Phosphorescent OLED and hole transporting materials for phosphorescent OLEDs

Patent metadata

Field	Value
Publication number	US-10243146-B2
Application number	US-201314436386-A
Country	US
Kind code	B2
Filing date	Oct 17, 2013
Priority date	Oct 17, 2012
Publication date	Mar 26, 2019
Grant date	Mar 26, 2019

Abstract

The present invention relates to phosphorescent organic light-emitting diodes (OLEDs) comprising a hole-transporting or a hole-transporting and an electron-blocking layer comprising an N,N,N′,N′-tetraaryl-phenylene-3,5-diamine or an N,N,N′,N′-tetraaryl-1,1′-biphenyl-3,3′-diamine matrix compound and to new N,N,N′,N′-tetraarylsubstituted m-arylene diamine compounds useful as hole-transporting and electron-blocking layer matrices in phosphorescent OLEDs.

First claim

The invention claimed is:

1. An organic light emitting device comprising an anode, a cathode, at least one emitting layer comprising a phosphorescent emitter, and at least one hole transporting or electron blocking layer comprising a compound represented by general formula (I), wherein the at least one emitting layer, and the at least one hole transporting or electron blocking layer are arranged between the anode and the cathode:

wherein R 1 -R 20 are independently selected from hydrogen, C1-C20 alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C3-C20 cycloalkyloxy, C7-C20 arylalkyl, C6-C20 aryl, or C2-C20 heteroaryl;
at least one of R 1 -R 5 and at least one of R 11 -R 15 is C6-C20 aryl or C2-C20 heteroaryl;
at least two of R 6 -R 10 and at least two of R 16 -R 20 are methyl, or at least one of R 6 -R 10 and at least one of R 16 -R 20 are selected from C2-C20 alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C3-C20 cycloalkyloxy, C7-C20 arylalkyl, C6-C20 aryl, or C2-C20 heteroaryl;
x is 0, and wherein R 22 is selected from the same substituents as R 1 -R 20 .

2. The device according to claim 1 , wherein at least one of R 1 -R 5 and at least one of R 11 -R 15 is selected from C6-C20 aryl or C2-C20 heteroaryl, and the R 1 -R 5 and R 11 -R 15 substituents not selected from C6-C20 aryl or C2-C20 heteroaryl are hydrogen.

3. The device according to claim 1 , wherein at least one of R 1 -R 5 and at least one of R 11 -R 15 is phenyl, and the other R 1 -R 5 and R 11 -R 15 substituents are hydrogen.

4. The device according to claim 1 , wherein at least two of R 6 -R 10 and at least two of R 16 -R 20 are methyl.

5. The device according to claim 1 , wherein at least one of R 6 -R 10 and at least one of R 16 -R 20 is selected from C2-C20 alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C3-C20 cycloalkyloxy, C7-C20 arylalkyl, C6-C20 aryl, or C2-C20 heteroaryl.

6. An organic light emitting device comprising an anode, a cathode, at least one emitting layer comprising a phosphorescent emitter, and at least one hole transporting or electron blocking layer comprising a compound represented by general formula (I), formula (II), or formula (III), wherein the at least one emitting layer, and the at least one hole transporting or electron blocking layer are arranged between the anode and the cathode:

wherein R 1 -R 20 are independently selected from hydrogen, C1-C20 alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C3-C20 cycloalkyloxy, C7-C20 arylalkyl, C6-C20 aryl, or C2-C20 heteroaryl; and
at least one of R 1 -R 5 and at least one of R 11 -R 15 is C6-C20 aryl or C2-C20 heteroaryl;
at least two of R 6 -R 10 and at least two of R 16 -R 20 are methyl, or at least one of R 6 -R 10 and at least one of R 16 -R 20 are selected from C2-C20 alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C3-C20 cycloalkyloxy, C7-C20 arylalkyl, C6-C20 aryl, or C2-C20 heteroaryl;
x is 0, and wherein R 22 is selected from C1-C20 alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C3-C20 cycloalkyloxy, C7-C20 arylalkyl, C6-C20 aryl, or C2-C20 heteroaryl.

7. The device according to claim 6 , wherein at least one of R 1 -R 5 and at least one of R 11 -R 15 is selected from C6-C20 aryl or C2-C20 heteroaryl, and the R 1 -R 5 and R 11 -R 15 substituents not selected from C6-C20 aryl or C2-C20 heteroaryl are hydrogen.

8. The device according to claim 6 , wherein at least one of R 1 -R 5 and at least one of R 11 -R 15 is phenyl, and the other R 1 -R 5 and R 11 -R 15 substituents are hydrogen.

9. The device according to claim 6 , wherein at least two of R 6 -R 10 and at least two of R 16 -R 20 are methyl.

10. The device according to claim 6 , wherein at least one layer comprising the compound of formula (I) is electrically doped.

11. The device according to claim 10 , wherein the layer comprising the compound of formula (I) comprises at least one doped portion and at least one portion that is un-doped or comprises less dopant than the doped portion.

12. The device according to claim 6 , wherein at least one of R 6 -R 10 and at least one of R 16 -R 20 is selected from C2-C20 alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C3-C20 cycloalkyloxy, C7-C20 arylalkyl, C6-C20 aryl, or C2-C20 heteroaryl.

13. The device according to claim 6 , wherein at least one layer comprising the compound of formula (I) is electrically doped.

14. The device according to claim 13 , wherein the layer comprising the compound of formula (I) comprises at least one doped portion and at least one portion that is un-doped or comprises less dopant than the doped portion.

Assignees

• Novaled Gmbh

Inventors

• Zoellner Mike
• Wutke Jens
• Burkhardt Martin

Classifications

• C07D213/38

  having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom · CPC title

• C07C217/94

  having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton · CPC title

• C07D471/04

  Ortho-condensed systems · CPC title

• C07D209/82

  Carbazoles; Hydrogenated carbazoles · CPC title

• C07C211/56

  the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups · CPC title