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EP-3989305-B1 - ORGANIC ELECTRONIC DEVICE COMPRISING A COMPOUND OF FORMULA (I), AND DISPLAY DEVICE COMPRISING THE ORGANIC ELECTRONIC DEVICE.

EP3989305B1EP 3989305 B1EP3989305 B1EP 3989305B1EP-3989305-B1

Inventors

  • NÜLLEN, MAX PETER
  • SCHULZE, Benjamin
  • WUDARCZYK, Jakob Jacek

Dates

Publication Date
20260513
Application Date
20201022

Claims (14)

  1. An organic electronic device comprising an anode layer (120), a cathode layer (190) and a charge generation layer (CGL), wherein the charge generation layer comprises a p-type charge generation layer (135) and a n-type charge generation player (185), wherein the p-type charge generation layer comprises a compound of formula (I) whereby A 1 is selected from formula (II) X 1 is selected from CR 1 or N; X 2 is selected from CR 2 or N; X 3 is selected from CR 3 or N; X 4 is selected from CR 4 or N; X 5 is selected from CR 5 or N; R 1 , R 2 , R 3 , R 4 and R 5 , if present, are independently selected from CN, partially fluorinated or perfluorinated C 1 to C 8 alkyl, halogen, Cl, F, D or H, whereby when any of R 1 , R 2 , R 3 , R 4 and R 5 is present, then the corresponding X 1 , X 2 , X 3 , X 4 and X 5 is not N; with the proviso that one of the following requirements a) to e) are fulfilled: a) At least one R 1 , R 2 , R 3 , R 4 and R 5 is independently selected from CN, partially flurorinated or perfluorinated C 1 to C 8 alkyl, halogen, Cl, F, and at least one remaining R 1 , R 2 , R 3 , R 4 and R 5 is selected D or H; b) R 1 or R 2 are selected from CN or partially flurorinated or perfluorinated C 1 to C 8 alkyl and at least one remaining R 1 to R 5 is independently selected from CN, partially flurorinated or perfluorinated C 1 to C 8 alkyl, halogen, Cl or F; c) R3 is selected from partially flurorinated or perfluorinated C 1 to C 8 alkyl and at least one of R 1 , R 2 , R 4 and R 5 is independently selected from CN, partially flurorinated or perfluorinated C 1 to C 8 alkyl, halogen, Cl or F; d) at least two R 1 to R 5 are independently selected from CN or partially flurorinated or perfluorinated C 1 to C 8 alkyl; or e) at least one X 1 to X 5 is N and at least two X 1 to X 5 are selected from CR 1 to CR 5 ; A 2 and A 3 are independently selected from formula (III) wherein Ar is independently selected from substituted or unsubstituted C 6 to C 18 aryl and substituted or unsubstituted C 2 to C 18 heteroaryl, wherein the substituents on Ar are independently selected from CN, partially or perfluorinated C 1 to C 6 alkyl, halogen, Cl, F, D; and wherein "*" denotes the binding position; and wherein the n-type charge generation layer comprises a metal dopant, and R' is selected from Ar, substituted or unsubstituted C 6 to C 18 aryl or C 3 to C 18 heteroaryl, partially flurorinated or perfluorinated C 1 to C 8 alkyl, halogen, F or CN.
  2. The device of any of the claims 1, whereby the p-type charge generation layer comprises a compound of formula (IV) whereby B 1 is selected from formula (V) B 3 and B 5 are Ar and B 2 , B 4 and B 6 are R; X 1 is selected from CR 1 or N; X 2 is selected from CR 2 or N; X 3 is selected from CR 3 or N; X 4 is selected from CR 4 or N; X 5 is selected from CR 5 or N; R 1 , R 2 , R 3 , R 4 and R 5 , if present, are independently selected from CN, partially fluorinated or perfluorinated C 1 to C 8 alkyl, halogen, Cl, F, D or H, whereby when any of R 1 , R 2 , R 3 , R 4 and R 5 is present, then the corresponding X 1 , X 2 , X 3 , X 4 and X 5 is not N; with the proviso that one of the following requirements a) to e) are fulfilled: a) At least one R 1 , R 2 , R 3 , R 4 and R 5 is independently selected from CN, partially flurorinated or perfluorinated C 1 to C 8 alkyl, halogen, Cl, F, and at least one remaining R 1 , R 2 , R 3 , R 4 and R 5 is selected D or H; b) R 1 or R 2 are selected from CN or partially flurorinated or perfluorinated C 1 to C 8 alkyl and at least one remaining R 1 to R 5 is independently selected from CN, partially flurorinated or perfluorinated C 1 to C 8 alkyl, halogen, Cl or F; c) R 3 is selected from partially flurorinated or perfluorinated C 1 to C 8 alkyl and at least one of R 1 , R 2 , R 4 and R 5 is independently selected from CN, partially flurorinated or perfluorinated C 1 to C 8 alkyl, halogen, Cl or F; d) at least two R 1 to R 5 are independently selected from CN or partially flurorinated or perfluorinated C 1 to C 8 alkyl; or e) at least one X 1 to X 5 is N and at least two X 1 to X 5 are selected from CR 1 to CR 5 ; and R' is selected from Ar, substituted or unsubstituted C 6 to C 18 aryl or C 3 to C 18 heteroaryl, partially flurorinated or perfluorinated C 1 to C 8 alkyl, halogen, F or CN; wherein Ar is independently selected from substituted or unsubstituted C 6 to C 18 aryl and substituted or unsubstituted C 2 to C 18 heteroaryl, wherein the substituents on Ar are independently selected from CN, partially or perfluorinated C 1 to C 6 alkyl, halogen, Cl, F, D.
  3. The device of claim 1 or 2, whereby in formula (II) or (V) R 3 is selected from CN or partially flurorinated or perfluorinated C 1 to C 8 alkyl and at least one R 1 , R 2 , R 4 , R 5 is selected from H or D.
  4. The device of any of the claims 1 to 3, whereby in formula (II) or (V) at least one X 1 to X 5 is N and at least one R 1 to R 5 is selected from CN, partially flurorinated or perfluorinated C 1 to C 8 alkyl, halogen, Cl, F.
  5. The device of any of the claims 1 to 4, whereby in formula (II) or (V) R 1 to R 5 are independently selected from CN, partially flurorinated or perfluorinated C 1 to C 8 alkyl, halogen, Cl, F
  6. The device of any of the claims 1 to 5, whereby A 2 and A 3 are identical.
  7. The device of any of the claims 1 to 6, whereby A 1 is different from A 2 and/or A 3 .
  8. The organic electronic device of any of the claims 1 to 7, whereby the p-type charge generation layer comprises a composition comprising a compound of formula (IV) and at least one compound of formula (IVa) to (IVd)
  9. The organic electronic device of any of the claims 1 to 8, wherein the p-type charge generation layer further comprises a substantially covalent matrix compound.
  10. The organic electronic device of any of the claims 1 to 9, further comprising a hole injection layer, wherein the hole injection layer is arranged between the anode layer and the charge generation layer and whereby the hole injection layer comprises a compound of formula (I) or (IV).
  11. The organic electronic device of any of the claims 1 to 10, whereby the p-type charge generation layer and the hole injection layer comprise an identical compound of formula (I) or (IV).
  12. The organic electronic device of any of the claims 1 to 11, whereby the p-type charge generation layer and the hole injection layer comprise an identical substantially covalent matrix compound.
  13. The organic electronic device of any of the claims 1 to 12, whereby the electronic organic device is an electroluminescent device, preferably an organic light emitting diode.
  14. A display device comprising an organic electronic device according to any of the claims 1 to 13.

Description

Organic electronic device comprising a compound of formula (I), and display device comprising the organic electronic device. Technical Field The present invention relates to an organic electronic device comprising a compound of formula (I), and a display device comprising the organic electronic device. Background Art Organic electronic devices, such as organic light-emitting diodes OLEDs, which are self-emitting devices, have a wide viewing angle, excellent contrast, quick response, high brightness, excellent operating voltage characteristics, and color reproduction. A typical OLED comprises an anode, a hole transport layer HTL, an emission layer EML, an electron transport layer ETL, and a cathode, which are sequentially stacked on a substrate. In this regard, the HTL, the EML, and the ETL are thin films formed from organic compounds. When a voltage is applied to the anode and the cathode, holes injected from the anode move to the EML, via the HTL, and electrons injected from the cathode move to the EML, via the ETL. The holes and electrons recombine in the EML to generate excitons. When the excitons drop from an excited state to a ground state, light is emitted. The injection and flow of holes and electrons should be balanced, so that an OLED having the above-described structure has excellent efficiency and/or a long lifetime. Performance of an organic light emitting diode may be affected by characteristics of the semiconductor layer, and among them, may be affected by characteristics of metal complexes which are also contained in the semiconductor layer. There remains a need to improve performance of organic semiconductor materials, semiconductor layers, as well as organic electronic devices thereof, in particular to achieve improved operating voltage stability over time through improving the characteristics of the compounds comprised therein. Compounds for organic optoeletronic devices are inter alia disclosed in the EP 3 382 770 (A1), US 2010 / 288 362 (A1), EP 3 336 918 (A1), EP 3 233 787 (B1), EP 3 667 755 (A1), CN 108 774515 (A), and CN 109 081 791 (A). DISCLOSURE An aspect of the present invention provides an organic electronic device according to the claims comprising an anode layer, a cathode layer and a charge generation layer, wherein the charge generation layer comprises a p-type charge generation layer and a n-type charge generation layer, wherein the p-type charge generation layer comprises a compound of formula (I) whereby A1 is selected from formula (II) 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 or N;X5 is selected from CR5 or N;R1, R2, R3, R4 and R5 (if present) are independently selected from CN, partially fluorinated or perfluorinated C1 to Cs alkyl, halogen, Cl, F, D or H, whereby when any of R1, R2, R3, R4 and R5 is present, then the corresponding X1, X2, X3, X4 and X5 is not N;with the proviso that one of the following requirements a) to e) are fulfilled: a) At least one R1, R2, R3, R4 and R5 is independently selected from CN, partially flurorinated or perfluorinated C1 to Cs alkyl, halogen, Cl, F, and at least one remaining R1, R2, R3, R4 and R5 is selected D or H;b) R1 or R2 are selected from CN or partially flurorinated or perfluorinated C1 to Cs alkyl and at least one remaining R1 to R5 is independently selected from CN, partially flurorinated or perfluorinated C1 to Cs alkyl, halogen, Cl or F;c) R3 is selected from partially flurorinated or perfluorinated C1 to C8 alkyl and at least one of R1, R2, R4 and R5 is independently selected from CN, partially flurorinated or perfluorinated C1 to Cs alkyl, halogen, Cl or F;d) at least two R1 to R5 are independently selected from CN or partially flurorinated or perfluorinated C1 to Cs alkyl; ore) at least one X1 to X5 is N and at least two X1 to X5 are selected from CR1 to CR5;A2 and A3 are independently selected from formula (III) 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 CN, partially or perfluorinated C1 to C6 alkyl, halogen, Cl, F, D; andR' is selected from Ar, substituted or unsubstituted C6 to C18 aryl or C3 to C18 heteroaryl, partially flurorinated or perfluorinated C1 to C8 alkyl, halogen, F or CN. It should be noted that throughout the application and the claims any An, Bn, Rn etc. always refer to the same moieties, unless otherwise noted. In the present specification, when a definition is not otherwise provided, "substituted" refers to one substituted with a deuterium, C1 to C12 alkyl and C1 to C12 alkoxy. However, in the present specification "aryl substituted" refers to a substitution with one or more aryl groups, which themselves may be substituted with one or more aryl and/or heteroaryl groups. Correspondingly, in the present specification "heteroaryl substituted" refers to a substitution with one