MATERIALS FOR ELECTRONIC DEVICES

• US 20200136045A1
• Filed: 06/25/2018
• Published: 04/30/2020
• Est. Priority Date: 06/28/2017
• Status: Active Application

• Current Assignee: Merck Patent GmbH (Merck & Co., Inc.)
• Original Assignee: Merck Patent GmbH (Merck & Co., Inc.)
• Inventors: MONTENEGRO, Elvira, MUJICA-FERNAUD, Teresa, MAIER-FLAIG, Florian, VOGES, Frank
• Application Number:
  US16/624,043
• Publication Number:
  US 20200136045A1
• Time in Patent Office: Days
• CPC Class Codes: C01B 33/00 Silicon; Compounds thereof C01B6/00, C01B21/00, C01B23/00 take precedence; persilicates C01B15/14; carbides C01B32/956
• CPC Class Codes: C07C 211/54 having amino groups bound to two or three six-membered aromatic rings
• CPC Class Codes: C07C 211/56 the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
• CPC Class Codes: C07C 211/59 the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
• 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 321/28 Sulfides, hydropolysulfides, or polysulfides having thio groups bound to carbon atoms of six-membered aromatic 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 209/94 containing carbocyclic rings other than six-membered
• CPC Class Codes: C07D 219/02 with only hydrogen, 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: C09K 11/025 non-luminescent particle coatings or suspension media
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1011 Condensed systems
• CPC Class Codes: C09K 2211/1014 bridged by heteroatoms, e.g. N, P, Si or B
• 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 50/17 Carrier injection layers
• CPC Class Codes: H10K 50/18 Carrier blocking layers
• 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: Y02E 10/549 : Organic PV cells

Abstract

The present application relates to a spirobifluorene derivative of a specific formula (I) which is suitable for use in electronic devices.

Claims

1-14. -14. (canceled)

15. A compound of a Formula (I)

16. The compound according to claim 15, wherein index k is 0, so that the group Ar^L is not present, and the spirobifluorene and the nitrogen atom of the amine are directly connected with each other.

17. The compound according to claim 15, wherein groups Ar¹ and Ar² are, identically or differently, selected from radicals derived from a group selected from the group consisting of phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, fluorenyl, benzofluorenyl, spirobifluorenyl, indenofluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, benzofuranyl, benzothiophenyl, indolyl, quinolinyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl and triazinyl, where the groups may each be substituted by one or more radicals R³, or from combinations of 2 or 3 radicals derived from those groups, where the groups may each be substituted by one or more radicals R³.

18. The compound according to claim 15, wherein 2, 3, or 4 indices n are equal to 1, and the rest of the indices n is equal to 0.

19. The compound according to claim 15, wherein the compound has not more than one radical R¹ bonded to each aromatic six-ring of the spirobifluorene.

20. The compound according to claim 15, wherein groups R¹ are selected, identically or differently on each occurrence, from straight-chain alkyl, alkoxy or thioalkyl groups having 1 to 20 C atoms, which may optionally be substituted by one or more groups F, and from branched or cyclic alkyl, alkoxy or thioalkyl groups having 3 to 20 C atoms, which may optionally be substituted by one or more groups F.

21. The compound according to claim 15, wherein the groups R¹ conform to one of the following formulae

22. The compound according to claim 15, wherein the compound conforms to one of Formulae (I-A-1) to (I-A-9) and (I-B-1) to (I-B-9)

23. A process for preparation of the compound according to claim 15, which comprises the reactions stepsmetallation of a biphenyl derivative which has a reactive group in a position which is ortho to the phenyl-phenyl bond;

2) adding the metallated biphenyl derivative to a fluorenone derivative which has a group A in its 1-position;

where the group A is selected from i) X, or ii) —

Ar—

X, or iii) —

NAr₂, or iv) —

Ar—

NAr₂, where Ar is aromatic or heteroaromatic group, and where X is a reactive group; and

3) cyclisation of the resulting addition product to a spirobifluorene derivative under acidic conditions or with a Lewis acid.

24. An oligomer, polymer or dendrimer, comprising one or more compounds of Formula (I) according to claim 15, where the bond(s) to the polymer, oligomer or dendrimer may be localised at any positions in Formula (I) substituted by R¹, R² or R³.

25. The formulation, comprising at least one compound of Formula (I) according to claim 15 and at least one solvent.

26. The formulation, comprising at least one polymer, oligomer or dendrimer according to claim 24, and at least one solvent.

27. An electronic device, comprising at least one compound according to claim 15, or at least one polymer, oligomer or dendrimer according to claim 24.

28. An organic electroluminescent device, comprising anode, cathode and at least one emitting layer, where at least one organic layer of the device, which is an emitting layer, a hole transport layer, an electron blocking layer or a hole injection layer, comprises the at least one compound according to claim 15.