Materials for organic electroluminescent devices

Patent metadata

Field	Value
Publication number	US-9199972-B2
Application number	US-201013510143-A
Country	US
Kind code	B2
Filing date	Oct 28, 2010
Priority date	Nov 17, 2009
Publication date	Dec 1, 2015
Grant date	Dec 1, 2015

Abstract

The present invention relates to organic electroluminescent devices which comprise fluorene derivatives and spiro bifluorene derivatives as matrix material for phosphorescent emitters.

First claim

The invention claimed is:

1. A compound of the formula (1), (2), (3a) or (3b),

where the following applies to the symbols and indices used:
Ar is on each occurrence, identically or differently, a heteroaryl group selected from the group consisting of triazine, pyrazine, pyrimidine, pyridazine, pyridine, pyrazole, imidazole, oxazole, 1,3,4-oxadiazole, benzimidazole or thiazole, each of which is optionally substituted by one or more groups R 1 ;
X is a group of the formula (4), where the dashed bond in each case indicates the bond to the two benzene rings:

or X is on each occurrence, identically or differently, a divalent bridge selected from B(Ar 2 ), C(Ar 2 ) 2 , C(Ar 1 Ar 2 ), Si(Ar 2 ) 2 , C═C(Ar 2 ) 2 or C═NAr 2 ;
X 1 is on each occurrence, identically or differently, X or a divalent bridge selected from B(R 1 ), C(R 1 ) 2 , Si(R 1 ) 2 , C═C(R 1 ) 2 , C═NR 1 , B(Ar 1 ), C(Ar 1 ) 2 , Si(Ar 1 ) 2 , C═C(Ar 1 ) 2 or C═NAr 1 ;
R 1 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, CHO, N(Ar 1 ) 2 , C(═O)Ar 1 , P(═O)(Ar 1 ) 2 , S(═O)Ar 1 , S(═O) 2 Ar 1 ,CR 2 ═CR 2 Ar 1 , CN, NO 2 , Si(R 2 ) 3 , B(OR 2 ) 2 , B(R 2 ) 2 , B(N(R 2 ) 2 ), OSO 2 R 2 , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, each of which is optionally substituted by one or more radicals R 2 , where one or more, preferably non-adjacent CH 2 groups is optionally replaced by R 2 C═CR 2 , C≡C, Si(R 2 ) 2 , Ge(R 2 ) 2 , Sn(R 2 ) 2 , C═O, C═S, C═Se, 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, I, CN or NO 2 , or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R 2 , or an aryloxy or hetero-aryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R 2 , or an aralkyl or heteroaralkyl group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R 2 ; two or more adjacent substituents R 1 here may also form a mono- or polycyclic, aliphatic or aromatic ring system with one another;
Ar 1 is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which is optionally substituted by one or more radicals R 2 ; two radicals Ar 1 which are bonded to the same nitrogen, phosphorus or boron atom may here also be linked to one another by a single bond or a bridge selected from B(R 2 ), C(R 2 ) 2 , Si(R 2 ) 2 , C═O, C═NR 2 , C═C(R 2 ) 2 , O, S, S═O, SO 2 , N(R 2 ), P(R 2 ) and P(═O)R 2 ;
R 2 is on each occurrence, identically or differently, H, D or an aliphatic, aromatic and/or heteroaromatic organic radical having 1 to 20 C atoms, in which, in addition, H atoms is optionally replaced by D or F; two or more adjacent substituents R 2 here may also form a mono- or polycyclic, aliphatic or aromatic ring system with one another;
n is 0 or 1;
m is 0, 1,2 or 3;
o is 0, 1, 2, 3 or 4 if m=0 and is 0, 1, 2 or 3 if m=1;
p, q are on each occurrence, identically or differently, 0 or 1, with the proviso that p+q is equal to 1 or 2;
where the compound of the formula (1), (2), (3a) or (3b) contains at least one group Ar 2 , where Ar 2 is selected from a carbazole group, an azacarbazole group, a cis- or trans-indenocarbazole group, a cis- or trans-indenoazacarbazole group or a cis- or trans-indolocarbazole group, each of which is optionally substituted by one or more radicals R 1 , where two or more adjacent substituents R 1 , together with the atoms to which they are bonded, may also form a mono- or polycyclic, aliphatic or aromatic ring system with one another, with the proviso that the group Ar 2 is not in conjugation with the group Ar.

2. The compound according to claim 1 , wherein the following applies to the symbols in the compounds of the formulae (1), (2), (3a) and (3b):
Ar is on each occurrence, identically or differently, triazine, pyrimidine or pyrazine, in particular triazine, each of which is optionally substituted by one or more radicals R 1 ;
X is on each occurrence, identically or differently, a group of the formula (4), where the dashed bond in each case indicates the bond to the two benzene rings;
X 1 is, identically or differently on each occurrence, a divalent bridge selected from C(R 1 ) 2 , Si(R 1 ) 2 or C═C(R 1 ) 2 ;
R 1 is on each occurrence, identically or differently, H, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 8 C atoms or an aromatic or heteroaromatic ring system having 5 to 20 aromatic ring atoms, each of which is optionally substituted by one or more radicals R 2 , or an aryloxy or heteroaryloxy group having 5 to 20 aromatic ring atoms, which is optionally substituted by one or more radicals R 2 , or a combination of these systems; two or more adjacent substituents R 1 here may also form a mono- or polycyclic, aliphatic or aromatic ring system with one another;
Ar 1 is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 20, which is optionally substituted by one or more radicals R 2 ; two radicals Ar 1 which are bonded to the same nitrogen, phosphorus or boron atom may here also be linked to one another by a single bond or a bridge selected from C(R 2 ) 2 , C═O, O, S and N(R 2 );
R 2 is on each occurrence, identically or differently, H, D or an aliphatic, aromatic and/or heteroaromatic organic radical having 1 to 10 C atoms, in which, in addition, H atoms is optionally replaced by F; two or more adjacent substituents R 2 here may also form a mono- or polycyclic, aliphatic or aromatic ring system with one another;
Ar 2 is on each occurrence selected from carbazole, azacarbazole, indenocarbazole and indolocarbazole, each of which may also be substituted by one or more radicals R 1 ;
the other symbols and indices have the meanings indicated in claim 1 .

3. The compound according to claim 2 , wherein
X 1 is C(R 1 ) 2 ;
Ar 1 is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 10, aromatic ring atoms, which is optionally substituted by one or more radicals R 2 ; two radicals Ar 1 which are bonded to the same nitrogen, phosphorus or boron atom may here also be linked to one another by a single bond or a bridge selected from C(R 2 ) 2 , C═O, O, S and N(R 2 );
R 2 is on each occurrence, identically or differently, H, D or an aliphatic, aromatic and/or heteroaromatic organic radical having 1 to 6 C atoms, in which, in addition, H atoms is optionally replaced by F; two or more adjacent substituents R 2 here may also form a mono- or polycyclic, aliphatic or aromatic ring system with one another.

4. The compound according to claim 1 , wherein the compound is selected from compounds of the formulae (5) to (12),

where the symbols and indices have the same meanings as described in claim 1 .

5. The compound according to claim 1 , wherein the compound is selected from compounds of the formulae (13) to (20),

Assignees

• Parham Amir Hossain
• Kaiser Joachim
• Gerhard Anja
• Kroeber Jonas Valentin
• Anémian Rémi Manouk
• Merck Patent Gmbh

Inventors

• Parham Amir Hossain
• Kaiser Joachim
• Gerhard Anja
• Kroeber Jonas Valentin
• Anémian Rémi Manouk

Classifications

• C07D471/04

  Ortho-condensed systems · CPC title

• C07D403/10 Primary

  linked by a carbon chain containing aromatic rings · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• Y02E10/549

  Organic PV cells · CPC title

• C09B57/10

  Metal complexes of organic compounds not being dyes in uncomplexed form · CPC title