Charge Generation Layer Comprising a Compound of Formula (I), Organic Electronic Device and Display Device Comprising the Charge Generation Layer as Well as Compounds of Formula (I)

Abstract

The present invention relates to a charge generation layer comprising a compound of formula (I). The invention further relates to organic electronic devices and display devices comprising the charge generation layer as well as compounds of formula (I).

Claims

1. A charge generation layer comprising a first charge generation layer and a second charge generation layer, wherein the first charge generation layer comprises a compound of formula (I) ##STR01093## wherein in formula (I) A.sup.1 is independently selected from a group of formula (II) ##STR01094## wherein Ar.sup.1 is independently selected from substituted or unsubstituted C.sub.6 to C.sub.36 aryl and substituted or unsubstituted C.sub.2 to C.sub.36 heteroaryl; wherein for the case that Ar.sup.1 is substituted, one or more of the substituents are independently selected from the group consisting of an electron-withdrawing group, F, CN, partially fluorinated alkyl, perfluorinated alkyl, and NO.sub.2; A.sup.2 and A.sup.3 are independently selected from a group of formula (III) ##STR01095## wherein Ar.sup.2 is independently selected from substituted or unsubstituted C.sub.6 to C.sub.36 aryl and substituted or unsubstituted C.sub.2 to C.sub.36 heteroaryl; wherein for the case that Ar.sup.2 is substituted, one or more of the substituents are independently selected from the group consisting of an electron-withdrawing group, F, CN, partially fluorinated alkyl, perfluorinated alkyl, and NO.sub.2; and wherein each R is independently selected from substituted or unsubstituted C.sub.6 to C.sub.18 aryl, C.sub.3 to C.sub.18 heteroaryl, electron-withdrawing group, partially fluorinated C.sub.1 to C.sub.8 alkyl, perfluorinated C.sub.1 to C.sub.8 alkyl, halogen, F or CN; wherein the compound of formula (I) has an absorption maximum .sub.max at 459 nm when measured in DCM at a concentration of 10.sup.5 to 10.sup.4 mol/L at 20 C., an absorption maximum .sub.max at 494 nm when calculated with the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) by TDDFT using the hybrid functional PBE0 with a def2-SVP basis set in the gas phase and including the first 30 singlet transitions from optimized geometry using the hybrid functional B3LYP with a 6-31G* basis set in the gas phase, and/or an integral of 50 a.u.nm in an UV-Vis Spectrum in the range of 400 to 650 nm, when calculated with the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) by TDDFT using the hybrid functional PBE0 with a def2-SVP basis set in the gas phase and including the first 30 singlet transitions from optimized geometry using the hybrid functional B3LYP with a 6-31G* basis set in the gas phase; wherein the first charge generation layer comprises an organic hole transport compound and wherein the second charge generation layer comprises an organic electron transport compound and a metal dopant.

2. Charge generation layer according to claim 1, wherein the charge generation layer is not a charge generation layer selected from the group consisting of: a) a charge generation layer, wherein the first charge generation layer comprises 10.1 vol % of a compound of formula (I) wherein A.sup.1, A.sup.2 and A.sup.3 are selected according to the following: ##STR01096## and N-([1,1-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-diphenyl-9H-fluoren-2-amine, wherein the first charge generation layer has a thickness of 86 nm, and the second charge generation layer contains 99 vol.-% 2,2-(1,3-Phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 vol.-% Li, wherein the second charge generation layer has a thickness of 10 nm; b) a charge generation layer, wherein the first charge generation layer comprises 9.8 vol % of a compound of formula (I) wherein A.sup.1, A.sup.2 and A.sup.3 are selected according to the following: ##STR01097## and N-([1,1-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-diphenyl-9H-fluoren-2-amine, wherein the first charge generation layer has a thickness of 86 nm, and the second charge generation layer contains 99 vol.-% 2,2-(1,3-Phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 vol.-% Li, wherein the second charge generation layer has a thickness of 10 nm; c) a charge generation layer, wherein the first charge generation layer comprises 12 vol % of a compound of formula (I) wherein A.sup.1, A.sup.2 and A.sup.3 are selected according to the following: ##STR01098## and N-([1,1-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-diphenyl-9H-fluoren-2-amine, wherein the first charge generation layer has a thickness of 86 nm, and the second charge generation layer contains 99 vol.-% 2,2-(1,3-Phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 vol.-% Li, wherein the second charge generation layer has a thickness of 10 nm; d) a charge generation layer, wherein the first charge generation layer comprises 9.6 vol % of a compound of formula (I) wherein A.sup.1, A.sup.2 and A.sup.3 are selected according to the following: ##STR01099## and N-([1,1-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-spirobi[fluoren]-2-amine, wherein the first charge generation layer has a thickness of 81 nm, and the second charge generation layer contains 99 vol.-% 2,2-(1,3-Phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 vol.-% Li, wherein the second charge generation layer has a thickness of 10 nm; e) a charge generation layer, wherein the first charge generation layer comprises 10.1 vol % of a compound of formula (I) wherein A.sup.1, A.sup.2 and A.sup.3 are selected according to the following: ##STR01100## and N-([1,1-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-spirobi[fluoren]-2-amine, wherein the first charge generation layer has a thickness of 81 nm, and the second charge generation layer contains 99 vol.-% 2,2-(1,3-Phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 vol.-% Li, wherein the second charge generation layer has a thickness of 10 nm; f) a charge generation layer, wherein the first charge generation layer comprises 9.9 vol % of a compound of formula (I) wherein A.sup.1, A.sup.2 and A.sup.3 are selected according to the following: ##STR01101## and N-([1,1-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-spirobi[fluoren]-2-amine, wherein the first charge generation layer has a thickness of 86 nm, and the second charge generation layer contains 99 vol.-% 2,2-(1,3-Phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 vol.-% Li, wherein the second charge generation layer has a thickness of 10 nm; g) a charge generation layer, wherein the first charge generation layer comprises 10.8 vol % of a compound of formula (I) wherein A.sup.1, A.sup.2 and A.sup.3 are selected according to the following: ##STR01102## and N-([1,1-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-spirobi[fluoren]-2-amine, wherein the first charge generation layer has a thickness of 86 nm, and the second charge generation layer contains 99 vol.-% 2,2-(1,3-Phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 vol.-% Li, wherein the second charge generation layer has a thickness of 10 nm; h) a charge generation layer, wherein the first charge generation layer comprises 11.8 vol % of a compound of formula (I) wherein A.sup.1, A.sup.2 and A.sup.3 are selected according to the following: ##STR01103## and N-([1,1-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-spirobi[fluoren]-2-amine, wherein the first charge generation layer has a thickness of 86 nm, and the second charge generation layer contains 99 vol.-% 2,2-(1,3-Phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 vol.-% Li, wherein the second charge generation layer has a thickness of 10 nm; i) a charge generation layer, wherein the first charge generation layer comprises 9.9 vol % of a compound of formula (I) wherein A.sup.1, A.sup.2 and A.sup.3 are selected according to the following: ##STR01104## and N-([1,1-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine, wherein the first charge generation layer has a thickness of 10 nm, and the second charge generation layer contains 99 vol.-% 2,2-(1,3-Phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 vol.-% Li, wherein the second charge generation layer has a thickness of 10 nm; j) a charge generation layer, wherein the first charge generation layer comprises 10.3 vol % of a compound of formula (I) wherein A.sup.1, A.sup.2 and A.sup.3 are selected according to the following: ##STR01105## and N-([1,1-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine, wherein the first charge generation layer has a thickness of 10 nm, and the second charge generation layer contains 99 vol.-% 2,2-(1,3-Phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 vol.-% Li, wherein the second charge generation layer has a thickness of 10 nm; k) a charge generation layer, wherein the first charge generation layer comprises 10.3 vol % of a compound of formula (I) wherein A.sup.1, A.sup.2 and A.sup.3 are selected according to the following: ##STR01106## and N-([1,1-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine, wherein the first charge generation layer has a thickness of 10 nm, and the second charge generation layer contains 99 vol.-% 2,2-(1,3-Phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 vol.-% Li, wherein the second charge generation layer has a thickness of 10 nm; l) a charge generation layer, wherein the first charge generation layer comprises 5 vol % of a compound of formula (I) wherein A.sup.1, A.sup.2 and A.sup.3 are selected according to the following: ##STR01107## and N-([1,1-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-spirobi[fluoren]-4-amine, wherein the first charge generation layer has a thickness of 10 nm, and the second charge generation layer contains 99 vol.-% 2,2-(1,3-Phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 vol.-% or 3 vol.-% Li, wherein the second charge generation layer has a thickness of 10 nm; m) a charge generation layer, wherein the first charge generation layer comprises 5 vol % of a compound of formula (I) wherein A.sup.1, A.sup.2 and A.sup.3 are selected according to the following: ##STR01108## and N-([1,1-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-spirobi[fluoren]-4-amine, wherein the first charge generation layer has a thickness of 10 nm, and the second charge generation layer contains 99 vol.-% 2,2-(1,3-Phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 vol.-% or 3 vol.-% Li, wherein the second charge generation layer has a thickness of 10 nm; n) a charge generation layer, wherein the first charge generation layer comprises 5 vol % or 10 vol % of a compound of formula (I) wherein A.sup.1, A.sup.2 and A.sup.3 are selected according to the following: ##STR01109## and N-([1,1-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-spirobi[fluoren]-4-amine, wherein the first charge generation layer has a thickness of 10 nm, and the second charge generation layer contains 99 vol.-% 2,2-(1,3-Phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 vol.-% or 3 vol.-% Li, wherein the second charge generation layer has a thickness of 10 nm; o) a charge generation layer, wherein the first charge generation layer comprises 5 vol % or 10 vol % of a compound of formula (I) wherein A.sup.1, A.sup.2 and A.sup.3 are selected according to the following: ##STR01110## and N-([1,1-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-spirobi[fluoren]-4-amine, wherein the first charge generation layer has a thickness of 10 nm, and the second charge generation layer contains 99 vol.-% 2,2-(1,3-Phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 vol.-% or 3 vol.-% Li, wherein the second charge generation layer has a thickness of 10 nm; p) a charge generation layer, wherein the first charge generation layer comprises 10 vol % of a compound of formula (I) wherein A.sup.1, A.sup.2 and A.sup.3 are selected according to the following: ##STR01111## and N-([1,1-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-spirobi[fluoren]-4-amine, wherein the first charge generation layer has a thickness of 10 nm, and the second charge generation layer contains 99 vol.-% 2,2-(1,3-Phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 vol.-% or 3 vol.-% Li, wherein the second charge generation layer has a thickness of 10 nm; q) a charge generation layer, wherein the first charge generation layer comprises 10 vol % of a compound of formula (I) wherein A.sup.1, A.sup.2 and A.sup.3 are selected according to the following: ##STR01112## and N-([1,1-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-spirobi[fluoren]-4-amine, wherein the first charge generation layer has a thickness of 10 nm, and the second charge generation layer contains 99 vol.-% 2,2-(1,3-Phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 vol.-% or 3 vol.-% Li, wherein the second charge generation layer has a thickness of 10 nm; r) a charge generation layer, wherein the first charge generation layer comprises 10 vol % of a compound of formula (I) wherein A.sup.1, A.sup.2 and A.sup.3 are selected according to the following: ##STR01113## and N-([1,1-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-spirobi[fluoren]-4-amine, wherein the first charge generation layer has a thickness of 10 nm, and the second charge generation layer contains 99 vol.-% 2,2-(1,3-Phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 vol.-% or 3 vol.-% Li, wherein the second charge generation layer has a thickness of 10 nm; s) a charge generation layer, wherein the first charge generation layer comprises 10 wt % of a compound of formula (I) wherein A.sup.1, A.sup.2 and A.sup.3 are selected according to the following: ##STR01114## wherein the first charge generation layer has a thickness of 10 nm, and the second charge generation layer contains 99 vol.-% 2,2-(1,3-Phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 vol.-% Li, wherein the second charge generation layer has a thickness of 10 nm; t) a charge generation layer, wherein the first charge generation layer comprises 10 wt % of a compound of formula (I) wherein A.sup.1, A.sup.2 and A.sup.3 are selected according to the following: ##STR01115## wherein the first charge generation layer has a thickness of 10 nm, and the second charge generation layer contains 99 vol.-% 2,2-(1,3-Phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 vol.-% Li, wherein the second charge generation layer has a thickness of 10 nm; u) a charge generation layer, wherein the first charge generation layer comprises 10 wt % of a compound of formula (I) wherein A.sup.1, A.sup.2 and A.sup.3 are selected according to the following: ##STR01116## wherein the first charge generation layer has a thickness of 10 nm, and the second charge generation layer contains 99 vol.-% 2,2-(1,3-Phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 vol.-% Li, wherein the second charge generation layer has a thickness of 10 nm; v) a charge generation layer, wherein the first charge generation layer comprises 10 vol % or 10 wt % of a compound of formula (I) wherein A.sup.1, A.sup.2 and A.sup.3 are selected according to the following: ##STR01117## and N-([1,1-biphenyl]-2-yl)-N-(9.9-dimethyl-9H-fluoren-2-yl)-9,9spirobi[fluoren]-2-amine, wherein the first charge generation layer has a thickness of 10 nm, and the second charge generation layer contains 99 vol.-% 2,2-(1,3-Phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 vol.-% Li, wherein the second charge generation layer has a thickness of 15 nm; w) a charge generation layer, wherein the first charge generation layer comprises 10 vol % or 10 wt % of a compound of formula (I) wherein A.sup.1, A.sup.2 and A.sup.3 are selected according to the following: ##STR01118## and N-([1,1-biphenyl]-2-yl)-N-(9.9-dimethyl-9H-fluoren-2-yl)-9,9spirobi[fluoren]-2-amine, wherein the first charge generation layer has a thickness of 10 nm, and the second charge generation layer contains 99 vol.-% 2,2-(1,3-Phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 vol.-% Li, wherein the second charge generation layer has a thickness of 15 nm; and x) a charge generation layer, wherein the first charge generation layer comprises 10 vol % or 10 wt % of a compound of formula (I) wherein A.sup.1, A.sup.2 and A.sup.3 are selected according to the following: ##STR01119## and N-([1,1-biphenyl]-2-yl)-N-(9.9-dimethyl-9H-fluoren-2-yl)-9,9spirobi[fluoren]-2-amine, wherein the first charge generation layer has a thickness of 10 nm, and the second charge generation layer contains 99 vol.-% 2,2-(1,3-Phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 vol.-% Li, wherein the second charge generation layer has a thickness of 15 nm.

3. Charge generation layer according to claim 1, wherein the organic electron transport compound comprises 15 covalently bound atoms.

4. Charge generation layer according to claim 1, wherein the metal dopant is Yb or a metal alloy comprising a metal selected from the group consisting of Li and Yb.

5. Charge generation layer according to claim 1, wherein the organic electron transport compound has a LUMO when calculated by DFT using B3LYP/6-31G* of <1.75 eV.

6. Charge generation layer according to claim 1, wherein the compound of formula (I) has an absorption maximum .sub.max at 455 nm when measured in DCM at a concentration of 10.sup.5 to 10.sup.4 mol/L at 20 C.

7. Charge generation layer according to claim 1, wherein the compound of formula (I) has an absorption maximum .sub.max at 475 nm.

8. Charge generation layer according to claim 1, wherein the compound of formula (I) has a LUMO expressed in the absolute scale referring to vacuum energy level being zero when 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 in the range from 5.7 eV to 4.7 eV.

9. Organic electronic device comprising a charge generation layer according to claim 1.

10. Organic electronic device comprising at least two vertically stacked electroluminescent units and a charge generation layer according to claim 1, wherein each electroluminescent unit comprises at least one light-emitting layer.

11. Organic electronic device according to claim 9, comprising at least three or at least four vertically stacked electroluminescent units, wherein each electroluminescent unit comprises at least one light-emitting layer.

12. Display device comprising a plurality of organic electronic devices according to claim 9.

13. Display device according to claim 12, wherein at least two of the plurality of the organic electronic devices share as charge generation layer a common charge generation layer, wherein the common charge generation layer is a charge generation layer according to claim 1.

14. A compound according to formula (XI) ##STR01120## wherein in formula (XI) A.sup.1 is selected from a group of formula (XIIa) ##STR01121## wherein 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; X.sup.5 is selected from CR.sup.5 or N; R.sup.1 (if present) is selected from electron-withdrawing group, CN, partially fluorinated or perfluorinated C.sub.1 to C.sub.8 alkyl, NO.sub.2, halogen, Cl, F, D or H, R.sup.2, R.sup.3 and R.sup.5(if present) are independently selected from electron-withdrawing group, CN, partially fluorinated or perfluorinated C.sub.1 to C.sub.8 alkyl, NO.sub.2, halogen, Cl, F, D or H, R.sup.4 is selected from CN, and partially fluorinated or perfluorinated C.sub.1 to C.sub.8 alkyl, whereby when any of R.sup.1, R.sup.2, R.sup.3 and R.sup.5 is present, then the corresponding X.sup.1, X.sup.2, X.sup.3, and X.sup.5 is not N; and wherein in formula (XI) A.sup.2 and A.sup.3 are independently selected from formula (XIII) ##STR01122## 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 electron-withdrawing group, CN, partially or perfluorinated C.sub.1 to C.sub.6 alkyl, halogen, NO.sub.2, Cl, F, D; and R is selected from 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.

15. Compound according to claim 14, wherein compound of formula (XI) is selected from a compound of formula (XI) ##STR01123## wherein in formula (XI) A.sup.1 is selected from a group of formula (XIIa) ##STR01124## wherein 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; X.sup.5 is selected from CR.sup.5 or N; R.sup.1 (if present) is selected from electron-withdrawing group, CN, partially fluorinated or perfluorinated C.sub.1 to C.sub.8 alkyl, NO.sub.2, halogen, Cl, F, D or H, R.sup.2, R.sup.3 and R.sup.5(if present) are independently selected from electron-withdrawing group, CN, partially fluorinated or perfluorinated C.sub.1 to C.sub.8 alkyl, NO.sub.2, halogen, Cl, F, D or H, R.sup.4 is selected from CN, and partially fluorinated or perfluorinated C.sub.1 to C.sub.8 alkyl, whereby when any of R.sup.1, R.sup.2, R.sup.3 and R.sup.5 is present, then the corresponding X.sup.1, X.sup.2, X.sup.3, and X.sup.5 is not N; and wherein in formula (XI) A.sup.2 and A.sup.3 are independently selected from formula (XIII) ##STR01125## 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 electron-withdrawing group, CN, partially or perfluorinated C.sub.1 to C.sub.6 alkyl, halogen, NO.sub.2, Cl, F, D; and R is selected from 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; and wherein the compound of formula (XI) comprises at least five CN groups; wherein in formula (XIIa) if X.sup.n is N and X.sup.n+1 is CR.sup.n+1 then R.sup.n+1 cannot be CN (with n=1 to 4); and wherein in formula (XIIa) if X.sup.n is N and X.sup.n+1 is CR.sup.n1 then R.sup.n1 cannot be CN (with n=1 to 4).

16. Compound according to claim 14, wherein compound of formula (XI) is selected from a compound of formula (XI) ##STR01126## whereby A.sup.1 is selected from formula (XIIb) ##STR01127## wherein 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; R.sup.1 (if present) is selected from electron-withdrawing group, CN, partially fluorinated or perfluorinated C.sub.1 to C.sub.8 alkyl, NO.sub.2, halogen, Cl, F, D or H, R.sup.2, and R.sup.3 (if present) are independently selected from electron-withdrawing group, CN, partially fluorinated or perfluorinated C.sub.1 to C.sub.8 alkyl, NO.sub.2, halogen, Cl, F, D or H, R.sup.4 is selected from CN, and partially fluorinated or perfluorinated C.sub.1 to C.sub.8 alkyl, whereby when any of R.sup.1, R.sup.2, and R.sup.3 and is present, then the corresponding X.sup.1, X.sup.2, and X.sup.3 is not N; with the proviso that when R.sup.1 and R.sup.4 are present and only R.sup.1 or R.sup.4 is selected from CN, then R.sup.2, R.sup.3 and the remaining R.sup.1 or R.sup.4 are independently selected from CN, and partially fluorinated or perfluorinated C.sub.1 to C.sub.8 alkyl, D, or R.sup.2 and R.sup.3 are selected from CN, partially fluorinated or perfluorinated C.sub.2 to C.sub.8 alkyl, halogen, Cl, F, D, or H, or R.sup.2, R.sup.3 and the remaining R.sup.1 or R.sup.4 are independently selected from CN, partially fluorinated or perfluorinated C.sub.1 to C.sub.8 alkyl, halogen, Cl, F, D; or with the proviso that when R.sup.1 and R.sup.4 are present and only R.sup.1 or R.sup.4 is selected from perfluorinated C.sub.1, then R.sup.2 and R.sup.3 are independently selected from partially fluorinated or perfluorinated C.sub.2 to C.sub.8 alkyl, halogen, Cl, F, D, or H; or R.sup.2, R.sup.3 and the remaining R.sup.1 or R.sup.4 is selected from CN, partially fluorinated or perfluorinated C.sub.1 to C.sub.8 alkyl, halogen, Cl, F, D; or with the proviso that when X.sup.1 is N and R.sup.4 is selected from CN then R.sup.2, R.sup.3, are selected from (if present) H or D, or R.sup.2 and R.sup.3 are independently selected from CN, partially fluorinated or perfluorinated C.sub.1 to C.sub.8 alkyl, halogen, Cl, F, D, but R.sup.2 and R.sup.3 cannot be both CN, or R.sup.2 is selected from partially fluorinated or perfluorinated C.sub.2 to C.sub.8 alkyl, halogen, Cl, F, D or H; or with the proviso that when X.sup.1 is N and R.sup.4 is selected from perfluorinated C.sub.1 alkyl, then R.sup.2 is selected from partially fluorinated or perfluorinated C.sub.2 to C.sub.8 alkyl, halogen, Cl, F, D or R.sup.3 is selected from CN, partially fluorinated or perfluorinated C.sub.1 to C.sub.8 alkyl, halogen, Cl, F, D, or R.sup.2 and R.sup.3, are independently selected from CN, partially fluorinated or perfluorinated C.sub.1 to C.sub.8 alkyl, halogen, Cl, F, D, or R.sup.2 and R.sup.3 are independently selected from (if present) H or D; and wherein in formula (XI) A.sup.2 and A.sup.3 are independently selected from formula (XIII) ##STR01128## 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 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.

17. Compound according to claim 14, wherein compound of formula (XI) is selected from a compound of formula (XI) ##STR01129## whereby A.sup.1 is selected from formula (XIIb) ##STR01130## wherein 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; R.sup.1 (if present) is selected from electron-withdrawing group, CN, partially fluorinated or perfluorinated C.sub.1 to C.sub.8 alkyl, NO.sub.2, halogen, Cl, F, D or H, R.sup.2, and R.sup.3 (if present) are independently selected from partially fluorinated or perfluorinated C.sub.1 to C.sub.8 alkyl, NO.sub.2, halogen, Cl, F, D or H, and if X.sup.3 is N then R.sup.4 of CR.sup.4 of X.sup.4 cannot be CN; if X.sup.2 is N and X.sup.1 is CR.sup.1 then R.sup.1 cannot be CN; R.sup.4 is selected from CN, and partially fluorinated or perfluorinated C.sub.1 to C.sub.8 alkyl, whereby when any of R.sup.1, R.sup.2, and R.sup.3 and is present, then the corresponding X.sup.1, X.sup.2, and X.sup.3 is not N; with the proviso that when R.sup.1 and R.sup.4 are present and only R.sup.1 or R.sup.4 is selected from CN, then R.sup.2, R.sup.3 and the remaining R.sup.1 or R.sup.4 are independently selected from CN, and partially fluorinated or perfluorinated C.sub.1 to C.sub.8 alkyl, D, or R.sup.2 and R.sup.3 are selected from CN, partially fluorinated or perfluorinated C.sub.2 to C.sub.8 alkyl, halogen, Cl, F, D, or H, or R.sup.2, R.sup.3 and the remaining R.sup.1 or R.sup.4 are independently selected from CN, partially fluorinated or perfluorinated C.sub.1 to C.sub.8 alkyl, halogen, Cl, F, D; or with the proviso that when R.sup.1 and R.sup.4 are present and only R.sup.1 or R.sup.4 is selected from perfluorinated C.sub.1, then R.sup.2 and R.sup.3 are independently selected from partially fluorinated or perfluorinated C.sub.2 to C.sub.8 alkyl, halogen, Cl, F, D, or H; or R.sup.2, R.sup.3 and the remaining R.sup.1 or R.sup.4 is selected from CN, partially fluorinated or perfluorinated C.sub.1 to C.sub.8 alkyl, halogen, Cl, F, D; or with the proviso that when X.sup.1 is N and R.sup.4 is selected from CN then R.sup.2, R.sup.3, are selected from (if present) H or D, or R.sup.2 and R.sup.3 are independently selected from CN, partially fluorinated or perfluorinated C.sub.1 to C.sub.8 alkyl, halogen, Cl, F, D, but R.sup.2 and R.sup.3 cannot be both CN, or R.sup.2 is selected from partially fluorinated or perfluorinated C.sub.2 to C.sub.8 alkyl, halogen, Cl, F, D or H; or with the proviso that when X.sup.1 is N and R.sup.4 is selected from perfluorinated C.sub.1 alkyl, then R.sup.2 is selected from partially fluorinated or perfluorinated C.sub.2 to C.sub.8 alkyl, halogen, Cl, F, D or R.sup.3 is selected from CN, partially fluorinated or perfluorinated C.sub.1 to C.sub.8 alkyl, halogen, Cl, F, D, or R.sup.2 and R.sup.3, are independently selected from CN, partially fluorinated or perfluorinated C.sub.1 to C.sub.8 alkyl, halogen, Cl, F, D, or R.sup.2 and R.sup.3 are independently selected from (if present) H or D; and wherein in formula (XI) A.sup.2 and A.sup.3 are independently selected from formula (XIII) ##STR01131## 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 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; and wherein the compound of formula (XI) comprises at least five CN groups.

18. Compound according to claim 1, wherein A.sup.1 in the compound according to formula (XI) is selected from one of the following formulae: ##STR01132## ##STR01133##

19. Compound according to claim 1, wherein A.sup.1 in the compound according to formula (XI) is selected from one of the following formulae: ##STR01134##

20. Compound according to claim 1, wherein A.sup.1 in the compound according to formula (XI) is selected from one of the following formulae: ##STR01135## and wherein the compound of formula (XI) comprises at least five CN groups.

21. Compound according to claim 15, wherein A.sup.2 and A.sup.3 in the compound according to formula (XI) are independently selected from one of the following formulae: ##STR01136## ##STR01137## ##STR01138## ##STR01139##

22. Compound according to claim 15, wherein A.sup.2 and A.sup.3 in the compound according to formula (XI) are independently selected from one of the following formulae: ##STR01140## ##STR01141## ##STR01142## ##STR01143##

23. Compound according to claim 15, wherein A.sup.2 and A.sup.3 in the compound according to formula (XI) are independently selected from one of the following formulae: ##STR01144## ##STR01145## ##STR01146## and wherein the compound of formula (XI) comprises at least five CN groups.

24. Compound according to claim 14, wherein the compound of formula (XI) is selected from a compound of formula (XIV) ##STR01147## wherein 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; R.sup.1 (if present) is selected from electron-withdrawing group, CN, partially fluorinated or perfluorinated C.sub.1 to C.sub.8 alkyl, NO.sub.2, halogen, Cl, F, D or H, R.sup.2, and R.sup.3 (if present) are independently selected from electron-withdrawing group, CN, partially fluorinated or perfluorinated C.sub.1 to C.sub.8 alkyl, NO.sub.2, halogen, Cl, F, D or H, R.sup.4 is selected from CN, and partially fluorinated or perfluorinated C.sub.1 to C.sub.8 alkyl, whereby when any of R.sup.1, R.sup.2, and R.sup.3 is present, then the corresponding X.sup.1, X.sup.2, and X.sup.3 is not N; wherein R is selected from 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 each X.sup.1 is selected from CR.sup.1 or N; each X.sup.2 is selected from CR.sup.2 or N; each X.sup.3 is selected from CR.sup.3 or N; each X.sup.4 is selected from CR.sup.4 or N; each X.sup.5 is selected from CR.sup.5 or N; each R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 (if present) are independently selected from electron-withdrawing group, F, 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.

Description

DESCRIPTION OF THE DRAWINGS

[0798] 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.

[0799] 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.

[0800] FIG. 1 is a schematic sectional view of an OLED comprising a charge generation layer, according to an exemplary embodiment of the present invention.

[0801] 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.

[0802] Hereinafter, the figures are illustrated in more detail with reference to examples. However, the present disclosure is not limited to the following figures.

[0803] 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.

[0804] FIG. 1 is a schematic sectional view of an OLED 100, according to one exemplary embodiment of the present invention.

[0805] 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).

[0806] 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.

[0807] 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, a 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, a second hole blocking layer (EBL) 156, a second electron transport layer (ETL) 161, an electron injection layer (EIL) 180 and a cathode layer 190. The HIL may comprise a compound of Formula (I).

[0808] 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 (EIL) 180 and a cathode layer 190 are formed, in that order or the other way around.

[0809] While not shown in FIGS. 1 and 2, 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.

[0810] 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

[0811] The invention is furthermore illustrated by the following examples which are illustrative only and non-binding.

[0812] Compounds of formula (I) may be prepared as described in EP2180029A1 and WO2016097017A1.

UV-VIS Absorption Measurement in Solution

[0813] Experimental absorption spectra were recorded on a Shimadzu UV-2401 PC Series Spectrophotometer. For sample preparation the material is weighed into an aluminum crucible, which is then inserted into a 25 mL measuring flask. The related micro balance has a mass change readability in the 1-2 g range. The flask is then filled up to the mark with dichloromethane (Spectroscopy grade, transmission 90% for 248 nm according to manufacturer) and shaken until the material is completely dissolved, yielding a solution with a concentration of 10-4-10-5 mol/L. For measurement the solution is put into a standard cuvette (Hellma 110-QS: quartz, d=10 mm, with PTFE stopper). The spectrum is recorded at a slit width of 1 nm at a sampling interval of 0.5 nm at an ambient temperature of 20 C. From all spectra the background absorption of the pure solvent is subtracted which was measured immediately prior to the measurement using the same measurement conditions. The results are shown in Table 1.

Optical Absorptance Measurement of p-Type Charge Generation Layer

[0814] Mixed films of N-([1,1-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-spirobi[fluoren]-2-amine and a p-dopant according to Table 2 with a thickness of 35 nm on quartz substrates (EN08, 99.98% SiO2, GVB GmbH) are prepared by thermal evaporation in a vacuum system (Cluster Tool, Sunic System Ltd.) at a deposition rate of 1 /s and a pressure of approximately 3 e-7 mbar. The samples are stored in glovebox with pure nitrogen atmosphere until the measurement takes place (maximum 1 hour of air exposure). Reflectance and transmittance are measured using a Filmetrics F10-RT Spectrometer with a spectral range of 380 nm to 1050 nm. An empty quartz substrate is used for reflectance standard. Absorptance is automatically calculated by subtracting reflectance and transmittance values from 100%. The results are shown in Table 2.

Glass Transition Temperature

[0815] The glass transition temperature (Tg) 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.

Calculated HOMO and LUMO

[0816] 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.

Calculated Absorption Area or Maximal Absorption

[0817] Calculations were carried out with the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany).

[0818] LUMO and HOMO energies and the resulting HOMO-LUMO-gap were calculated using the hybrid functional B3LYP with a 6-31G* basis set in the gas phase. The thus obtained optimized geometries were used to run TDDFT calculations applying the hybrid functional PBE0 with a def2-SVP basis set in the gas phase and including the first 30 singlet transitions. The calculated singlet transitions were used to calculate the absorption spectra by applying a Gaussian fit (=215-850 nm, SD=20, 200 sampling points) from which transitions below 350 nm were excluded.

[0819] To calculate the general absorption in a relevant wavelength area (k=400-650 nm, blue and green emission) the integral below the calculated UV TDDFT spectrum was determined.

Calculated Bond Dissociation Energy (BDE)

[0820] All the calculations were performed with the program package ORCA Version 5.0.3-f.1 (Department of theory and spectroscopy, Max Planck Institute fr Kohlenforschung Kaiser Wilhelm Platz 1, 45470 Muelheim/Ruhr, Germany).

[0821] Homolytic Bond dissociation Energies (BDE), the amount of energy needed to break apart one mole of covalently bonded gases into a pair of radicals, were calculated accordingly a reported procedure (J. Phys. Chem. A, 1999, 103, 11, 1653-1661).

[0822] Molecular geometries were optimized with the DFT functional BP86 and the Def2-SVP basis set in the gas phase, if more than one conformer was available, we selected the conformer at lower energy. The optimized geometries were identified as minima by frequency analysis.

[0823] From the optimized geometry, G.sup.(BP86/Def2SVP) and Electronic Energy.sup.(BP86/Def2SVP) were obtained at the same level of geometry. In a second calculation the Electronic Energy.sup.(B3LYP/Def2TZVP) was obtained from a single point calculation performed with the DFT functional B3LYP and the Def2-TZVP basis set in the gas phase.

[0824] Energy corrected values were obtained as:

[00001]$\left(G^{\left(\mathrm{BP}86/\mathrm{Def}2\mathrm{SVP}\right)}-\mathrm{Electronic}{\mathrm{Energy}}^{\left(\mathrm{BP}86/\mathrm{Def}2\mathrm{SVP}\right)}\right)+\mathrm{Electronic}{\mathrm{Energy}}^{\left(B3\mathrm{LYP}/\mathrm{Def}2\mathrm{TZVP}\right)}.$

General Procedure for Fabrication of OLEDs

[0825] For bottom emission devices, see Table 2, a 15/cm.sup.2 glass substrate with 90 nm ITO (available from Corning Co.) was cut to a size of 50 mm50 mm0.7 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.

[0826] Then N-([1,1-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-spirobi[fluoren]-2-amine was vacuum deposited with 12 vol % of compound according to formula (I) or a comparative compound according to Table 2 to form a hole injection layer having a thickness 10 nm.

[0827] Then N-([1,1-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-spirobi[fluoren]-2-amine was vacuum deposited, to form a first hole transport layer having a thickness of 130 nm

[0828] Then N,N-bis(4-(dibenzo[b,d]furan-4-yl)phenyl)-[1,1:4,1-terphenyl]-4-amine was vacuum deposited on the HTL, to form an electron blocking layer (EBL) having a thickness of 5 nm.

[0829] 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 blue-emitting EML with a thickness of 20 nm.

[0830] Then 2-(3-(9,9-dimethyl-9H-fluoren-2-yl)-[1,1-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine was vacuum deposited to form a first hole blocking layer having a thickness of 25 nm.

[0831] Then an-type CGL having a thickness of 15 nm is formed on the ETL1 by co-depositing 99 vol.-% (3-(10-(3-(2,6-diphenylpyrimidin-4-yl)phenyl)anthracen-9-yl)phenyl)dimethylphosphine oxide] having energy level of the LUMO of 1.80 eV, expressed in the absolute scale referring to vacuum energy level being zero when 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 and 1 vol.-% Yb.

[0832] Then a p-type CGL having a thickness of 20 nm is formed on the first n-type CGL by co-depositing N-([1,1-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-spirobi[fluoren]-2-amine with 20 vol % compound according to formula (I) or a comparative example according to table 3.

[0833] Then a second hole transport layer having a thickness of 11 nm is formed on the first p-type CGL by depositing N-([1,1-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-spirobi[fluoren]-2-amine.

[0834] Then a second electron blocking layer having a thickness of 5 nm is formed on the second hole transport layer by depositing N,N-bis(4-(dibenzo[b,d]furan-4-yl)phenyl)-[1,1:4,1-terphenyl]-4-amine,

[0835] 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 second EBL, to form a second blue-emitting EML with a thickness of 20 nm.

[0836] Then 2-(3-(9,9-dimethyl-9H-fluoren-2-yl)-[1,1-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine was vacuum deposited to form a second hole blocking layer having a thickness of 10 nm is formed on the second blue-emitting EML.

[0837] Then, 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 were vacuum deposited on the second hole blocking layer to form a second electron transport layer having a thickness of 25 nm.

[0838] Al is evaporated at a rate of 0.01 to 1 /s at 10.sup.7 mbar to form a cathode with a thickness of 100 nm.

[0839] 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.

[0840] 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/cm.sup.2.

[0841] 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.

[0842] 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.

[0843] 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.

[0844] The increase in operating voltage AU is used as a measure of the operational voltage stability of the device. This increase is determined during the LT measurement and by subtracting the operating voltage after 1 hour after the start of operation of the device from the operating voltage after 100 hours.

U=[U100 h)U(1 h)]

[0845] or the operating voltage after 1 hour after the start of operation of the device from the operating voltage after 400 hours.

[00002]$U=[U400h)-U\left(1h\right)]$

[0846] The smaller the value of AU the better is the operating voltage stability.

Luminous Flux

[0847] The samples were placed individually into an integrating sphere and the luminous flux has been measured at a current density of 10 mA/cm.sup.2 using an Instrument Systems CAS-140CT array spectrometer (calibrated by Deutsche Akkreditierungsstelle (DAkkS)). As a constant current source a Keithley 2635 source measure unit has been used.

Technical Effect of the Invention

TABLE-US-00005 TABLE 1 Overview of physical parameters of radialenes Absorption Area 400- 650 nm abs(max) abs(max) TDDFT of organic TDDFT [a.u. nm] LUMO p-dopant of organic of organic DFT A.sup.1 A.sup.2 A.sup.3 in solution p-dopant p-dopant [eV] Comp [00811] [00812] [00813] 475 507 54.84 5.19 A1 [00814] [00815] [00816] 448 479 41.69 5.44 A2 [00817] [00818] [00819] 395 415 21.62 5.15 A3 [00820] [00821] [00822] 409 409 34.72 4.86 A4 [00823] [00824] [00825] 420 472 25.80 4.74 A5 [00826] [00827] [00828] 426 434 37.39 5.13 A6 [00829] [00830] [00831] 428 428 40.80 5.15 A7 [00832] [00833] [00834] 430 428 39.87 4.99 A8 [00835] [00836] [00837] 434 456 35.17 5.18 A9 [00838] [00839] [00840] 435 428 39.05 5.09 A10 [00841] [00842] [00843] 435 434 41.36 5.15 A11 [00844] [00845] [00846] 436 444 43.28 5.22 A12 [00847] [00848] [00849] 436 444 42.67 5.29 A13 [00850] [00851] [00852] 438 437 43.11 5.31 A14 [00853] [00854] [00855] 439 456 41.83 4.83 A15 [00856] [00857] [00858] 364 2.00 5.16 A55 [00859] [00860] [00861] 418 31.95 5.02 A65 [00862] [00863] [00864] 430 33.33 5.25 A66 [00865] [00866] [00867] 409 23.00 5.03 A16 [00868] [00869] [00870] 412 22.41 5.17 A17 [00871] [00872] [00873] 444 29.55 5.06 A18 [00874] [00875] [00876] 431 26.84 5.45 A72 [00877] [00878] [00879] 466 39.16 5.38 A62 [00880] [00881] [00882] 425 35.20 5.11 A31 [00883] [00884] [00885] 450 35.14 5.08 A59 [00886] [00887] [00888] 465 46.77 5.32 A79 [00889] [00890] [00891] 453 41.51 5.26 A77 [00892] [00893] [00894] 447 35.62 5.26 A57 [00895] [00896] [00897] 460 46.51 5.17 A58 [00898] [00899] [00900] 431 39.95 5.17 A68 [00901] [00902] [00903] 440 39.97 5.25 A70 [00904] [00905] [00906] 479 46.68 4.96 A74 [00907] [00908] [00909] 421 34.47 5.12 A76 [00910] [00911] [00912] 437 41.87 5.21 A19 [00913] [00914] [00915] 475 43.25 5.16 A69 [00916] [00917] [00918] 418 32.90 5.07 A71 [00919] [00920] [00921] 472 45.97 5.29 A78 [00922] [00923] [00924] 425 33.42 5.21 A73 [00925] [00926] [00927] 463 42.45 5.32 A75 [00928] [00929] [00930] 479 44.93 5.13 A56 [00931] [00932] [00933] 446 469 46.58 5.04 A20 [00934] [00935] [00936] 447 491 53.13 5.19 A21 [00937] [00938] [00939] 479 44.58 5.06 A22 [00940] [00941] [00942] 466 35.52 5.38 A23 [00943] [00944] [00945] 439 456 44.09 5.02 A24 [00946] [00947] [00948] 441 428 41.93 5.03 A25 [00949] [00950] [00951] 441 463 44.65 5.22 A26 [00952] [00953] [00954] 442 466 45.18 5.32 A27 [00955] [00956] [00957] 443 453 46.44 5.24 A28 [00958] [00959] [00960] 443 447 43.38 5.14 A29 [00961] [00962] [00963] 446 463 45.38 4.97 A61 [00964] [00965] [00966] 472 43.75 5.02 A60 [00967] [00968] [00969] 441 469 44.37 5.27 A64 [00970] [00971] [00972] 482 43.98 5.11 A63 [00973] [00974] [00975] 479 46.36 5.37 A67 [00976] [00977] [00978] 457 494 46.79 5.23 A32 [00979] [00980] [00981] 451 467 42.43 5.19 A33 [00982] [00983] [00984] 451 447 43.57 5.38 A34 [00985] [00986] [00987] 453 475 45.84 4.82 A35 [00988] [00989] [00990] 453 453 48.05 5.30 A36 [00991] [00992] [00993] 454 469 45.16 5.00 A37 [00994] [00995] [00996] 454 466 47.05 5.00 A38 [00997] [00998] [00999] 454 475 49.05 5.12 A39 [01000] [01001] [01002] 454 453 42.44 4.75 A40 [01003] [01004] [01005] 455 463 43.79 4.93 A41 [01006] [01007] [01008] 456 456 44.17 4.93 A42 [01009] [01010] [01011] 456 466 43.40 4.91 A43 [01012] [01013] [01014] 456 472 44.34 5.16 A44 [01015] [01016] [01017] 457 479 47.13 5.10 A45 [01018] [01019] [01020] 457 485 48.37 5.23 A46 [01021] [01022] [01023] 457 479 47.51 5.16 A47 [01024] [01025] [01026] 457 472 44.53 4.79 A48 [01027] [01028] [01029] 458 479 50.75 4.85 A49 [01030] [01031] [01032] 458 479 46.77 5.07 A50 [01033] [01034] [01035] 458 479 44.92 4.73 A51 [01036] [01037] [01038] 458 491 42.93 5.04 A52 [01039] [01040] [01041] 459 475 45.68 4.92 A53 [01042] [01043] [01044] 459 479 51.36 5.51 A54 [01045] [01046] [01047] 459 491 51.09 5.32 A80 [01048] [01049] [01050] 427 415 17.94 5.24

[0848] The compounds in particular the inventive compounds exhibits a low absorption in the range of 300 to 650 nm.

[0849] Thus, the compounds may be beneficial for providing an organic electronic device or a display device with increased brightness of a display or when a lower current density is used, the lifetime of the display can be increased.

TABLE-US-00006 TABLE 2 Optical absorptance of p-type charge generation layer (solid film) Absorption Area Abs. Integral Abs. Integral Abs. Integral abs(max) 300-650 nm visible blue green of organic p- TDDFT 380-780 nm 450-500 nm 500-600 nm dopant in [a.u. x nm] Conc. [a.u. x nm] [a.u. x nm] [a.u. x nm] p-Dopant* solution of organic p-dopant (vol %) of solid film of solid film of solid film Comp. 1 Comparative 475 54.84245 10 3509 604 818 Inv. 1 A9 435 39.05 10 3283 486 594 Inv. 2 A12 436 42.66625 10 3418 524 592 Inv. 3 A32 451 42.43 10 3258 522 648 Inv. 4 A1 448 41.69 10 3433 436 769 Inv. 5 A25 441 44.65 10 3103 459 603

[0850] It can be seen from Table 2 that a layer containing a radialene having a abs(max) below 459 nm and an organic hole transport compound exhibits a lower absorption of visible light in particular of the green and blue part of the visible light.

[0851] This may be beneficial for increasing the brightness of a display or when a lower current density is used, the lifetime of the display can be increased.

TABLE-US-00007 TABLE 3 Performace of the OLED containing the inventive charge generation layer abs abs(max) Absorption Area luminous relative (max) 300-650 nm [a.u. x nm] Voltage EQE Ceff at flux luminous of organic TDDFT calculated by at 15 at 15 15 at 10 flux at Org. p-dopant in [a.u. x nm] of TDDFT of organic mA/cm.sup.2 mA/cm.sup.2 mA/cm.sup.2 mA/cm.sup.2 10 mA/cm.sup.2 p-dopant solution organic p-dopant p-dopant [V] [%] [cd/A] [lm] [%] Comp. Com- 475 507 54.84 7.32 13.25 130.3 0.0194 100% Ex. 2 parative Ex. 1 A25 441 463 44.65 7.30 13.92 135.8 0.0218 112% Ex. 2 A12 436 444 42.67 7.34 13.46 130.7 0.0211 109%

[0852] According to Table 3, a higher luminous flux for the charge generation layer according to the invention could be measured.

[0853] This may be beneficial for increasing the brightness of a display or when a lower current density is used, the lifetime of the display can be increased.

TABLE-US-00008 TABLE 4 Glass transition temperature (Tg) A.sup.1 A.sup.2 A.sup.3 Tg A12 [01051] [01052] [01053] 81 Comp [01054] [01055] [01056] 91 C27 [01057] [01058] [01059] 163 C13 [01060] [01061] [01062] 138 C30 [01063] [01064] [01065] 152 C3 [01066] [01067] [01068] 134 C2 [01069] [01070] [01071] 100 C32 [01072] [01073] [01074] 140 C34 [01075] [01076] [01077] 136 C8 [01078] [01079] [01080] 107 C7 [01081] [01082] [01083] 132 C14 [01084] [01085] [01086] 134 C35 [01087] [01088] [01089] 157

TABLE-US-00009 TABLE 5 Bond dissociation energy (BDE) Bond dissociation energy (BDE) Compound [kcal/mol.sup.1] Comp. Ex. 1 [01090] 460 (bond between pyridinyl and CN) Comp. Ex.2 [01091] 470 (bond between pyridinyl and CN) Inv. ex. 1 [01092] 480 (bond between pyridinyl and CN)

[0854] 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.