Materials for organic electroluminescent devices

• US 10,454,041 B2
• Filed: 01/24/2017
• Issued: 10/22/2019
• Est. Priority Date: 02/23/2016
• Status: Active Grant

• Current Assignee: Merck Patent GmbH (Merck & Co., Inc.)
• Original Assignee: Merck Patent GmbH (Merck & Co., Inc.)
• Inventors: Mujica-Fernaud, Teresa, Montenegro, Elvira
• Primary Examiner(s): Sefer, Ahmed N
• Application Number:
  US16/079,151
• Publication Number:
  US 20190067576A1
• Time in Patent Office: 1,001 Days
• CPC Class Codes: C07C 17/263 by condensation reactions
• CPC Class Codes: C07C 17/269 of only halogenated hydrocarbons
• CPC Class Codes: C07C 17/35 by reactions not affecting the number of carbon or of halogen atoms in the reaction
• 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 211/61 with at least one of the condensed ring systems formed by three or more rings
• CPC Class Codes: C07C 25/18 Polycyclic aromatic halogenated hydrocarbons
• CPC Class Codes: C07C 25/22 with condensed 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: C07D 411/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: H10K 50/15 Hole transporting layers
• CPC Class Codes: H10K 50/171 Electron injection layers
• CPC Class Codes: H10K 50/18 Carrier blocking layers
• CPC Class Codes: H10K 85/322 comprising boron
• CPC Class Codes: H10K 85/631 Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
• 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 a process to produce compounds of the formula (1) which are suitable for use in electronic devices, as well as to intermediate compounds of formula (Int-1) and compounds of formula (1-1) and (1-2) obtained via the process. These compounds are particularly suitable for use organic electroluminescent devices. The present invention also relate to electronic devices, which comprise these compounds.

Claims

1. A process for the preparation of a compound according to formula (1),

2. The process according to claim 1, where the metalation reaction in the step (a-1-1) and (a-2-2) is a lithiation reaction or a grignard reaction and the amination reaction in step (b) is a Buchwald-Hartwig amination reaction.

3. The process according to claim 1, where X¹ is selected from Cl, Br, or I and X³ stands for —

B(OR^B)₂.

4. The process according to claim 1, where X¹ is Cl and X³ is a group (R^B-1),

5. The process according to claim 1, where the group Ar^L is selected from the groups of formulae (Ar^L-1) to (Ar^L-24),

6. The process according to claim 1, where the groups Ar¹ and Ar² are selected from the groups of formulae (A-1) to (A-48),