CONJUGATED OLIGOELECTROLYTE ELECTRON TRANSPORTING LAYERS

• US 20090230362A1
• Filed: 01/26/2009
• Published: 09/17/2009
• Est. Priority Date: 01/25/2008
• Status: Abandoned Application

• Current Assignee: Regents of the University of California (University of California)
• Original Assignee: Regents of the University of California (University of California)
• Inventors: Xu, Yunhua, Yang, Renqiang, Bazan, Guillermo C., Nguyen, Thuc-Quyen
• Application Number:
  US12/359,967
• Publication Number:
  US 20090230362A1
• Time in Patent Office: Days
• US Class Current: 252/512
• CPC Class Codes: C07D 233/56 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
• CPC Class Codes: C07D 333/06 with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
• CPC Class Codes: C07D 403/10 linked by a carbon chain containing aromatic rings
• CPC Class Codes: C07D 409/10 linked by a carbon chain containing aromatic rings
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1416 Condensed systems
• CPC Class Codes: C09K 2211/1425 Non-condensed systems
• CPC Class Codes: C09K 2211/145 containing oxygen as the only heteroatom
• CPC Class Codes: C09K 2211/1458 containing sulfur as the only heteroatom
• CPC Class Codes: C09K 2211/1466 containing nitrogen as the only heteroatom
• CPC Class Codes: C09K 2211/1483 containing nitrogen and sulfur as heteroatoms
• CPC Class Codes: H01G 9/2013 the electrolyte comprising ionic liquids, e.g. alkyl imidazolium iodide
• CPC Class Codes: H05B 33/14 characterised by the chemical or physical composition or the arrangement of the electroluminescent material , or by the simultaneous addition of the electroluminescent material in or onto the light source
• CPC Class Codes: H10K 2102/103 comprising indium oxides, e.g. ITO
• CPC Class Codes: H10K 50/14 Carrier transporting layers
• CPC Class Codes: H10K 50/171 Electron injection layers
• CPC Class Codes: H10K 85/1135 Polyethylene dioxythiophene [PEDOT]; Derivatives thereof
• CPC Class Codes: H10K 85/114 Poly-phenylenevinylene; Derivatives thereof
• CPC Class Codes: H10K 85/626 containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
• CPC Class Codes: H10K 85/654 comprising only nitrogen as heteroatom H10K85/652 takes precedence

Abstract

An organic electronic or an optoelectronic device containing a conjugated oligoelectrolyte. In more particularized embodiments, the conjugated oligoelectrolyte is the charge injection or transport layer. The conjugated oligoelectrolyte can be positively or negatively charged, and used in conjunction in a device with either or high or low work function metal.

Claims

1. An organic electronic or optoelectronic device containing a conjugated oligoelectrolyte.

2. The device of claim 1 wherein the conjugated oligoelectrolyte is the charge injection or transport layer.

3. The device of claim 1 wherein the oligoelectrolyte is a cationic conjugated oligoelectrolyte.

4. The device of claim 1 wherein the oligoelectrolyte is an anionic conjugated oligoelectrolyte.

5. The device of claim 1 wherein the conjugated oligoelectrolyte is selected from the group consisting of

where ‘

n’

is any integer between 1 and 20; and

where terminal end groups D¹ and D² are the same or different and can be a hydrogen, alkyl group, alkoxy group or any one of the following;

and where R¹ and R² can be the same or different and where R¹ and R² can be either;

i) (CH₂)_nN⁺BX⁻

, where ‘

B’

is Me₃, Ethyl₃, Propyl₃, Me₂Ethyl, MeEthyl₂, Me₂Propyl, MePropyl₂, or Ethyl₂Propyl;

‘

X’

is Br, CF₃SO₃, BIm₄, BAr^F₄, BF₄₁ PF₆, F₃CSO₃, BPh₄, BTh₄, BPhF₄₁ HPO₄²⁻

, or FeCN₆⁴; and

‘

n’

is an integer between 1 and 100;

or

ii) (CH₂)_nZ, where ‘

Z’

is SO₃⁻

Na⁺, SO₃⁻

K⁺, SO₃⁻

NH₄⁺, COO⁻

Na⁺, COO⁻

K⁺, COO⁻

NH₄⁺, PO₄³⁻

Na₃⁺, PO₄³⁻

K₃⁺, PO₄³⁻

or (NH₄)³⁺;

‘

n’

is an integer between 1 and 100.

6. The device of claim 3 wherein the cationic conjugated oligoelectrolyte any one of

where R¹ to R¹⁶ and R′

is (CH₂)_nN⁺BX⁻

and R¹ to R¹⁶ and R′

can be the same or different;

n is an integer between 1 and 20;

B is Me₃, Ethyl₃, Propyl₃, Me₂Ethyl, MeEthyl₂, Me₂Propyl, MePropyl₂, or Ethyl₂Propyl;

X is Br, CF₃SO₃₁ BIm₄, BArF₄, BF₄, PF₆, F₃CSO₃, BPh₄, BTh₄, BPhF₄, HPO₄²⁻

, or FeCN₆⁴;

Y¹ to Y⁶ is O, S, Se, or N—

R′

, and where Y¹ to Y⁶ can be the same or different;

m is an integer between 1 and 20;

and wherein Ar is one of the following

9. The device of claim 4 wherein the anionic conjugated oligoelectrolyte is any one of

where R¹ to R¹⁶ and R′

is (CH₂)_nZ and R¹ to R¹⁶ and R′

can be the same or different;

n is an integer between 1 and 20;

Z is SO₃⁻

Na⁺, SO₃⁻

K⁺, SO₃⁻

NH₄⁺, COO⁻

Na⁺, COO⁻

K⁺, COO⁻

NH₄⁺, PO₄³⁻

Na₃⁺, PO₄³⁻

K₃⁺, PO₄³⁻

, or (NH₄)³⁺;

Y¹ to Y⁶ is O S, Se, or N—

R′

, and where Y¹ to Y⁶ can be the same or different;

m is an integer between 1 and 20;

and wherein Ar is one of the following

11. The organic electronic device of claim 1 further comprising a high work function metal.

13. The organic electronic device of claim 1, further comprising a low work function metal.

7. The device of claim 7 wherein the cationic conjugated oligoelectrolyte wherein n is 6, B is Me₃ and X is BIm₄.

8. The device of claim 7 wherein the cationic conjugated oligoelectrolyte is any one of

10. The device of claim 10 wherein the anionic conjugated oligoelectrolyte is any one of

where n is 4, and Z is SO₃⁻

Na⁺.

12. The organic electronic device of claim 12 in which the high work function metal is Al.

14. A material used for an organic electronic device which contains at least a conjugated oligoelectrolyte.

15. A method of producing an organic electronic device containing a conjugated oligoelectrolyte.