IP Library Granted Patent US 8,053,094
Granted Patent B2
US 8,053,094 · App. 12/497,109 · Granted Nov 8, 2011

Organic light-emitting diodes and methods for assembly and enhanced charge injection

Assignee: Northwestern University
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Quick Facts
Patent No.
US 8,053,094
App. No.
12/497,109
Granted
Nov 8, 2011
Kind
B2
Abstract

New organic light-emitting diodes and related electroluminescent devices and methods for fabrication, using siloxane self-assembly techniques.

Claims (42)

1. A method of using an amine molecular component to enhance hole injection across the electrode-organic interface of a light emitting diode device, said method comprising:

providing an anode; and

incorporating an electroluminescent medium adjacent said anode, said medium comprising an amine molecular layer coupled to said anode, said amine molecular layer having at the least one of an arylamine molecular component and an arylalkylamine molecular component, each said component substituted with at least one silyl group; and

providing on said amine molecular layer a hole transport layer of molecular components having at least one of an arylamine molecular component and an arylalkylamine molecular component.

2. The method of claim 1 wherein said molecular layer components are compounds of formula

wherein n is an integer from 1-4;

R 2 -R 8 are independently selected from H, trichlorosilyl, trialkoxysilyl, dichlorosilyl, dialkoxysilyl, trichlorosilylalkyl, trialkoxysilylalkyl, dichlorosilylalkyl and dialkoxysilylalkyl, provided that at least one of R 2 -R 4 and least one of R 5 -R 8 is not H; and

Ar is an arylene group.

3. The method of claim 2 wherein said molecular layer components are selected from the group consisting of trichlorosilylalkyl-substituted triphenylamine, trialkoxysilylalkyl-substituted triphenylamine, trichlorosilylalkyl-substituted N,N,N′,N′-tetraphenyl-(1,1′-biphenyl)-4,4′-diamine and trialkoxysilylalkyl-substituted N,N,N′,N′-tetraphenyl-(1,1′-biphenyl)-4,4′-diamine.

4. The method of claim 3 wherein said molecular layer is spin-coated on said anode.

5. The method of claim 3 wherein said anode is immersed in a solution of said molecular layer components.

6. The method of claim 1 wherein a plurality of molecular layers are coupled to said anode.

7. The method of claim 1 wherein said hole transport layer is N,N-diphenyl-N,N-bis(3-methylphenyl)-(1,1′-biphenyl)-4,4′-diamine.

8. The method of claim 7 wherein said hole transport layer is spin-coated on said anode.

9. An electroluminescent device for generating light upon application of an electrical potential across two electrodes, said device comprising:

an anode;

at least one amine molecular layer coupled to said anode, said molecular layer having at least one of an arylamine molecular component and an arylalkylamine molecular component, each said component substituted with at least one silyl group;

a conductive layer of molecular components having at least one of an arylamine molecular component and an arylalkylamine molecular component; and

a cathode in electrical contact with said anode layer.

10. The device of claim 9 wherein said molecular layer components are compounds of formula

wherein

n is an integer from 1-4;

R 2 -R 8 are independently selected from H, trichlorosilyl, trialkoxysilyl, dichlorosilyl, dialkoxysilyl, trichlorosilylalkyl, trialkoxysilylalkyl, dichlorosilylalkyl and dialkoxysilylalkyl, provided that at least one of R 2 -R 4 and least one of R 5 -R 8 is not H; and

Ar is an arylene group.

11. The device of claim 10 wherein said molecular layer components are selected from the group consisting of trichlorosilylalkyl-substituted triphenylamine, trialkoxysilylalkyl-substituted triphenylamine, trichlorosilylalkyl-substituted N,N,N′,N′-tetraphenyl-(1,1′-biphenyl)-4,4′-diamine and trialkoxysilylalkyl-substituted N,N,N′,N′-tetraphenyl-(1,1′-biphenyl)-4,4′-diamine.

12. The device of claim 11 wherein said conductive layer is a hole transport layer of N,N-diphenyl-N,N-bis(3-methylphenyl)-(1,1′-biphenyl)-4,4′-diamine.

13. The device of claim 9 wherein a plurality of molecular layers are coupled to said anode.

14. An electroluminescent device for generating light upon application of an electrical potential across two electrodes, said device comprising:

an anode;

at least one molecular layer, coupled to said anode, of arylamine molecular components substituted with at least two silyl groups;

a hole transport layer of N,N′-diphenyl-N,N-bis(3-methylphenyl)-(1,1′-biphenyl)-4,4′-diamine molecular components, said hole transport layer substantially without crystallization sufficient for layer decohesion; and

a cathode in electrical contact with said anode.

15. The device of claim 14 wherein said molecular layer components are selected from the group consisting of trichlorosilylalkyl-substituted triphenylamine, trialkoxysilylalkyl-substituted triphenylamine, trichlorosilylalkyl-substituted N,N,N′,N-tetraphenyl-(1,1′-biphenyl)-4,4′-diamine and trialkoxysilylalkyl-substituted N,N,N′,N′-tetraphenyl-(1,1′-biphenyl)-4,4′-diamine.

16. The device of claim 14 wherein a plurality of molecular layers are coupled to said anode.

17. The device of claim 14 further including an electron transport layer.

18. An electroluminescent device for generating light upon application of an electrical potential across two electrodes, said device comprising:

an anode;

at least one molecular layer, coupled to said anode, of silylalkyl-substituted N,N,N′N′-tetraphenyl-(1,1′-biphenyl)-4,4′-diamine molecular components;

a hole transport layer of N,N′-diphenyl-N,N-bis(3-methylphenyl)-(1,1′-biphenyl)-4,4′-diamine molecular components and

a cathode in electrical contact with said anode.

19. The device of claim 18 further including, an electron transport layer.

20. The device of claim 18 wherein a plurality of molecular layers are coupled to said anode.

Assignments (4)
CONFIRMATORY LICENSE Recorded Jun 30, 2025
From: NORTHWESTERN UNIVERSITY
To: NATIONAL SCIENCE FOUNDATION
Reel/Frame 071756/0280 →
CONFIRMATORY LICENSE Recorded Dec 26, 2021
From: NORTHWESTERN UNIVERSITY
To: NATIONAL SCIENCE FOUNDATION
Reel/Frame 058477/0400 →
CONFIRMATORY LICENSE Recorded Dec 28, 2011
From: NORTHWESTERN UNIVERSITY
To: NATIONAL SCIENCE FOUNDATION
Reel/Frame 027456/0228 →
CONFIRMATORY LICENSE Recorded Dec 22, 2011
From: NORTHWESTERN UNIVERSITY
To: NATIONAL SCIENCE FOUNDATION
Reel/Frame 027437/0572 →
Continuity (5)
Continuation 10992624 · Nov 18, 2004
Continuation 10099131 · Mar 15, 2002
Continuation In Part 09187891 · Nov 6, 1998
Continuation In Part 08673600 · Jun 25, 1996
Related Publication 20090284145A1 · Nov 19, 2009