Compounds for electronic devices

Patent metadata

Field	Value
Publication number	US-9735371-B2
Application number	US-201214112344-A
Country	US
Kind code	B2
Filing date	Mar 23, 2012
Priority date	Apr 18, 2011
Publication date	Aug 15, 2017
Grant date	Aug 15, 2017

Abstract

The present invention relates to a compound of the formula (I), to the use of this compound in an electronic device, and to an electronic device comprising one or more compounds of the formula (I). The invention furthermore relates to the preparation of the compound of the formula (I) and to a formulation comprising one or more compounds of the formula (I).

First claim

The invention claimed is:

1. A compound of a formula (I)

wherein A is, identically or differently on each occurrence, a group of the following formula (II) or selected from the formulae (III-1) to (III-3):

wherein

Z is, identically or differently on each occurrence, CR 2 or N; and the dashed line emanating from the nitrogen atom represents the bond from the group A to the central benzene ring;
wherein the group Ar 1 is, identically or differently on each occurrence, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, optionally substituted by one or more radicals R 2 ;

and wherein furthermore:
R 1 is, identically or differently on each occurrence, Si(R 3 ) 3 , a straight-chain C 1 , C 2 , C 3 , C 4 , C 5 , C 6 , C 7 or C 8 -alkyl, and each of which is optionally substituted by one or more radicals R 3 , a branched C 3 , C 4 , C 5 , C 6 , C 7 or C 8 -alkyl, and each of which is optionally substituted by one or more radicals R 3 , a cyclic C 4 , C 5 or C 6 -alkyl, each of which is optionally substituted by one or more radicals R 3 , and wherein one or more CH 2 groups in the above-mentioned groups are optionally replaced by —R 3 C═CR 3 —, —C≡C—, Si(R 3 ) 2 , C═O, C═S, C═NR 3 , —C(═O)O—, —C(═O)NR 3 —, NR 3 , P(═O)(R 3 ), —O—, —S—, SO, or SO 2 , and wherein one or more H atoms in the above-mentioned groups are optionally replaced by D, F, Cl, Br, I, CN, or NO 2 , or an aromatic ring system having 6 to 60 aromatic ring atoms, optionally substituted by one or more radicals R 3 , or a heteroaromatic ring system having 5 to 60 aromatic ring atoms, which is not bonded via a ring nitrogen atom, and which is optionally substituted by one or more radicals R 3 , or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, optionally substituted by one or more radicals R 3 , or an aralkyl or heteroaralkyl group having 5 to 60 aromatic ring atoms, optionally substituted by one or more radicals R 3 ;
R 2 is, identically or differently on each occurrence, H, D, F, Cl, Br, I, B(OR 3 ) 2 , CHO, C(═O)R 3 , CR 3 ═C(R 3 ) 2 , CN, C(═O)OR 3 , C(═O)N(R 3 ) 2 , Si(R 3 ) 3 , N(R 3 ) 2 , NO 2 , P(═O)(R 3 ) 2 , OSO 2 R 3 , OR 3 , S(═O)R 3 , S(═O) 2 R 3 , a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 C atoms, a branched or cyclic alkyl, alkoxy or thio-alkyl group having 3 to 20 C atoms, or an alkenyl or alkynyl group having 2 to 20 C atoms, wherein the above-mentioned groups are optionally substituted by one or more radicals R 3 and wherein one or more CH 2 groups in the above-mentioned groups are optionally replaced by —R 3 C═CR 3 —, —C≡C—, Si(R 3 ) 2 , C═O, C═S, C═NR 3 , —C(═O)O—, —C(═O)NR 3 —, NR 3 , P(—O)(R 3 ), —O—, —S—, SO, or SO 2 , and wherein one or more H atoms in the above-mentioned groups are 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, optionally substituted by one or more radicals R 3 , or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, optionally substituted by one or more radicals R 3 , or an aralkyl or heteroaralkyl group having 5 to 60 aromatic ring atoms, optionally substituted by one or more radicals R 3 ;
R 3 is, identically or differently on each occurrence, H, D, F, Cl, Br, I, B(OR 4 ) 2 , CHO, C(═O)R 4 , CR 4 ═C(R 4 ) 2 , CN, C(═O)OR 4 , C(═O)N(R 4 ) 2 , Si(R 4 ) 3 , N(R 4 ) 2 , NO 2 , P(═OX(R 4 ) 2 , OSO 2 R 4 , OR 4 , S(═O)R 4 , S(═O) 2 R 4 , a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 C atoms, or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 C atoms, or an alkenyl or alkynyl group having 2 to 20 C atoms, wherein the above-mentioned groups are optionally substituted by one or more radicals R 4 and wherein one or more CH 2 groups in the above-mentioned groups are optionally replaced by —R 4 C═CR 4 —, —C≡C—, Si(R 4 ) 2 , C═O, C═S, C═NR 4 , —C(═O)O—, —C(═O)NR 4 —, NR 4 , P(═O)(R 4 ), —O—, —S—, SO, or SO 2 , and wherein one or more H atoms in the above-mentioned groups are 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, optionally substituted by one or more radicals R 4 , or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, optionally substituted by one or more radicals R 4 , or an aralkyl or heteroaralkyl group having 5 to 60 aromatic ring atoms, optionally substituted by one or more radicals R 4 , wherein two or more radicals R 3 are optionally linked to one another and optionally form a ring;
R 4 is, identically or differently on each occurrence, H, D, F, or an aliphatic, aromatic or heteroaromatic organic radical having 1 to 20 C atoms, in which, in addition, one or more H atoms are optionally replaced by D or F; two or more substituents R 4 are optionally linked to one another and optionally form a ring.

2. The compound of claim 1 , wherein the group Ar 1 is, identically or differently on each occurrence, an aryl group having 6 to 10 aromatic ring atoms.

3. The compound of claim 1 , wherein the group of the formula (II) is a group of the following formulae (II-1) and (II-3) to (II-11):

wherein
Z is, identically or differently on each occurrence, CR 2 or N.

4. The compound of claim 1 , wherein Ar 1 bonded to a common N atom in a group of the formula (II) are selected identically.

5. The compound of claim 1 , wherein the group R 1 is, identically or differently on each occurrence the straight-chain alkyl or the branched-chain alkyl, each of which is optionally substituted by one or more radicals R 3 , and wherein one or more CH 2 groups in the above-mentioned groups are optionally replaced by —C≡C—, —R 3 C═CR 3 —, Si(R 3 ) 2 , C═O, C═NR 3 , —NR 3 —, —O—, —S—, —C(═O)O—, or —C(═O)NR 3 —, or an aromatic ring system having 5 to 20 aromatic ring atoms, optionally substituted by one or more radicals R 3 , or a heteroaromatic ring system, not bonded via a ring nitrogen atom, optionally substituted by one or more radicals R 3 .

6. The compound of claim 5 , wherein the radicals R 1 in formula (I) are selected identically.

7. A process for the preparation of the compound of claim 1 wherein at least one intermediate of a formula (Z)

is reacted with at least one arylamino compound or at least one heterocyclic compound containing at least one NH function,
wherein
X is, identically or differently on each occurrence, any reactive group.

8. An oligomer, polymer, or dendrimer, comprising one or more compound of claim 1 , wherein bonds to the oligomer, polymer, or dendrimer, are optionally localised at any position in formula (I) which are substituted by R 1 , R 2 , or R 3 .

9. A formulation comprising at least one compound of claim 1 and at least one solvent.

10. A formulation comprising at least one oligomer, polymer, or dendrimer, of claim 8 and at least one solvent.

11. An e

Assignees

• Stoessel Philipp
• Buesing Arne
• Voges Frank
• Pflumm Christof
• Parham Amir Hossain
• Eberle Thomas
• Mujica-Fernaud Teresa
• Merck Patent Gmbh

Inventors

• Stoessel Philipp
• Buesing Arne
• Voges Frank
• Pflumm Christof
• Parham Amir Hossain
• Eberle Thomas
• Mujica-Fernaud Teresa

Classifications

• C09K2211/1022

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

• C09K2211/185

  of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd · CPC title

• H01L51/5016

  Electricity · mapped topic

• C09K2211/1037

  with sulfur · CPC title

• Y02E10/549

  Organic PV cells · CPC title