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US 2025/0081844 A1Published application
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)
AssigneeNovaled GmbH
InventorsMax Peter Nuellen, Benjamin Schulze, Jakob Jacek Wudarczyk, Steffen Runge, Thomas Rosenow, Peter Robaschik
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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).
Claims24
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)
- wherein in formula (I)
- A1 is independently selected from a group of formula (II)
- wherein Ar1 is independently selected from substituted or unsubstituted C6 to C36 aryl and substituted or unsubstituted C2 to C36 heteroaryl;
- wherein for the case that Ar1 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 —NO2;
- A2 and A3 are independently selected from a group of formula (III)
- wherein Ar2 is independently selected from substituted or unsubstituted C6 to C36 aryl and substituted or unsubstituted C2 to C36 heteroaryl;
- wherein for the case that Ar2 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 —NO2;
- and wherein each R′ is independently selected from substituted or unsubstituted C6 to C18 aryl, C3 to C18 heteroaryl, electron-withdrawing group, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, halogen, F or CN;
- wherein the compound of formula (I) has an absorption maximum λmax at ≤459 nm when measured in DCM at a concentration of 10−5 to 10−4 mol/L at 20° C., an absorption maximum λmax 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.
8 more elements
A compound according to formula (XI)
- wherein in formula (XI) A1 is selected from a group of formula (XIIa)
- wherein
- X1 is selected from CR1 or N;
- X2 is selected from CR2 or N;
- X3 is selected from CR3 or N;
- X4 is selected from CR4;
- X5 is selected from CR5 or N;
- R1 (if present) is selected from electron-withdrawing group, CN, partially fluorinated or perfluorinated C1 to C8 alkyl, —NO2, halogen, Cl, F, D or H,
- R2, R3 and R5(if present) are independently selected from electron-withdrawing group, CN, partially fluorinated or perfluorinated C1 to C8 alkyl, —NO2, halogen, Cl, F, D or H,
- R4 is selected from CN, and partially fluorinated or perfluorinated C1 to C8 alkyl, whereby when any of R1, R2, R3 and R5 is present, then the corresponding X1, X2, X3, and X5 is not N;
- and wherein in formula (XI) A2 and A3 are independently selected from formula (XIII)
- wherein Ar is independently selected from substituted or unsubstituted C6 to C18 aryl and substituted or unsubstituted C2 to C18 heteroaryl, wherein the substituents on Ar are independently selected from electron-withdrawing group, CN, partially or perfluorinated C1 to C6 alkyl, halogen, —NO2, Cl, F, D;
- and R′ is selected from substituted or unsubstituted C6 to C18 aryl or C3 to C18 heteroaryl, partially fluorinated or perfluorinated C1 to C8 alkyl, halogen, F or CN.
10 more elements
Dependencies are inferred from the claim text.