Organic semiconductive layer comprising phosphine oxide compounds

Patent metadata

Field	Value
Publication number	US-11950496-B2
Application number	US-201615777274-A
Country	US
Kind code	B2
Filing date	Nov 23, 2016
Priority date	Nov 23, 2015
Publication date	Apr 2, 2024
Grant date	Apr 2, 2024

Abstract

The present invention relates to an. organic semiconductive layer which is an electron transport layer and/or an electron injection layer and/or an n-type charge generation layer, the organic semiconductive layer comprising at least one compound of formula (1) wherein R 1 and R 2 are each independently selected from C 1 to C 16 alkyl; Ar 1 is selected from C 6 to C 14 arylene or C 3 to C 12 heteroarylene; Ar 2 is independently selected from C 14 to C 40 arylene or C 8 to C 40 heteroarylene; R 3 is independently selected from H, C 1 to C 12 alkyl or C 10 to C 20 aryl; wherein each of Ar 1 , Ar 2 and R 3 may each independently be unsubstituted or substituted with at least one C 1 to C 12 alky group; n is 0 or 1; and m is 1 in case of n=0; and m is 1 or 2 in case of n=1, phosphine oxide compounds comprised therein and to organic electroluminescent devices comprising such layers and compounds.

First claim

The invention claimed is:

1. Organic semiconductive layer which is an electron transport layer and/or an electron injection layer and/or an n-type charge generation layer, the organic semiconductive layer comprising (i) at least one compound of formula (1), and (ii) an alkali organic complex and/or an alkali halide:

wherein R 1 and R 2 are each independently selected from C 1 to C 4 alkyl;
Ar 1 is selected from C 6 to C 14 arylene or C 3 to C 12 heteroarylene;
Ar 2 is independently selected from C 14 to C 40 arylene comprising a conjugated system of at least 14 delocalized electrons or C 8 to C 40 heteroarylene;
R 3 is independently selected from H, C 1 to C 12 alkyl, or C 10 to C 20 aryl or heteroaryl;
wherein each of Ar 1 , Ar 2 and R 3 may each independently be unsubstituted or substituted with at least one C 1 to C 12 alkyl group;
n is 1; and
m is 1 or 2.

2. Organic semiconductive layer according to claim 1 , wherein Ar 1 is selected from a group consisting of phenylene, biphenylene, naphthylene, fluorenylene, pyridylene, quinolinylene and pyrimidinylene.

3. Organic semiconductive layer according to claim 1 , wherein Ar 2 is selected from a group consisting of anthracenylene, pyrenylene, phenanthrylene, carbazoylene, benzo[c]acridinylene, dibenzo[c,h]acridinylene, dibenzo[a,j]acridinylene or from a group of the following formulas (IVa) to (IVm)

4. Organic semiconductive layer according to claim 1 , wherein Ar 2 is selected from a group consisting of anthracenylene, pyrenylene, phenanthrylene, benzo[c]acridinylene, dibenzo[c,h]acridinylene and dibenzo[a,j]acridinylene.

5. Organic semiconductive layer according to claim 1 , wherein R 3 is selected from H, biphenyl, terphenyl, fluorenyl, naphthyl, phenanthryl, pyrenyl, carbazoyl, dibenzofuranyl or dinapthofuranyl.

6. Organic semiconductive layer according to claim 1 , selected from one of the following compounds a to g.

7. Organic semiconductive layer according to claim 1 further comprising a zero-valent metal dopant.

8. Organic electroluminescent device comprising the organic semiconductive layer according to claim 1 .

9. Organic semiconductive layer according to claim 1 , wherein Art is phenylene or biphenylene.

10. Organic semiconductive layer according to claim 1 , wherein
Ar 1 is phenylene or biphenylene;
Ar 2 is anthracenylene; and
R 3 is biphenyl or naphthyl.

11. Organic semiconductive layer according to claim 1 , wherein
Ar 1 is phenylene or biphenylene; and
Ar 2 is anthracenylene or naphthylene.

Assignees

• Novaled Gmbh

Inventors

• Senkovskyy Volodymyr

Classifications

• H10K50/16

  Electron transporting layers · CPC title

• H10K85/615 Primary

  Polycyclic condensed aromatic hydrocarbons, e.g. anthracene · CPC title

• C07F9/5325 Primary

  Aromatic phosphine oxides or thioxides (P-C aromatic linkage) · CPC title

• C07F9/5765

  condensed with carbocyclic rings or carbocyclic ring systems · CPC title

• C07F9/65068

  condensed with carbocyclic rings or carbocyclic ring systems · CPC title