IP Library Granted Patent US 7,201,859
Granted Patent B2
US 7,201,859 · App. 10/173,679 · Granted Apr 10, 2007

Hole transport layer and method for manufacturing the organic EL device by using the same

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Quick Facts
Patent No.
US 7,201,859
App. No.
10/173,679
Granted
Apr 10, 2007
Kind
B2
Abstract

The present invention discloses a hole transport layer of an organic EL display, comprising: a material including one of a PEDOT which is a mixture of a poly (3,4)-ethylenedioxythiophene and a polystyrenesulfonate, a PANI which is a mixture of a polyaniline and a polystyrenesulfonate, and an aromatic amine derivative; and an organic compound derivative having the general structure, R 1 R 2 MR 3 R 4 , where “M” denotes one metal selected from a group consisting of Ti, Pt and one metal among elements belonging to groups 3A and 4A of periods 3 to 5.

Claims (42)

1. A hole transport layer of an organic EL display, comprising:

one of a mixture of a poly (3,4)-ethylenedioxythiophene (PEDOT) and a polystyrenesulfonate, a mixture of a polyaniline (PANI) and a polystyrenesulfonate, and an aromatic amine derivative; and

an organic compound derivative having a structure with the following formula:

R 1 R 2 MR 3 R 4

wherein “M” denotes a metal selected from the group consisting of Ti, Pt, and metals belonging to groups 3A and 4A of periods 3 to 5, and “R 1 ” to “R 4 ” each denotes a functional group selected from the group consisting of a hydroxyl group, a hydrogen, a cyano group, a nitro group, an aryl group ranging from 6 to about 15 carbons, a fused aromatic group having a ring, an aromatic halide group, an alkylamine group, an aryloxy group, an arylamine group, an alkylepoxide group, a vinyl group, an alkylmercapto group, and an imide group.

2. The hole transport layer of claim 1 , wherein M includes a metal selected from the group consisting of Si, Sn, and Al.

3. The hole transport layer of claim 1 , wherein a concentration of the organic compound derivative ranges from about 0.0001 wt % to about 50 wt %.

4. The hole transport layer of claim 1 , further comprising, a surfactant.

5. The hole transport layer of claim 4 , wherein the surfactant includes one selected from a group consisting of an alkyl group, an alkylaryl group, a fluoroalkyl group, and an alkylsiloxane group, a sulfate, a sulfonate, a carboxylate, an amide, a betainic structures, and a quarternised ammonium group.

6. The hole transport layer of claim 5 , wherein the surfactant includes a non-ionic surfactant.

7. The hole transport layer of claim 6 , wherein the non-ionic surfactant is a non-ionic fluoride-based surfactant.

8. The hole transport layer of claim 4 , wherein the surfactant has a concentration ranging from about 0.1 wt % to about 0.3 wt %.

9. The hole transport layer of claim 1 , wherein the aromatic amine derivative is selected from the group consisting of:

wherein “Ph” is a benzene ring, “NA” denotes a naphthalene group, and “R 1 ” to “R 6 ” each denote a material selected from the group consisting of a hydrogen, an alkyl group ranging from 1 to about 20 carbons, a halogen group, a cyano group, a nitro group, an aryl group ranging from 6 to about 15 carbons, a fused aromatic group having a ring, an alkyamine group, an aryloxy group, and an arylamine group.

10. The hole transport layer of claim 1 , wherein a concentration of the PEDOT, the PANI or the aromatic amine derivative ranges from about 0.01 wt % to about 50 wt %.

11. A method for manufacturing an organic EL display having a hole transport layer, comprising:

preparing a hole transport layer material comprising:

one of a mixture of a poly (3,4)-ethylenedioxythiophene (PEDOT) and a polystyrenesulfonate, a mixture of a polyaniline (PANI) and a polystyrenesulfonate, and an aromatic amine derivative; and

an organic compound derivative having a structure with the following formula:

R 1 R 2 MR 3 R 4

wherein “M” denotes a metal selected from the group consisting of Ti, Pt, and metals belonging to groups 3A and 4A of periods 3 to 5, and “R 1 ” to “R 4 ” each denotes a functional group selected from the group consisting of a hydroxyl group, a hydrogen, a cyano group, a nitro group, an aryl group ranging from 6 to about 15 carbons, a fused aromatic group having a ring, an aromatic halide group, an alkylamine group, an aryloxy group, an arylamine group, an alkylepoxide group, a vinyl group, an alkylmercapto group, and an imide group,

depositing the hole transport layer material to form a hole transport layer; and

curing the hole transport layer by heat treatment to lower the surface energy of the hole transport layer.

12. The method of claim 11 , wherein the organic compound derivative has a central metal atom and has a molecular weight ranging from about 100 to about 10,000 g/mol.

13. The method of claim 12 , wherein the metal is selected from the group consisting of Ti, Pt and elements belonging to groups 3A and 4A of period 3 to period 5.

14. The method of claim 13 , wherein the elements belonging to groups 3A and 4A of periods 3 to 5 includes metals selected from a group consisting of Si, Sn and Al.

15. The method of claim 12 , wherein a concentration of the organic compound derivative ranges from about 0.0001 wt % to about 50 wt %.

16. The method of claim 11 , further comprising a surfactant.

17. The method of claim 16 , wherein the surfactant comprises a functional group selected from the group consisting of an alkyl group, an alkylaryl group, a fluoroalkyl group, and an alkylsiloxane group, a sulfate, a sulfonate, a carboxylate, an amide, a betainic structures, and a quarternised ammonium group.

18. The method of claim 17 , wherein the surfactant includes a non-ionic surfactant.

19. The method of claim 18 , wherein the non-ionic surfactant is a non-ionic fluoride-based surfactant.

20. The method of claim 16 , wherein the surfactant has a concentration ranging from about 0.1 wt % to about 0.3 wt %.

21. The method of claim 11 , further comprising:

forming an organic light-emitting layer by spin coating, ink-jet printing, vacuum deposition, or laser induced thermal imaging.

22. The method of claim 21 ,

wherein the hole transport layer includes a surfactant, and

wherein the organic light-emitting layer is formed using an ink-jet technique.

23. The method of claim 22 , wherein the surfactant is a non-ionic fluoride-based surfactant and has a concentration ranging from about 0.1 wt % to about 0.3 wt %.

24. A hole transport layer of an organic EL display, comprising:

one of a mixture of a poly (3,4)-ethylenedioxythiophene (PEDOT) and a polystyrenesulfonate, a mixture of a polyaniline (PANI) and a polystyrenesulfonate, and an aromatic amine derivative; and

a surfactant comprising a functional group selected from the group consisting of an alkylaryl group, a sulfate, a carboxylate, an amide, a betainic structures, and a quarternised ammonium group.

25. The hole transport layer of claim 24 , wherein the surfactant has a concentration ranging from about 0.1 wt % to about 0.3 wt %.

Assignments (1)
MERGER Recorded Aug 29, 2012
From: SAMSUNG MOBILE DISPLAY CO., LTD.
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 028870/0626 →