SPIROBIFLUORENE COMPOUNDS FOR ORGANIC ELECTROLUMINESCENT DEVICES

• US 20150065730A1
• Filed: 01/21/2013
• Published: 03/05/2015
• Est. Priority Date: 02/14/2012
• Status: Active Grant

• Current Assignee: Merck Patent GmbH (Merck & Co., Inc.)
• Original Assignee: Merck Patent GmbH (Merck & Co., Inc.)
• Inventors: Parham, Amir H., Stoessel, Philipp, Mujica-Fernaud, Teresa, Voges, Frank, Buesing, Arne, Montenegro, Elvira
• Granted Patent: US 9,812,648 B2
• Time in Patent Office: Days
• US Class Current: 548/440
• CPC Class Codes: C07C 211/54 having amino groups bound to two or three six-membered aromatic rings
• CPC Class Codes: C07C 211/58 Naphthylamines; N-substituted derivatives thereof
• CPC Class Codes: C07C 211/61 with at least one of the condensed ring systems formed by three or more 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 209/88 with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
• 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 333/76 Dibenzothiophenes
• 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 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 50/18 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 85/654 : comprising only nitrogen as heteroatom H10K85/652 takes precedence
• 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 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

1-15. -15. (canceled)

16. A compound of the following formula (1):

17. The compound according to claim 16, wherein the index i is 0.

18. The compound according to claim 16, selected from compounds of the following formulae (2) to (10),

19. The compound according to claim 16, selected from compounds of the following formulae (2a) to (10a),

20. The compound according to claim 16, selected from compounds of the following formulae (2b) to (10b),

21. The compound according to claim 16, wherein groups Ar¹ and Ar² are selected, identically or differently on each occurrence, from the groups of the following formulae (11) to (66)

22. The compound according to claim 21, wherein Ar¹ and Ar² are selected, identically or differently on each occurrence, from the groups of the formulae (11), (20) and (24), which optionally is substituted by one or more radicals R⁵.

23. The compound according to claim 16, wherein the groups Ar¹ and Ar² are selected differently from one another.

24. The compound according to claim 16, wherein R¹ to R⁴ are selected, identically or differently on each occurrence, from the group consisting of H, 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 optionally is substituted by one or more radicals R⁶, where one or more non-adjacent CH₂ groups optionally is replaced by 0 and where one or more H atoms optionally is 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 R⁶.

25. The compound according to claim 16, wherein the radical R⁵ which is bonded to Ar¹ or Ar² or Ar^S is selected, identically or differently on each occurrence, from the group consisting of H, F, CN, a straight-chain alkyl group having 1 to 10 C atoms, a branched or cyclic alkyl group having 3 to 10 C atoms or an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms, each of which optionally is substituted by one or more radicals R⁶.

26. The compound according to claim 21, wherein:

Ar¹, Ar² are, identically or differently, a group of one of the formulae (11) to (66);

or —

NAr¹Ar² stands for a group of one of the formulae (67) to (74);

27. A process for the preparation of the compound according to claim 16, which comprises introducing a diarylamino group by a C—

N coupling reaction between a 1- or 3- or 4-halogenated spirobifluorene and a diarylamine.

28. An electronic device which comprises the compound according to claim 16.

29. The electronic devise as claimed in claim 28, wherein the device is selected from the group consisting of an organic electroluminescent device, an organic integrated circuit, an organic field-effect transistor, an organic thin-film transistor, an organic light-emitting transistor, an organic solar cell, an organic dye-sensitised solar cell, an organic optical detector, an organic photoreceptor, an organic field-quench device, a light-emitting electrochemical cell, an organic laser diode and an organic plasmon emitting device.

30. An organic electroluminescent devices which comprises the compound according to claim 16 is comprised as hole-transport material in a hole-transport or hole-injection or exciton-blocking or electron-blocking layer, or is comprised as matrix material for fluorescent or phosphorescent emitters in an emitting layer.