MATERIALS FOR ORGANIC ELECTROLUMINESCENT DEVICES

• US 20180212149A1
• Filed: 07/01/2016
• Published: 07/26/2018
• Est. Priority Date: 07/29/2015
• Status: Active Grant

• Current Assignee: Merck Patent GmbH (Merck & Co., Inc.)
• Original Assignee: Merck Patent GmbH (Merck & Co., Inc.)
• Inventors: PFISTER, Jochen, MUJICA-FERNAUD, Teresa, MONTENEGRO, Elvira, STIEBER, Frank, VOGES, Frank
• Granted Patent: US 11,538,995 B2
• Time in Patent Office: Days
• CPC Class Codes: C07C 209/68 from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
• 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 2603/94 containing "free" spiro atoms
• CPC Class Codes: C07C 2603/97 containing five-membered rings
• 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: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: H10K 2101/10 Triplet emission
• 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 50/155 comprising dopants
• CPC Class Codes: H10K 50/156 comprising a multilayered structure
• CPC Class Codes: H10K 50/17 Carrier injection layers
• CPC Class Codes: H10K 50/18 Carrier blocking layers
• CPC Class Codes: H10K 85/615 Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
• CPC Class Codes: H10K 85/624 containing six or more rings
• CPC Class Codes: H10K 85/626 containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
• 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

1-17. -17. (canceled)

18. A compound of the formula (1),

19. The compound according to claim 18, wherein t+u=0 or 1.

20. The compound according to claim 18, wherein the index i is 0.

21. The compound according to claim 18, wherein the compound is selected from the compounds of the formulae (1-1) to (1-9),

22. The compound according to claim 18, wherein the compound is selected from the compounds of the formulae (1-1a) to (1-9a)

23. The compound according to claim 18, wherein the compound is selected from the compounds of the formulae (1-1b) to (1-9b)

24. The compound according to claim 18, wherein the group Ar^N is selected from the groups of formulae (20) to (84)

25. The compound according to claim 18, wherein R¹ to R⁴ are selected, identically or differently on each occurrence, from the group consisting of H, D, F, CN, a straight-chain alkyl or alkoxy group having 1 to 10 C atoms or a branched or cyclic alkyl or alkoxy group having 3 to 10 C atoms, each of which is optionally substituted by one or more radicals R⁸, where one or more non-adjacent CH₂ groups is optionally replaced by O and where one or more H atoms is optionally replaced by F, an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, which may in each case be substituted by one or more radicals R⁸.

26. The compound according to claim 18, wherein R⁵ is selected from the group consisting of H, D, F, CN, a straight-chain alkyl or alkoxy group having 1 to 10 C atoms or a branched or cyclic alkyl or alkoxy group having 3 to 10 C atoms, each of which is optionally substituted by one or more radicals R⁸, where one or more non-adjacent CH₂ groups is optionally replaced by O and where one or more H atoms is optionally replaced by F.

27. The compound according to claim 18, wherein R⁶ and R⁷ are selected, identically or differently on each occurrence, from the group consisting of H, D, F, CN, a straight-chain alkyl or alkoxy group having 1 to 10 C atoms or a branched or cyclic alkyl or alkoxy group having 3 to 10 C atoms, each of which is optionally substituted by one or more radicals R⁸, where one or more non-adjacent CH₂ groups is optionally replaced by O and where one or more H atoms is optionally replaced by F, an aryl or heteroaryl ring system having 5 to 14 aromatic ring atoms, which may in each case be substituted by one or more radicals R⁸.

28. The compound according to claim 18, wherein R⁰ is selected on each occurrence, identically or differently, from the group consisting of H, D, F, CN, a straight-chain alkyl or alkoxy group having 1 to 10 C atoms or a branched or cyclic alkyl or alkoxy group having 3 to 10 C atoms, each of which is optionally substituted by one or more radicals R⁸, where in each case one or more non-adjacent CH₂ groups is optionally replaced by O and where one or more H atoms is optionally replaced by D, F or CN, an aromatic or heteroaromatic ring system having 5 to 14 aromatic ring atoms, which may in each case be substituted by one or more radicals R⁸, where two substituents R⁰ may optionally form a monocyclic aliphatic ring system, which is optionally substituted by one or more radicals R⁸;

with the proviso that when two R⁰ are attached to the same C atom, then at least one R⁰ is selected from the group consisting of H, D, F, CN, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms, each of which is optionally substituted by one or more radicals R⁸.

29. The compound according to claim 18, wherein R⁰ is selected on each occurrence, identically or differently, from the group consisting of H, a straight-chain alkyl group having 1 to 10 C atoms or a branched or cyclic alkyl group having 3 to 10 C atoms, each of which is optionally substituted by one or more radicals R⁸.

30. A process for the preparation of the compound according to claim 18, which comprises introducing a diarylamino group by a C—

N coupling reaction between a diarylamine compound and a halogenated spirobifluorene compound.

31. A formulation comprising at least one compound according to claim 18 and at least one solvent.

32. An electronic device comprising the compound according to claim 18.

33. An organic electroluminescent device comprising the compound according to claim 18.

34. The electronic device according to claim 32, 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.

35. An organic electroluminescent device comprising the compound according to claim 18 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.