Carbazole derivatives for organic electroluminescence devices

Patent metadata

Field	Value
Publication number	US-9818948-B2
Application number	US-201214346187-A
Country	US
Kind code	B2
Filing date	Aug 23, 2012
Priority date	Sep 21, 2011
Publication date	Nov 14, 2017
Grant date	Nov 14, 2017

Abstract

The present invention describes carbazole derivatives formula (1), where the following applies to the symbols used: Y is on each occurrence, identically or differently, CR or N; X is selected from C(R1)2, O, S, PR1, P(═O)R1 or BR1; characterized in that at least one group R is present which stands, identically or differently on each occurrence, for a group of the following formula (2), and/or in that at least one group R1 is present which stands for a group of the following formula (3) or (4), in particular for use as triplet matrix materials in organic electroluminescent devices. The invention furthermore relates to a process for the preparation of the compounds according to the invention and to electronic devices comprising same.

First claim

The invention claimed is:

1. A compound of the formulae (6b), (7b) and (8b),

where the following applies to the symbols used:
R and R 1 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, N(R 2 ) 2 , N(Ar) 2 , C(═O)Ar, P(═O)Ar 2 , S(═O)Ar, S(═O) 2 Ar, CR 2 ═CR 2 Ar, CN, NO 2 , Si(R 2 ) 3 , B(OR 2 ) 2 , OSO 2 R 2 , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a branched or cyclic alkyl, 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 non-adjacent CH 2 groups is optionally replaced by R 2 C═CR 2 , Si(R 2 ) 2 , C═O, 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 heteroaryloxy group having 5 to 40 aromatic ring atoms, which is optionally substituted by one or more radicals R 2 , or an aralkyl or heteroaralkyl group having 5 to 40 aromatic ring atoms, which is optionally substituted by one or more radicals R 2 , or a combination of these systems; two or more substituents R here, together with the atoms to which they are bonded, or two substituents R 1 , together with the atom to which they are bonded, may also form a mono- or polycyclic, aliphatic or aromatic ring system with one another;
Ar is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which is optionally substituted by one or more radicals R 3 ;
R 2 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, N(R 3 ) 2 , N(Ar) 2 , C(═O)Ar, P(═O)Ar 2 , S(═O)Ar, S(═O) 2 Ar, CR 3 ═CR 3 Ar, CN, NO 2 , Si(R 3 ) 3 , B(OR 3 ) 2 , OSO 2 R 3 , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy 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 R 3 C═CR 3 , Si(R 3 ) 2 , C═O, 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 , 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 3 , or an aryloxy or heteroaryloxy group having 5 to 40 aromatic ring atoms, which is optionally substituted by one or more radicals R 3 , or an aralkyl or heteroaralkyl group having 5 to 40 aromatic ring atoms, which is optionally substituted by one or more radicals R 3 , or a combination of these systems;
R 3 is on each occurrence, identically or differently, H, D or an aliphatic hydrocarbon radical having 1 to 20 C atoms or an aryl or heteroaryl group having 5 to 40 ring atoms or a combination of these groups;
with the proviso that, if one or more of the groups R, R 1 , R 2 , R 3 , Ar or Ar 1 contain heteroaryl groups which do not conform to the formulae (2), (3) these are not electron-deficient heteroaryl groups;

wherein at least one group R is present which stands, identically or differently on each occurrence, for a group of the following formula (2),

where the dashed bond indicates the linking of the group of the formula (2), R 2 has the above-mentioned meanings, and furthermore:
Q is C if the group of the formula (2) is linked to Ar 1 or to the remainder of the molecule via this group; or is, identically or differently on each occurrence, CR 2 or N in the other cases;
Z is NR 2 or S;
Ar 1 is a divalent aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which is optionally substituted by one or more radicals R 2 ;
p is 0 or 1;
and/or in that at least one group R 1 is present which stands for a group of the following formula (3)

where the dashed bond indicates the linking of the group of the formula (3), R 2 , Ar 1 , Q and p have the above-mentioned meanings, and furthermore:
W is NR 2 , O or S, and
wherein in the compound of formula (6b) at least one group R is present which stands for a group of the formula (2) or at least one group R 1 is present which stands for a group of the formula (3); and
wherein in the compounds of formula (7b) or (8b) at least one group R is present which stands for a group of the formula (2).

2. The compound according to claim 1 , wherein the radical R 1 which is bonded to the nitrogen atom stands for an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may also be substituted by one or more radicals R 2 , or for a group of the formula (3).

3. The compound according to claim 1 where R 1 stands, identically or differently on each occurrence, for a straight-chain alkyl group having 1 to 10 C atoms or a branched or cyclic alkyl group having 3 to 10 C atoms, each of which is optionally substituted by one or more radicals R 2 , where one or more non-adjacent CH 2 groups is optionally replaced by R 2 C═CR 2 , C≡C, Si(R 2 ) 2 , C═O, O, S or CONR 2 and where one or more H atoms is optionally replaced by D, F or CN, or for an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may also be substituted by one or more radicals R 2 ; the radicals R 1 here may also form an aromatic or aliphatic ring system with one another.

4. The compound according to claim 1 , wherein the groups of the formulae (2) to (3) are selected from the groups of the formulae (2a) to (3a),

where the symbols and indices used have the meanings given in claim 1 , and, in formula (2a) and (3a), no group R 2 is bonded at the position at which the group is linked to Ar 1 or the remainder of the molecule.

5. The compound according to claim 1 , wherein the groups of the formulae (2) to (3) are selected from the structures of the formulae (2b), (2c), (2d), (3b), (3c), and (3d),

where the dashed bond indicates the linking of the group to the remainder of the molecule, and the other symbols and indices used have the meanings given in claim 1 .

6. Compound according to claim 4 , wherein the radicals R 2 which are bonded to a carbon atom in formula (2a) to (3a) stand for H.

7. Compound according to claim 5 , wherein the radicals R 2 which are bonded to a carbon atom in formula (2b), (2c), (2d), (3b), (3c), and (3d), stand for H.

8. The compound according to claim 1 , wherein Z or W stands for NR 2 , where R 2 stands for an aromatic or heteroaromatic ring system.

9. A process for the preparation of a the compound according to claim 1 , which comprises introducing the group of the formula (2) or (3) by a Suzuki coupling, an Ullmann coupling or by a Hartwig-Buchwald coupling.

10. A mixture comprising at least one compound according to claim 1 and at least one fluorescent or phosphorescent dopant.

11. A formulation comprising at least one compound according to claim 1 and one or more s

Assignees

• Jatsch Anja
• Parham Amir Hossain
• Pflumm Christof
• Stoessel Philipp
• Kroesser Jonas Valentin
• Anémian Rémi Manouk
• Eberle Thomas
• Merck Patent Gmbh

Inventors

• Jatsch Anja
• Parham Amir Hossain
• Pflumm Christof
• Stoessel Philipp
• Kroesser Jonas Valentin
• Anémian Rémi Manouk
• Eberle Thomas

Classifications

• C07D405/14 Primary

  containing three or more hetero rings · CPC title

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title

• C09K2211/1096

  containing other heteroatoms · CPC title

• C07D495/14

  Ortho-condensed systems · CPC title

• C07D405/04

  directly linked by a ring-member-to-ring-member bond · CPC title