Organic iridium compositions and their use in electronic devices
View Patent ↗The present invention provides novel polymer compositions comprising 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). Type (1) organic iridium compositions are referred to herein as comprising “organic iridium complexes”. In one aspect, the polymeric component may be an electroactive polymer. The novel polymer compositions of the invention are useful in optoelectronic electronic devices such as OLED devices and photovoltaic devices. In one aspect, the invention provides novel polymer compositions useful in the preparation of OLED devices exhibiting enhanced color properties and light output efficiencies.
1. A 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 composition according to claim 1 , wherein said polymeric component comprises at least one electroactive polymer.
3. The composition according to claim 1 , wherein said polymeric component comprises at least one electroluminescent polymer.
4. The composition according to claim 1 , wherein said polymeric component comprises at least one polyfluorene.
5. The composition 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 C3-C40 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 from 0 to 5.
6. The composition 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.
7. The composition according to claim 1 , wherein the cyclometallated ligand is derived from a styrylisoquinoline 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.
8. The composition according to claim 1 , wherein the cyclometallated ligand
is derived from a 1-phenylisoquinoline, a 2-phenylpyridine, a 1-styrylisoquinoline, or a combination thereof.
9. The composition 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 composition 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 composition 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 composition according to claim 1 , wherein said 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.
13. A 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.
14. The light emitting polymer composition according to claim 13 , wherein said electroluminescent polymer is selected from the group consisting of poly(n-vinylcarbazole) (PVK), poly(n-vinylcarbazole) derivatives, polyfluorene, poly(9,9-dihexylfluorene), poly9,9-dioctylfluorene), poly{9,9-bis(3,6-dioxaheptyl)-fluorene-2,7-diyl}, poly(paraphenylene) (“PPP”), poly(2-decyloxy-1,4-phenylene), poly(2,5-diheptyl-1,4-phenylene), poly(p-phenylene vinylene) (“PPV”), and mixtures thereof.
15. The light emitting polymer composition according to claim 13 , wherein said electroluminescent polymer is a polyfluorene.
16. The light emitting polymer composition according to claim 13 , 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.
17. The light emitting polymer composition according to claim 13 , 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.
18. The light emitting polymer composition according to claim 13 , wherein the electroluminescent polymer component is a blue light emitting electroluminescent polymer.
19. The light emitting polymer composition according to claim 18 , wherein the organic iridium complex is characterized by a lowest accessible triplet state energy T1 and the blue light emitting electroluminescent polymer is characterized by a lowest accessible triplet state energy T2, wherein T1 is less than T2.
20. The light emitting polymer composition according to claim 13 , wherein the organic iridium complex is at least 10 percent deuterated.
21. The light emitting polymer composition according to claim 13 , wherein the organic iridium complex is at least 60 percent deuterated.
22. The light emitting polymer composition according to claim 13 , wherein said 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.
23. A polymer composition comprising:
a polymeric component; and
at least one organic iridium complex having structure XLIV