Materials for organic electroluminescent devices

Patent metadata

Field	Value
Publication number	US-9324954-B2
Application number	US-201113988351-A
Country	US
Kind code	B2
Filing date	Oct 27, 2011
Priority date	Nov 24, 2010
Publication date	Apr 26, 2016
Grant date	Apr 26, 2016

Abstract

The present invention relates to compounds of the formula (1) and formula (2) which are suitable for use in electronic devices, in particular in organic electroluminescent devices.

First claim

The invention claimed is:

1. A compound of the formula (1) or formula (2),

where the following applies to the symbols used:
pym is a pyrimidine, which is optionally substituted by one or more radicals R;
Cb is a carbazole derivative which contains at least 2 bridges, in which, in addition, one or more C atoms is optionally replaced by N and which is optionally substituted by one or more radicals R 2 ;
R, R 1 and R 2 are selected on each occurrence, identically or differently, and are H, D, F, Cl, Br, I, CN, NO 2 , N(Ar) 2 , N(R 3 ) 2 , C(═O)Ar, C(═O)R 3 , P(═O)(Ar) 2 , a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms or an alkenyl or alkynyl group having 2 to 40 C atoms, each of which is optionally substituted by one or more radicals R 3 , where one or more non-adjacent CH 2 groups is optionally replaced by R 3 C═CR 3 , C≡C Si(R 3 ) 2 , C═O, C═S, C═NR 3 , P(═O)(R 3 ), SO, SO 2 , NR 3 , O, S or CONR 3 and where one or more H atoms is optionally replaced by D, F, Cl, Br, I, CN or NO 2 , an aromatic or heteroaromatic ring system having 5 to 80 aromatic ring atoms, which may in each case be substituted by one or more radicals R 3 , an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R 3 , or an aralkyl or heteroaralkyl group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R 3 , where two or more adjacent substituents R 2 may optionally form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system, which is optionally substituted by one or more radicals R 3 ;
R 3 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, CN, NO 2 , N(Ar) 2 , N(R 4 ) 2 , C(═O)Ar, C(═O)R 4 , P(═O)(Ar) 2 , a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms or an alkenyl or alkynyl group having 2 to 40 C atoms, each of which is optionally substituted by one or more radicals R 3 , where one or more non-adjacent CH 2 groups is optionally replaced by R 4 C═CR 4 , Si(R 4 ) 2 , C═O, C═S,C═Se, C═NR 4 , P(═O)(R 4 ), SO, SO 2 , NR 4 , O, S or CONR 4 and where one or more H atoms is optionally replaced by D, F, Cl, Br, I, CN or NO 2 , an aromatic or hetero-aromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R 4 , an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R 4 , or an aralkyl or heteroaralkyl group having 5 to 60 aromatic ring atoms, where two or more adjacent substituents R 3 may optionally form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system, which is optionally substituted by one or more radicals R 4 ;
Ar is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5-30 aromatic ring atoms, which is optionally substituted by one or more non-aromatic radicals R 4 ; two radicals Ar here which are bonded to the same N atom or P atom may also be bridged to one another by a single bond or a bridge selected from N(R 4 ), C(R 4 ) 2 , O or S;
R 4 is H, D, F, CN, an aliphatic hydrocarbon radical having 1 to 20 C atoms, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, in which one or more H atoms is optionally replaced by D, F, Cl, Br, I or CN, where two or more adjacent substituents R 4 may form a mono- or polycyclic, aliphatic, aromatic or heteroaromatic ring system with one another;
the following compounds are excluded from the invention:

2. The compound according to claim 1 , wherein the compounds of the formula (1) are selected from the compounds of the formulae (1 a), (1 b) or (1 c) and in that the compounds of the formula (2) are compounds of the formula (2a),

where the symbols used have the meanings given in claim 1 .

3. The compound according to claim 1 , wherein R 1 represents H or an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms, which is optionally substituted by one or more radicals R 3 .

4. The compound according to claim 1 , wherein the group pym is selected from the groups of the formulae (3), (4) or (5),

Where the symbols used have the meanings given in claim 1 and the dashed bond indicates the bond to the phenyl group in formula (1) or (2).

5. The compound according to claim 4 , wherein the group pym is selected from the formulae (3a), (4a) and (5a),

Where the symbols used have the meanings given in claim 1 and the dashed bond represents the bond from the pyrimidine to the phenyl group of the formula (1) or (2).

6. The compound according to claim 1 , wherein R stands, identically or differently on each occurrence, for H, an alkyl group having 1 to 10 C atoms or for an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms, which is optionally substituted by one or more radicals R 3 .

7. The compound according to claim 1 , wherein the group Cb is selected from the groups of the formulae (6) to (22),

where the symbols used have the meanings given in claim 1 , the dashed bond represents the bond from the carbazole derivative to the phenyl group of the formula (1) or (2) and
X is on each occurrence, identically or differently, CR 2 or N, where a maximum of 2 symbols X per ring stand for N;
Y is on each occurrence, identically or differently, C(R 2 ) 2 , NR 2 , O or S;
n is 0 or 1, where n equals 0 means that no group Y is bonded at this position and instead radicals R 2 are bonded to the corresponding carbon atoms.

8. The compound according to claim 7 , wherein the symbol X stands, identically or differently on each occurrence, for CR 2 .

9. The compound according to claim 7 , wherein the symbol X stands, identically or differently on each occurrence, CH.

10. The compound according to claim 1 , wherein the substituent R 2 , which is bonded directly to a nitrogen atom in the bridge of a carbazole derivative, stands for an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms, which may also be substituted by one or more radicals R 3 .

11. The compound according to claim 1 , wherein the group Cb is selected from the groups of the formulae (7), (8), (10), (11), (13), (14), (16) to (19), (21) and (22),

where the symbols used have the meanings given in claim 1 , the dashed b

Assignees

• Parham Amir Hossain
• Pflumm Christof
• Anémian Rémi Manouk
• Spreitzer Hubert
• Merck Patent Gmbh

Inventors

• Parham Amir Hossain
• Pflumm Christof
• Anémian Rémi Manouk
• Spreitzer Hubert

Classifications

• C07D487/02

  in which the condensed system contains two hetero rings · CPC title

• C07D403/14

  containing three or more hetero rings · CPC title

• C09B57/00

  Other synthetic dyes of known constitution · 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

• C09K2211/1007

  Non-condensed systems · CPC title