IP Library › Granted Patent US 8,039,123

Granted Patent B2

US 8,039,123 · App. 11/727,593 · Granted Oct 18, 2011

Phosphorescent heteronuclear copper(I)-iridium(III) complex and organic electroluminescence device using the same

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Quick Facts

Patent No.: US 8,039,123
App. No.: 11/727,593
Granted: Oct 18, 2011
Kind: B2

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Abstract

Provided are a high-efficiency, photoluminescent heteronuclear copper (I)-iridium (III) complex and an organic electroluminescent device using the complex. The photoluminescent heteronuclear copper (I)-iridium (III) complex can be used to form an organic layer of an organic electroluminescent device, can emit light of 590-630 nm as a high-efficiency, photoluminescent material, and provides a high brightness and a low turn-on voltage.

Claims (69)

1. A heteronuclear copper (I)-iridium (III) complex represented by a formula selected from the group consisting of Formulae 1 through 3:

where A-X—B is a mononegative bidentate auxiliary ligand containing a hetero atom X;

X is N, P, S, or O;

CyN is 1,2,4-triazole, a substituted or unsubstituted C 3 -C 60 hetero ring group including nitrogen bound to iridium (III), or a substituted or unsubstituted C 3 -C 60 heteroaryl group including nitrogen bound to iridium;

CyC is a substituted or unsubstituted C 4 -C 60 cyclic group including carbon bound to iridium, a substituted or unsubstituted C 3 -C 60 hetero ring group including carbon bound to iridium, a substituted or unsubstituted C 6 -C 60 aryl group including carbon bound to iridium, or a substituted or unsubstituted C 3 -C 60 heteroaryl group including carbon bound to iridium; and

CyN-CyC is a cyclometalating ligand coordinated to iridium via the nitrogen of the CyN and the carbon of the CyC, and, alternative to the above definition of CyN and CyC, CyN-CyC is optionally

Where R 11 , R 12 , R 13 and R 14 are each independently selected from the group consisting of hydrogen, a halogen atom, —OR, —N(R) 2 , —P(R) 2 , —POR, —PO 2 R, —PO 3 R, —SR, —Si(R) 3 , —B(R) 2 , —B(OR) 2 , —C(O)R, —C(O)OR, —C(O)N(R), —CN, —NO 2 , —SO 2 , —SOR, —SO 2 R, —SO 3 R, a C 1 -C 20 alkyl group, and a C 6 -C 20 aryl group, wherein R is selected from the group consisting of hydrogen, a halogen atom, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 1 -C 10 alkoxy group, a substituted or unsubstituted C 2 -C 20 alkenyl group, a substituted or unsubstituted C 2 -C 20 alkenyl group, a substituted or unsubstituted C 1 -C 20 heteroalkyl, a substituted or unsubstituted C 6 -C 40 aryl group, a substituted or unsubstituted C 7 -C 40 arylalkyl group, a substituted or unsubstituted C 7 -C 40 alkylaryl group, a substituted or unsubstituted C 2 -C 40 heteroaryl group, and a substituted or unsubstituted C 3 -C 40 heteroarylalkyl group.

2. The heteronuclear copper(I)-iridium(III) complex of claim 1 , wherein the cyclometalating ligand CyN-CyC is represented by one of the formulae:

where the cyclometalating ligand CyN-CyC is mono-substituted or multi-substituted with at least one of R 11 , R 12 , R 13 , R 14 , and R 15 , and R 11 , R 12 , R 13 , R 14 , and R 15 are each independently selected from the group consisting of hydrogen, a halogen atom, —OR, —N(R) 2 , —P(R) 2 , —POR, —PO 2 R, —PO 3 R, —SR, —Si(R) 3 , —B(R) 2 , —B(OR) 2 , —C(O)R, —C(O)OR, —C(O)N(R), —CN, —NO 2 , —SO 2 , —SOR, —SO 2 R, —SO 3 R, a C 1 -C 20 alkyl group, and a C 6 -C 20 aryl group;

R is selected from the group consisting of hydrogen, a halogen atom, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 1 -C 10 alkoxy group, a substituted or unsubstituted C 2 -C 20 alkenyl group, a substituted or unsubstituted C 2 -C 20 alkynyl group, a substituted or unsubstituted C 1 -C 20 heteroalkyl, a substituted or unsubstituted C 6 -C 40 aryl group, a substituted or unsubstituted C 7 -C 40 arylalkyl group, a substituted or unsubstituted C 7 -C 40 alkylaryl group, a substituted or unsubstituted C 2 -C 40 heteroaryl group, and a substituted or unsubstituted C 3 -C 40 heteroarylalkyl group; and

Z is S, O, or NR 0 where R 0 is hydrogen or a C 1 -C 20 alkyl group.

3. The heteronuclear copper(I)-iridium(III) complex of claim 1 , wherein the ligand A-X—B is represented by one of the formulae below:

where the ligands A-X—B are mono-substituted or multi-substituted with at least one of R 1 , R 2 , R 3 , and R 4 , and R 1 , R 2 , R 3 , and R 4 are each independently selected from the group consisting of hydrogen, a halogen atom, —OR, —N(R) 2 , —P(R) 2 , —POR, —PO 2 R, —PO 3 R, —SR, —Si(R) 3 , —B(R) 2 , —B(OR) 2 , —C(O)R, —C(O)OR, —C(O)N(R), —CN, —NO 2 , —SO 2 , —SOR, —SO 2 R, —SO 3 R, a C 1 -C 20 alkyl group, and a C 6 -C 20 aryl group; and

4. The heteronuclear copper(I)-iridium(III) complex of claim 1 , wherein CyN is selected from the group consisting of pyrrolidine, morpholine, thiomorpholine, thiazolidine, pyridine, 4-methoxypyridine, quinoline, pyrrole, indole, pyrazine, pyrazole, imidazole, pyrimidine, quinazoline, thiazole, oxazole, triazine, and 1,2,4-triazole;

CyC is selected from the group consisting of cyclohexane, cyclopentane, tetrahydrofuran, 1,3-dioxane, 1,3-dithiane, 1,3-dithiolane, 1,4-dioxa-8-azaspiro[4,5]decane, 1,4-dioxaspiro[4,5]decan-2-one, phenyl, 1,3-benzodioxole, biphenyl, naphthalene, anthracene, azulene, thiophene, furan2(5H)-furanone, pyridine, coumarin, imidazole, 2-phenylpyridine, 2-benzothiazole, 2-benzooxazole, 1-phenylpyrazole, 1-naphthylpyrazole,5-(4-methoxyphenyl) pyrazole, 2,5-bisphenyl-1,3,4-oxadiazole, 2,3-benzofuran, and 2-(4-biphenyl)-6-phenyl benzooxazole; and

A and B are independently selected from the group consisting of cyclohexyl, cyclopentyl, cyclooctyl, phenyl, 1,3-benzodioxole, biphenyl, naphthalene, anthracene, azulene, thiophene, furan2(5H)-furanone, pyridine, coumarin, imidazole, 2-phenylpyridine, 2-benzothiazole, 2-benzooxazole, 1-phenylpyrazole, 1-naphthylpyrazole, 5-(4-methoxyphenyl)pyrazole, 2, 5-bisphenyl-1,3,4-oxadiazole, 2,3-benzofuran and 2-(4 -biphenyl)-6-phenyl benzooxazole.

5. An organic electroluminescent device comprising an organic layer between a pair of electrodes, the organic layer containing the copper(I)-iridium (III) complex of claim 1 .

6. The organic electroluminescent device of claim 5 , wherein the organic layer is an emitting layer.

7. The organic electroluminescent device of claim 6 , wherein the amount of the copper (I)-iridium (III) complex is in a range of 1-30 parts by weight based on 100 parts by the total weight of the emitting layer.

8. The organic electroluminescent device of claim 5 , wherein the organic layer further comprises at least one host selected from the group consisting of a polymer host, a mixed host of a polymer and a low-molecular weight material, a low-molecular weight host, and a non-emitting polymer matrix.

9. The organic electroluminescent device of claim 5 , wherein the organic layer further comprises one of a green luminescent material and a blue luminescent material.

10. A heteronuclear copper (I)-iridium (III) complex represented by Formula 1:

where A-X—B is a mononegative bidentate auxiliary ligand containing a hetero atom X;

X is N, P, S, or O;

CyN is a substituted or unsubstituted C 3 -C 60 hetero ring group including nitrogen bound to iridium (III), or a substituted or unsubstituted C 3 -C 60 heteroaryl group including nitrogen bound to iridium;

CyN-CyC indicates a cyclometalating ligand coordinated to iridium via the nitrogen of the CyN and the carbon of the CyC.

11. The heteronuclear copper(I)-iridium(III) complex of claim 10 , being a compound represented by Formula 6:

12. A heteronuclear copper(I)-iridium(III) complex represented by Formula 2:

where A-X—B is a mononegative bidentate auxiliary ligand containing a hetero atom X;

X is N, P, S, or O;

CyN-CyC indicates a cyclometalating ligand coordinated to iridium via the nitrogen of the CyN and the carbon of the CyC.

13. The heteronuclear copper(I)-iridium(III) complex of claim 12 , being a compound represented by one of Formulae 7 and 8:

14. A heteronuclear copper(I)-iridium(III) complex represented by Formula 3:

where A-X—B is a mononegative bidentate auxiliary ligand containing a hetero atom X;

X is N, P, S, or O;

CyN-CyC indicates a cyclometalating ligand coordinated to iridium via the nitrogen of the CyN and the carbon of the CyC.

15. The heteronuclear copper(I)-iridium(III) complex of claim 14 , being a compound represented by Formula 4:

where X is N, P, S, or O;

NCyX is a substituted or unsubstituted C 3 -C 60 hetero ring group including nitrogen bound to iridium (III) and including hetero atom X or a substituted or unsubstituted C 3 -C 60 heteroaryl group including nitrogen bound to iridium and including hetero atom X; and

CyN-CyC and NCyX-CCy are cyclometalating ligands coordinated to iridium via the nitrogen of the CyN and the carbon of the CyC.

16. The heteronuclear copper(I)-iridium(III) complex of claim 15 . wherein the NCyX-CCy is one of the groups represented by formulae:

where the NCyX-CCy is mono-substituted or multi-substituted with at least one of R 1 and R 2 , and R 1 and R 2 are each independently selected from the group consisting of hydrogen, a halogen atom, —OR, —N(R) 2 , —P(R) 2 , —POR, —PO 2 R, —PO 3 R, —SR, —Si(R) 3 , —B(R) 2 , —B(OR) 2 , —C(O)R, —C(O)OR, —C(O)N(R), —CN, —NO 2 , —SO 2 , —SOR, —SO 2 R, —SO 3 R, a C 1 -C 20 alkyl group, and a C 6 -C 20 aryl group; and

R is selected from the group consisting of hydrogen, a halogen atom, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 1 -C 10 alkoxy group, a substituted or unsubstituted C 2 -C 20 alkenyl group, a substituted or unsubstituted C 2 -C 20 alkynyl group, a substituted or unsubstituted C 1 -C 20 heteroalkyl, a substituted or unsubstituted C 6 -C 40 aryl group, a substituted or unsubstituted C 7 -C 40 arylalkyl group, a substituted or unsubstituted C 7 -C 40 alkylaryl group, a substituted or unsubstituted C 7 -C 40 heteroaryl group, and a substituted or unsubstituted C 3 -C 40 heteroarylalkyl group.

17. The heteronuclear copper (I)-iridium(III) complex of claim 14 , being a compound represented by Formula 5:

where X is N, P, S, or O;

NCy is a substituted or unsubstituted C 4 -C 60 cyclic group including nitrogen bound to iridium (III), a substituted or unsubstituted C 3 -C 60 hetero ring group including nitrogen bound to iridium, a substituted or unsubstituted C 3 -C 60 aryl group including nitrogen bound to iridium, or a substituted or unsubstituted C 3 -C 60 heteroaryl group including nitrogen bound to iridium;

CCyX is a substituted or unsubstituted C 3 -C 60 hetero ring group including carbon bound to iridium (III) and including hetero atom X or a substituted or unsubstituted C 3 -C 60 heteroaryl group including carbon bound to iridium and including hetero atom X; and

CyN-CyC and NCy-CCyX indicate cyclometalating ligands coordinated to iridium via the nitrogen of the CyN and the carbon of the CyC.

18. The heteronuclear copper(I)-iridium(III) complex of claim 16 , wherein the NCy-CCyX is one of the groups represented by formulae below:

where the NCy-CCyX is mono-substituted or multi-substituted with at least one of R 1 and R 2 , and R 1 and R 2 are each independently selected from the group consisting of hydrogen, a halogen atom, —OR, —N(R) 2 , —P(R) 2 , —POR, —PO 2 R, —PO 3 R, —SR, —Si(R) 3 , —B(R) 2 , —B(OR) 2 , —C(O)R, —C(O)OR, —C(O)N(R), —CN, —NO 2 , —SO 2 , —SOR, —SO 2 R, —SO 3 R, a C 1 -C 20 alkyl group, and a C 6 -C 20 aryl group; and R is selected from the group consisting of hydrogen, a halogen atom, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 1 -C 10 alkoxy group, a substituted or unsubstituted C 2 -C 20 alkenyl group, a substituted or unsubstituted C 2 -C 20 alkynyl group, a substituted or unsubstituted C 1 -C 20 heteroalkyl, a substituted or unsubstituted C 6 -C 40 aryl group, a substituted or unsubstituted C 7 -C 40 arylalkyl group, a substituted or unsubstituted C 7 -C 40 alkylaryl group, a substituted or unsubstituted C 2 -C 40 heteroaryl group, and a substituted or unsubstituted C 3 -C 40 heteroarylalkyl group.

19. The heteronuclear copper(I)-iridium(III) complex of claim 14 , being a compound of one of Formulae 9 and 10:

20. A method of preparing a copper (I)-iridium (III) complex represented by one selected from the group consisting of Formulae 1 through 3, the method comprising:

reacting a compound [(3,5-(CF 3 ) 2 Pz)-Cu] 3 represented by Formula 11 with a compound of Formula 12:

where A-X—B is a mononegative bidentate auxiliary ligand containing a hetero atom X;

X is N, P, S, or O;

CyN-CyC indicates a cyclometalating ligand coordinated to iridium via the nitrogen of the CyN and the carbon of the CyC.

21. A copper (I)-iridium (III) complex prepared by the method of claim 20 .

Assignments (1)

MERGER Recorded Sep 21, 2012

From: SAMSUNG MOBILE DISPLAY CO., LTD.

To: SAMSUNG DISPLAY CO., LTD.

Reel/Frame 029241/0599 →