IP Library Granted Patent US 8,815,639
Granted Patent B2
US 8,815,639 · App. 13/868,924 · Granted Aug 26, 2014

Hole transport compositions and related devices and methods (II)

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Quick Facts
Patent No.
US 8,815,639
App. No.
13/868,924
Granted
Aug 26, 2014
Kind
B2
Abstract

A composition comprising: at least one compound comprising a hole transporting core, wherein the core is covalently bonded to a first arylamine group and also covalently bonded to a second arylamine group different from the first, and wherein the compound is covalently bonded to at least one intractability group, wherein the intractability group is covalently bonded to the hole transporting core, the first arylamine group, the second arylamine group, or a combination thereof, and wherein the compound has a molecular weight of about 5,000 g/mole or less. Blended mixtures of arylamine compounds, including fluorene core compounds, can provide good film formation and stability when coated onto hole injection layers. Solution processing of OLEDs is a particularly important application.

Claims (26)

1. A method comprising:

providing a substrate comprising a hole injection layer,

coating the substrate with at least one ink comprising at least one hole transport arylamine compound comprising intractability groups to form a coated substrate, wherein the hole transport arylamine compound comprises a hole transporting core, wherein the hole transporting core is covalently bonded to a first arylamine group and also to a second arylamine group, wherein the intractability groups are covalently bonded to the hole transporting core, the first arylamine group, or the second arylamine group, or a combination thereof, wherein the hole transporting arylamine compound has a molecular weight of about 5,000 g/mole or less, and wherein the hole transporting arylamine compound comprises at least one sulfur heteroatom,

heating the coated substrate.

2. The method of claim 1 , wherein the ink comprises at least two hole transport materials comprising intractability groups.

3. The method of claim 1 , wherein the compound is a first compound, and the composition further comprises at least one additional second compound, different from the first compound, which activates a polymerization reaction for the composition.

4. The method of claim 1 , wherein the compound is a first compound, and the composition further comprises at least one additional second compound, different from the first compound, which comprises para-styrene units.

5. The method of claim 1 , wherein the compound is a first compound, and the composition further comprises at least one additional second arylamine compound, different from the first arylamine compound, wherein the second arylamine compound has only one crosslinking group.

6. The method of claim 1 , wherein the compound is a first compound, and the composition further comprises at least one second arylamine compound, different from the first arylamine compound, wherein the second arylamine compound has three or more crosslinking groups.

7. The method of claim 1 , wherein the intractability groups are polymerizable groups.

8. The method of claim 1 , wherein the hole transporting core comprises the at least one sulfur heteroatom.

9. The method of claim 1 , wherein the hole transporting compound comprises an optionally substituted thiophene moiety.

10. The method of claim 1 , wherein the hole transport core comprises at least one optionally substituted thiophene moiety.

11. The method of claim 1 , wherein the hole transport core comprises at least two optionally substituted thiophene moieties.

12. The method of claim 1 , wherein the hole transporting compound comprises at least one optionally substituted benzodithiophene moiety.

13. The method of claim 1 , wherein the hole transport core comprises at least one optionally substituted benzodithiophene moiety.

14. The method of claim 1 , wherein the hole transport core comprises at least one optionally substituted moiety represented by:

15. The method of claim 1 , wherein the hole transporting core comprises both O and S heteroatoms.

16. The method of claim 1 , wherein the hole transporting core comprises at least one sulfur atom and at least one oxygen atom, wherein the sulfur and oxygen atoms are positioned in the compound so that a sulfur-oxygen intramolecular interaction is present.

17. A method comprising:

providing a substrate comprising a hole injection layer,

coating the substrate with at least one ink comprising at least one hole transport arylamine compound comprising intractability groups to form a coated substrate, wherein the hole transport arylamine compound comprises a hole transporting core, wherein the hole transporting core is covalently bonded to a first arylamine group and also to a second arylamine group, wherein the intractability groups are covalently bonded to the hole transporting core, the first arylamine group, or the second arylamine group, or a combination thereof, wherein the compound has a molecular weight of about 5,000 g/mole or less, and wherein the hole transporting compound comprises an optionally substituted triphenylene group,

heating the coated substrate.

18. The method of claim 17 , wherein the first and/or the second arylamine group comprises the optionally substituted triphenylene group.

19. The method of claim 17 , wherein the hole transporting compound comprises at least one optionally substituted moiety represented by:

20. The method of claim 17 , wherein the hole transporting compound comprises at least one optionally substituted moiety represented by:

Assignments (8)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 16, 2016
From: SOLVAY USA, INC.
To: NISSAN CHEMICAL INDUSTRIES, LTD.
Reel/Frame 039767/0225 →
RELEASE OF SECURITY INTEREST Recorded Mar 31, 2014
From: SOLVAY AMERICA, INC.
To: PLEXTRONICS, INC.
Reel/Frame 032568/0641 →
RELEASE OF SECURITY INTEREST Recorded Mar 31, 2014
From: SOLVAY AMERICA, INC.
To: PLEXTRONICS, INC.
Reel/Frame 032568/0619 →
RELEASE OF SECURITY INTEREST Recorded Mar 31, 2014
From: SOLVAY AMERICA, INC.
To: PLEXTRONICS, INC.
Reel/Frame 032568/0742 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 31, 2014
From: PLEXTRONICS, INC.
To: SOLVAY USA INC.
Reel/Frame 032568/0780 →
SECURITY AGREEMENT Recorded Jan 30, 2014
From: PLEXTRONICS, INC.
To: SOLVAY AMERICA, INC.
Reel/Frame 032141/0680 →
SECURITY AGREETMENT Recorded Sep 23, 2013
From: PLEXTRONICS, INC.
To: SOLVAY AMERICA, INC.
Reel/Frame 031347/0336 →
SECURITY AGREEMENT Recorded May 24, 2013
From: PLEXTRONICS, INC.
To: SOLVAY AMERICA, INC.
Reel/Frame 030486/0137 →