ORGANIC PHOTOSENSITIVE DEVICES

• US 20100000606A1
• Filed: 05/11/2009
• Published: 01/07/2010
• Est. Priority Date: 03/26/2004
• Status: Abandoned Application

• Current Assignee: Mark Thompson, Peter Djurovich
• Original Assignee: Mark Thompson, Peter Djurovich
• Inventors: Thompson, Mark E., Djurovich, Peter
• Application Number:
  US12/355,475
• Publication Number:
  US 20100000606A1
• Time in Patent Office: Days
• US Class Current: 136/263
• CPC Class Codes: C07F 15/0033 Iridium compounds
• CPC Class Codes: C07F 15/0086 Platinum compounds
• CPC Class Codes: H10K 30/151 the wide bandgap semiconductor comprising titanium oxide, e.g. TiO2
• CPC Class Codes: H10K 30/50 Photovoltaic [PV] devices
• CPC Class Codes: H10K 85/342 comprising iridium
• CPC Class Codes: H10K 85/346 comprising platinum
• CPC Class Codes: H10K 85/361 Polynuclear complexes, i.e. complexes comprising two or more metal centers
• CPC Class Codes: Y02E 10/549 Organic PV cells

Abstract

The present invention generally relates to organic photosensitive optoelectronic devices. More specifically, it is directed to organic photovoltaic devices, e.g., organic solar cells. More specifically, it is directed to organic photosensitive optoelectronic devices that comprise a cyclometallated organometallic compound as a light absorbing material.

Claims

1. An organic photosensitive optoelectronic device comprising:

an anode;

an active region comprising a cyclometallated organometallic material; and

a cathode,

wherein the device produces a photogenerated current when illuminated with light.

2. The organic photosensitive optoelectronic device of claim 1, wherein the cyclometallated organometallic material comprises an Ir or Pt atom.

3. The organic photosensitive optoelectronic device of claim 1, wherein the device further comprises a blocking layer.

4. The organic photosensitive optoelectronic device of claim 1, wherein the cyclometallated organometallic material has the formula I

wherein

M is a transition metal having a molecular weight greater than 40;

Z is N or C,

the dotted line represents an optional double bond,

R¹, R², R³ and R⁴ are independently selected from H, alkyl, or aryl, and additionally or alternatively, one or more of R¹ and R², R² and R³, and R³ and R⁴ together from independently a 5 or 6-member cyclic group, wherein said cyclic group is cycloalkyl, cycloheteroalkyl, aryl or heteroaryl; and

wherein said cyclic group is optionally substituted by one or more substituents Q;

each substituent Q is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aralkyl, CN, CF₃, NR₂, NO₂, OR, halo, and aryl, and additionally, or alternatively, two Q groups on adjacent ring atoms form a fused 5- or 6-membered aromatic group;

each R is independently selected from H, alkyl, aralkyl, aryl and heteroaryl;

(X and Y), separately or in combination, are an ancillary ligand;

a is 1 to 3; and

b is 0 to 2;

with the proviso that the sum of a and b is 2 or 3.

5. The organic photosensitive optoelectronic device of claim 1, wherein the cyclometallated organometallic material has the formula

wherein

M is a transition metal having a molecular weight greater than 40;

ring A is an aromatic heterocyclic ring or a fused aromatic heterocyclic ring with at least one nitrogen atom that coordinates to the metal M;

Z is selected from carbon or nitrogen;

each R⁵ is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aralkyl, CN, CF₃, NR₂, NO₂, OR, halo, and aryl, and additionally, or alternatively, two R⁵ groups on adjacent ring atoms form a fused 5- or 6-membered aromatic group;

each R⁶ is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aralkyl, CN, CF₃, NR₂, NO₂, OR, halo, and aryl, and additionally, or alternatively, two R⁶ groups on adjacent ring atoms form a fused 5- or 6-membered aromatic group;

each R is independently selected from H, alkyl, aralkyl, aryl and heteroaryl;

(X and Y), separately or in combination, are an ancillary ligand;

n is 0 to 4;

m is 0 to 4;

a is 1 to 3; and

b is 0 to 2;

with the proviso that the sum of a and b is 2 or 3.

6. The organic photosensitive optoelectronic device of claim 5, wherein the cyclometallated organometallic material has the formula

wherein

M is a transition metal having a molecular weight greater than 40;

ring A is an aromatic heterocyclic ring or a fused aromatic heterocyclic ring with at least one nitrogen atom that coordinates to the metal M;

each R⁵ is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aralkyl, CN, CF₃, NR₂, NO₂, OR, halo, and aryl, and additionally, or alternatively, two R⁵ groups on adjacent ring atoms form a fused 5- or 6-membered aromatic group;

each R⁶ is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aralkyl, CN, CF₃, NR₂, NO₂, OR, halo, and aryl, and additionally, or alternatively, two R⁶ groups on adjacent ring atoms form a fused 5- or 6-membered aromatic group;

each R is independently selected from H, alkyl, aralkyl, aryl and heteroaryl;

(X and Y), separately or in combination, are an ancillary ligand;

n is 0 to 4;

m is 0 to 4;

a is 1 to 3; and

b is 0 to 2;

with the proviso that the sum of a and b is 2 or 3.

7. The organic photosensitive optoelectronic device of claim 5, wherein the cyclometallated organometallic material has the formula IV

wherein

M is a transition metal having a molecular weight greater than 40;

ring A is an aromatic heterocyclic ring or a fused aromatic heterocyclic ring with at least one nitrogen atom that coordinates to the metal M;

each R⁵ is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aralkyl, CN, CF₃, NR₂, NO₂, OR, halo, and aryl, and additionally, or alternatively, two R⁵ groups on adjacent ring atoms form a fused 5- or 6-membered aromatic group;

each R⁶ is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aralkyl, CN, CF₃, NR₂, NO₂, OR, halo, and aryl, and additionally, or alternatively, two R⁶ groups on adjacent ring atoms form a fused 5- or 6-membered aromatic group;

each R is independently selected from H, alkyl, aralkyl, aryl and heteroaryl;

(X and Y), separately or in combination, are an ancillary ligand;

n is 0 to 4; and

m is 0 to 4.

8. The organic photosensitive optoelectronic device of claim 7, wherein the cyclometallated organometallic material has the formula V

wherein

M is a transition metal having a molecular weight greater than 40;

each R⁵ is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aralkyl, CN, CF₃, NR₂, NO₂, OR, halo, and aryl, and additionally, or alternatively, two R⁵ groups on adjacent ring atoms form a fused 5- or 6-membered aromatic group;

each R⁶ is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aralkyl, CN, CF₃, NR₂, NO₂, OR, halo, and aryl, and additionally, or alternatively, two R⁶ groups on adjacent ring atoms form a fused 5- or 6-membered aromatic group;

each R is independently selected from H, alkyl, aralkyl, aryl and heteroaryl;

(X and Y), separately or in combination, are an ancillary ligand;

n is 0 to 4; and

m is 0 to 4.

9. The organic photosensitive optoelectronic device of claim 7, wherein M is Pt.

10. The organic photosensitive optoelectronic device of claim 7, wherein the cyclometallated organometallic material forms π

-stacked chains.

11. The organic photosensitive optoelectronic device of claim 9, wherein the cyclometallated organometallic material has the formula

12. The organic photosensitive optoelectronic device of claim 1, wherein the cyclometallated organometallic material absorbs light in the red or near IR portion of the spectrum.

13. The organic photosensitive optoelectronic device of claim 1, wherein the device is a photovoltaic device.

14. The organic photosensitive optoelectronic device of claim 1, wherein the device is a photodetector.

15. The organic photosensitive optoelectronic device of claim 1, wherein the device is a photoconductor.

16. The organic photosensitive optoelectronic device of claim 1, wherein the device comprises multiple subcells in series.