IP Library Granted Patent US 8,057,908
Granted Patent B2
US 8,057,908 · App. 12/267,347 · Granted Nov 15, 2011

Hole transport layer compositions and related diode devices

Assignee: Northwestern University
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Quick Facts
Patent No.
US 8,057,908
App. No.
12/267,347
Granted
Nov 15, 2011
Kind
B2
Abstract

Hole transport layer compositions comprising a silylated aryl amine and a polymeric component, to enhance performance of an associated electroluminescent device.

Claims (30)

1. A device comprising a substrate; and a hole transport composition comprising a polymeric hole transport component and a product selected from:

(a) a sorption product of said substrate and a silylated aryl amine component,

(b) an intermolecular cross-linking product of two silylated aryl amine components, and

(c) combinations of a said sorption product and a said intermolecular cross-linking product;

wherein said silylated aryl amine component is of a formula selected from

where Ar is arylene; n is an integer ranging from 1 to 4; R 1 -R 7 are independently selected from H and alkyl moieties ranging from C 1 to C 6 , each said alkyl moiety comprising a hydrolyzable silyl group, and wherein at least one of R 1 -R 3 and at least one of R 4 -R 7 is one of said alkyl moieties, and

wherein each silyl group of each said product comprises three silicon-oxygen bonds.

2. The device of claim 1 wherein R 1 -R 7 are selected from a C 1 -C 6 alkyl moiety comprising a group selected from trihalosilyl and trialkoxysilyl.

3. The device of claim 2 wherein Ar is phenylene and n is 2.

4. The device of claim 2 wherein R 1 -R 7 are independently selected from trihalosilylalkyl and trialkoxysilylalkyl moieties.

5. The device of claim 4 wherein one of R 1 -R 3 is a trichlorosilylpropyl moiety, and one of R 4 -R 7 is a trichlorosilylpropyl moiety.

6. The device of claim 5 wherein Ar is phenylene and n is 2.

7. The device of claim 1 wherein said polymeric component is a poly(fluorene).

8. The device of claim 1 wherein said polymeric component is selected from TFB, BT and combinations thereof.

9. The device of claim 8 wherein said silylated aryl amine component is of a formula where Ar is phenylene and n is 2.

10. The device of claim 9 wherein said polymeric component is selected from TFB, BT and combinations thereof.

11. The device of claim 1 wherein said substrate is selected from an anode, where said hole transport composition comprises a sorption product, and an anode configuration comprising an anode and a second hole transport polymer on an anode of said device, where said hole transport composition comprises an intermolecular cross-linking product.

12. The device of claim 11 wherein said second hole transport polymer is PEDOT-PSS.

13. A device comprising a substrate; and a hole transport composition comprising a polymeric component selected from TFB, BT and combinations thereof and a silylated aryl amine component of a formula

where R 4 -R 7 are independently selected from H and alkyl moieties ranging from C 1 -C 6 , each said alkyl moiety further comprising a hydrolyzable silyl group, and wherein at least one of R 4 -R 7 is one of said alkyl moieties.

14. The device of claim 13 wherein at least two of R 4 -R 7 comprise a C 2 -C 4 alkyl moiety.

15. The device of claim 14 wherein each of R 4 and R 5 is H, and each of R 6 and R 7 comprises a C 2 -C 4 alkyl moiety.

16. The device of claim 15 wherein each of said R 6 and R 7 moieties further comprise a silyl group selected from halosilyl and alkoxysilyl.

17. The device of claim 13 wherein said polymeric component comprises TFB.

18. A device comprising a substrate; and a hole transport composition comprising a polymeric hole transport component and a silylated aryl amine component of a formula selected from

where Ar is arylene; n is an integer ranging from 1 to 4; R 1 -R 7 are independently selected from H and alkyl moieties ranging from C 1 to C 6 , each said alkyl moiety comprising a hydrolyzable silyl group comprising three hydrolyzable groups bonded to silicon, and wherein at least one of R 1 -R 3 and at least one of R 4 -R 7 is one of said alkyl moieties.

19. The device of claim 18 wherein at least one of R 1 -R 3 is a trichlorosilylpropyl moiety; and at least one of R 4 -R 7 is a trichlorosilylpropyl moiety.

20. The device of 19 wherein Ar is phenylene and n is 2.

21. The device of claim 18 wherein said polymeric component is selected from TFB, BT and combinations thereof.

22. The device of claim 18 wherein said silylated aryl amine component is of a formula where Ar is phenylene and n is 2.

Assignments (2)
CONFIRMATORY LICENSE Recorded Nov 3, 2015
From: NORTHWESTERN UNIVERSITY
To: NATIONAL SCIENCE FOUNDATION
Reel/Frame 037040/0438 →
CONFIRMATORY LICENSE Recorded Apr 9, 2015
From: NORTHWESTERN UNIVERSITY
To: NATIONAL SCIENCE FOUNDATION
Reel/Frame 035398/0971 →
Continuity (3)
Continuation 11009883 · Dec 10, 2004
Provisional Application 60528325 · Dec 10, 2003
Related Publication 20090062440A1 · Mar 5, 2009