Compositions with 2,3-disubstituted indoles as charge transport materials, and display devices fabricated therefrom

Patent metadata

Field	Value
Publication number	US-9966537-B2
Application number	US-201515539856-A
Country	US
Kind code	B2
Filing date	Dec 22, 2015
Priority date	Dec 29, 2014
Publication date	May 8, 2018
Grant date	May 8, 2018

Abstract

Provided is a composition comprising a compound selected from Structure 1, as described herein:

First claim

The invention claimed is:

1. A composition comprising a compound of Structure 1:

wherein R 1 through R 24 are each, independently, selected from the following: a hydrogen, a hydrocarbyl, a substituted hydrocarbyl, a cyano, an alkoxy, an aryloxy, or a NR′ 2 wherein R′ is selected from an aryl or a heteroaryl; and
wherein, optionally, two or more of R 1 to R 24 form one or more ring structures; and
wherein Z is selected from group (1) or (2):

 and

wherein, optionally, one or more hydrogens may be substituted with deuterium.

2. The composition of claim 1 , wherein R 1 through R 24 are each independently selected from the following: hydrogen, an unsubstituted hydrocarbyl, or an substituted hydrocarbyl.

3. The composition of claim 1 , wherein R 1 through R 24 are each hydrogen.

4. The composition of claim 1 , wherein the Z is group (1):

5. The composition of claim 1 , wherein Structure 1 is the following Structure 1a:

6. The composition of claim 1 , wherein Z is group (2):

7. The composition of claim 6 , wherein Structure 1 is Structure 2a:

8. The composition of claim 1 , wherein the compound of Structure 1has a HOMO level of −5.00 eV to −4.40 eV.

9. The composition of claim 1 , wherein the Z group of group 1, when attached to a carbazole via the nitrogen atom of the carbazole, provides an electrochemical stability within ±3.0 × 10 -5 A, for at least 2 repeated cyclic voltammograms, each with a voltage range from 1.6 V to 0 V.

10. A film formed from the composition of claim 1 .

11. An electronic device comprising at least one component formed from the film of claim 10 .

12. An electronic device comprising at least one component formed from the composition of claim 1 .

13. The electronic device of claim 12 , wherein the component is a hole transport layer.

14. The electronic device of claim 13 , further comprising a hole injection layer, an emitting layer, an electron charge transport layer, and/or an electron injection layer.

15. A composition comprising a compound of Structure 2:

wherein R 1 through R 24 are each, independently, selected from the following: a hydrogen, a hydrocarbyl, a substituted hydrocarbyl, a cyano, an alkoxy, an aryloxy, or a NR′ 2 wherein R′ is selected from an aryl or a heteroaryl; and
wherein, optionally, two or more of R 1 to R 24 form one or more ring structures; and
wherein Z is selected from group (1a) or (2a):

wherein for group 1a, Ra and Rb are each independently an alkyl, and wherein at least one of Ra and/or Rb comprises at least two carbon atoms; and for group 2a, Rc and Rd are each independently an alkyl, and wherein at least one of Rc and/or Rd comprises at least two carbon atoms; and
wherein, optionally, one or more hydrogens may be substituted with deuterium.

Assignees

• Dow Global Technologies Llc

Inventors

• Gray Kaitlyn
• Wright Robert
• Spencer Liam
• Devore David
• Pearson David
• Feng Jichang
• Yan jing jing
• Feng Shaoguang

Classifications

• C07D209/86

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system · CPC title

• H01L51/0061 Primary

  Electricity · mapped topic

• H01L51/5088

  Electricity · mapped topic

• H01L51/5012

  Electricity · mapped topic

• H01L51/5092

  Electricity · mapped topic