Organic electroluminescent device

Patent metadata

Field	Value
Publication number	US-9337430-B2
Application number	US-201214355342-A
Country	US
Kind code	B2
Filing date	Oct 11, 2012
Priority date	Nov 1, 2011
Publication date	May 10, 2016
Grant date	May 10, 2016

Abstract

The present invention relates to electronic devices, in particular organic electroluminescent devices, comprising compounds of the formula (1), to the corresponding compounds, and to a process for the preparation of these compounds.

First claim

The invention claimed is:

1. A compound of the formula (11) or formula (12),

where the following applies to the symbols and indices used:
X is, identically or differently on each occurrence, CR or N; or two adjacent groups X in formula (11) or formula (12) stand for a group of the following formula (9) or (10),

where
E stands for NR, CR 2 , O or S;
Z stands, identically or differently on each occurrence, for CR or N and
^ indicate the corresponding adjacent groups X in formula (11) or formula (12);
Ar 1 is an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms, which may be substituted by one or more radicals R and which contains no aryl or heteroaryl groups having more than two aromatic six-membered rings condensed directly onto one another;
Y is —C(═O)—N(Ar 1 )—, C(R 1 ) 2 , or C(═O);
R is selected, identically or differently on each occurrence, from the group consisting of H, D, F, CN, N(Ar 2 ) 2 , C(═O)Ar 2 , a straight-chain alkyl or alkoxy group having 1 to 10 C atoms or a branched or cyclic alkyl or alkoxy group having 3 to 10 C atoms or an alkenyl group having 2 to 10 C atoms, each of which may be substituted by one or more radicals R 2 , where one or more non-adjacent CH 2 groups may be replaced by O and where one or more H atoms may be replaced by D or F, an aromatic or heteroaromatic ring system having 5 to 30 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 30 aromatic ring atoms, which may be substituted by one or more radicals R 2 ;
R 1 is selected on each occurrence, identically or differently, from the group consisting of H, D, F, Cl, Br, I, CN, NO 2 , N(Ar 2 ) 2 , N(R 2 ) 2 , C(═O)Ar 2 , C(═O)R 2 , P(═O)(Ar 2 ) 2 , 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 or an alkenyl or alkynyl group having 2 to 40 C atoms, each of which may be substituted by one or more radicals R 2 , where one or more non-adjacent CH 2 groups may be replaced by R 2 C═CR 2 , C≡C, Si(R 2 ) 2 , C═O, C═S, C═NR 2 , P(═O)(R 2 ), SO, SO 2 , NR 2 , O, S or CONR 2 and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 , 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 , an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R 2 , or a combination of these systems, where two or more adjacent substituents R or two or more adjacent substituents R 1 may optionally form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system, which may be substituted by one or more radicals R 2 and which contains no aryl or heteroaryl groups having more than two aromatic six-membered rings condensed directly onto one another; a radical R on Ar 1 may furthermore also form an aliphatic ring system with a radical R on Ar; with the proviso that an aryl or heteroaryl group having more than two aryl groups condensed directly onto one another is not formed by ring formation of the radicals R or R 1 ;
Ar 2 is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5-30 aromatic ring atoms, which may be substituted by one or more non-aromatic radicals R 2 and which contains no aryl or heteroaryl groups having more than two aromatic six-membered rings condensed directly onto one another; two radicals Ar 2 which are bonded to the same N atom or P atom may also be bridged to one another here by a single bond or a bridge selected from N(R 2 ), C(R 2 ) 2 or O;
R 2 is selected from the group consisting of H, D, F, CN, an aliphatic hydrocarbon radical having 1 to 20 C atoms, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, in which one or more H atoms may be replaced by D, F, Cl, Br, I or CN, where two or more adjacent substituents R 2 may form a mono- or polycyclic, aliphatic, aromatic or heteroaromatic ring system with one another;
n is on each occurrence, identically or differently, 0 or 1, where n =0 means that no group Y is present and instead a substituent R is bonded or a heteroatom of the group Ar is present in the positions on Ar in which Y is bonded in formula (12);
with the proviso that the radicals on Ar 1 do not contain a lactam group
the following compounds are excluded from the invention:

2. Process for the preparation of the compound according to claim 1 comprising:
bond formation between the nitrogen of a lactam and Ar 1 ;
followed by an oxidation to the corresponding lactum.

3. The electronic device which comprises the compound according to claim 1 .

4. The electronic device as claimed in claim 3 , wherein the device is an organic electroluminescent device.

5. An electronic device comprising a compound of the formula (11) or (12),

where the following applies to the symbols and indices used:
X is, identically or differently on each occurrence, CR or N; or two adjacent groups X in formula (11) or formula (12) stand for a group of the following formula (9) or (10),

where
E stands for NR, CR 2 , O or S;
Z stands, identically or differently on each occurrence, for CR or N and
^ indicate the corresponding adjacent groups X in formula (11) or formula (12);
Ar 1 is an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms, which may be substituted by one or more radicals R and which contains no aryl or heteroaryl groups having more than two aromatic six-membered rings condensed directly onto one another;
Y is —C(═O)—N(Ar 1 )—, C(R 1 ) 2 , or C(═O);
R is selected, identically or differently on each occurrence, from the group consisting of H, D, F, CN, N(Ar 2 ) 2 , C(═O)Ar 2 , a straight-chain alkyl or alkoxy group having 1 to 10 C atoms or a branched or cyclic alkyl or alkoxy group having 3 to 10 C atoms or an alkenyl group having 2 to 10 C atoms, each of which may be substituted by one or more radicals R 2 , where one or more non-adjacent CH 2 groups may be replaced by O and where one or more H atoms may be replaced by D or F, an aromatic or heteroaromatic ring system having 5 to 30 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 30 aromatic ring atoms, which may be substituted by one or more radicals R 2 ;
R 1 is selected on each occurrence, identically or differently, from the group consisting of H, D, F, Cl, Br, I, CN, NO 2 , N(Ar 2 ) 2 , N(R 2 ) 2 , C(═O)Ar 2 , C(═O)R 2 , P(═O)(Ar 2 ) 2 , 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 or an alkenyl or alkynyl group having 2 to 40 C atoms, each of which may be substituted by one or more radicals R 2 , where one or more non-adjacent CH 2 groups may be replaced by R 2 C═CR 2 , C≡C, Si(R 2 ) 2 , C

Assignees

• Merck Patent Gmbh

Inventors

• Parham Amir Hossain
• Pflumm Christof
• Jatsch Anja
• Eberle Thomas
• Stoessel Philipp

Classifications

• C07D401/10

  linked by a carbon chain containing aromatic rings · CPC title

• C09K2211/1011

  Condensed systems · CPC title

• C07D401/04

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

• C07D491/22

  in which the condensed system contains four or more hetero rings · CPC title

• C07D221/18

  Ring systems of four or more rings · CPC title