Electron injection layer for an organic light-emitting diode (OLED)

Patent metadata

Field	Value
Publication number	US-12563963-B2
Application number	US-201616062974-A
Country	US
Kind code	B2
Filing date	Dec 14, 2016
Priority date	Dec 18, 2015
Publication date	Feb 24, 2026
Grant date	Feb 24, 2026

Abstract

The invention relates to Organic light emitting diode comprising at least one emission layer, an electron injection layer and at least one cathode electrode, wherein: the electron injection layer comprises an organic phosphine compound, wherein the electron injection layer is free of a metal, metal salt, metal complex and metal organic compound;the cathode electrode comprises at least a first cathode electrode layer, whereinthe first cathode electrode layer comprises a first zero-valent metal selected from the group comprising alkali metal, alkaline earth metal, rare earth metal and/or a group 3 transition metal; andthe electron injection layer is arranged in direct contact to the first cathode electrode layer.

First claim

The invention claimed is:

1 . Organic light emitting diode comprising at least one emission layer, an electron injection layer and at least one cathode electrode, wherein:
the electron injection layer comprises an organic phosphine compound, wherein the electron injection layer is free of a metal, metal salt, metal complex and metal organic compound; the cathode electrode comprises at least a first cathode electrode layer and at least a second cathode electrode layer, wherein the first cathode electrode layer comprises a first zero-valent metal selected from Yb; and the composition of the first cathode electrode layer differs from the composition of the second cathode electrode layer, wherein the second cathode electrode layer comprises at least an additional metal, wherein the additional metal is an MgAg alloy; and wherein the electron injection layer is arranged in direct contact to the first cathode electrode layer; the first cathode electrode layer does not comprise or consist of an organic compound; the organic light emitting diode is a top emission device; and the organic phosphine compound of the electron injection layer is a compound having the Formula Ia:

wherein:
X is selected from O, S, or Se;
R 1 and R 2 are independently selected from C 1 to C 12 alkyl, substituted or unsubstituted C 6 to C 20 aryl or substituted or unsubstituted C 5 to C 20 heteroaryl; or R 1 and R 2 are bridged with an alkene-di-yl group forming with the P atom a substituted or unsubstituted five, six or seven membered ring; and
A 1 is phenyl or selected from Formula (II):

wherein
R 3 is selected from C 1 to C 8 alkane-di-yl, substituted or unsubstituted C 6 to C 20 arylene, or substituted or unsubstituted C 5 to C 20 heteroarylene; or
A 1 is selected from Formula (III)

wherein
n is selected from 0 or 1;
m is selected from 1 or 2;
o is selected from 1 or 2;
and m is 1 if o is 2;
Ar 1 is selected from substituted or unsubstituted C 6 to C 20 arylene and substituted or unsubstituted C 5 to C 20 heteroarylene;
Ar 2 is selected from substituted or unsubstituted C 18 to C 40 arylene and substituted or unsubstituted C 10 to C 40 heteroarylene;
R 4 is selected from H, C 1 to C 12 alkyl, substituted or unsubstituted C 6 to C 20 aryl and substituted or unsubstituted C 5 to C 20 heteroaryl.

2 . The organic light emitting diode according to claim 1 , wherein the first cathode electrode layer is free of a metal halide and/or free of a metal organic complex.

3 . The organic light emitting diode according to claim 1 , further comprising at least one electron transport layer comprising at least one matrix compound, wherein the electron injection layer is contacting sandwiched between the first cathode electrode layer and the electron transport layer.

4 . The organic light emitting diode according to claim 1 , wherein
Ar 1 is selected from substituted C 6 to C 20 arylene, and/or substituted C 5 to C 20 heteroarylene, wherein the C 6 to C 20 arylene, and/or C 5 to C 20 heteroarylene is substituted with at least one C 1 to C 12 alkyl and/or at least one C 1 to C 12 heteroalkyl group; Ar 2 is selected from substituted C 18 to C 40 arylene and/or substituted C 10 to C 40 heteroarylene, wherein the C 18 to C 40 arylene and/or C 10 to C 40 heteroarylene is substituted with at least one C 1 to C 12 alkyl and/or at least one C 1 to C 12 heteroalkyl group.

5 . The organic light emitting diode according to claim 1 , wherein:
R 1 and R 2 are independently selected from substituted C 6 to C 20 aryl, or substituted C 5 to C 20 heteroaryl, wherein the C 6 to C 20 aryl, and/or C 5 to C 20 heteroaryl is substituted with at least one C 1 to C 12 alkyl and/or at least one C 1 to C 12 heteroalkyl group; and/or R 3 is independently selected from substituted C 6 to C 20 arylene, or substituted C 5 to C 20 heteroarylene, wherein the C 6 to C 20 arylene, and/or C 5 to C 20 heteroarylene is substituted with at least one C 1 to C 12 alkyl and/or at least one C 1 to C 12 heteroalkyl group; and/or R 4 is independently selected from substituted C 6 to C 20 aryl, or substituted C 5 to C 20 heteroaryl, wherein the C 6 to C 20 aryl, and/or Cs to C 20 heteroaryl is substituted with at least one C 1 to C 12 alkyl and/or at least one C 1 to C 12 heteroalkyl group.

6 . The organic light emitting diode according to claim 1 , wherein for
o=2 the organic phosphine compound of the electron injection layer is a compound having the Formula Ib:

or
o=1 the organic phosphine compound of the electron injection layer is a compound having the Formula Ic, Id, Ie or If:

7 . The organic light emitting diode according to claim 1 , wherein
R 1 and R 2 is independently selected from C 1 to C 4 alkyl, unsubstituted or substituted C 6 to C 10 aryl, or unsubstituted or substituted C 5 to C 10 heteroaryl, wherein the C 6 to C 10 aryl, and/or C 5 to C 10 heteroaryl is substituted with at least one C 1 to C 12 alkyl and/or at least one C 1 to C 12 heteroalkyl group; and/or X is O or S; and/or R 3 is selected from C 1 to C 6 alkane-di-yl, unsubstituted or substituted C 6 to C 10 arylene or unsubstituted or substituted C 5 to C 10 heteroarylene; and/or R 4 is selected from H, phenyl, biphenyl, terphenyl, fluorenyl, naphthyl, anthranyl, phenanthryl, pyrenyl, carbazoyl, dibenzofuranyl, dinapthofuranyl; and/or n is 0 or 1; m is 1 or 2 and n is 0 or 1, or m is 2 and n is 2; and/or Ar 1 is selected from phenylene, biphenylene, terphenylene, naphthylene, fluorenylene, pyridylene, quinolinylene, and pyrimidinylene; and/or Ar 2 is selected from fluorenylene, anthranylene, pyrenylene, phenanthrylene, carbazoylene, benzo[c]acridinylene, dibenzo[c,h]acridinylene, dibenzo[a,j]acridinylene.

8 . The organic light emitting diode according to claim 1 , wherein R 1 , R 2 , R 3 , R 4 , Ar 1 and/or Ar 2 are unsubstituted.

9 . The organic light emitting diode according to claim 1 , wherein Ar 2 is selected from a compound according to Formula IVa to IVh:

10 . The organic light emitting diode according to claim 1 , wherein the compound of Formula (Ia) is selected from a compound according to:

Assignees

• Novaled Gmbh

Inventors

• Senkovskyy Volodymyr
• Ganier Jerome
• Rothe Carsten

Classifications

• C07F9/65685

  the ring phosphorus atom being part of a phosphine oxide or thioxide · CPC title

• C07F9/65517

  condensed with carbocyclic rings or carbocyclic ring systems · CPC title

• C07F9/5765

  condensed with carbocyclic rings or carbocyclic ring systems · CPC title

• C07F9/5728

  condensed with carbocyclic rings or carbocyclic ring systems · CPC title

• C07F9/5333

  Arylalkane phosphine oxides or thioxides (C07F9/5329 takes precedence) · CPC title