Triphenylene-based materials for organic electroluminescent devices

Patent metadata

Field	Value
Publication number	US-9985226-B2
Application number	US-201113879530-A
Country	US
Kind code	B2
Filing date	Sep 16, 2011
Priority date	Oct 15, 2010
Publication date	May 29, 2018
Grant date	May 29, 2018

Abstract

The present invention relates to compounds of the formula (1) and (2)

which are suitable for use in electronic devices, in particular organic electroluminescent devices.

First claim

The invention claimed is:

1. A neutral compound of the formula (1),

where the following applies to the symbols and indices used:
X is on each occurrence, identically or differently, BR 2 , Si(R 2 ) 2 or NR 2 ;
or X is, for n=0, a group of the following formula (3),

A is Si; the dashed bonds on A indicate the bonding to the triphenylene;
Y is BR 2 , O, S, NR 2 , PR 2 or P(═O)R 2 ;
Z is on each occurrence, identically or differently, CR 1 or N, with the proviso that a maximum of two groups Z per ring stand for N;
Ar 1 is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more non-aromatic radicals R 3 ; two radicals Ar 1 which are bonded to the same N atom or P atom may also be bridged to one another by a single bond or a bridge selected from N(R 4 ), C(R 4 ) 2 , O or S;
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 1 ) 2 , N(R 3 ) 2 , C(═O)Ar 1 , C(═O)R 3 , P(═O)(Ar 1 ) 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, where the alkyl, alkoxy, thioalkyl, alkenyl or alkynyl group is optionally substituted by one or more radicals R 3 and where one or more non-adjacent CH 2 groups is optionally replaced by R 3 C═CR 3 , C≡C, Si(R 3 ) 2 , Ge(R 3 ) 2 , Sn(R 3 ) 2 , C═O, C═S, C═Se, 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 , 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 , an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R 3 , or a combination of these systems, where two or more adjacent substituents R 1 which are bonded to the same benzene ring may optionally form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system;
R 2 is selected on each occurrence, identically or differently, from the group consisting of a straight-chain alkyl group having 1 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 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 , C≡C, 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 , where two substituents R 2 which are bonded to the same carbon, silicon, germanium or tin atom may optionally form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system with one another, which is optionally substituted by one or more radicals R 3 ;
R 3 is selected on each occurrence, identically or differently, from the group consisting of H, D, F, Cl, Br, I, CN, NO 2 , N(R 4 ) 2 , C(═O)Ar 1 , C(═O)R 4 , P(═O)(Ar 1 ) 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, where the alkyl, alkoxy, thioalkyl, alkenyl or alkynyl group is optionally substituted by one or more radicals R 4 , where one or more non-adjacent CH 2 groups is optionally replaced by R 4 C═CR 4 , C≡C, Si(R 4 ) 2 , C═O, C═NR 4 , P(═O)(R 4 ), SO, SO 2 , NR 4 , O, S or CONR 4 and where one or more H atoms is optionally replaced by D, F, Cl, Br, I, CN or NO 2 , an aromatic or hetero-aromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R 4 , an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R 4 , or a combination of these systems, where two or more adjacent substituents R 3 may optionally form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system, which is optionally substituted by one or more radicals R 4 ;
R 4 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 is optionally replaced by D, F, Cl, Br, I, CN or an alkyl group having 1 to 5 C atoms, where two or more adjacent substituents R 4 may form a mono- or polycyclic, aliphatic, aromatic or heteroaromatic ring system with one another;
n is 0 or 1.

2. The compound according to claim 1 , wherein the compound is selected from the compounds of the formulae (4) to (6),

where the symbols used have the meanings given in claim 1 .

3. The compound according to claim 1 , wherein the compound is selected from the compounds of the formulae (4a) to (6a),

where the symbols used have the meanings given in claim 1 .

4. The compound according claim 1 , wherein the compound of formula (1) is selected from the group consisting of formula (4), (4a), (5), (5a), (6), or (6a),

wherein, in compounds of the formula (1) where n=0 or in compounds of the formula (4) or formula (4a), X is selected from the group consisting of Si(R 2 ) 2 and N(R 2 ) and R 2 stands, identically or differently on each occurrence, for an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which may in each case also be substituted by one or more radicals R 3 and where two radicals R 2 may also form an aromatic ring system with one another;
and in that, in compounds of the formula (1) where X=formula (3) or in compounds of the formula (5) or formula (5a), the two triphenylene moieties which are bonded to A are in each case substituted identically and A stands for silicon;
and in that, in compounds of the formula (1) where n=1 or in compounds of the formula (6) or formula (6a), the group X—Y—X is Si(R 2 ) 2 —O—Si(R 2 ) 2 .

5. A process for the preparation of the compound according to claim 1 which comprises reacting 1,12-dilithiotriphenylene derivatives with electrophiles or by reaction of halogen- or amino-substituted triphenylene derivatives in a metal-catalyzed coupling reaction.

6. An oligomer, polymer or dendrimer containing one or more of the compounds according to claim 1 , where one or more bonds are present from the compound to the polymer, oligomer or dendrimer.

7. An electronic device which comprises the compound according to claim 1 .

8. An electronic device which comprises the oligomer, polymer or dendrimer according to claim 6 .

9. The electronic device as claimed in claim 7 , wherein the device is selected from the group consisting of organic electroluminescent de

Assignees

• Stoessel Philipp
• Joosten Dominik
• Buesing Arne
• Merck Patent Gmbh

Inventors

• Stoessel Philipp
• Joosten Dominik
• Buesing Arne

Classifications

• H10K85/6576

  comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene · CPC title

• H10K85/6572

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

• H10K85/636

  comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom · CPC title

• H10K85/624

  containing six or more rings · CPC title

• C07D409/14

  containing three or more hetero rings · CPC title