MATERIALS FOR ORGANIC ELECTROLUMINESCENT DEVICES

• US 20180219156A1
• Filed: 06/28/2016
• Published: 08/02/2018
• Est. Priority Date: 07/22/2015
• Status: Abandoned Application

• Current Assignee: Merck Patent GmbH (Merck & Co., Inc.)
• Original Assignee: Merck Patent GmbH (Merck & Co., Inc.)
• Inventors: MUJICA-FERNAUD, TERESA, MONTENEGRO, Elvira, GROSSMANN, Tobias, PFISTER, Jochen
• Application Number:
  US15/746,257
• Publication Number:
  US 20180219156A1
• 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 307/91 Dibenzofurans; Hydrogenated dibenzofurans
• CPC Class Codes: C07D 333/76 Dibenzothiophenes
• CPC Class Codes: H10K 2101/10 Triplet emission
• CPC Class Codes: H10K 2101/90 Multiple hosts in the emissive layer
• 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 50/17 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 85/6574 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 m+n=0 or 1.

20. The compound according to claim 18, wherein X is selected from the group consisting of C(R⁰)₂, O, S, and SO₂ and r is equal to 0.

21. The compound according to claim 18, wherein X is C(R⁰)₂ and r is equal to 0.

22. The compound according to claim 18, wherein the group N(Ar)² is a group A of formula (2) as defined in claim 18.

23. The compound according to claim 18, wherein the compound is selected from the compounds of the formulae (1-1) to (1-6),

24. The compound according to claim 18, wherein the compound is selected from the compounds of the formulae (1-1a) to (1-6a)

25. The compound according to claim 18, wherein the compound is selected from the compounds of the formulae (1-1b) to (1-6b)

26. The compound according to claim 18, wherein R is 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 may be substituted by one or more radicals R⁴, 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, an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms, which may in each case be substituted by one or more radicals R⁴.

27. The compound according to claim 18, wherein R² 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 may be substituted by one or more radicals R⁴, where in each case one or more non-adjacent CH₂ groups may be replaced by O or S and where one or more H atoms may be replaced by F, an aryl or heteroaryl ring system having 5 to 24 aromatic ring atoms, which may in each case be substituted by one or more radicals R⁴, an aryloxy or heteroaryloxy group having 5 to 24 aromatic ring atoms, which may be substituted by one or more radicals R⁴, a thioaryl or thio-heteroaryl group having 5 to 24 aromatic ring atoms, which may be substituted by one or more radicals R⁴, where two or more adjacent substituents R², may optionally form a mono- or polycyclic, aliphatic ring system or aromatic ring system, which may be substituted by one or more radicals R⁴.

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 may be substituted by one or more radicals R⁴, where in each case one or more non-adjacent CH₂ groups may be replaced by O and where one or more H atoms may be 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 R⁴, where two substituents R⁰ may optionally form a monocyclic aliphatic ring system, which may be substituted by one or more radicals R⁴.

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 may be substituted by one or more radicals R⁴.

30. A process for the preparation of the compound according to claim 18, wherein the diarylamino groups A and N(Ar)² are introduced by a C—

N coupling reaction between a 1- or 4-halogenated spirobifluorene and a diarylamine groups A or N(Ar)².

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

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

33. An electronic device comprising at least one compound according to claim 18,

34. The electronic device according to claim 33, wherein the device is selected from the group consisting of organic electroluminescent device, organic integrated circuit, organic field-effect transistor, organic thin-film transistor, organic light-emitting transistor, organic solar cell, dye-sensitised organic solar cell, organic optical detector, organic photoreceptor, organic field-quench device, light-emitting electrochemical cell, organic laser diode and organic plasmon emitting device.

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.