Organometallic complex and organic electroluminescence device using the same
View Patent ↗Provided are an organometallic complex providing highly efficient phosphorescence and an organic electroluminescence device using the organometallic complex represented by Formula 1: ML m L′ n where M is Ir, Os, Pt, Pb, Re, Ru or Pd, L and L′ are different bidentate ligands, m is 1, 2 or 3, and n is 3−m. The organometallic complex can be used to form an organic layer of the organic electroluminescence device, efficiently emits light of a wavelength corresponding to red light, and has high brightness and low operating voltage.
1. An organometallic complex represented by Formula 1:
ML 2 L′ (1)
where M is Ir;
L 2 and L′ are different bidentate ligands; and
ML 2 of Formula 1 is represented by one of Formulas 4, 5, and 7 through 9:
where, R 1 , R 2 , R 3 and R 4 are each independently at least one selected from the group consisting of hydrogen, a halogen atom, a carboxyl group, an amino group, a nitro group, a cyano group, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 1 -C 20 alkoxy group, a substituted or unsubstituted C 2 -C 20 alkenyl, a substituted or unsubstituted C 2 -C 20 alkynyl group, a substituted or unsubstituted C 1 -C 20 heteroalkyl group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 7 -C 30 arylalkyl group, a substituted or unsubstituted C 5 -C 30 heteroaryl group, and a substituted or unsubstituted C 3 -C 30 heteroarylalkyl group.
2. The organometallic complex of claim 1 , wherein the bidentate ligand L′ is represented by one of Formulas 11 through 19:
where, R 1 , R 2 , R 3 and R 4 are each independently at least one selected from the group consisting of a halogen atom, a carboxyl group, an amino group, a nitro group, a cyano group, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 1 -C 20 alkoxy group, a substituted or unsubstituted C 2 -C 20 alkenyl, a substituted or unsubstituted C 1 -C 20 alkynyl group, a substituted or unsubstituted C 1 -C 20 heteroalkyl group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 7 -C 30 arylalkyl group, a substituted or unsubstituted C 5 -C 30 heteroaryl group, and a substituted or unsubstituted C 3 -C 30 heteroarylalkyl group.
3. The organometallic complex of claim 1 , wherein the compound represented by Formula 1 is represented by one of Formulas 22, 25, 26 or 28:
4. An organic electroluminescence device including an organic layer comprising an organometallic complex of claim 1 .
5. An organometallic complex represented by Formula 1:
ML 2 L′ (1)
where M is Ir;
L 2 and L′ are different bidentate ligands; and
ML 2 of Formula 1 is represented by one of Formulas 4, 5, and 7 through 9:
where, R 1 , R 2 , R 3 and R 4 are each independently at least one selected from the group consisting of hydrogen, a halogen atom, a carboxyl group, an amino group, a nitro group, a cyano group, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 1 -C 20 alkoxy group, a substituted or unsubstituted C 2 -C 20 alkenyl, a substituted or unsubstituted C 2 -C 20 alkynyl group, a substituted or unsubstituted C 1 -C 20 heteroalkyl group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 7 -C 30 arylalkyl group, a substituted or unsubstituted C 5 -C 30 heteroaryl group, and a substituted or unsubstituted C 3 -C 30 heteroarylalkyl group; and
L′ is represented by Formulas 11 through 19:
where, R 1 , R 2 , R 3 and R 4 are each independently at least one selected from the group consisting of a halogen atom, a carboxyl group, an amino group, a nitro group, a cyano group, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 1 -C 20 alkoxy group, a substituted or unsubstituted C 2 -C 20 alkenyl, a substituted or unsubstituted C 2 -C 20 alkynyl group, a substituted or unsubstituted C 1 -C 20 heteroalkyl group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 7 -C 30 arylalkyl group, a substituted or unsubstituted C 5 -C 30 heteroaryl group, and a substituted or unsubstituted C 3 -C 30 heteroarylalkyl group.
6. An organic electroluminescence device having an organic layer comprising an organometallic complex of claim 5 .
7. An organic electroluminescence device, comprising:
a pair of electrodes; and
an organic layer interposed between the pair of electrodes, the organic layer comprising an organometallic complex represented by Formula 1:
ML 2 L′ (1)
where M is Ir;
L 2 and L′ are different bidentate ligands; and
ML 2 of Formula 1 is represented by one of Formulas 4, 5, and 7 through 9:
where, R 1 , R 2 , R 3 and R 4 are each independently at least one selected from the group consisting of hydrogen, a halogen atom, a carboxyl group, an amino group, a nitro group, a cyano group, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 1 -C 20 alkoxy group, a substituted or unsubstituted C 2 -C 20 alkenyl, a substituted or unsubstituted C 2 -C 20 alkynyl group, a substituted or unsubstituted C 1 -C 20 heteroalkyl group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 7 -C 30 arylalkyl group, a substituted or unsubstituted C 5 -C 30 heteroaryl group, and a substituted or unsubstituted C 3 -C 30 heteroarylalkyl group.
8. The organic electroluminescence device of claim 7 , wherein the organic layer comprising an organometallic complex of Formula (1) is a light emitting layer.
9. The organic electroluminescence device of claim 8 , wherein the organometallic complex is in an amount of 1 to 30 parts by weight based on 100 parts by weight of all the materials used to form the light emitting layer.
10. The organic electroluminescence device of claim 7 , wherein the organic layer further comprises one of green phosphorescent materials or blue phosphorescent materials.
11. The organic electroluminescence device of claim 7 , wherein the bidentate ligand L′ is represented by one of Formulas 11 through 19:
where, R 1 , R 2 , R 3 and R 4 are each independently at least one selected from the group consisting of a halogen atom, a carboxyl group, an amino group, a nitro group, a cyano group, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 1 -C 20 alkoxy group, a substituted or unsubstituted C 2 -C 20 alkenyl, a substituted or unsubstituted C 2 -C 20 alkynyl group, a substituted or unsubstituted C 1 -C 20 heteroalkyl group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 7 -C 30 arylalkyl group, a substituted or unsubstituted C 5 -C 30 heteroaryl group, and a substituted or unsubstituted C 3 -C 30 heteroarylalkyl group.
12. The organic electroluminescence device of claim 7 , wherein the compound represented by Formula 1 is represented by one of Formulas 22, 25, 26 or 28:
13. The organic electroluminescence device of claim 7 , wherein the organic layer further comprises at least one host selected from the group consisting of a polymer host, a mixture host comprising a polymer and a small molecule, a small molecule host, and a non-emitting polymer matrix.