Anthracene derivatives and their use in organic electroluminescent devices

Patent metadata

Field	Value
Publication number	US-9017825-B2
Application number	US-9653606-A
Country	US
Kind code	B2
Filing date	Dec 7, 2006
Priority date	Dec 8, 2005
Publication date	Apr 28, 2015
Grant date	Apr 28, 2015

Abstract

The present invention relates to anthracene derivatives which are suitable for use in organic electroluminescent devices, and to organic electroluminescent devices containing these anthracene derivatives.

First claim

The invention claimed is:

1. An organic electroluminescent device comprising a compound of formula (1)

wherein
Ar 1 is, identically or differently on each occurrence, either a) an aryl which is a condensed aryl group having 10 to 16 aromatic ring atoms optionally substituted by one or more R′, with the proviso that the aryl is substituted by at most one aryl or heteroaryl, or b) an optionally bridged biaryl group, with the proviso that the biaryl group is unsubstituted or substituted with R 1″ where
R 1 ′ is identically or differently on each occurrence, H, F, CN, N(R 2 ) 2 , a straight-chain alkyl, or alkoxy group having up to 40 C atoms optionally substituted by one or more radicals R 2 , and wherein one or more H atoms are optionally replaced by F or CN or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 C atoms optionally substituted by one or more radicals R 2 , or an aryloxy or heteroaryloxy group having 5 to 24 aromatic ring atoms optionally substituted by one or more radicals R 2 ;

Ar 2 is 1,4-naphthylene, optionally substituted by one or more radicals R 1 ;
R 1 is, identically or differently on each occurrence, H, F, CN, N(R 2 ) 2 , a straight-chain alkyl, or alkoxy group having up to 40 C atoms optionally substituted by one or more radicals R 2 , and wherein one or more H atoms are optionally replaced by F, or CN or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 C atoms optionally substituted by one or more radicals R 2 ,-and wherein one or more H atoms are optionally replaced by F or CN, or an aryl or heteroaryl group having 5 to 30 aromatic ring atoms optionally substituted by one or more radicals R 2 , or an aryloxy or heteroaryloxy group having 5 to 24 aromatic ring atoms optionally substituted by one or more radicals R 2 ;
R 2 is, identically or differently on each occurrence, H or a hydrocarbon radical having up to 20 C atoms, wherein said radical is aliphatic, aromatic or a combination of aliphatic and aromatic, and wherein one or more H atoms are optionally replaced by F;
n is, identically or differently on each occurrence, 0, 1, 2, 3, or 4;
m is 1,
and wherein said compound is employed as host material together with a blue emitting dopant.

2. The device of claim 1 , wherein R 1 is, identically or differently on each occurrence, H, F, a straight-chain alkyl or alkoxy group having up to 6 C atoms, wherein one or more H atoms are optionally replaced by F; a branched or cyclic alkyl or alkoxy group having 3 to 10 C atoms, wherein one or more H atoms are optionally replaced by F; or an aryl or heteroaryl group having 5 to 14 aromatic ring atoms.

3. The device of claim 1 , wherein n is 0, 1 or 2.

4. The device of claim 1 , wherein n is 0 or 1.

5. The device of claim 1 , wherein the two groups Ar 1 are identical and identically substituted.

6. The device of claim 1 , wherein said device comprises an anode, a cathode, at least one emitting layer, and optionally further layers selected from the group consisting of hole-injection layers, hole-transport layers, electron-transport layers, electron-injection layers, charge-generation layers, and combinations thereof.

7. A process for producing the device of claim 1 , comprising applying at least one compound of of formula (1), optionally together with a dopant and/or other compounds, via a sublimation process or from solution or by a printing process.

8. The device as claimed in claim 1 , wherein Ar 1 which is a condensed aryl group is, identically or differently on each occurrence, 1-naphthyl, 2-naphthyl, 9-anthryl, 2-phenanthrenyl, 9-phenanthrenyl; and Ar 1 which is an optionally bridged biaryl group is, identically or differently on each occurrence, an ortho-biphenyl or 2-fluorenyl group.

9. The device as claimed in claim 1 , wherein Ar 1 which is a condensed aryl group is identically or differently on each occurrence, 1-naphthyl, 2-naphthyl, 9-phenanthrenyl; and Ar 1 which is an optionally bridged biaryl group is, identically or differently on each occurrence, an ortho-biphenyl or 2-fluorenyl group.

10. The device of claim 1 , wherein R 1 identically or differently on each occurrence, is H, F, a straight-chain alkyl or alkoxy group having up to 6 C atoms, wherein one or more H atoms are optionally replaced by F; a branched or cyclic alkyl or alkoxy group having 3 to 10 C atoms, wherein one or more H atoms are optionally replaced by F.

11. The device as claimed in claim 1 , wherein R 1 is, identically or differently on each occurrence, H, F, straight-chain alkyl groups having 1 to 4 C atoms, branched alkyl groups having 3 to 5 C atoms or cyclic alkyl groups having 5 to 10 C atoms, where in each case one or more H atoms may be replaced by F, or aryl or heteroaryl groups having 6 to 10 aromatic ring atoms.

12. The device of claim 1 , wherein m is 1 and n is 0 or 1.

Assignees

• Heil Holger
• Buesing Arne
• Stoessel Philipp
• Merck Patent Gmbh

Inventors

• Heil Holger
• Buesing Arne
• Stoessel Philipp

Classifications

• Y10S428/917

  Electroluminescent · CPC title

• H05B33/14

  characterised by the chemical or physical composition or the arrangement of the electroluminescent material {, or by the simultaneous addition of the electroluminescent material in or onto the light source} · CPC title

• C09K2211/1014

  bridged by heteroatoms, e.g. N, P, Si or B · CPC title

• Y02E10/549

  Organic PV cells · CPC title

• C09K2211/1011

  Condensed systems · CPC title