MATERIALS FOR ORGANIC ELECTROLUMINESCENT DEVICES

• US 20180370938A1
• Filed: 11/28/2016
• Published: 12/27/2018
• Est. Priority Date: 12/16/2015
• Status: Abandoned Application

• Current Assignee: Merck Patent GmbH (Merck & Co., Inc.)
• Original Assignee: Merck Patent GmbH (Merck & Co., Inc.)
• Inventors: VOGES, Frank, MUJICA-FERNAUD, Teresa, MONTENEGRO, Elvira, ANEMIAN, Remi Manouk
• Application Number:
  US16/061,774
• Publication Number:
  US 20180370938A1
• Time in Patent Office: Days
• CPC Class Codes: C07C 211/61 with at least one of the condensed ring systems formed by three or more rings
• CPC Class Codes: C07C 2603/18 Fluorenes; Hydrogenated fluorenes
• CPC Class Codes: C07C 2603/93 Spiro compounds
• CPC Class Codes: C07D 209/86 with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
• CPC Class Codes: C07D 307/91 Dibenzofurans; Hydrogenated dibenzofurans
• CPC Class Codes: C07D 333/76 Dibenzothiophenes
• CPC Class Codes: C07D 407/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07D 407/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 409/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 50/15 Hole transporting layers
• CPC Class Codes: H10K 85/633 comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
• CPC Class Codes: H10K 85/636 comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
• CPC Class Codes: H10K 85/6572 comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
• CPC Class Codes: H10K 85/6574 comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
• CPC Class Codes: H10K 85/6576 comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
• CPC Class Codes: Y02E 10/549 Organic PV cells

Abstract

The present invention relates to compounds of the formula (1) which are suitable for use in electronic devices, in particular organic electroluminescent devices, and to electronic devices which comprise these compounds.

Claims

1-18. -18. (canceled)

19. A compound of the formula (1),

20. The compound according to claim 19, wherein m+n=0.

21. The compound according to claim 19, wherein the index i is 0.

22. The compound according to claim 19, wherein Ar² is selected from the groups of formulae (Ar2-3) to (Ar2-6),

23. The compound according to claim 19, wherein the group Ar¹ is selected from the groups of formula (Ar1-2),

24. The compound according to claim 19, wherein the group Ar² is selected from the groups of the following formulae (Ar2-7) to (Ar2-10),

25. The compound according to claim 24, wherein a+b≤

1 and c+d≤

1.

26. The compound according to claim 24, wherein c=d=0.

27. The compound according to claim 19, wherein E¹, E² and/or E³ are, identically or differently, selected from C(R⁰)₂, O, S and N(R⁰).

28. The compound according to claim 19, wherein R⁰ is selected on each occurrence, identically or differently, from the group consisting of H, D, F, CN, Si(R²)₃, straight-chain alkyl groups having 1 to 10 C atoms or branched or cyclic alkyl groups having 3 to 10 C atoms, each of which may be substituted by one or more radicals R², where in each case one or more H atoms may be replaced by F, and aryl or heteroaryl groups having 5 to 40 aromatic ring atoms, which may in each case be substituted by one or more radicals R², where two adjacent substituents R⁰ may form a mono- or polycyclic, aliphatic ring system or aromatic ring system, which may be substituted by one or more radicals R².

29. The compound according to claim 19, wherein the group Ar² is selected from the group of formulae (Ar2-7-1) to (Ar2-10-1),

30. The compound according to claim 19, wherein Ar^L is selected from aromatic or heteroaromatic ring systems having 5 to 14 aromatic ring atoms, which may in each case also be substituted by one or more radicals R².

31. Compound according to claim 19, wherein

R, R¹ are selected, identically or differently on each occurrence, from the group consisting of H, D, F, CN, straight-chain alkyl or alkoxy groups having 1 to 10 C atoms or branched or cyclic alkyl or alkoxy groups having 3 to 10 C atoms, each of which may be substituted by one or more radicals R², where one or more non-adjacent CH₂ groups may be replaced by O and where one or more H atoms may be replaced by F, and aromatic or heteroaromatic ring systems having 5 to 24 aromatic ring atoms, which may in each case be substituted by one or more radicals R².

32. A process for the preparation of the compound according to claim 19, which comprises introducing a diarylamino group by a C—

N coupling reaction between a 1- or 3- or 4-halogenated spirobifluorene and a diarylamine or triarylamine.

33. A formulation comprising at least one compound according to claim 19 and at least one solvent.

34. An electronic device comprising at least one compound according to claim 19.

35. The electronic device as claimed in claim 34, wherein the device is selected from the group consisting of organic electroluminescent devices, organic integrated circuits, organic field-effect transistors, organic thin-film transistors, organic light-emitting transistors, organic solar cells, dye-sensitised organic solar cells, organic optical detectors, organic photoreceptors, organic field-quench devices, light-emitting electrochemical cells, organic laser diodes and organic plasmon emitting devices.

36. An organic electroluminescent device which comprises the compound according to claim 19 is employed as hole-transport material in a hole-transport or hole-injection or exciton-blocking or electron-blocking layer or as matrix material for fluorescent or phosphorescent emitters.