Electronic devices comprising organic iridium compositions
View Patent ↗The present invention provides electronic devices comprising novel polymer compositions which provide for enhanced device performance. The polymer compositions employed comprise a polymeric component and a novel organic iridium compound comprising at least one cyclometallated ligand and at least one ketopyrrole ligand. The organic iridium compounds used in the polymer compositions are referred to as Type (1) organic iridium compositions and are constituted such that no ligand of the novel organic iridium compound has a number average molecular weight of 2,000 grams per mole or greater (as measured by gel permeation chromatography). In one aspect, the polymeric component may be an electroactive polymer. In one aspect, the present invention provides optoelectronic devices, such as OLED devices and photovoltaic devices. In another aspect, the invention provides OLED devices exhibiting enhanced color properties and light output efficiencies.
1. An organic light emitting device comprising:
a cathode;
an anode;
an electroluminescent material; and
a polymer composition, said polymer composition comprising:
a polymeric component; and
at least one organic iridium complex of structure I
wherein each of the ligands
is independently at each occurrence a cyclometallated ligand which may be the same or different;
R 1 is a C 3 -C 40 aromatic radical, a C 1 -C 50 aliphatic radical, or a C 3 -C 40 cycloaliphatic radical;
R 2 is independently at each occurrence a deuterium atom, a halogen, a nitro group, an amino group, a C 3 -C 40 aromatic radical, a C 1 -C 50 aliphatic radical, or a C 3 -C 40 cycloaliphatic radical; and
“a” is an integer from 0 to 3.
2. The organic light emitting device according to claim 1 , wherein the cyclometallated ligand is derived from a phenylisoquinoline compound having structure II
wherein R 3 is independently at each occurrence a deuterium atom, a halogen, a nitro group, an amino group, a C 3 -C 40 aromatic radical, a C 1 -C 50 aliphatic radical, or a C 3 -C 40 cycloaliphatic radical;
R 4 is independently at each occurrence a deuterium atom, a halogen, a nitro group, an amino group, a C 3 -C 40 aromatic radical, a C 1 -C 50 aliphatic radical, or a C 3 -C 40 cycloaliphatic radical;
“m” is an integer from 0 to 6; and
“n” is an integer ranging from 0 to 5.
3. The organic light emitting device according to claim 1 , wherein the cyclometallated ligand is derived from a 2-phenylpyridine compound having structure III
wherein R 5 is independently at each occurrence a deuterium atom, a halogen, a nitro group, an amino group, a C 3 -C 40 aromatic radical, a C 1 -C 50 aliphatic radical, or a C 3 -C 40 cycloaliphatic radical;
R 6 is independently at each occurrence a deuterium atom, a halogen, a nitro group , an amino group, a C 3 -C 40 aromatic radical, a C 1 -C 50 aliphatic radical, or a C 3 -C 40 cycloaliphatic radical;
“p” is an integer from 0 to 4; and
“q” is an integer from 0 to 5.
4. The organic light emitting device according to claim 1 , wherein the cyclometallated ligand is derived from a styryl isoquinoline compound having structure IV
wherein R 7 is independently at each occurrence a deuterium atom, a halogen, a nitro group , an amino group, a C 3 -C 40 aromatic radical, a C 1 -C 50 aliphatic radical, or a C 3 -C 40 cycloaliphatic radical;
R 8 is independently at each occurrence a deuterium atom, a halogen, a nitro group, an amino group, a C 3 -C 40 aromatic radical, a C 1 -C 50 aliphatic radical, or a C 3 -C 40 cycloaliphatic radical;
“d” is an integer from 0 to 6; and
“e” is an integer from 0 to 5.
5. The organic light emitting device according to claim 1 , wherein the cyclometallated ligand
is derived from a 1-phenylisoquinoline, a 2-phenylpyridine, a 1-styrylisoquinoline, or a combination thereof.
6. The organic light emitting device according to claim 1 , wherein the cyclometallated ligand is derived from 1-phenylisoquinoline.
7. The organic light emitting device according to claim 1 , wherein the cyclometallated ligand is derived from 2-phenylpyridine.
8. The organic light emitting device according to claim 1 , wherein the cyclometallated ligand is derived from 1-styrylisoquinoline.
9. The organic light emitting device according to claim 1 , wherein said complex comprises a ketopyrrole ligand derived from a ketopyrrole having structure V
wherein R 1 is a C 3 -C 40 aromatic radical, a C 1 -C 50 aliphatic radical, or a C 3 -C 40 cycloaliphatic radical;
R 2 is independently at each occurrence a deuterium atom, a halogen, a nitro group, an amino group, a C 3 -C 40 aromatic radical, a C 1 -C 50 aliphatic radical, or a C 3 -C 40 cycloaliphatic radical; and
“a” is an integer from 0 to 3.
10. The organic light emitting device according to claim 1 , wherein said organic iridium complex has structure VII
wherein R 2 is independently at each occurrence a deuterium atom, a halogen, a nitro group, an amino group, a C 3 -C 40 aromatic radical, a C 1 -C 50 aliphatic radical, or a C 3 -C 40 cycloaliphatic radical;
R 3 is independently at each occurrence a deuterium atom, a halogen, a nitro group, an amino group, a C 3 -C 40 aromatic radical, a C 1 -C 50 aliphatic radical, or a C 3 -C 40 cycloaliphatic radical;
R 4 is independently at each occurrence a deuterium atom, a halogen, a nitro group, an amino group, a C 3 -C 40 aromatic radical, a C 1 -C 50 aliphatic radical, or a C 3 -C 40 cycloaliphatic radical;
R 9 is independently at each occurrence a deuterium atom, a halogen, a nitro group, an amino group, a C 3 -C 40 aromatic radical, a C 1 -C 50 aliphatic radical, or a C 3 -C 40 cycloaliphatic radical;
“a” is an integer from 0 to 3;
“m” is an integer from 0 to 6;
“n” is an integer from 0 to 4; and
“s” is an integer from 0 to 5.
11. The organic light emitting device according to claim 1 , wherein said organic iridium complex has structure IX
wherein R 2 is independently at each occurrence a deuterium atom, a halogen, a nitro group, an amino group, a C 3 -C 40 aromatic radical, a C 1 -C 50 aliphatic radical, or a C 3 -C 40 cycloaliphatic radical;
R 5 is independently at each occurrence a deuterium atom, a halogen, a nitro group, an amino group, a C 3 -C 40 aromatic radical, a C 1 -C 50 aliphatic radical, or a C 3 -C 40 cycloaliphatic radical;
R 6 is independently at each occurrence a deuterium atom, a halogen, a nitro group, an amino group, a C 3 -C 40 aromatic radical, a C 1 -C 50 aliphatic radical, or a C 3 -C 40 cycloaliphatic radical;
R 9 is independently at each occurrence a deuterium atom, a halogen, a nitro group, an amino group, a C 3 -C 40 aromatic radical, a C 1 -C 50 aliphatic radical, or a C 3 -C 40 cycloaliphatic radical;
“a” is an integer from 0 to 3;
“p” is an integer from 0 to 4;
“q” is an integer from 0 to 4; and
“s” is an integer from 0 to 5.
12. The organic light emitting device according to claim 1 , wherein said organic iridium complex has structure XI
wherein R 2 is independently at each occurrence a deuterium atom, halogen, a nitro group, an amino group, a C 3 -C 40 aromatic radical, a C 1 -C 50 aliphatic radical, or a C 3 -C 40 cycloaliphatic radical;
R 7 is independently at each occurrence a deuterium atom, halogen, a nitro group, an amino group, a C 3 -C 40 aromatic radical, a C 1 -C 50 aliphatic radical, or a C 3 -C 40 cycloaliphatic radical;
R 8 is independently at each occurrence a deuterium atom, halogen, a nitro group, an amino group, a C 3 -C 40 aromatic radical, a C 1 -C 50 aliphatic radical, or a C 3 -C 40 cycloaliphatic radical;
R 9 is independently at each occurrence a deuterium atom, halogen, a nitro group, an amino group, a C 3 -C 40 aromatic radical, a C 1 -C 50 aliphatic radical, or a C 3 -C 40 cycloaliphatic radical;
“a” is an integer from 0 to 3;
“d” is an integer from 0 to 6;
“e” is an integer from 0 to 5; and
“s” is an integer from 0 to 5.
13. The organic light emitting device according to claim 1 , wherein said electroluminescent material is a light emitting polymer.
14. The organic light emitting device according to claim 1 wherein said electroluminescent material is a blue light emitting polymer.
15. The organic light emitting device according to claim 1 , further comprising at least one of a hole transport layer and an electron transport layer.
16. An organic light emitting device comprising:
a cathode;
an anode; and
a light emitting polymer composition, said light emitting polymer composition comprising:
an electroluminescent polymer component; and
at least one organic iridium complex of structure I
wherein each of the ligands
is independently at each occurrence a cyclometallated ligand which may be the same or different;
R 1 is a C 3 -C 40 aromatic radical, a C 1 -C 50 aliphatic radical, or a C 3 -C 40 cycloaliphatic radical;
R 2 is independently at each occurrence a deuterium atom, a halogen, a nitro group, an amino group, a C 3 -C 40 aromatic radical, a C 1 -C 50 aliphatic radical, or a C 3 -C 40 cycloaliphatic radical; and
“a” is an integer from 0 to 3.
17. The organic light emitting device according to claim 16 , wherein said organic iridium complex has structure VII
wherein R 2 is independently at each occurrence a deuterium atom, a halogen, a nitro group, an amino group, a C 3 -C 40 aromatic radical, a C 1 -C 50 aliphatic radical, or a C 3 -C 40 cycloaliphatic radical;
R 3 is independently at each occurrence a deuterium atom, a halogen, a nitro group, an amino group, a C 3 -C 40 aromatic radical, a C 1 -C 50 aliphatic radical, or a C 3 -C 40 cycloaliphatic radical;
R 4 is independently at each occurrence a deuterium atom, a halogen, a nitro group, an amino group, a C 3 -C 40 aromatic radical, a C 1 -C 50 aliphatic radical, or a C 3 -C 40 cycloaliphatic radical;
R 9 is independently at each occurrence a deuterium atom, a halogen, a nitro group, an amino group, a C 3 -C 40 aromatic radical, a C 1 -C 50 aliphatic radical, or a C 3 -C 40 cycloaliphatic radical;
“a” is an integer from 0 to 3;
“m” is an integer from 0 to 6;
“n” is an integer from 0 to 4; and
“s” is an integer from 0 to 5.
18. The organic light emitting device according to claim 16 , wherein said organic iridium complex has structure IX
wherein R 2 is independently at each occurrence a deuterium atom, a halogen, a nitro group, an amino group, a C 3 -C 40 aromatic radical, a C 1 -C 50 aliphatic radical, or a C 3 -C 40 cycloaliphatic radical;
R 5 is independently at each occurrence a deuterium atom, a halogen, a nitro group, an amino group, a C 3 -C 40 aromatic radical, a C 1 -C 50 aliphatic radical, or a C 3 -C 40 cycloaliphatic radical;
R 6 is independently at each occurrence a deuterium atom, a halogen, a nitro group, an amino group, a C 3 -C 40 aromatic radical, a C 1 -C 50 aliphatic radical, or a C 3 -C 40 cycloaliphatic radical;
R 9 is independently at each occurrence a deuterium atom, a halogen, a nitro group, an amino group, a C 3 -C 40 aromatic radical, a C 1 -C 50 aliphatic radical, or a C 3 -C 40 cycloaliphatic radical;
“a” is an integer from 0 to 3;
“p” is an integer from 0 to 4;
“q” is an integer from 0 to 4; and
“s” is an integer from 0 to 5.
19. The organic light emitting device according to claim 16 , wherein organic iridium complex has structure XI
wherein R 2 is independently at each occurrence a deuterium atom, a halogen, a nitro group, an amino group, a C 3 -C 40 aromatic radical, a C 1 -C 50 aliphatic radical, or a C 3 -C 40 cycloaliphatic radical;
R 7 is independently at each occurrence a deuterium atom, a halogen, a nitro group, an amino group, a C 3 -C 40 aromatic radical, a C 1 -C 50 aliphatic radical, or a C 3 -C 40 cycloaliphatic radical;
R 8 is independently at each occurrence a deuterium atom, a halogen, a nitro group, an amino group, a C 3 -C 40 aromatic radical, a C 1 -C 50 aliphatic radical, or a C 3 -C 40 cycloaliphatic radical;
R 9 is independently at each occurrence a deuterium atom, a halogen, a nitro group, an amino group, a C 3 -C 40 aromatic radical, a C 1 -C 50 aliphatic radical, or a C 3 -C 40 cycloaliphatic radical;
“a” is an integer from 0 to 3;
“d” is an integer from 0 to 6;
“e” is an integer from 0 to 5; and
“s” is an integer from 0 to 5.
20. An organic light emitting device comprising:
a cathode;
an anode;
an electroluminescent material; and
an organic iridium complex having structure XXVIII