Phenanthrene compounds for organic electronic devices

• US 10,446,759 B2
• Filed: 10/13/2017
• Issued: 10/15/2019
• Est. Priority Date: 06/06/2012
• Status: Active Grant

• Current Assignee: Merck Patent GmbH (Merck & Co., Inc.)
• Original Assignee: Merck Patent GmbH (Merck & Co., Inc.)
• Inventors: Mujica-Fernaud, Teresa, Buesing, Arne, Voges, Frank, Kroeber, Jonas
• Primary Examiner(s): Clark, Gregory D
• Application Number:
  US15/783,333
• Publication Number:
  US 20180102479A1
• Time in Patent Office: 732 Days
• CPC Class Codes: C07C 209/60 by condensation or addition reactions, e.g. Mannich reaction, addition of ammonia or amines to alkenes or to alkynes or addition of compounds containing an active hydrogen atom to Schiff's bases, quinone imines, or aziranes
• 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 217/80 having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
• CPC Class Codes: C07C 2601/14 The ring being saturated
• CPC Class Codes: C07C 2603/18 Fluorenes; Hydrogenated fluorenes
• CPC Class Codes: C07C 2603/26 Phenanthrenes; Hydrogenated phenanthrenes
• CPC Class Codes: C07C 2603/52 containing five condensed rings
• CPC Class Codes: C07C 2603/54 containing more than five condensed rings
• 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 209/94 containing carbocyclic rings other than six-membered
• CPC Class Codes: C07D 213/06 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
• CPC Class Codes: C07D 213/16 containing only one pyridine ring
• 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 221/08 Aza-anthracenes
• CPC Class Codes: C07D 223/26 having a double bond between positions 10 and 11
• CPC Class Codes: C07D 265/38 [b, e]-condensed with two six-membered rings
• CPC Class Codes: C07D 279/22 with carbon atoms directly attached to the ring nitrogen atom
• CPC Class Codes: C07D 307/91 Dibenzofurans; Hydrogenated dibenzofurans
• CPC Class Codes: C07D 307/93 : condensed with a ring other than six-membered
• CPC Class Codes: C07D 311/80 : Dibenzopyrans; Hydrogenated dibenzopyrans
• CPC Class Codes: C07D 333/76 : Dibenzothiophenes
• CPC Class Codes: C07D 405/04 : directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07D 405/12 : linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 407/12 : linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 471/06 : Peri-condensed systems
• CPC Class Codes: C07D 487/04 : Ortho-condensed systems
• CPC Class Codes: C09B 19/00 : Oxazine dyes
• CPC Class Codes: C09B 21/00 : Thiazine dyes
• CPC Class Codes: C09B 57/008 : Triarylamine dyes containing no other chromophores
• CPC Class Codes: C09B 69/008 : Dyes containing a substituent, which contains a silicium atom
• CPC Class Codes: C09K 11/06 : containing organic luminescent materials
• CPC Class Codes: C09K 2211/1007 : Non-condensed systems
• 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: C09K 2211/1029 : containing one nitrogen atom as the heteroatom
• CPC Class Codes: C09K 2211/1088 : containing oxygen as the only heteroatom
• CPC Class Codes: C09K 2211/1092 : containing sulfur as the only heteroatom
• 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 50/181 : Electron blocking layers
• CPC Class Codes: H10K 85/615 : Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
• 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 invention relates to specific phenanthrenes, the use of the compound in an electronic device, and an electronic device containing at least one of said compounds. The invention further relates to a method for producing the compound and a formulation and composition containing one or more of the compounds.

Claims

1. A compound of the general formula (1)

2. The compound according to claim 1, wherein the compound is of the general formula

3. The compound according to claim 1, wherein the compound has the general formula (5)

4. The compound according to claim 3, wherein the compound has the general (6)

5. The compound according to claim 3, wherein the compound has the general (7)

6. The compound according to claim 1, wherein L is an aromatic ring system selected from the group consisting of biphenylenes, terphenylenes and the compounds of the formula (101a) and (101b),

7. The compound according to claim 6, wherein Y is C(R²)₂ or NR².

8. The compound according to claim 1, wherein L is a single bond, so that the amine group is bonded directly to the phenanthrene.

9. The compound according to claim 1, wherein the compound contains in total at least 26 ring atoms.

10. The compound according to claim 1, wherein the compound contains only one amine group.

11. A process for the preparation of the compound according to claim 1 which comprises a one-step Buchwald coupling by reaction of a phenanthrene derivative which contains a leaving group with Ar²—

NH—

Ar¹.

12. A process for the preparation of the compound according to claim 1 which comprises a two-step Buchwald coupling by stepwise reaction of a phenanthrene derivative which contains a leaving group with (1) Ar²—

NH₂ and (2) NH₂—

Ar¹.

13. An oligomer, polymer or dendrimer containing one or more compounds according to claim 1, where the bond(s) to the polymer, oligomer or dendrimer is optionally localised at any position in formula (1) which are substituted by R¹, R⁴ or R².

14. A composition comprising one or more compound according to claim 1 and at least one further organically functional material selected from the group consisting of fluorescent emitters, phosphorescent emitters, host materials, matrix materials, electron-transport materials, electron-injection materials, hole-conductor materials, hole-injection materials, electron-blocking materials and hole-blocking materials.

15. A formulation comprising at least one compound according to claim 1 and at least one solvent.

16. An electronic device comprising at least one compound according to claim 1.

17. The electronic device according to claim 16, wherein the device is selected from organic integrated circuits (O—

ICs), organic field-effect transistors (OFETs), organic thin-film transistors (O-TFTs), organic light-emitting transistors (OLETs), organic solar cells (O-SCs), organic optical detectors, organic photoreceptors, organic field-quench devices (O-FQDs), light-emitting electrochemical cells (LECs), organic laser diodes (O-lasers) and organic electroluminescent devices (OLEDs).

18. An electronic device which is selected from the group of organic electroluminescent devices, which comprises the compound according to claim 1 employed in one or more of the following functions:

as hole-transport material in a hole-transport or hole-injection layer,

as matrix material in an emitting layer,

as electron-blocking material,

as exciton-blocking material.

19. The compound according to claim 1, wherein the compound is of the formula

20. The compound according to claim 1, wherein the compound is of the formula

21. A compound of the general formula (1)

22. A compound of the general formula (1)

23. A compound of the general formula (1)

24. A compound of the general formula (1)

25. An oligomer, polymer or dendrimer containing one or more compounds of the formula (I), where the bond(s) to the polymer, oligomer or dendrimer is optionally localised at any desired positions in formula (1) which are substituted by R¹, R⁴ or R²;