Materials for electronic devices

Patent metadata

Field	Value
Publication number	US-2018019397-A1
Application number	US-201515520987-A
Country	US
Kind code	A1
Filing date	Oct 2, 2015
Priority date	Oct 24, 2014
Publication date	Jan 18, 2018
Grant date	—

Abstract

The present application relates to a material comprising a monoarylamine of a formula (A) and a p-dopant of a defined formula. The present application further relates to the use of said material in an organic layer of an electronic device, the device preferably being an organic electroluminescent device (OLED).

First claim

1 .- 19 . (canceled)

20 . A material comprising a compound A of a formula (A)

where the variables that occur are:
Z is CR 1 ;
Ar 1 is the same or different at each instance and is an aromatic ring system which has 6 to 30 aromatic ring atoms and is optionally substituted by one or more R 1 radicals, or a heteroaromatic ring system which has 5 to 30 aromatic ring atoms and is optionally substituted by one or more R 1 radicals; Ar 1 groups here is optionally bonded to one another via R 1 radicals;
R 1 is the same or different at each instance and is selected from H, D, F, C(═O)R 2 , CN, Si(R 2 ) 3 , P(═O)(R 2 ) 2 , OR 2 , S(═O)R 2 , S(═O) 2 R 2 , straight-chain alkyl or alkoxy groups having 1 to 20 carbon atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 carbon atoms, alkenyl or alkynyl groups having 2 to 20 carbon atoms, aromatic ring systems having 6 to 30 aromatic ring atoms, and heteroaromatic ring systems having 5 to 30 aromatic ring atoms; where two or more R 1 radicals is optionally joined to one another and may form a ring; where the alkyl, alkoxy, alkenyl and alkynyl groups mentioned and the aromatic ring systems and heteroaromatic ring systems mentioned may each be substituted by one or more R 2 radicals; and where one or more CH 2 groups in the alkyl, alkoxy, alkenyl and alkynyl groups mentioned is optionally replaced by —R 2 C═CR 2 —, —C≡C—, Si(R 2 ) 2 , C═O, C═NR 2 , —C(═O)O—, —C(═O)NR 2 —, P(═O)(R 2 ), —O—, —S—, SO or SO 2 ;
R 2 is the same or different at each instance and is selected from H, D, F, CN, alkyl groups having 1 to 20 carbon atoms, aromatic ring systems having 6 to 30 aromatic ring atoms and heteroaromatic ring systems having 5 to 30 aromatic ring atoms; where two or more R 2 radicals is optionally joined to one another and may form a ring; and where the alkyl groups, aromatic ring systems and heteroaromatic ring systems mentioned is optionally substituted by F or CN;

and a compound P which is a complex of bismuth.

21 . The material according to claim 20 , wherein the compound A does not contain a fused aryl group having more than 10 aromatic ring atoms nor a fused heteroaryl group having more than 14 aromatic ring atoms.

22 . The material according to claim 20 , wherein, in the compound A, the Ar 1 group is the same or different at each instance and is an aromatic ring system which has 6 to 24 aromatic ring atoms and is optionally substituted by one or more R 1 radicals, or a heteroaromatic ring system which has 5 to 24 ring atoms and is optionally substituted by one or more R 1 radicals.

23 . The material according to claim 20 , wherein, in the compound A, the Ar 1 group is a group which is optionally substituted by one or more R 1 radicals and is selected from the group consisting of phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, phenanthryl, fluoranthenyl, fluorenyl, indenofluorenyl, spirobifluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, acridyl and phenanthridyl.

24 . The material according to claim 20 , wherein the compound P is a complex of bismuth in the (III) oxidation state.

25 . The material according to claim 20 , wherein the compound P is a complex of bismuth having at least one ligand L which is an organic compound.

26 . The material according to claim 25 , wherein the ligand L is singly negatively charged.

27 . The material according to claim 25 , wherein the group in the ligand L that binds to the bismuth atom is selected from the group consisting of carboxylic acid groups, thiocarboxylic acid groups, carboxamide groups and carboximide groups.

28 . The material according to claim 25 , wherein the ligand L is selected from fluorinated benzoic acid derivatives, fluorinated or non-fluorinated phenylacetic acid derivatives and fluorinated or non-fluorinated acetic acid derivatives.

29 . The material according to claim 20 , wherein the compound P is present in the material as a dopant in a concentration of 0.1% to 30%.

30 . A layer for use in an electronic device, comprising the material according to claim 20 .

31 . A formulation comprising the material according to claim 20 and at least one solvent.

32 . A process for producing a layer according to claim 30 , which comprises applying compound A and compound P together from the gas phase.

33 . A process for producing a layer which comprises applying a formulation comprising the material according to claim 20 and a solvent from the liquid phase.

34 . An electronic device selected from organic electroluminescent devices, organic integrated circuits, organic field-effect transistors, organic thin-film transistors, organic light-emitting transistors, organic solar cells, organic optical detectors, organic photoreceptors, organic field-quench devices, organic light-emitting electrochemical cells and organic laser diodes, comprising a material according to claim 20 .

35 . The organic electroluminescent device according to claim 34 , wherein the device includes the material in a hole-transporting layer disposed between anode and emitting layer, with one or more further layers present between the layer comprising the material and the emitting layer.

36 . The organic electroluminescent device according to claim 35 , wherein the HOMO levels of the hole-transporting layer (HTL) and the one layer between hole-transporting layer and emitting layer (EBL) meet the following condition:
HOMO(HTL)<=HOMO(EBL).

37 . The organic electroluminescent device according to claim 35 , wherein the one or more further layers disposed between the layer comprising the material and the emitting layer comprise one or more identical or different compounds of the formula (A).

38 . The organic electroluminescent device according to claim 34 , wherein the device comprises the material in a layer directly adjoining the anode.

Assignees

• Merck Patent Gmbh
• Osram Oled Gmbh

Inventors

• Kaiser Joachim
• Pflumn Christof
• Jaeger Arndt
• Dobbertin Thomas
• Schmid Guenter

Classifications

• Y02E10/549

  Organic PV cells · CPC title

• H01L51/006 Primary

  Electricity · mapped topic

• H01L51/5012

  Electricity · mapped topic

• H01L51/0058

  Electricity · mapped topic

• H01L51/0077

  Electricity · mapped topic