Organic Compound of Formula (I) for Use in Organic Electronic Devices, a Composition Comprising a Compound of Formula (IV) and at Least One Compound of Formula (IVa) to (IVd), an Organic Semiconductor Layer Comprising the Compound or Composition, an Organic Electronic Device Comprising the Organic Semiconductor Layer, and a Display Device Comprising the Organic Electronic Device

Abstract

The present invention relates to a compound of formula (I) for use in organic electronic devices, a composition comprising a compound of formula (IV) and at least one compound of formula (IVa) to (IVd), an organic semiconductor layer comprising the compound or composition, an organic electronic device comprising the organic semiconductor layer, and a display device comprising the organic electronic device.

Claims

1. A compound of formula (I) ##STR00338## whereby A.sup.1 is selected from formula (II) ##STR00339## 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 and R.sup.5 (if present) are independently selected from CN, CF.sub.3, halogen, Cl, F, H or D; R.sup.2, R.sup.3, and R.sup.4 (if present) are independently selected from CN, partially fluorinated or perfluorinated C.sub.1 to C.sub.8 alkyl, halogen, Cl, F, H or D; 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 of R.sup.1 and R.sup.5 is present and independently selected from CN or CF.sub.3; A.sup.2 is selected from formula (III) ##STR00340## wherein Ar is independently selected from substituted C.sub.6 to C.sub.18 aryl and substituted 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; 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; wherein the asterix “*” denotes the binding position; wherein each Ar is substituted by at least two CN groups; A.sup.3 is selected from formula (II) or formula (III); and A.sup.1 and A.sup.2 are selected differently.

2. The compound of claim 1, selected of the formula (IV) ##STR00341## whereby B.sup.1 is selected from formula (V) ##STR00342## 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, wherein the compound comprises less than nine CN groups.

4. The compound of claim 1, wherein both of R.sup.1 and R.sup.5 are present and independently selected from CN or CF.sub.3.

5. The compound of claim 1, wherein R′ is selected from partially fluorinated or perfluorinated C.sub.1 to C.sub.8 alkyl, F or CN.

6. The compound of claim 1, wherein Ar comprises two adjacent CN groups.

7. A composition comprising a compound of formula (IV) and at least one compound of formula (IVa) to (IVd) ##STR00343##

8. An organic semiconductor layer, whereby the organic semiconductor layer comprises a compound of claim 1.

9. An organic electronic device comprising an anode layer, a cathode layer, and at least one organic semiconductor layer, wherein the organic semiconductor layer is arranged between the anode layer and the cathode layer, and wherein the organic semiconductor layer is an organic semiconductor layer according to claim 8.

10. The organic electronic device of claim 9, wherein the organic electronic device further comprises a charge generation layer, wherein the charge generation layer comprises a p-type charge generation layer and a n-type charge generation layer.

11. The organic electronic device of claim 9, wherein the organic electronic device further comprises a hole injection layer.

12. The organic electronic device of claim 11, wherein the p-type charge generation layer and the hole injection layer comprise the same compound of formula (I).

13. The organic electronic device of claim 11, wherein the p-type charge generation layer and the hole injection layer comprise an identical substantially covalent matrix compound.

14. The organic electronic device of claim 11, wherein the organic electronic device is an electroluminescent device.

15. A display device comprising an organic electronic device according to claim 11.

Description

DESCRIPTION OF THE DRAWINGS

[0233] 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.

[0234] 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.

[0235] FIG. 1 is a schematic sectional view of an organic electronic device, according to an exemplary embodiment of the present invention;

[0236] FIG. 2 is a schematic sectional view of an organic light-emitting diode (OLED), according to an exemplary embodiment of the present invention;

[0237] FIG. 3 is a schematic sectional view of an OLED, according to an exemplary embodiment of the present invention.

[0238] FIG. 4 is a schematic sectional view of an OLED, according to an exemplary embodiment of the present invention.

[0239] FIG. 5 is a schematic sectional view of an OLED, according to an exemplary embodiment of the present invention.

[0240] FIG. 6 is a schematic sectional view of an OLED comprising a charge generation layer, according to an exemplary embodiment of the present invention.

[0241] FIG. 7 is a schematic sectional view of a stacked OLED comprising a charge generation layer, according to an exemplary embodiment of the present invention.

[0242] Hereinafter, the figures are illustrated in more detail with reference to examples. However, the present disclosure is not limited to the following figures.

[0243] 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.

[0244] 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 a 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.

[0245] 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 a 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.

[0246] 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.

[0247] Referring to FIG. 3, the OLED 100 includes a substrate 110, an anode layer 120, a hole injection layer (HIL) 130 which may comprise a compound of formula (I), a hole transport layer (HTL) 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 electron injection layer (EIL) 180 and a cathode layer 190.

[0248] FIG. 4 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 that comprises a first anode sub-layer 121, a second anode sub-layer 122 and a third anode sub-layer 123, and a hole injection layer (HIL) 130. The HIL 130 is disposed on the anode layer 120. Onto the HIL 130, an hole transport layer (HTL) 140, a first emission layer (EML) 150, a hole blocking layer (HBL) 155, an electron transport layer (ETL) 160, and a cathode layer 190 are disposed. The hole injection layer 130 may comprise a compound of formula (I).

[0249] FIG. 5 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 that comprises a first anode sub-layer 121, a second anode sub-layer 122 and a third anode sub-layer 123, and a hole injection layer (HIL) 130. The HIL 130 is disposed on the anode layer 120. Onto the HIL 130, a hole transport layer (HTL) 140, an electron blocking layer (EBL) 145, a first emission layer (EML) 150, a hole blocking layer (HBL) 155, an electron transport layer (ETL) 160, an electron injection layer (EIL) 180 and a cathode layer 190 are disposed. The hole injection layer 130 may comprise a compound of formula (I).

[0250] Referring to FIG. 6 the organic electronic device 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 also comprise a compound of formula (I).

[0251] Referring to FIG. 7 the organic electronic device 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) 180 and a cathode layer 190. The HIL may also comprise a compound of formula (I).

[0252] While not shown in FIG. 1 to FIG. 7, a capping and/or 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.

[0253] 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

[0254] The invention is furthermore illustrated by the following examples which are illustrative only and non-binding.

[0255] Compounds of formula (I) may be prepared as described in EP2180029A1 and WO2016097017A1.

Melting Point

[0256] The melting point (mp) is determined as peak temperatures from the DSC curves of the above TGA-DSC measurement or from separate DSC measurements (Mettler Toledo DSC822e, heating of samples from room temperature to completeness of melting with heating rate 10 K/min under a stream of pure nitrogen. Sample amounts of 4 to 6 mg are placed in a 40 μL Mettler Toledo aluminum pan with lid, a <1 mm hole is pierced into the lid).

Glass Transition Temperature

[0257] The glass transition temperature, also named Tg, is measured in ° C. and determined by Differential Scanning Calorimetry (DSC).

[0258] 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.

Rate Onset Temperature

[0259] The rate onset temperature (T.sub.RO) is determined by loading 100 mg compound into a VTE source. As VTE source a point source for organic materials may be used as supplied by Kurt J. Lesker Com-pany (www.lesker.com) or CreaPhys GmbH (http://www.creaphys.com). The VTE source is heated at a constant rate of 15 K/min at a pressure of less than 10.sup.−5 mbar and the temperature inside the source measured with a thermocouple. Evaporation of the compound is detected with a QCM detector which detects deposition of the compound on the quartz crystal of the detector. The deposition rate on the quartz crystal is measured in Angstrom per second. To determine the rate onset temperature, the deposition rate is plotted against the VTE source temperature. The rate onset is the temperature at which noticeable deposition on the QCM detector occurs. For accurate results, the VTE source is heated and cooled three time and only results from the second and third run are used to determine the rate onset temperature.

[0260] To achieve good control over the evaporation rate of an organic compound, the rate onset temperature may be in the range of 200 to 255° C. If the rate onset temperature is below 200° C. the evaporation may be too rapid and therefore difficult to control. If the rate onset temperature is above 255° C. the evaporation rate may be too low which may result in low tact time and decomposition of the organic compound in VTE source may occur due to prolonged exposure to elevated temperatures.

[0261] The rate onset temperature is an indirect measure of the volatility of a compound. The higher the rate onset temperature the lower is the volatility of a compound.

Calculated HOMO and LUMO

[0262] 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.

General Procedure for Fabrication of OLEDs with a Transparent Cathode, Wherein the Organic Semiconductor Laver is a Hole Injection Layer

[0263] For Examples 1-1 to 1-6 and comparative example 1-1 in Table 3, a glass substrate with an anode layer comprising a first anode sub-layer of 120 nm Ag, a second anode sub-layer of 8 nm ITO and a third anode sub-layer of 10 nm ITO was cut to a size of 50 mm×50 mm×0.7 mm, ultrasonically washed with water for 60 minutes and then with isopropanol for 20 minutes. The liquid film was removed in a nitrogen stream, followed by plasma treatment, to prepare the anode layer. The plasma treatment was performed in nitrogen atmosphere or in an atmosphere comprising 98 vol.-% nitrogen and 2 vol.-% oxygen.

[0264] Then, Biphenyl-4-yl(9,9-diphenyl-9H-fluoren-2-yl)-[4-(9-phenyl-9H-carbazol-3-yl) phenyl]-amine as matrix compound and compound of formula (I) were co-deposited in vacuum on the anode layer, to form a hole injection layer (HIL) having a thickness of 10 nm. The percentage compound of formula (I) in the HIL can be seen in Table 3.

[0265] Then, Biphenyl-4-yl(9,9-diphenyl-9H-fluoren-2-yl)-[4-(9-phenyl-9H-carbazol-3-yl) phenyl]-amine was vacuum deposited on the HIL, to form a HTL having a thickness of 123 nm.

[0266] Then N-([1,1′-biphenyl]-4-yl)-9,9-diphenyl-N-(4-(triphenylsilyl)phenyl)-9H-fluoren-2-amine (CAS 1613079-70-1) was vacuum deposited on the HTL, to form an electron blocking layer (EBL) having a thickness of 5 nm.

[0267] Then 97 vol.-% H09 (Sun Fine Chemicals, Korea) as EML host and 3 vol.-% BD200 (Sun Fine Chemicals, Korea) as fluorescent blue emitter dopant were deposited on the EBL, to form a blue-emitting first emission layer (EML) with a thickness of 20 nm.

[0268] Then a hole blocking layer was 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 EML.

[0269] Then the electron transporting layer having a thickness of 31 nm was 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.-% of LiQ.

[0270] Then an electron injection layer having a thickness of 2 nm was formed on the ETL by depositing Ytterbium.

[0271] Then Ag:Mg (90:10 vol.-%) was evaporated at a rate of 0.01 to 1 Å/s at 10.sup.−7 mbar to form a cathode layer with a thickness of 13 nm on the electron injection layer.

[0272] Then, Biphenyl-4-yl(9,9-diphenyl-9H-fluoren-2-yl)-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-amine was deposited on the cathode layer to form a capping layer with a thickness of 75 nm.

[0273] 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.

[0274] General Procedure for Fabrication of OLEDs with a Transparent Cathode, Wherein the Organic Semiconductor Layer is a p-CGL

[0275] For OLEDs comprising a CGL, see Examples 2-1 and 2-2 and comparative example 2-1 in Table 4, 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.

[0276] 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.

[0277] Then, a hole injection layer (HIL) having a thickness of 10 nm is formed on the anode layer by co-depositing compound F11 and 2,2′,2″-(cyclopropane-1,2,3-triylidene)tris(2-(p-cyanotetrafluorophenyl)acetonitrile) CC3. The hole injection layer comprises 8 wt.-% CC3 and 92 wt.-% F11.

[0278] Then, a first hole transport layer (HTLT) having a thickness of 34 nm is formed on the IL by depositing F11.

[0279] 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.

[0280] 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 EML host and 3 vol.-% BD200 (Sun Fine Chemicals, Korea) as fluorescent blue dopant.

[0281] 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.

[0282] 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.

[0283] 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.

[0284] 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 4.

[0285] Then, a second hole transport layer (HTL2) having a thickness of 81 nm is formed on the p-CGL by depositing F11.

[0286] Then, an electron injection layer (EIL) having a thickness of 2 nm is formed on the HTL2 by depositing Yb.

[0287] 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.

[0288] Then, a capping layer having a thickness of 75 nm is formed on the cathode layer by depositing compound of formula F3.

[0289] 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.

[0290] 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.

[0291] 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.

[0292] 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.

[0293] 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.

[0294] 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.

[0295] The increase in operating voltage U over time “U(100-1h)” is measured by determining the difference in operating voltage at 30 mA/cm.sup.2 after 1 hour and after 100 hours.

Technical Effect of the Invention

[0296] In Table 1 are shown LUMO levels for Examples A1 to A57. 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 6-31 G* basis set in the gas phase.

TABLE-US-00003 TABLE 1 Structure of the inventive compounds A1 to A49 and their LUMOs LUMO Compound A.sup.1 A.sup.2 A.sup.3 [eV] A1  [00179] [00180] [00181] −4.91 A2  [00182] [00183] [00184] −5.22 A3  [00185] [00186] [00187] −5.44 A4  [00188] [00189] [00190] −5.27 A5  [00191] [00192] [00193] −5.10 A6  [00194] [00195] [00196] −5.29 A7  [00197] [00198] [00199] −5.25 A8  [00200] [00201] [00202] −5.00 A9  [00203] [00204] [00205] −5.25 A10 [00206] [00207] [00208] −4.96 A11 [00209] [00210] [00211] −5.24 A12 [00212] [00213] [00214] −5.22 A13 [00215] [00216] [00217] −5.27 A14 [00218] [00219] [00220] −5.39 A15 [00221] [00222] [00223] −5.29 A16 [00224] [00225] [00226] −4.79 A17 [00227] [00228] [00229] −5.15 A18 [00230] [00231] [00232] −5.25 A19 [00233] [00234] [00235] −5.24 A20 [00236] [00237] [00238] −5.24 A21 [00239] [00240] [00241] −5.38 A22 [00242] [00243] [00244] −5.26 A23 [00245] [00246] [00247] −5.14 A24 [00248] [00249] [00250] −4.78 A25 [00251] [00252] [00253] −5.42 A26 [00254] [00255] [00256] −5.32 A27 [00257] [00258] [00259] −5.18 A28 [00260] [00261] [00262] −5.28 A29 [00263] [00264] [00265] −5.26 A30 [00266] [00267] [00268] −5.27 A31 [00269] [00270] [00271] −4.80 A32 [00272] [00273] [00274] −5.45 A33 [00275] [00276] [00277] −5.35 A34 [00278] [00279] [00280] −5.21 A35 [00281] [00282] [00283] −5.31 A36 [00284] [00285] [00286] −5.30 A37 [00287] [00288] [00289] −5.30 A38 [00290] [00291] [00292] −4.82 A39 [00293] [00294] [00295] −5.30 A40 [00296] [00297] [00298] −5.23 A41 [00299] [00300] [00301] −5.06 A42 [00302] [00303] [00304] −5.26 A43 [00305] [00306] [00307] −5.20 A44 [00308] [00309] [00310] −5.38 A45 [00311] [00312] [00313] −5.14 A46 [00314] [00315] [00316] −5.35 A47 [00317] [00318] [00319] −5.35 A48 [00320] [00321] [00322] −5.27 A49 [00323] [00324] [00325] −5.26

TABLE-US-00004 TABLE 2 Properties of comparative examples 1 and 2 and compounds of formula (I) mp Tg T.sub.RO Name A.sup.1 A.sup.2 A.sup.3 (° C.) (° C.) (° C.) Comparative compound 1 (CC1) [00326] [00327] [00328] 210  65 116 Comparative compound 2 (CC2) [00329] [00330] [00331] 209  78 136 Inventive compound 1 [00332] [00333] [00334] 311 135 199 Inventive compound 2 [00335] [00336] [00337] 300 134 208

[0297] Table 2 shows the physical properties of compounds of formula (I) and comparative compounds 1 and 2.

[0298] A higher Tg and Tm may be beneficial and a higher rate onset temperature T.sub.RO temperature (in other words lower volatility) may be advantageous for improved processing, in particular in mass production. Additionally, the lower LUMO may be beneficial for performance of organic electronic devices, see Table 1.

[0299] Table 3 shows device data obtained for comparative compound 1 (comparative example 1-1) and inventive compounds 1 and 2 (examples 1-1 to 1-6).

[0300] As can be seen Table 3, the operating voltage and voltage stability over time of Examples 1-1 to 1-6 is substantially improved over comparative example 1-1.

TABLE-US-00005 TABLE 3 Performance of an organic electronic device comprising a transparent cathode and a hole injection layer comprising a compound of formula (I) Percentage of compound of Voltage U(1-100 h) formula (I) at 15 at 30 Compound of in HIL mA/cm.sup.2 mA/cm.sup.2 formula (I) [wt.-%] [V] [V] Comparative CC1 6.0 4.04 0.665 example 1-1 Example 1-1 Inventive 1.1 3.78 0.016 compound 1 Example 1-2 Inventive 1.3 3.78 0.014 compound 1 Example 1-3 Inventive 2.0 3.78 0.012 compound 1 Example 1-4 Inventive 1.3 3.90 0.046 compound 2 Example 1-5 Inventive 1.7 3.82 0.025 compound 2 Example 1-6 Inventive 2.1 3.86 0.026 compound 2

[0301] Table 4 shows device data obtained for comparative compound 2 (comparative example 2-1) and inventive compounds 1 and 2 (examples 2-1 to 2-2).

[0302] As can be seen Table 4, the operating voltage and voltage stability over time of Examples 1-1 to 1-6 is substantially improved over comparative example 1-1.

TABLE-US-00006 TABLE 4 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 Percentage of compound of Voltage U(1-100 h) formula (I) at 15 at 30 Compound of in p-CGL mA/cm.sup.2 mA/cm.sup.2 formula (I) [wt.-%] [V] [V] Comparative CC2 10 6.34 0.036 example 2-1 Example 2-1 Inventive 10 6.04 0.025 compound 1 Example 2-2 Inventive 10 6.2 0.025 compound 2

[0303] A lower operating voltage may be beneficial for improved battery life, in particular in mobile devices.

[0304] An improved voltage stability over time U(100-1 h) may be beneficial for improved stability over time of organic electronic devices.

[0305] 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.