 nm. The composition of the p-CGL can be seen in Table 6.

[0270] Then, a second hole transport layer (HTL2) having a thickness of 81 nm is formed on the p-CGL by depositing a substantially covalent matrix compound. The composition of the second hole transport layer is the same as of the first hole transport layer.

[0271] Then, an electron injection layer (EIL) having a thickness of 2 nm is formed on the HTL2 by depositing Yb.

[0272] Then, the cathode layer having a thickness of 13 nm is formed on the EIL by co-depositing Ag:Mg (90:10 vol.-%) at a rate of 0.01 to 1 Å/s at 10.sup.−7 mbar.

[0273] Then, a capping layer having a thickness of 75 nm is formed on the cathode layer by depositing compound of formula F3.

[0274] The OLED stack is protected from ambient conditions by encapsulation of the device with a glass slide. Thereby, a cavity is formed, which includes a getter material for further protection.

[0275] To assess the performance of the inventive examples compared to the prior art, the current efficiency is measured at 20° C. The current-voltage characteristic is determined using a Keithley 2635 source measure unit, by sourcing a voltage in V and measuring the current in mA flowing through the device under test. The voltage applied to the device is varied in steps of 0.1V in the range between 0V and 10V. Likewise, the luminance-voltage characteristics and CIE coordinates are determined by measuring the luminance in cd/m.sup.2 using an Instrument Systems CAS-140CT array spectrometer (calibrated by Deutsche Akkreditierungsstelle (DAkkS)) for each of the voltage values. The cd/A efficiency at 10 mA/cm2 is determined by interpolating the luminance-voltage and current-voltage characteristics, respectively.

[0276] In bottom emission devices, the emission is predominately Lambertian and quantified in percent external quantum efficiency (EQE). To determine the efficiency EQE in % the light output of the device is measured using a calibrated photodiode at 10 mA/cm2.

[0277] In top emission devices, the emission is forward directed, non-Lambertian and also highly dependent on the micro-cavity. Therefore, the efficiency EQE will be higher compared to bottom emission devices. To determine the efficiency EQE in % the light output of the device is measured using a calibrated photodiode at 10 mA/cm.sup.2.

[0278] Lifetime LT of the device is measured at ambient conditions (20° C.) and 30 mA/cm.sup.2, using a Keithley 2400 sourcemeter, and recorded in hours.

[0279] The brightness of the device is measured using a calibrated photo diode. The lifetime LT is defined as the time till the brightness of the device is reduced to 97% of its initial value.

[0280] The increase in operating voltage U over time “U rise (100-1 h)” is measured by determining the difference in operating voltage at 30 mA/cm.sup.2 after 1 hour and after 50 hours.

[0281] The increase in operating voltage U over time “U rise (400-1 h)” is measured by determining the difference in operating voltage at 30 mA/cm.sup.2 after 1 hour and after 400 hours.

Technical Effect of the Invention

[0282] In Table 2 are shown LUMO levels for Examples A1 to A82. LUMO levels were calculated with the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) by applying the hybrid functional B3LYP with a 6-31G* basis set in the gas phase

TABLE-US-00004 TABLE 2 Structure of the inventive compounds A1 to A82 and their LUMOs LUMO A.sup.1 A.sup.2 A.sup.3 [eV] A1 [00286] [00287] [00288] −5.36 A2 [00289] [00290] [00291] −5.25 A3 [00292] [00293] [00294] −5.34 A4 [00295] [00296] [00297] −5.29 A5 [00298] [00299] [00300] −5.19 A6 [00301] [00302] [00303] −5.05 A7 [00304] [00305] [00306] −5.15 A8 [00307] [00308] [00309] −5.22 A9 [00310] [00311] [00312] −5.14 A10 [00313] [00314] [00315] −5.17 A11 [00316] [00317] [00318] −5.17 A12 [00319] [00320] [00321] −5.19 A13 [00322] [00323] [00324] −5.29 A14 [00325] [00326] [00327] −5.20 A15 [00328] [00329] [00330] −5.19 A16 [00331] [00332] [00333] −5.26 A17 [00334] [00335] [00336] −5.51 A18 [00337] [00338] [00339] −5.36 A19 [00340] [00341] [00342] −5.39 A20 [00343] [00344] [00345] −5.29 A21 [00346] [00347] [00348] −5.15 A22 [00349] [00350] [00351] −5.25 A23 [00352] [00353] [00354] −5.24 A24 [00355] [00356] [00357] −5.27 A25 [00358] [00359] [00360] −5.12 A26 [00361] [00362] [00363] −5.16 A27 [00364] [00365] [00366] −5.23 A28 [00367] [00368] [00369] −5.26 A29 [00370] [00371] [00372] −5.12 A30 [00373] [00374] [00375] −5.24 A31 [00376] [00377] [00378] −5.22 A32 [00379] [00380] [00381] −5.06 A33 [00382] [00383] [00384] −5.15 A34 [00385] [00386] [00387] −5.26 A35 [00388] [00389] [00390] −5.33 A36 [00391] [00392] [00393] −5.24 A37 [00394] [00395] [00396] −5.35 A38 [00397] [00398] [00399] −5.55 A39 [00400] [00401] [00402] −5.38 A40 [00403] [00404] [00405] −5.42 A41 [00406] [00407] [00408] −5.32 A42 [00409] [00410] [00411] −5.18 A43 [00412] [00413] [00414] −5.28 A44 [00415] [00416] [00417] −5.26 A45 [00418] [00419] [00420] −5.27 A46 [00421] [00422] [00423] −5.60 A47 [00424] [00425] [00426] −5.39 A48 [00427] [00428] [00429] −5.45 A49 [00430] [00431] [00432] −5.35 A50 [00433] [00434] [00435] −5.21 A51 [00436] [00437] [00438] −5.31 A52 [00439] [00440] [00441] −5.30 A53 [00442] [00443] [00444] −5.30 A54 [00445] [00446] [00447] −5.33 A55 [00448] [00449] [00450] −5.24 A56 [00451] [00452] [00453] −5.28 A57 [00454] [00455] [00456] −5.35 A58 [00457] [00458] [00459] −5.19 A59 [00460] [00461] [00462] −5.19 A60 [00463] [00464] [00465] −5.19 A61 [00466] [00467] [00468] −5.30 A62 [00469] [00470] [00471] −5.58 A63 [00472] [00473] [00474] −5.32 A64 [00475] [00476] [00477] −5.39 A65 [00478] [00479] [00480] −5.14 A66 [00481] [00482] [00483] −5.13 A67 [00484] [00485] [00486] −5.17 A68 [00487] [00488] [00489] −5.36 A69 [00490] [00491] [00492] −5.31 A70 [00493] [00494] [00495] −5.37 A71 [00496] [00497] [00498] −5.34 A72 [00499] [00500] [00501] −5.32 A73 [00502] [00503] [00504] −5.15 A74 [00505] [00506] [00507] −5.18 A75 [00508] [00509] [00510] −5.42 A76 [00511] [00512] [00513] −5.33 A77 [00514] [00515] [00516] −5.28 A78 [00517] [00518] [00519] −5.22 A79 [00520] [00521] [00522] −5.50 A80 [00523] [00524] [00525] −5.29 A81 [00526] [00527] [00528] −5.40 A82 [00529] [00530] [00531] −5.26

[0283] Additionally two comparative compounds 1 and 2 were used, the structure of which is shown in Table 3.

TABLE-US-00005 TABLE 3 Structure of the comparative examples 1 and 2 A.sup.1 A.sup.2 A.sup.3 Comparative compound 1 (CC1) [00532] [00533] [00534] Comparative compound 2 (CC2) [00535] [00536] [00537]

[0284] In Table 4 are shown some physical properties of several inventive compounds and the two comparative compounds 1 and 2:

TABLE-US-00006 TABLE 4 Physical properties of three compounds of formula (I) and comparative compounds 1 and 2 LUMO TGA5% Tg [eV] [° C.] [° C.] Comparative compound 1 (CC1) −4.58 264  65 Comparative compound 2 (CC2) −4.90 270  78 Compound A1 −5.36 419 n/obs Compound A2 −5.30 381 130 Compound A30 −5.24 403 n/obs Compound A55 −5.24 396 n/obs Compound A76 −5.19 339 107

[0285] As can be seen in Table 4, compounds of formula (I) may have improved LUMO values, reduced volatility as determined by TGA5% and/or improved glass transition temperatures.

[0286] In Table 5 are shown data for bottom emission devices. The light is emitted through the transparent anode and substrate.

[0287] In comparative example 1-1 the p-CGL comprises a substantially covalent matrix compound of formula F11 and comparative compound CC1. The LUMO of CC1 is −4.58 eV and the Tg is 65° C., see Table 4. The operating voltage U is 9.83 V. Lifetime and voltage rise over time were not determined due to the high operating voltage.

[0288] In comparative example 1-2, the p-CGL comprises a substantially covalent matrix compound of formula F11 and comparative compound CC2. The LUMO of CC2 is −4.9 eV the Tg is 78° C., see Table 4. The operating voltage U is improved to 8.04 V. The lifetime is 144 hours and the voltage rise over time (100-1 h) is 0.09 V and the voltage rise over time (400-1 h) is 0.193 V.

[0289] In example 1-1, the p-CGL comprises a substantially covalent matrix compound of formula F11 and compound of formula (I) A1. The LUMO of A1 is −5.36 eV, see Table 4. The operating voltage U is improved to 7.58 V. The lifetime is improved to 153 hours and the voltage rise over time (100-1 h) is improved to 0.059 V and the voltage rise over time (400-1 h) is improved to 0.13 V.

[0290] In example 1-2, the amount of compound of formula (I) A1 in the p-CGL has been increased from 5 to 10 vol.-% compared to example 1-1. The operating voltage U is further improved to 7.38 V. The lifetime is unchanged at 153 hours and the voltage rise over time (100-1 h) is 0.054 V and the voltage rise over time (400-1 h) is 0.124 V.

[0291] In example 1-3, the p-CGL comprises a substantially covalent matrix compound of formula F11 and compound of formula (I) A55. The LUMO of A55 is −5.24 eV, see Table 4. The operating voltage U is improved to 7.47 V. The lifetime is improved to 156 hours and the voltage rise over time (100-1 h) is improved to 0.062 V and the voltage rise over time (400-1 h) is improved to 0.135 V.

[0292] In example 1-4, the p-CGL comprises a substantially covalent matrix compound of formula F11 and compound of formula (I) A30. The LUMO of A30 is −5.24 eV, see Table 4. The operating voltage U is improved to 7.45 V. The lifetime is improved to 151 hours and the voltage rise over time (100-1 h) is improved to 0.086 V and the voltage rise over time (400-1 h) is improved to 0.185 V.

[0293] In example 1-5, the p-CGL comprises a substantially covalent matrix compound of formula F11 and compound of formula (I) A76. The LUMO of A76 is −5.19 eV, see Table 4. The operating voltage U is improved to 7.43 V. The lifetime is improved to 157 hours and the voltage rise over time (100-1 h) is improved to 0.049 V and the voltage rise over time (400-1 h) is improved to 0.122 V.

[0294] In comparative example 1-3 the p-CGL and the HIL comprise a substantially covalent matrix compound of formula F11 and comparative compound CC1. The operating voltage U is >12 V. Lifetime and voltage rise over time were not determined due to the high operating voltage.

[0295] In comparative example 1-4, the p-CGL and the HIL comprise a substantially covalent matrix compound of formula F11 and comparative compound CC2. The operating voltage U is improved to 8.11 V. The lifetime is 150 hours and the voltage rise over time (100-1 h) is 0.092 V and the voltage rise over time (400-1 h) is 0.175 V.

[0296] In Example 1-6, the p-CGL and the HIL comprise a substantially covalent matrix compound of formula F11 and compound of formula (I) A1. The operating voltage U is improved to 7.61 V. The lifetime is improved to 159 hours and the voltage rise over time (100-1 h) is 0.077 V and the voltage rise over time (400-1 h) is 0.166 V.

[0297] In Example 1-7, the amount of compound of formula (I) A1 in the p-CGL has been increased from 5 to 10 vol.-% compared to example 1-3. The operating voltage U is further improved to 7.36 V. The lifetime is further improved to 168 hours and the voltage rise over time (100-1 h) is improved to 0.054 V and the voltage rise over time (400-1 h) is improved to 0.134 V.

[0298] In Example 1-8, the p-CGL and the HIL comprise a substantially covalent matrix compound of formula F11 and compound of formula (I) A2. The operating voltage U is improved to 7.61 V. The lifetime is improved to 157 hours and the voltage rise over time (100-1 h) is 0.083 V and the voltage rise over time (400-1 h) is 0.204 V.

[0299] In Example 1-9, the amount of compound of formula (I) A2 in the p-CGL has been increased from 5 to 10 vol.-% compared to Example 1-8. The operating voltage U is further improved to 7.39 V. The lifetime is further improved to 159 hours and the voltage rise over time (100-1 h) is improved to 0.063 V and the voltage rise over time (400-1 h) is improved to 0.173 V.

[0300] In Table 6 are shown data for top emission devices. The light is emitted through the transparent cathode.

[0301] In comparative example 2-1 the p-CGL comprises a substantially covalent matrix compound of formula F11 and comparative compound CC1. The operating voltage U is >12 V. In comparative example 2-2, the p-CGL comprises a substantially covalent matrix compound of formula F11 and comparative compound CC2. The operating voltage U is improved to 6.77 V.

[0302] In example 2-1, the p-CGL comprises a substantially covalent matrix compound of formula F11 and compound of formula (I) A1. The operating voltage U is further improved to 6.26 V.

[0303] In example 2-2, the amount of compound of formula (I) A1 in the p-CGL has been increased from 5 to 10 vol.-% compared to example 1-1. The operating voltage U is further improved to 6.13 V.

[0304] In example 2-3, the p-CGL comprises a substantially covalent matrix compound of formula F11 and compound of formula (I) A55. The operating voltage U is improved to 6.24 V compared to comparative example 2-2.

[0305] In example 2-4, the p-CGL comprises a substantially covalent matrix compound of formula F11 and compound of formula (I) A30. The operating voltage U is improved to 6.17 V compared to comparative example 2-2.

[0306] In example 2-5, the p-CGL comprises a substantially covalent matrix compound of formula F11 and compound of formula (I) A76. The operating voltage U is improved to 6.08 V compared to comparative example 2-2.

[0307] In comparative Example 2-3 the p-CGL and the HIL comprise a substantially covalent matrix compound of formula F11 and comparative compound CC1. The operating voltage U is >12 V.

[0308] In comparative Example 2-4, the p-CGL and the HIL comprise a substantially covalent matrix compound of formula F11 and comparative compound CC2. The operating voltage U is improved to 6.92 V.

[0309] In Example 2-6, the p-CGL and the HIL comprise a substantially covalent matrix compound of formula F11 and compound of formula (I) A1. The operating voltage U is further improved to 6.36 V.

[0310] In Example 2-7, the amount of compound of formula (I) A1 in the p-CGL has been increased from 5 to 10 vol.-% compared to example 1-3. The operating voltage U is further improved to 6.22 V.

[0311] A low operating voltage U may be beneficial for reduced power consumption and improved battery life, in particular in mobile devices.

[0312] The particular combinations of elements and features in the above detailed embodiments are exemplary only; the interchanging and substitution of these teachings with other teachings in this and the patents/applications incorporated by reference are also expressly contemplated. As those skilled in the art will recognize, variations, modifications, and other implementations of what is described herein can occur to those of ordinary skill in the art without departing from the spirit and the scope of the invention as claimed. Accordingly, the foregoing description is by way of example only and is not intended as limiting. In the claims, the word “comprising” does not exclude other elements or steps, and the indefinite article “a” or “an” does not exclude a plurality. The mere fact that certain measures are recited in mutually different dependent claims does not indicate that a combination of these measured cannot be used to advantage. The invention's scope is defined in the following claims and the equivalents thereto. Furthermore, reference signs used in the description and claims do not limit the scope of the invention as claimed.

TABLE-US-00007 TABLE 5 Organic electronic devices comprising a transparent anode, a p-type charge generation layer (p-CGL) comprising a compound of formula (I) and a substantially organic matrix compound HIL p-CGL Amount Amount LT at U rise U rise Compound compound of Compound compound of U at 15 30 (100-1 h) at (400-1 h) at Matrix of formula formula (I) Matrix of formula formula (I) mA/cm.sup.2 mA/cm.sup.2 30 mA/cm.sup.2 30 mA/cm.sup.2 compund (I) [vol.-%] compund (I) [vol.-%] [V] [h] [V] [V] Comparative F11 CC3 5 F11 CC1 5 9.83 — — — example 1-1 F11 Comparative F11 CC3 5 F11 CC2 5 8.04 144 0.09 0.193 example 1-2 Example 1-1 F11 CC3 5 F11 A1 5 7.58 153 0.059 0.13 Example 1-2 F11 CC3 5 F11 A1 10 7.38 153 0.054 0.124 Example 1-3 F11 CC3 5 F11 A55 10 7.47 156 0.062 0.135 Example 1-4 F11 CC3 5 F11 A30 10 7.45 151 0.086 0.185 Example 1-6 F11 CC3 5 F11 A76 10 7.43 157 0.049 0.122 Comparative F11 CC1 5 F11 CC1 5 >12 — — — example 1-3 Comparative F11 CC2 5 F11 CC2 5 8.11 150 0.092 0.175 example 1-4 Example 1-6 F11 A1 5 F11 A1 5 7.61 159 0.077 0.166 Example 1-7 F11 A1 5 F11 A1 10 7.36 168 0.054 0.134 Example 1-8 F11 A2 5 F11 A2 5 7.61 157 0.083 0.204 Example 1-9 F11 A2 5 F11 A2 10 7.39 159 0.063 0.173

TABLE-US-00008 TABLE 6 Organic electronic devices comprising a transparent cathode, a p-type charge generation layer (p-CGL) comprising a compound of formula (I) and a substantially organic matrix compound HIL p-CGL Amount Amount Compound compound of Compound compound of U at 15 Matrix of formula formula (I) Matrix of formula formula (I) mA/cm.sup.2 compund (I) [ vol.-%] compund (I) [ vol.-%] [V] Comparative F11 CC3 5 F11 CC1 5 >12 example 2-1 Comparative F11 CC3 5 F11 CC2 5 6.77 example 2-2 Example 2-1 F11 CC3 5 F11 A1 5 6.26 Example 2-2 F11 CC3 5 F11 A1 10 6.13 Example 2-3 F11 CC3 5 F11 A55 10 6.24 Example 2-4 F11 CC3 5 F11 A30 10 6.17 Example 2-5 F11 CC3 5 F11 A76 10 6.08 Comparative F11 CC1 5 F11 CC1 5 >12 Example 2-3 Comparative F11 CC2 5 F11 CC2 5 6.92 Example 2-4 Example 2-6 F11 A1 5 F11 A1 5 6.36 Example 2-7 F11 A1 5 F11 A1 10 6.22