Electron-accepting compound and composition for charge-transporting film, and luminescent element using same

Patent metadata

Field	Value
Publication number	US-11316112-B2
Application number	US-201816136961-A
Country	US
Kind code	B2
Filing date	Sep 20, 2018
Priority date	Mar 24, 2016
Publication date	Apr 26, 2022
Grant date	Apr 26, 2022

Abstract

The present invention provides with an electron-accepting compound having a structure of the following formula (1):

First claim

The invention claimed is:

1. An electron-accepting compound having a structure of the following formula (1):

wherein
Ar is each independently a substituted or unsubstituted aromatic ring group or a fluorine-substituted alkyl group, wherein at least one Ar is represented by the following formula (3):

wherein Ar 7 is a substituent and F 4 represents a substitution with four fluorine atoms,
F 4 represents a substitution with four fluorine atoms,
F (5-a) represents a substitution with (5-a) fluorine atom(s),
k each independently represents an integer of 0 to 5,
a each independently represents an integer of 0 to 5,
k+a is 1 to 10, and
X + represents a counter cation having a structure of the following formula (2):

wherein Ar 5 and Ar 6 are each independently an aromatic ring group which may have a substituent,
wherein X + does not represent octyloxy diphenyl iodonium.

2. The electron-accepting compound according to claim 1 , wherein k is 0, a is 1.

3. The electron-accepting compound according to claim 1 , wherein Ar 7 is represented by the following formula (4)

4. The electron-accepting compound according to claim 1 , wherein the formula (2) is represented by the following formula (5):

wherein Ar 8 and Ar 9 represent a substituent.

5. The electron-accepting compound according to claim 1 , wherein at least one Ar has a crosslinkable group.

6. A composition suitable for a charge-transporting film, comprising the electron-accepting compound according to claim 1 and a hole-transporting compound.

7. The composition according to claim 6 , wherein the hole-transporting compound is an aromatic tertiary amine compound.

8. The composition according to claim 6 , which further comprises a solvent.

9. The composition according to claim 8 , wherein the solvent contains at least one solvent selected from the group consisting of an ether-based solvent and an ester-based solvent.

10. The composition according to claim 6 , which is used for a hole injection layer of an organic electroluminescent element.

11. An organic electroluminescent element comprising a hole injection layer and a luminescent layer between an anode and a cathode and emitting light by electric energy, wherein the hole injection layer is a layer formed by applying and drying the composition for a charge-transporting film according to claim 6 to form a film.

12. A display using the organic electroluminescent element according to claim 11 .

13. A lighting device using the organic electroluminescent element according to claim 11 .

14. A light-emitting device using the organic electroluminescent element according to claim 11 .

15. A method for manufacturing an organic electroluminescent element comprising a hole injection layer and a luminescent layer between an anode and a cathode and that emits light by electric energy, the method comprising applying the composition of claim 8 to a substrate and drying the composition to form the hole injection layer.

16. An electron-accepting compound having a crosslinkable group, comprising the compound of claim 1 .

17. The electron-accepting compound according to claim 16 , wherein k is 0, a is 1.

18. The electron-accepting compound according to claim 16 , wherein Ar 7 is represented by the following formula (4)

19. The electron-accepting compound according to claim 16 , wherein the formula (2) is represented by the following formula (5):

wherein Ar 8 and Ar 9 represent a substituent.

20. The electron-accepting compound according to claim 16 , wherein at least one Ar of the formula (1) has a crosslinkable group selected from the crosslinking groups represented by the following formulae (Z-1) to (Z-7):

wherein * represents a bonding point and wherein the formulae (Z-1) to (Z-7) optionally further comprises a cyclic/non-cyclic aliphatic group-derived groups having 30 or less carbon atoms, an aryl groups having 30 or less carbon atoms, an alkyloxy group having 30 or less carbon atoms, or an aralkyl group having 30 or less carbon atoms.

21. The electron-accepting compound according to claim 16 , wherein at least one Ar of the formula (1) has a crosslinkable group selected from the crosslinking groups represented by the following formulae (7) and (8):

wherein * represents a bonding point and wherein the formulae (7) and (8) optionally further comprise a substituent selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, an aromatic ring group having 1 to 5 aromatic rings, a hydrocarbon ring group, an alkyl group, an alkenyl group, an alkynyl group, an aralkyl group, an alkyloxy group, an aryloxy group, an alkylthio group, an arylthio group, an alkyl ketone group, and an aryl ketone group and adjacent substituents may be combined to form a ring, and the aromatic ring group having 1 to 5 aromatic rings, the hydrocarbon ring group, the alkyl group, the alkenyl group, the alkynyl group, the aralkyl group, the alkyloxy group, the aryloxy group, the alkylthio group, the arylthio group, the alkyl ketone group, or the aryl ketone group optionally further comprise a substituent selected from the group consisting of a halogen atom, an alkyl group, and an aryl group.

22. A composition for a charge-transporting film, comprising the electron-accepting compound according to claim 16 and a hole-transporting compound.

23. The composition for a charge-transporting film according to claim 22 , wherein the hole-transporting compound is an aromatic tertiary amine compound.

24. The composition for charge-transporting according to claim 22 , wherein the hole-transporting compound has a crosslinkable group.

25. The composition for a charge-transporting film according to claim 22 , which further comprises a solvent.

26. The composition for a charge-transporting film according to claim 25 , wherein the solvent contains at least one solvent selected from the group consisting of an ether-based solvent and an ester-based solvent.

27. A method for forming a charge-transporting film, the method comprising applying a composition comprising the compound according to claim 25 to a substrate and drying the composition to form the charge-transporting film.

28. The method according to claim 27 , wherein the composition further comprises a charge-transporting compound, the charge-transporting compound is a charge-transporting polymer compound and has a crosslinkable group.

Assignees

• Mitsubishi Chem Corp

Inventors

• Gorohmaru Hideki
• Okabe Kazuki
• Iida Koichiro
• Umemoto Tomokazu
• Bando Yoshimasa
• Ishibashi Koichi
• KAJIYAMA Yoshiko
• Abe Tomohiro

Classifications

• H10K71/00

  Manufacture or treatment specially adapted for the organic devices covered by this subclass · CPC title

• H10K85/611

  Charge transfer complexes · CPC title

• C07F5/027 Primary

  Organoboranes and organoborohydrides · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• C08G2261/314

  Condensed aromatic systems, e.g. perylene, anthracene or pyrene · CPC title