Compounds for electronic devices

Patent metadata

Field	Value
Publication number	US-9608208-B2
Application number	US-201213985671-A
Country	US
Kind code	B2
Filing date	Jan 18, 2012
Priority date	Feb 17, 2011
Publication date	Mar 28, 2017
Grant date	Mar 28, 2017

Abstract

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

First claim

The invention claimed is:

1. A compound of a formula (I), (II) or (III)

where the following applies to the symbols occurring:
Z is on each occurrence, identically or differently, CR 2 or N;
X and Y are on each occurrence, identically or differently, a divalent group selected from the group consisting of BR 2 , C(R 2 ) 2 , C═NR 2 , C═C(R 2 ) 2 , C═S, Si(R 2 ) 2 , NR 1 , PR 2 , P(═O)R 2 , O, S, S═O and S(═O) 2 ;
R 1 is on each occurrence, identically or differently, an aromatic having 6 to 60 aromatic ring atoms or a heteroaromatic ring system having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R 3 and which is optionally linked to a substituent R 2 on the skeleton or an atom of the skeleton;
R 2 is on each occurrence, identically or differently, 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 , N(Ar 1 ) 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 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, where the above-mentioned groups may each be substituted by one or more radicals R 3 and where one or more adjacent or non-adjacent CH 2 groups in the above-mentioned groups is optionally replaced by —R 3 C═CR 3 —, Si(R 3 ) 2 , Ge(R 3 ) 2 , Sn(R 3 ) 2 , C═O, C═S, C═Se, C═NR 3 , —C(═O)O—, —C(═O)NR 3 —, NR 3 , P(═O)(R 3 ), —O—, —S—, SO or SO 2 and where one or more H atoms in the above-mentioned groups is optionally replaced by D, F, Cl, Br, I, CN or NO 2 , or an aromatic having 6 to 60 aromatic ring atoms or a 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 having 6 to 60 aromatic ring atoms or a heteroaryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R 3 , where two or more radicals R 2 is optionally linked to one another and may form a ring or a ring system;
R 3 is on each occurrence, identically or differently, 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(═O)(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, where the above-mentioned groups may each be substituted by one or more radicals R 4 and where one or more adjacent or non-adjacent CH 2 groups in the above-mentioned groups is optionally replaced by —R 4 C═CR 4 —, —C≡C—, Si(R 4 ) 2 , Ge(R 4 ) 2 , Sn(R 4 ) 2 , C═O, C═S, C═Se, C═NR 4 , —C(═O)O—, —C(═O)NR 4 —, NR 4 , P(═O)(R 4 ), —O—, —S—, SO or SO 2 and where one or more H atoms in the above-mentioned groups is optionally replaced by D, F, Cl, Br, I, CN or NO 2 , or an aromatic having 6 to 60 aromatic ring atoms or a heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R 4 , or an aryloxy having 6 to 60 aromatic ring atoms or a heteroaryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R 4 , where two or more radicals R 3 is optionally linked to one another and may form a ring or a ring system;
R 4 is, identically or differently on each occurrence, H, D, F or an aliphatic, aromatic and/or heteroaromatic organic radical having 1 to 20 C atoms, in which, in addition, one or more H atoms is optionally replaced by D or F; two or more substituents R 4 here may also be linked to one another and form a ring or a ring system; and
Ar 1 is on each occurrence, identically or differently, an aromatic having 6 to 60 aromatic ring atoms or a heteroaromatic ring system having 5 to 30 aromatic ring atoms, which is optionally substituted by one or more radicals R 3 .

2. The compound according to claim 1 , wherein there are 0, 1 or 2 groups Z per aromatic six-membered ring of a compound of the formula (I), (II) or (III) are equal to N, and the remaining groups Z are equal to CR 2 .

3. The compound according to claim 1 , wherein X is C═O, NR 1 , O, S, S═O or S(═O) 2 .

4. The compound according to claim 1 , wherein Y is C(R 2 ) 2 , NR 1 , O or S.

5. The compound according to claim 1 , wherein R 2 is selected on each occurrence, identically or differently, from H, D, F, CN, Si(R 3 ) 3 , N(R 3 ) 2 or a straight-chain alkyl or alkoxy group having 1 to 20 C atoms or a branched or cyclic alkyl or alkoxy group having 3 to 20 C atoms, where the above-mentioned groups may each be substituted by one or more radicals R 3 and where one or more adjacent or non-adjacent CH 2 groups in the above-mentioned groups is 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 having 6 to 60 aromatic ring atoms or a heteroaromatic ring system having 5 to 20 aromatic ring atoms, which may in each case be substituted by one or more radicals R 3 , where two or more radicals R 2 is optionally linked to one another and may form a ring or a ring system.

6. The compound according to claim 1 , wherein at least one group R 1 or R 2 is present which is selected from
heteroaryl groups having 1 to 20 C atoms, which may optionally be bonded via one or more divalent aryl groups bonded in between and which is optionally substituted by one or more radicals R 3 ,
aromatic having 6 to 60 aromatic ring atoms or a heteroaromatic ring systems having 5 to 20 aromatic ring atoms, which is optionally substituted by one or more radicals R 3 , and
arylamine groups, which is optionally substituted by one or more radicals R 3 .

7. The compound according to claim 6 , wherein the heteroaryl groups are selected from the group consisting of pyridine, pyrimidine, pyridazine, pyrazine, triazine and benzimidazole, each of which is optionally substituted by one or more radicals R 3 , and the aromatic or heteroaromatic ring systems are selected from the group consisting of naphthyl, anthracenyl, phenanthrenyl, benzanthracenyl, pyrenyl, biphenyl, terphenyl and quaterphenyl, each of which is optionally substituted by one or more radicals R 3 .

8. A process for the preparation of the compound according to claim 1 , comprising at least the following steps:
(a) a coupling reaction between the pyrrole nitrogen atom and an aryl or heteroaryl group; and
(b) a ring-closure reaction between the pyrrole ring and the aryl or heteroaryl group coupled in step (a).

9. An oligomer, polymer or dendrimer comprising one or more compounds according to claim 1 , where the bond(s) to the polymer, oligomer or dendrimer is optionally localised at any positions in formula (I), (II) or (III) that are substituted by R 1 or R 2 .

10. A formulation comprising at least one compound according to claim 1 and at least one solvent.

11. A formulation comprising at least one polymer, oligomer or dendrimer according to claim 9 and at least one solvent.

12. An electronic device comprising the compound according to claim 1 .

13. An electronic device comprising the polymer according to claim 9 .

14. An organic electroluminescent device comprising the compound according to claim 1 .

15. An organic electroluminesce

Assignees

• Martynova Irina
• Parham Amir Hossain
• Pflumm Christof
• Merck Patent Gmbh

Inventors

• Martynova Irina
• Parham Amir Hossain
• Pflumm Christof

Classifications

• H10K85/6572

  comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole · CPC title

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title

• H01L51/0073

  Electricity · mapped topic

• C07F9/6561

  containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings · CPC title