Compounds for organic electroluminescent devices

Patent metadata

Field	Value
Publication number	US-9627626-B2
Application number	US-201113979545-A
Country	US
Kind code	B2
Filing date	Dec 15, 2011
Priority date	Jan 13, 2011
Publication date	Apr 18, 2017
Grant date	Apr 18, 2017

Abstract

The present invention relates to aromatic nitrogen heterocycles, and to electronic devices, in particular organic electroluminescent devices, which comprise these aromatic nitrogen heterocycles, in particular in a hole-injection layer and/or in a hole-transport layer and/or in a hole-blocking layer and/or in an electron-transport layer and/or in an emitting layer.

First claim

The invention claimed is:

1. A compound of the formula (2) and (5),

where the following applies to the symbols used:
R is on each occurrence, identically, H, D, F, Cl, Br, I, CHO, N(R 1 ) 2 , N(Ar) 2 , C(═O)R 1 , C(═O)Ar, P(═O)(R 1 ) 2 , F(═O)(Ar) 2 , S(═O)Ar, S(═O) 2 Ar, CR 1 ═CR 1 Ar, CN, NO 2 , Si(R 1 ) 3 , B(OR 1 ) 2 , B(R 1 ) 2 , B(Ar) 2 , B(N(R 1 ) 2 ) 2 , P(R 1 ) 2 , OSO 2 R 1 , COOH, COOR 1 , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, each of which is optionally substituted by one or more radicals R 1 , where one or more non-adjacent CH 2 groups is optionally replaced by R 1 C═CR 1 , C≡C, Si(R 1 ) 2 , Ge(R 1 ) 2 , Sn(R 1 ) 2 , C═O, C═S, C═Se, C═NR 1 , P(═O)(R 1 ), SO, SO 2 , NR 1 , O, S or CONR 1 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 1 , or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R 1 , or a combination of these systems; two adjacent radicals R here may in each case form a mono- or polycyclic, aliphatic, aromatic or heteroaromatic ring system with one another;
R 1 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, CHO, 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 , B(R 2 ) 2 , B(N(R 2 ) 2 ) 2 , OSO 2 R 2 , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkenyl, alkynyl, 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 , C≡C, Si(R 2 ) 2 , Ge(R 2 ) 2 , Sn(R 2 ) 2 , C═O, C═S, C═Se, 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 60 aromatic ring atoms, which is optionally substituted by one or more radicals R 2 , or a combination of these systems;
Ar is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which is optionally substituted by one or more non-aromatic radicals R 1 ; two radicals Ar which are bonded to the same nitrogen or phosphorus atom may also be linked to one another here by a single bond or a bridge selected from the group consisting of B(R 2 ), C(R 2 ) 2 , Si(R 2 ) 2 , C═O, C═NR 2 , C═C(R 2 ) 2 , O, S, S═O, SO 2 , N(R 2 ), P(R 2 ) and P(═O)R 2 ;
R 2 is on each occurrence, identically or differently, H, D or an aliphatic, aromatic and/or heteroaromatic hydrocarbon radical having 1 to 20 C atoms, in which, in addition, H atoms is optionally replaced by F; two or more adjacent substituents R 2 here may also form a mono- or polycyclic, aliphatic or aromatic ring system with one another.

2. The compound according to claim 1 wherein the heteroaromatic skeleton has C3h or C2v symmetry.

3. The compound according to claim 1 wherein R stands, identically on each occurrence, for H, F, C(═O)Ar, P(═O)(Ar) 2 , CN, 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 1 , where one or more H atoms is optionally replaced by F or CN, or an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which may in each case be substituted by one or more radicals R 1 .

4. An organic electroluminescent device which comprises the compound according to claim 1 is employed as electron-transport material or as hole-blocking material in an electron-transport layer or in a hole-blocking layer and/or in that the compound according to claim 1 is employed as charge-generation material in a charge-generation layer and/or in that the compound according to claim 1 is employed as matrix material for an emitting compound for a phosphorescent compound.

5. The compound according to claim 1 wherein R is on each occurrence, identically, H, F, N(Ar) 2 , CN, 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 1 .

6. The compound according to claim 1 wherein R is on each occurrence, identically, F, N(Ar) 2 , CN, 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 1 .

7. A process for the preparation of the compound according to claim 1 , which comprises the following reaction steps:
a) synthesizing the corresponding halogenated skeleton; and
b) conversion of the halogen into the substituent.

8. An oligomer, polymer or dendrimer containing one or more compounds according to claim 1 , where one or more radicals R represent bonds from the compound to the polymer, oligomer or dendrimer.

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

10. The electronic device as claimed in claim 9 , wherein the device is selected from the group consisting of an organic electroluminescent device, an organic integrated circuit, an organic field-effect transistor, an organic thin-film transistor, an organic light-emitting transistor, an organic solar cell, a dye-sensitised solar cell, an organic optical detector, an organic photoreceptor, an organic field-quench device, a light-emitting electrochemical cell, an organic laser diode and an organic plasmon emitting device.

11. An organic electroluminescent device which comprises the compound according to claim 1 is used in a hole-injection or hole-transport layer.

12. An organic electroluminescent device which comprises one of the following structures a) or b):
a) anode-hole-injection layer comprising at least one compound according to claim 1 hole-transport layer-emitting layer-cathode;
or
b) anode-hole-injection layer-hole-transport layer comprising at least one compound according to claim 1 hole-transport layer-emitting layer-cathode,
where the electroluminescent device may also comprise further layers in addition to the said layers.

13. An organic electroluminescent device which comprises the compound according to claim 1 is employed as electron-transport material or as hole-blocking material in an electron-transport layer or in a hole-blocking layer and/or in that the compound according to claim 1 is employed as charge-generation material in a charge-generation layer and/or in that the compound according to claim 1 is employed as matrix material for an emitting compound.

Assignees

• Stoessel Philipp
• Buesing Arne
• Breuning Esther
• Pflumm Christof
• Hossain Amir
• Eberle Thomas
• Mujica-Fernaud Teresa
• Merck Patent Gmbh

Inventors

• Stoessel Philipp
• Buesing Arne
• Breuning Esther
• Pflumm Christof
• Hossain Amir
• Eberle Thomas
• Mujica-Fernaud Teresa

Classifications

• H10K85/6572

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

• C07D487/22 Primary

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

• H01L51/0072 Primary

  Electricity · mapped topic

• C09B57/00

  Other synthetic dyes of known constitution · CPC title

• H01L51/5088

  Electricity · mapped topic