Organic Compound of Formula (I) for Use in Organic Electronic Devices, an Organic Electronic Device Comprising a Compound of Formula (I) and a Display Device Comprising the Organic Electronic Device

Abstract

The present invention relates to a compound of formula (I) and an organic electronic device comprising a semiconductor layer which comprises a compound of formula (I).

Claims

1. A compound of formula (I) ##STR00124## whereby A.sup.1 is selected from formula (II) ##STR00125## 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; R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 (if present) are independently selected from CN, partially fluorinated or perfluorinated C.sub.1 to C.sub.8 alkyl, halogen, Cl, F, D or H, 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; with the proviso that at least one R.sup.1 to R.sup.5 is selected from D or H, and either R.sup.1 and/or R.sup.5 are independently selected from CN, partially fluorinated or perfluorinated C.sub.1 to C.sub.8 alkyl, or at least one R.sup.n and R.sup.n+1 (with n=1 to 4) are independently selected from CN, partially fluorinated or perfluorinated C.sub.1 to C.sub.8 alkyl; A.sup.2 and A.sup.3 are independently selected from formula (III) ##STR00126## 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 flurorinated or perfluorinated C.sub.1 to C.sub.8 alkyl, halogen, F or CN; and wherein the asterix “*” denotes the binding position.

2. The compound of claim 1, selected of the formula (IV) ##STR00127## whereby B.sup.1 is selected from formula (V) ##STR00128## B.sup.3 and B.sup.5 are Ar and B.sup.2, B.sup.4 and B.sup.6 are R′.

3. The compound of claim 1, whereby A.sup.1 and A.sup.3 are not identical.

4. The compound of claim 1, whereby X.sup.3 is CR.sup.3 and R.sup.3 is selected from partially fluorinated or perfluorinated C.sub.1 to C.sub.8 alkyl, halogen, Cl, F, D or H.

5. The compound of claim 1, whereby either X.sup.1 and/or X.sup.5 are C—CN.

6. The compound of claim 1, whereby X.sup.1 and/or X.sup.2 are C—CN.

7. The compound of claim 1, whereby X.sup.1 and X.sup.3 are C—CN.

8. The compound of claim 1, whereby at least three R.sup.1 to R.sup.5 are independently selected from CN, partially flurorinated or perfluorinated C.sub.1 to C.sub.8 alkyl, halogen, Cl, F; or one of X.sup.1 and X.sup.5 is N and one of R.sup.1 to R.sup.5 is independently selected from CN, partially flurorinated or perfluorinated C.sub.1 to C.sub.8 alkyl, halogen, Cl, F.

9. The compound claim 1, whereby two of X.sup.1 and X.sup.5 are N and two of R.sup.1 to R.sup.5 are independently selected from CN, partially fluorinated or perfluorinated C.sub.1 to C.sub.8 alkyl.

10. An organic electronic device comprising an anode layer, a cathode layer and at least one organic semiconductor layer, wherein the at least one organic semiconductor layer is arranged between the anode layer and the cathode layer; and wherein the at least one organic semiconductor layer comprises a compound of claim 1.

11. The organic electronic device of claim 10, whereby the organic semiconductor layer comprises a composition comprising a compound of formula (IV) and at least one compound of formula (IVa) to (IVd) ##STR00129##

12. The organic electronic device of claim 10, whereby the organic electronic device comprises at least one photoactive layer, wherein the at least one photoactive layer is arranged between the anode layer and the cathode layer and at least one of the at least one organic semiconductor layers is arranged between the anode layer and the at least one photoactive layer.

13. The organic electronic device of claim 10, whereby the organic electronic device comprises at least two photoactive layers, wherein at least one of the at least one organic semiconductor layers is arranged between the first and the second photoactive layer.

14. The organic electronic device of claim 10, whereby the electronic organic device is an electroluminescent device.

15. A display device comprising an organic electronic device according to claim 10.

Description

DESCRIPTION OF THE DRAWINGS

[0242] 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.

[0243] 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.

[0244] FIG. 1 is a schematic sectional view of an organic electronic device, according to an exemplary embodiment of the present invention;

[0245] FIG. 2 is a schematic sectional view of an organic light-emitting diode (OLED), according to an exemplary embodiment of the present invention;

[0246] FIG. 3 is a schematic sectional view of an OLED, according to an exemplary embodiment of the present invention.

[0247] FIG. 4 is a schematic sectional view of a tandem OLED comprising a charge generation layer, according to an exemplary embodiment of the present invention.

[0248] FIG. 5 is a schematic sectional view of a tandem OLED comprising a charge generation layer, according to an exemplary embodiment of the present invention.

[0249] Hereinafter, the figures are illustrated in more detail with reference to examples. However, the present disclosure is not limited to the following figures.

[0250] 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.

[0251] FIG. 1 is a schematic sectional view of an organic electronic device 100, according to an exemplary embodiment of the present invention. The organic electronic device 100 includes a substrate 110, an anode layer 120 and a hole injection layer (HIL) (130) which may comprise compound of Formula (I). The HIL 130 is disposed on the anode layer 120. Onto the HIL 130, a photoactive layer (PAL) 170 and a cathode layer 190 are disposed.

[0252] FIG. 2 is a schematic sectional view of an organic light-emitting diode (OLED) 100, according to an exemplary embodiment of the present invention. The OLED 100 includes a substrate 110, an anode layer 120 and a hole injection layer (HIL) 130 which may comprise compound of Formula (I). The HIL 130 is disposed on the anode layer 120. Onto the HIL 130, a hole transport layer (HTL) 140, an emission layer (EML) 150, an electron transport layer (ETL) 160, an electron injection layer (EIL) 180 and a cathode layer 190 are disposed. Instead of a single electron transport layer 160, optionally an electron transport layer stack (ETL) can be used.

[0253] FIG. 3 is a schematic sectional view of an OLED 100, according to another exemplary embodiment of the present invention. FIG. 3 differs from FIG. 2 in that the OLED 100 of FIG. 3 comprises an electron blocking layer (EBL) 145 and a hole blocking layer (HBL) 155.

[0254] Referring to FIG. 3, the OLED 100 includes a substrate 110, an anode layer 120, a hole injection layer (HIL) 130 which may comprise compound of Formula (I), a hole transport layer (HTL) 140, an electron blocking layer (EBL) 145, an emission layer (EIL) 150, a hole blocking layer (HBL) 155, an electron transport layer (ETL) 160, an electron injection layer (EIL) 180 and a cathode layer 190.

[0255] FIG. 4 is a schematic sectional view of an OLED 100, according to another exemplary embodiment of the present invention. FIG. 4 differs from FIGS. 2 and 3 in that the OLED 200 of FIG. 4 comprises a charge generation layer (CGL) and an additional electron transport layer (ETL) 161 which replace the hole injection layer (HIL) 130 of OLED 100 in FIG. 3. Referring to FIG. 4 the OLED 200 includes a substrate 110, an anode 120, a first electron transport layer (ETL1) 161, an n-type charge generation layer (n-type CGL) 185, a p-type charge generation layer (p-type GCL) 135 which may comprise compound of Formula (I), a first hole transport layer (HTL) 140, a first electron blocking layer (EBL) 145, a first emission layer (EIL) 150, a first hole blocking layer (HBL) 155, a second electron transport layer (ETL2) 160, and a cathode 190.

[0256] 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 120 is formed, on the anode electrode 120, a first electron transport layer 161, an n-type CGL 185, a p-type CGL 135, 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 a second electron transport layer 160, and a cathode 190 are formed, in that order or the other way around.

[0257] FIG. 5 is a schematic sectional view of a tandem OLED 100, according to another exemplary embodiment of the present invention. FIG. 5 differs from FIG. 4 in that the OLED 100 of FIG. 5 further comprises a second emission layer.

Referring to FIG. 5 the OLED 200 includes a substrate 110, an anode 120, a hole injection layer (HIL) 130 which may comprise compound of Formula (I), a first hole transport layer (HTL) 140, a first electron blocking layer (EBL) 145, a first emission layer (EIL) 150, a first hole blocking layer (HBL) 155, a first electron transport layer (ETL) 160, an n-type charge generation layer (n-type CGL) 185, a p-type charge generation layer (p-type 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 (EMIL) 151, a second hole blocking layer (EBL) 156, a second electron transport layer (ETL) 161, an electron injection layer (EIL) 180 and a cathode 190.

[0258] 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 120 is formed, on the anode electrode 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-type CGL 185, a p-type 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 (EIL) 180 and a cathode 190 are formed, in that order or the other way around.

[0259] While not shown in FIG. 1 to 5, a sealing and/or capping 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.

[0260] 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

[0261] The invention is furthermore illustrated by the following examples which are illustrative only and non-binding.

[0262] Compounds of formula (I) may be prepared as described in EP2180029A1 or WO2016097017A1.

Calculated HOMO and LUMO

[0263] 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

[0264] The term “TGA5%” denotes the temperature at which 5% weight loss occurs during thermogravimetric analysis and is measured in ° C.
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.

[0265] 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.

[0266] According to one embodiment, the TGA5% value of compound of formula (I) is selected in the range of ≥280° C. and ≤390° C.; preferably of ≥290° C. and ≤380° C., also preferred of ≥295° C. and ≤370° C.

General Procedure for Fabrication of OLEDs

[0267] For bottom emission devices, see Table 3 and 5, a 15 Ω/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 layer.

[0268] Then, compound of formula F3 and compound of formula (I) according to Table 3 and 5 were co-deposited in vacuum on the anode layer, to form a HIL having a thickness of 10 nm. In comparative examples 1 and 2, comparative compounds 1 and 2 were used instead of compounds of formula (I). The composition of the HIL can be seen in Table 3 and 5.

[0269] Then, compound of formula F3 was vacuum deposited on the HIL, to form a first HTL having a thickness of 128 nm.

[0270] Then N,N-bis(4-(dibenzo[b,d]furan-4-yl)phenyl)-[1,1′:4′,1″-terphenyl]-4-amine (CAS 1198399-61-9) was vacuum deposited on the HTL, to form an electron blocking layer (EBL) having a thickness of 5 nm.

[0271] Then 97 vol.-% H09 (Sun Fine Chemicals, Korea) as EML host and 3 vol.-% BD200 (Sun Fine Chemicals, Korea) as fluorescent blue dopant were co-deposited on the EBL, to form a first blue-emitting EML with a thickness of 20 nm.

[0272] Then the hole blocking layer (HBL) is formed with a thickness of 5 nm by depositing 2-(3′-(9,9-dimethyl-9H-fluoren-2-yl)-[1,1′-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine on the emission layer.

[0273] Then, the electron transporting layer (ETL) having a thickness of 25 nm is formed on the hole blocking layer by co-depositing 50 wt.-% 4′-(4-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)naphthalen-1-yl)-[1,1′-biphenyl]-4-carbonitrile and 50 wt.-% LiQ.

[0274] Then, the cathode layer having a thickness of 100 nm is formed on the ETL by depositing Al at a rate of 0.01 to 1 Å/s at 10-7 mbar.

[0275] 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.

Organic Electronic Device Comprising a Charge Generation Layer (CGL)

[0276] For devices comprising a CGL, see Table 4, a 15 Ω/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 layer.

[0277] Then, the first electron transporting layer (ETL1) having a thickness of 30 nm is formed on the anode layer by co-depositing 50 wt.-% 4′-(4-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)naphthalen-1-yl)-[1,1′-biphenyl]-4-carbonitrile and 50 wt.-% LiQ.

[0278] Then, the n-type CGL having a thickness of 15 nm is formed on the ETL1 by co-depositing 99 vol.-% 2,2′-(1,3-Phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 vol.-% Li.

[0279] Then, the p-type CGL having a thickness of 10 nm is formed on the n-type CGL by co-depositing a substantially covalent matrix compound and a compound of formula (I). The composition of the p-type CGL can be seen in Table 4.

[0280] Then, the hole transport layer (HTL) having a thickness of 86 nm is formed on the p-type CGL by depositing a substantially covalent matrix compound. The composition of the HTL can be seen in Table 4.

[0281] Then, an electron blocking layer (EBL) having a thickness of 5 nm is formed on the HTL by depositing N-([1,1′-biphenyl]-4-yl)-9,9-diphenyl-N-(4-(triphenylsilyl)phenyl)-9H-fluoren-2-amine.

[0282] Then, an emission layer (EML) having a thickness of 20 nm is formed on the EBL by co-depositing 97 vol.-% H09 (Sun Fine Chemicals, Korea) as EML host and 3 vol.-% BD200 (Sun Fine Chemicals, Korea) as fluorescent blue dopant.

[0283] Then the hole blocking layer (HBL) is formed with a thickness of 5 nm is formed on the 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.

[0284] Then, the second electron transporting layer (ETL2) having a thickness of 25 nm is formed on the hole blocking layer by co-depositing 50 wt.-% 4′-(4-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)naphthalen-1-yl)-[1,1′-biphenyl]-4-carbonitrile and 50 wt.-% LiQ.

[0285] Then, the cathode layer having a thickness of 100 nm is formed on the ETL2 by depositing Al at a rate of 0.01 to 1 Å/s at 10-7 mbar.

[0286] 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.

[0287] 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 U 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.

[0288] 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.

[0289] In top emission devices, the emission is forward directed, non-Lambertian and also highly dependent on the mirco-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.

[0290] 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.

[0291] 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.

Technical Effect of the Invention

[0292] In Table 1 are shown LUMO levels and TGA5%-temperatures (when available) for Examples A1 to A31 and comparative example 1 and 2 (=C1 and C2). Table 2 shows the structure of comparative examines C1 and C2.

[0293] 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.

[0294] Comparative compound 1 has a LUMO level of −4.58 eV and a TGA5% value of 265° C.

[0295] Comparative compound 2 has a LUMO level of −4.79 eV and a TGA5% value of 268° C. Comparative compound 2 differs from comparative compound 1 in the number of CF.sub.3 groups. In comparative compound 2, two fluorine atoms have been replaced by CF.sub.3 groups. As can be seen in Table 1, the LUMO level of compounds of formula (I) is more negative compared to comparative compound 1. A more negative LUMO level is beneficial, as matrix compounds with more negative HOMO level are enabled. However, the volatility is very similar.

[0296] In inventive compound A1, the LUMO level is −4.82 eV and thereby more negative than the LUMO level of comparative compound 2. Additionally, the volatility is substantially improved at 297° C. Inventive compound A1 differs from comparative compound 2 in at least one of A.sup.1-A.sup.3.

[0297] In inventive compounds A2 to A31 the LUMO level and/or TGA5% value are improved compared to comparative compounds 1 and 2.

TABLE-US-00002 TABLE 1 Properties of compounds of formula (I) and comparative compounds 1 and 2 LUMO [eV] TGA5% [° C.] C1 −4.58 265 C2 −4.79 268 A1 −4.82 297 A2 −4.83 304 A3 −4.92 331 A4 −4.95 319 A5 −4.99 309 A6 −5.12 300 A7 −5.16 328 A8 −5.09 332 A9 −5.07 361 A10 −4.73 320 A11 −4.91 324 A12 −4.71 n/a A13 −5.07 n/a A14 −4.91 n/a A15 −5.36 n/a A16 −5.00 n/a A17 −5.25 n/a A18 −5.18 n/a A19 −5.12 n/a A20 −5.23 n/a A21 −5.07 n/a A22 −5.15 n/a A23 −4.93 n/a A24 −5.21 n/a A25 −5.26 n/a A26 −5.17 n/a A27 −5.13 n/a A28 −5.25 n/a A29 −5.37 n/a A30 −5.32 n/a A31 −5.34 n/a

TABLE-US-00003 TABLE 2 Structure of the comparative compounds 1 and 2 A.sup.1 A.sup.2 A.sup.3 Comparative compound 1 [00118] [00119] [00120] Comparative compound 2 [00121] [00122] [00123]

[0298] In Table 3 performance data for organic electroluminescent devices comprising a hole injection layer (HIL) comprising comparative and inventive compounds are shown:

TABLE-US-00004 TABLE 3 Organic electronic devices comprising an hole injection layer (HIL) comprising comparative and inventive compounds. Percentage of compound U at 10 EQE at 10 LT at 30 Compound of of formula (I) in HIL mA/cm.sup.2 mA/cm.sup.2 mA/cm.sup.2 formula (I) [vol.-%] [V] [%] [h] Comparative C1 12 6.28 10.5 <10 example 1 Comparative C2 10 4.51 9.4 100 example 2 Example 1 A3 12 3.75 9.6 128 Example 2 A3 10 3.77 9.6 131 Example 3 A1 12 3.76 9.8 141 Example 4 A1 10 3.79 9.8 148

[0299] As can be seen from Table 3, the operating voltage U for all devices is lower than for the comparative compounds. The external quantum efficiency EQE is improved over comparative examples 1 and 2.

[0300] A low operating voltage and improved efficiency may be beneficial for reduced power consumption and improved battery life, in particular in mobile devices.

[0301] Additionally, the lifetime LT are increased over the comparative examples 1 and 2.

[0302] An improved LT is beneficial for improved long-term stability of organic electronic devices.

[0303] In Table 4 performance data for organic electroluminescent devices comprising a p-type charge injection layer (p-type CGL) comprising inventive compounds are shown.

TABLE-US-00005 TABLE 4 Organic electronic devices comprising a p-type charge injection layer (p-type CGL) comprising inventive compounds Percentage compound of Composition formula (1) in U at 15 EQE LT97 at of the p-type p-type CGL Composition mA/cm.sup.2 (cd/A/y) at 30 mA/cm.sup.2 CGL [vol.-%] of the HTL [V] 15 mA/cm.sup.2 [h] Example 5 F5:A5 10 F5 5.20 8.88 150 Example 6 F5:A6 10 F5 5.21 8.93 98

[0304] A high EQE may be beneficial for reduced power consumption and improved battery life, in particular in mobile devices.

[0305] An improved LT97 may be beneficial for long lifetime of organic electronic devices.

[0306] In Table 5 performance data for organic electroluminescent devices comprising a hole injection layer (HIL) comprising comparative and inventive compounds are shown:

TABLE-US-00006 TABLE 5 Organic electronic devices comprising an hole injection layer (HIL) comprising comparative and inventive compounds. Percentage of compound U at 10 EQE at 10 LT at 30 Compound of of formula (I) in HIL mA/cm.sup.2 mA/cm.sup.2 mA/cm.sup.2 formula (I) [wt.-%] [V] [%] [h] Example 7 A3 8 3.81 9.67 137 Example 8 A3 10 3.77 9.65 131 Example 9 A3 12 3.75 9.63 128 Example 10 A1 8 3.90 9.82 159 Example 11 A1 10 3.79 9.80 148 Example 12 A1 12 3.76 9.80 141 Example 13 A4 12 3.71 9.82 129 Example 14 A10 12 4.57 9.85 137 Example 15 A10 18 3.92 9.66 150 Example 16 A11 8 3.92 9.90 143 Example 17 A11 12 3.78 9.81 135 Example 18 A7 4 3.71 9.88 117 Example 19 A7 6 3.70 9.84 115 Example 20 A23 10 3.79 9.69 130 Example 21 A23 14 3.74 9.68 127 Example 22 A15 4 3.73 9.95 149 Example 23 A15 6 3.72 9.91 159

[0307] As can be seen from Table 5, the performance of OLEDs is in comparable range to Examples 1 to 4 in Table 3. Performance of examples 7 to 23 is improved over comparative examples 1 and 2, see Table 3.

[0308] 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.