Materials for organic electroluminescent devices

Patent metadata

Field	Value
Publication number	US-9312495-B2
Application number	US-201113823401-A
Country	US
Kind code	B2
Filing date	Aug 16, 2011
Priority date	Sep 15, 2010
Publication date	Apr 12, 2016
Grant date	Apr 12, 2016

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.

First claim

The invention claimed is:

1. A compound of the formula (1),

where the following applies to the symbols and indices used:
Ar is, identically or differently on each occurrence, an aromatic ring system selected from the group consisting of benzene, naphthalene, phenanthrene, fluorene, spirobifluorene, dibenzofuran and dibenzothiophene, each of which is optionally substituted by one or more radicals R 1 ;
Ar 1 and Ar 2 are, identically or differently on each occurrence, selected from the groups of the formulae (5) to (28),

where the dashed bond indicates the position of the bond to the nitrogen;
R is on each occurrence, identically or differently, and are H, D, F, Cl, Br, I, CN, Si(R 2 ) 3 , 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, each of which is optionally substituted by one or more radicals R 2 , where in each case one or more non-adjacent CH 2 groups is optionally replaced by Si(R 2 ) 2 , C═NR 2 , P(═O)(R 2 ), SO, SO 2 , NR 2 , O, S or CONR 2 and where one or more H atoms is optionally replaced by D, F, Cl, Br or I, an aromatic or heteroaromatic ring system having 6 to 60 C atoms selected from the group consisting of benzene, naphthalene, phenanthrene, fluorene, spirobifluorene, dibenzofuran and dibenzothiophene, which may in each case be substituted by one or more radicals R 2 , or a combination of two, three, four or five of these groups, which may in each case be identical or different, an aryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R 2 , or an aralkyl group having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R 2 , where two or more adjacent substituents R or two or more adjacent substituents R 1 may optionally form a mono- or polycyclic, aliphatic ring system, which is optionally substituted by one or more radicals R 2 ;
R 1 are on each occurrence, identically or differently, and are H, D, F, CN, a straight-chain alkyl having 1 to 40 C atoms or a branched or cyclic alkyl group having 3 to 40 C atoms, or an aromatic or heteroaromatic ring system having 6 to 60 C atoms selected from the group consisting of benzene, naphthalene, phenanthrene, dibenzofuran and dibenzothiophene, or a combination of two, three, four or five of these groups, which may in each case be identical or different;
R 2 is on each occurrence, identically or differently, is H, D, F, Cl, Br, I, Si(R 3 ) 3 , 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, 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 Si(R 3 ) 2 , 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 or I, an aromatic ring system having 6 to 60 C atoms selected from the group consisting of benzene, naphthalene, phenanthrene, fluorene, spirobifluorene or a combination of two, three, four or five of these groups, which may in each case be identical or different, which may in each case be substituted by one or more radicals R 3 , an aryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R 3 , or an aralkyl 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 mono- or polycyclic, aliphatic ring system, which is optionally substituted by one or more radicals R 3 ;
R 3 is selected from the group consisting of H, D, F, an aliphatic hydrocarbon radical having 1 to 20 C atoms, an aromatic ring system having 6 to 30 C atoms, in which one or more H atoms is optionally replaced by D or F, where two or more adjacent substituents R 3 may form a mono- or polycyclic, aliphatic ring system with one another;
m is 0, 1, 2 or 3;
n is on each occurrence, identically or differently, 0, 1, 2, 3 or 4;
p is 0, 1 or 2;
the following compounds are excluded from the invention:

2. The compound according to claim 1 of the formula (2), formula (3a), (3b), (4a) or formula (4b),

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

3. The compound according to claim 1 , wherein the groups Ar 1 and Ar 2 are selected, identically or differently on each occurrence, from the groups of the formulae (5a) to (28a),

where the symbols used have the meanings given in claim 1 , and the dashed bond indicates the position of the bond from the group to the nitrogen.

4. The compound according to claim 1 , wherein Ar 1 is a group of the formula (6), (7), (8), (9) or (21).

5. The compound according to claim 3 , wherein Ar 1 is a group of the formula (6a), (7a), (8a), (9a) or (21a).

6. The compound according to claim 1 , wherein the groups Ar 1 and Ar 2 are different from one another.

7. A compound of the formula (1),

where the following applies to the symbols and indices used:
Ar is, identically or differently on each occurrence, an aromatic ring system selected from the group consisting of benzene, naphthalene, phenanthrene, fluorene, spirobifluorene, dibenzofuran and dibenzothiophene, each of which is optionally substituted by one or more radicals R 1 ;
the group —NAr 1 Ar 2 has the structure of one of the formulae (29), (30), (31) or (32) or in that the group —Ar—NAr 1 Ar 2 has the structure of one of the formulae (33), (34), (35) or (36),

and the dashed bond indicates the bond to the spirobifluorene or to Ar;

and the dashed bond indicates the bond to the spirobifluorene;
where
R is on each occurrence, identically or differently, and are H, D, F, Cl, Br, I, CN, Si(R 2 ) 3 , 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, each of which is optionally substituted by one or more radicals R 2 , where in each case one or more non-adjacent CH, groups is optionally replaced by Si(R 2 ) 2 , C═NR 2 , P(═O)(R 2 ), SO, SO 2 , NR 2 , O, S or CONR 2 and where one or more H atoms is optionally replaced by D, F, Cl,

Assignees

• Pflumm Christof
• Parham Amir Hossain
• Brocke Constanze
• Montenegro Elvira
• Voges Frank
• Heil Holger
• Buesing Arne
• Merck Patent Gmbh

Inventors

• Pflumm Christof
• Parham Amir Hossain
• Brocke Constanze
• Montenegro Elvira
• Voges Frank
• Heil Holger
• Buesing Arne

Classifications

• C07D219/02

  with only hydrogen, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system · CPC title

• C09K2211/1037

  with sulfur · CPC title

• C09K2211/1033

  with oxygen · CPC title

• C07C2603/94

  containing "free" spiro atoms · 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