IP Library Granted Patent US 9,293,739
Granted Patent B2
US 9,293,739 · App. 14/367,426 · Granted Mar 22, 2016

Process and materials for making contained layers and devices made with same

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Quick Facts
Patent No.
US 9,293,739
App. No.
14/367,426
Granted
Mar 22, 2016
Kind
B2
Abstract

There is provided a process for forming a contained second layer over a first layer, including the steps: forming the first layer including a fluorinated material and having a first surface energy; treating the first layer with a priming layer; exposing the priming layer patternwise with radiation having a wavelength greater than 300 nm, resulting in exposed areas and unexposed areas; developing the priming layer to effectively remove the priming layer from the unexposed areas resulting in a first layer having a patterned priming layer, wherein the patterned priming layer has a second surface energy that is higher than the first surface energy; and forming the second layer by liquid deposition on the patterned priming layer on the first layer. The priming layer includes an aromatic amine compound and a photoinitiator.

Claims (52)

1. A process for forming a contained second layer over a first layer, said process comprising:

forming the first layer comprising a fluorinated material and having a first surface energy;

treating the first layer with a priming layer consisting essentially of an aromatic amine compound and a photoinitiator;

exposing the priming layer patternwise with radiation having a wavelength greater than 300 nm, resulting in exposed areas and unexposed areas;

developing the priming layer to effectively remove the priming layer from the unexposed areas resulting in the first layer having a patterned priming layer, wherein the patterned priming layer has a second surface energy that is higher than the first surface energy; and

forming the second layer by liquid deposition on the patterned priming layer on the first layer, wherein exposing is carried out through the first layer.

2. The process of claim 1 , wherein developing is carried out by treating with a liquid.

3. The process of claim 1 , wherein developing is carried out by evaporation.

4. The process of claim 1 , wherein developing is carried out by contacting an outermost surface of the unexposed areas with an absorbent surface.

5. The process of claim 1 , wherein developing is carried out by contacting an outermost surface of the unexposed areas with an adhesive surface.

6. A process for making an organic electronic device comprising a support having thereon an electrode, a first organic active layer, and a second organic active layer, said process comprising

forming the first organic active layer comprising a fluorinated material and having a first surface energy over the electrode;

treating the first organic active layer with a priming layer consisting essentially of an aromatic amine compound and a photoinitiator;

exposing the priming layer patternwise with radiation having a wavelength greater than 300 nm, resulting in exposed areas and unexposed areas;

developing the priming layer to effectively remove the priming layer from the unexposed areas resulting in the first layer having a patterned priming layer, wherein the patterned priming layer has a second surface energy that is higher than the first surface energy; and

forming the second organic active layer by liquid deposition on the pattern of priming layer on the first organic active layer, wherein exposing is carried out through the support.

7. The process of claim 6 , wherein the first active layer is a hole injection layer and the second active layer is selected from the group consisting of a hole transport layer and a photoactive layer.

8. The process of claim 7 , wherein the hole injection layer comprises a conductive polymer and a fluorinated acid polymer.

9. The process of claim 7 , wherein the hole injection layer consists essentially of a conductive polymer doped with a fluorinated acid polymer and inorganic nanoparticles.

10. The process of claim 7 , wherein the second active layer is a hole transport layer and further comprising forming a photoactive layer by liquid deposition on the hole transport layer.

11. The process of claim 6 , wherein the aromatic amine compound is a material selected from the group consisting of polymeric triarylamines, polycarbazoles, polymeric triarylamines having conjugated moieties which are connected in a non-planar configuration, copolymers of fluorene and triarylamine, deuterated analogs thereof, and combinations thereof.

12. A process for making an organic electronic device comprising a support having thereon an electrode, a first organic active layer, and a second organic active layer, said process comprising

forming the first organic active layer comprising a fluorinated material and having a first surface energy over the electrode;

treating the first organic active layer with a priming layer consisting essentially of an aromatic amine compound and a photoinitiator;

exposing the priming layer patternwise with radiation having a wavelength greater than 300 nm, resulting in exposed areas and unexposed areas;

developing the priming layer to effectively remove the priming layer from the unexposed areas resulting in the first layer having a patterned priming layer, wherein the patterned priming layer has a second surface energy that is higher than the first surface energy; and

forming the second organic active layer by liquid deposition on the patterned priming layer on the first organic active layer, wherein the aromatic amine compound has one of formulas (1) through (9):

where:

Ar is the same or different at each occurrence and is an aryl group;

L is a linking group;

M is the same or different at each occurrence and is an aromatic group;

a and b represent relative mole fractions, such that a+b=1; and

n is an integer greater than 0.

13. A process for forming a contained second layer over a first layer, said process comprising:

forming the first layer comprising a fluorinated material and having a first surface energy;

treating the first layer with a priming layer consisting essentially of an aromatic amine compound and a photoinitiator;

exposing the priming layer patternwise with radiation having a wavelength greater than 300 nm, resulting in exposed areas and unexposed areas;

developing the priming layer to effectively remove the priming layer from the unexposed areas resulting in the first layer having a patterned priming layer, wherein the patterned priming layer has a second surface energy that is higher than the first surface energy; and

forming the second layer by liquid deposition on the patterned priming layer on the first layer, wherein the aromatic amine compound has no polymerizable or crosslinkable groups.

14. The process of claim 13 , wherein developing is carried out by treating with a liquid.

15. The process of claim 13 , wherein developing is carried out by evaporation.

16. The process of claim 13 , wherein developing is carried out by contacting an outermost surface of the unexposed areas with an absorbent surface.

17. The process of claim 13 , wherein developing is carried out by contacting an outermost surface of the unexposed areas with an adhesive surface.

18. A process for making an organic electronic device comprising a support having thereon an electrode, a first organic active layer, and a second organic active layer, said process comprising

forming the first organic active layer comprising a fluorinated material and having a first surface energy over the electrode;

treating the first organic active layer with a priming layer consisting essentially of an aromatic amine compound and a photoinitiator;

exposing the priming layer patternwise with radiation having a wavelength greater than 300 nm, resulting in exposed areas and unexposed areas;

developing the priming layer to effectively remove the priming layer from the unexposed areas resulting in the first layer having a patterned priming layer, wherein the patterned priming layer has a second surface energy that is higher than the first surface energy; and

forming the second organic active layer by liquid deposition on the patterned priming layer on the first organic active layer, wherein the aromatic amine compound has no polymerizable or crosslinkable groups.

19. The process of claim 18 , wherein the first active layer is a hole injection layer and the second active layer is selected from the group consisting of a hole transport layer and a photoactive layer.

20. The process of claim 19 , wherein the hole injection layer comprises a conductive polymer and a fluorinated acid polymer.

21. The process of claim 19 , wherein the hole injection layer consists essentially of a conductive polymer doped with a fluorinated acid polymer and inorganic nanoparticles.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 22, 2019
From: E. I. DU PONT DE NEMOURS AND COMPANY
To: LG CHEM, LTD.
Reel/Frame 050150/0482 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 23, 2014
From: FENNIMORE, ADAM; MACKARA, STEVEN R.
To: E. I. DUPONT DE NEMOURS AND COMPANY
Reel/Frame 033155/0127 →