IP Library › Granted Patent US 8,945,723

Granted Patent B2

US 8,945,723 · App. 12/081,214 · Granted Feb 3, 2015

Organometallic complexes and organic electroluminescence device using the same

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Patent No.: US 8,945,723
App. No.: 12/081,214
Granted: Feb 3, 2015
Kind: B2

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Abstract

An organometallic complex that increases an energy band gap between HOMO and triplet MLCT states, and enables highly efficient phospholuminescence and can be used for an organic electroluminescent device. The organometallic complex, which is suitably used for forming an organic layer of the organic electroluminescent device, provides a luminescence maximum emission in the wavelength range of 400-650 nm, and induces white electroluminescence when combined with green or red luminescent materials.

Claims (119)

1. An organometallic complex represented by Formula 1:

wherein M is a metal selected from the group consisting of Ir, Os, Pt, Pb, Re, Ru, and Pd;

CyN is selected from the group consisting of a substituted C 3 -C 60 heterocyclic group containing nitrogen bonded to said M, an unsubstituted C 3 -C 60 heterocyclic group containing nitrogen bonded to said M, a substituted C 3 -C 60 heteroaryl group containing nitrogen bonded to said M, and an unsubstituted C 3 -C 60 heteroaryl group containing nitrogen bonded to said M;

CyC is selected from the group consisting of an unsubstituted C 4 -C 60 carbocyclic group containing carbon bonded to said M, a substituted C 4 -C 60 carbocyclic group containing carbon bonded to said M, an unsubstituted C 3 -C 60 heterocyclic group containing carbon bonded to said M, a substituted C 3 -C 60 heterocyclic group containing carbon bonded to said M, an unsubstituted C 6 -C 60 aryl containing carbon bonded to said M, a substituted C 6 -C 60 aryl containing carbon bonded to said M, an unsubstituted C 3 -C 60 heteroaryl containing carbon bonded to said M, and a substituted C 3 -C 60 heteroaryl containing carbon bonded to said M;

the CyN-CyC formed by said CyN and said CyC is a cyclometalating ligand bonded to said M through nitrogen (N) of said CyN and carbon (C) of said CyC;

each substituent of the CyN-CyC is independently selected from the group consisting of a halogen atom, —OR, —N(R)(R′), —P(R)(R′), —POR, —PO 2 R, —PO 3 R, —SR, —Si(R)(R′)(R″), —B(R)(R′), —B(OR)(OR′), —C(O)R, —C(O)OR, —C(O)N(R), —CN, —NO 2 , —SO 2 , —SOR, —SO 2 R, —SO 3 R, substituted or unsubstituted C 1 -C 20 alkyl, and substituted or unsubstituted C 6 -C 20 aryl, the substituents are alternatively joined to form a substituted or unsubstituted 4- to 7-membered carbocyclic group or a substituted or unsubstituted 4- to 7-membered heterocyclic group, the R, R′ and R″ are independently selected from the group consisting of hydrogen, a substituted or unsubstituted C 1 -C 20 alkyl, substituted or unsubstituted C 1 -C 20 alkoxy, substituted or unsubstituted C 2 -C 20 alkenyl, substituted or unsubstituted C 2 -C 20 alkynyl, substituted or unsubstituted C 1 -C 20 heteroalkyl, substituted or unsubstituted C 6 -C 40 aryl, substituted or unsubstituted C 7 -C 40 arylalkyl, substituted or unsubstituted C 7 -C 40 alkylaryl, substituted or unsubstituted C 2 -C 40 heteroaryl, and substituted or unsubstituted C 3 -C 40 heteroarylalkyl;

alternatively, the CyN-CyC is represented by the Formula 1a:

wherein R 1 , R 2 , R 3 , and R 4 are independently selected from the group consisting of hydrogen, halogen atom, —OR a , —N(R a ) 2 , —P(R a ) 2 , —POR a , —PO 2 R a , —PO 3 R a , —SR a , —Si(R a ) 3 , —B(R a ) 2 , —B(OR a ) 2 , —C(O)R a , —C(O)OR a , —C(O)N(R a ), —CN, —NO 2 , —SO 2 , —SOR a , —SO 2 R a , —SO 3 R a , C 1 -C 20 alkyl, and C 6 -C 20 aryl, and R a is selected from the group consisting of hydrogen, a substituted or unsubstituted C 1 -C 20 alkyl, substituted or unsubstituted C 1 -C 20 alkoxy, substituted or unsubstituted C 2 -C 20 alkenyl, substituted or unsubstituted C 2 -C 20 alkynyl, substituted or unsubstituted C 1 -C 20 heteroalkyl, substituted or unsubstituted C 6 -C 40 aryl, substituted or unsubstituted C 7 -C 40 arylalkyl, substituted or unsubstituted C 7 -C 40 alkylaryl, substituted or unsubstituted C 2 -C 40 heteroaryl, and substituted or unsubstituted C 3 -C 40 heteroarylalkyl;

A is either an unsubstituted imidazole containing nitrogen bonded to said M, or one containing nitrogen bonded to said M selected from the group consisting of substituted or unsubstituted triethylamine, propylamine, cyclohexylamine, pyrrolidine, pyrroline, piperidine, indole, azaindole, carbazole, indazole, norharman, harman, aniline, oxazole, thiazole, pyrrole, benzimidazole, benzotriazole, benzoxazole, benzothiazole, benzoselenazole, benzothiadiazole, isoxazole, isothiazole, oxadiazole, thiadiazole, anthranyl, triazine, benzisoxazole, quinoline, benzoquinoline, acridine, thiazoline, quinuclidine, imidazoline, oxazoline, thiazoline, and isoquinoline;

X is a monoanionic monodentate ligand; and

n is one of 1 and 2.

2. The organometallic complex of claim 1 , wherein the CyN-CyC is represented by one of the following Formulas:

wherein R 1 , R 2 , R 3 , R 4 , and R 5 are independently selected from the group consisting of hydrogen, halogen atom, —OR b , —N(R b ) 2 , —P(R b ) 2 , —POR b , —PO 2 R b , —PO 3 R b , —SR b , —Si(R b ) 3 , —B(R b ) 2 , —B(OR b ) 2 , —C(O)R b , —C(O)OR b , —C(O)N(R b ), —CN, —NO 2 , —SO 2 , —SOR b , —SO 2 R b , —SO 3 R b , a C 1 -C 20 alkyl, or a C 6 -C 20 aryl group, and R b is selected from the group consisting of hydrogen, a substituted or unsubstituted C 1 -C 20 alkyl, substituted or unsubstituted C 1 -C 20 alkoxy, substituted or unsubstituted C 2 -C 20 alkenyl, substituted or unsubstituted C 2 -C 20 alkynyl, substituted or unsubstituted C 1 -C 20 heteroalkyl, substituted or unsubstituted C 6 -C 40 aryl, substituted or unsubstituted C 7 -C 40 arylalkyl, substituted or unsubstituted C 7 -C 40 alkylaryl, substituted or unsubstituted C 2 -C 40 heteroaryl, and substituted or unsubstituted C 3 -C 40 heteroarylalkyl; and

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

3. The organometallic complex of claim 1 , wherein said X is selected from the group consisting of —F, —Cl, —Br, —I, —CN, —CN(R 11 ), —SCN, and —OCN, and R 11 is a substituted or unsubstituted C 1 -C 20 alkyl group.

4. The organometallic complex of claim 1 , wherein said M is one of Ir and Pt.

5. An organometallic complex represented by one selected from the group consisting of compounds represented by Formulae 2, 3, and 5 through 14:

wherein M is a metal selected from the group consisting of Ir, Os, Pt, Pb, Re, Ru, and Pd;

the CyN-CyC formed by said CyN and said CyC is a cyclometalating ligand bonded to said M through nitrogen (N) of said CyN and carbon (C) of said CyC;

each substituent of the CyN-CyC is independently selected from the group consisting of a halogen atom, —OR, —N(R)(R′), —P(R)(R′), —POR, —PO 2 R, —PO 3 R, —SR, —Si(R)(R′)(R″), —B(R)(R′), —B(OR)(OR′), —C(O)R, —C(O)OR, —C(O)N(R), —CN, —NO 2 , —SO 2 , —SOR, —SO 2 R, —SO 3 R, substituted or unsubstituted C 1 -C 20 alkyl, and substituted or unsubstituted C 6 -C 20 aryl, the substituents are alternatively joined to form a substituted or unsubstituted 4- to 7-membered carbocyclic group or a substituted or unsubstituted 4- to 7-membered heterocyclic group, the R, R′ and R″ are independently selected from the group consisting of hydrogen, a substituted or unsubstituted C 1 -C 70 alkyl, substituted or unsubstituted C 1 -C 20 alkoxy, substituted or unsubstituted C 2 -C 20 alkenyl, substituted or unsubstituted C 2 -C 20 alkynyl, substituted or unsubstituted C 1 -C 20 heteroalkyl, substituted or unsubstituted C 6 -C 40 aryl, substituted or unsubstituted C 7 -C 40 arylalkyl, substituted or unsubstituted C 7 -C 40 alkylaryl, substituted or unsubstituted C 2 -C 40 heteroaryl, and substituted or unsubstituted C 3 -C 40 heteroarylalkyl;

alternatively, the CyN-CyC is represented by the Formula 1a:

wherein R 1 , R 2 , R 3 , and R 4 are independently selected from the group consisting of hydrogen, halogen atom, —OR a , —N(R a ) 2 , —P(R a ) 2 , —POR a , —PO 2 R a , —PO 3 R a , —SR a , —Si(R a ) 3 , —B(R a ) 2 , —B(OR a ) 2 , —C(O)R a , —C(O)OR a , —C(O)N(R a ), —CN, —NO 2 —SO 2 , —SOR a , —SO 2 R a , —SO 3 R a , C 1 -C 20 alkyl, and C 6 -C 20 aryl, and R a is selected from the group consisting of hydrogen, a substituted or unsubstituted C 1 -C 20 alkyl, substituted or unsubstituted C 1 -C 20 alkoxy, substituted or unsubstituted C 2 -C 20 alkenyl, substituted or unsubstituted C 2 -C 20 alkynyl, substituted or unsubstituted C 1 -C 20 heteroalkyl, substituted or unsubstituted C 6 -C 40 aryl, substituted or unsubstituted C 7 -C 40 arylalkyl, substituted or unsubstituted C 7 -C 40 alkylaryl, substituted or unsubstituted C 2 -C 40 heteroaryl, and substituted or unsubstituted C 3 -C 40 heteroarylalkyl;

R 6 and R 7 are independently selected from the group consisting of hydrogen, halogen atom, —OR c , —N(R c ) 2 , —P(R c ) 2 , —POR c , —PO 2 R c , —PO 3 R c , SR c , —Si(R c ) 3 , —B(R c ) 2 , —B(OR c ) 2 , —C(O)R c , —C(O)OR c , —C(O)N(R c ), —CN, —NO 2 , —SO 2 , —SOW, —SO 2 R c , —SO 3 R c , substituted or unsubstituted C 1 -C 20 alkyl, substituted or unsubstituted C 6 -C 20 aryl or substituted or unsubstituted C 2 -C 20 heteroaryl group, and R c is selected from the group consisting of hydrogen, a substituted or unsubstituted C 1 -C 20 alkyl, substituted or unsubstituted C 1 -C 20 alkoxy, substituted or unsubstituted C 2 -C 20 alkenyl, substituted or unsubstituted C 2 -C 20 alkynyl, substituted or unsubstituted C 1 -C 20 heteroalkyl, substituted or unsubstituted C 6 -C 40 aryl, substituted or unsubstituted C 7 -C 40 arylalkyl, substituted or unsubstituted C 7 -C 40 alkylaryl, substituted or unsubstituted C 2 -C 40 heteroaryl, and substituted or unsubstituted C 3 -C 40 heteroarylalkyl;

substituents of R 6 and R 7 , which are substituted at different positions, are alternatively interconnected to form a substituted or unsubstituted fused 4-7 atom ring;

R 8 , R 9 , and R 10 are independently a substituted or unsubstituted C 1 -C 20 alkyl, a substituted or unsubstituted C 6 -C 20 aryl or substituted or unsubstituted C 2 -C 20 heteroaryl group;

X is selected from the group consisting of F, Cl, Br, I, CN, CN(R 11 ), SCN or OCN, R 11 is selected from the group consisting of hydrogen, a substituted or unsubstituted C 1 -C 20 alkyl, substituted or unsubstituted C 1 -C 20 alkoxy, substituted or unsubstituted C 2 -C 20 alkenyl, substituted or unsubstituted C 2 -C 20 alkynyl, substituted or unsubstituted C 1 -C 20 heteroalkyl, substituted or unsubstituted C 6 -C 40 aryl, substituted or unsubstituted C 7 -C 40 arylalkyl, substituted or unsubstituted C 7 -C 40 alkylaryl, substituted or unsubstituted C 2 -C 40 heteroaryl, and substituted or unsubstituted C 3 -C 40 heteroarylalkyl; and

n is one of 1 and 2.

6. An organic electroluminescent device, comprising:

a first electrode;

a second electrode; and

an organic layer between said first electrode and said second electrode, said organic layer comprising an organometallic complex represented by Formula 1:

wherein M is a metal selected from the group consisting of Ir, Os, Pt, Pb, Re, Ru, and Pd;

the CyN-CyC formed by said CyN and said CyC is a cyclometalating ligand bonded to said M through nitrogen (N) of said CyN and carbon (C) of said CyC;

alternatively, the CyN-CyC is represented by the Formula 1a:

A is either imidazole containing nitrogen bonded to said M, or one containing nitrogen bonded to said M selected from the group consisting of substituted or unsubstituted triethylamine, propylamine, cyclohexylamine, pyrrolidine, pyrroline, piperidine, indole, azaindole, carbazole, indazole, norharman, harman, aniline, oxazole, thiazole, pyrrole, benzimidazole, benzotriazole, benzoxazole, benzothiazole, benzoselenazole, benzothiadiazole, isoxazole, isothiazole, oxadiazole, thiadiazole, anthranyl, triazine, benzisoxazole, quinoline, benzoquinoline, acridine, thiazoline, quinuclidine, imidazoline, oxazoline, thiazoline, and isoquinoline;

X is a monoanionic monodentate ligand; and

n is one of 1 and 2.

7. The organic electroluminescent device of claim 6 , wherein the CyN-CyC is represented by one of the following Formulas:

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

8. The organic electroluminescent device of claim 6 , wherein said X is selected from the group consisting of —F, —Cl, —Br, —I, —CN, —CN(R 11 ), —SCN, and —OCN, and R 11 is a substituted or unsubstituted C 1 -C 20 alkyl group.

9. The organic electroluminescent device of claim 6 , wherein said M is one of Ir and Pt.

10. An organic electroluminescent device comprising:

a first electrode;

a second electrode; and

an organic layer between said first electrode and said second electrode, said organic layer comprising an organometallic complex represented by one selected from the group consisting of compounds represented by Formulae 2 through 14:

wherein M is a metal selected from the group consisting of Ir, Os, Pt, Pb, Re, Ru, and Pd;

the CyN-CyC formed by said CyN and said CyC is a cyclometalating ligand bonded to said M through nitrogen (N) of said CyN and carbon (C) of said CyC;

each substituent of the CyN-CyC is independently selected from the group consisting of a halogen atom, —OR, —N(R)(R′), —P(R)(R′), —POR, —PO 2 R, —PO 3 R, —SR, —Si(R)(R′)(R″), —B(R)(R′), —B(OR)(OR′), —C(O)R, —C(O)OR, —C(O)N(R), —CN, —NO 2 , —SO 2 , —SOR, —SO 2 R, —SO 3 R, substituted or unsubstituted C 1 -C 20 alkyl, and substituted or unsubstituted C 6 -C 20 aryl, the substituents are alternatively joined to form a substituted or unsubstituted 4- to 7-membered carbocyclic group or a substituted or unsubstituted 4- to 7-membered heterocyclic group, the R, R′ and R″ are independently selected from the group consisting of hydrogen, a substituted or unsubstituted C 1 -C 70 alkyl, substituted or unsubstituted C 1 -C 20 alkoxy, substituted or unsubstituted C 2 -C 20 alkenyl, substituted or unsubstituted C 2 -C 20 alkynyl, substituted or unsubstituted C 1 -C 20 heteroalkyl, substituted or unsubstituted C 6 -C 40 aryl, substituted or unsubstituted C 7 -C 40 arylalkyl, substituted or unsubstituted C 7 -C 40 alkylaryl, substituted or unsubstituted C 2 -C 40 heteroaryl, and substituted or unsubstituted C 3 -C 40 heteroarylalkyl;

alternatively, the CyN-CyC is represented by the Formula 1a:

wherein R 1 , R 2 , R 3 , and R 4 are independently selected from the group consisting of hydrogen, halogen atom, —OR a , —N(R a ) 2 , —P(R a ) 2 , —POR a , —PO 2 R a —PO 3 R a , —SR a , —Si(R a ) 3 , —B(R a ) 2 —, —B(OR a ) 2 , —C(O)R a , —C(O)OR a , —C(O)N(R a ), —CN, —NO 2 —SO 2 , —SOR a , —SO 2 R a —SO 3 R a , C 1 -C 20 alkyl, and C 6 -C 20 aryl, and R a is selected from the group consisting of hydrogen, a substituted or unsubstituted C 1 -C 20 alkyl, substituted or unsubstituted C 1 -C 20 alkoxy, substituted or unsubstituted C 2 -C 20 alkenyl, substituted or unsubstituted C 2 -C 20 alkynyl, substituted or unsubstituted C 1 -C 20 heteroalkyl, substituted or unsubstituted C 6 -C 40 aryl, substituted or unsubstituted C 7 -C 40 arylalkyl, substituted or unsubstituted C 7 -C 40 alkylaryl, substituted or unsubstituted C 2 -C 40 heteroaryl, and substituted or unsubstituted C 3 -C 40 heteroarylalkyl;

R 6 and R 7 are independently selected from the group consisting of hydrogen, halogen atom, —OR c , —N(R c ) 2 , —P(R c ) 2 , —POR c , —PO 2 R c , —PO 3 R c , —SR c , —Si(R c ) 3 , —B(R c ) 2 , —B(OR c ) 2 , —C(O)R c , —C(O)OR c , —C(O)N(R c ), —CN, —NO 2 , —SO 2 , —SOW, —SO 2 R c , —SO 3 R c , substituted or unsubstituted C 1 -C 20 alkyl, substituted or unsubstituted C 6 -C 20 aryl or substituted or unsubstituted C 2 -C 20 heteroaryl group, and R c is selected from the group consisting of hydrogen, a substituted or unsubstituted C 1 -C 20 alkyl, substituted or unsubstituted C 1 -C 20 alkoxy, substituted or unsubstituted C 2 -C 20 alkenyl, substituted or unsubstituted C 2 -C 20 alkynyl, substituted or unsubstituted C 1 -C 20 heteroalkyl, substituted or unsubstituted C 6 -C 40 aryl, substituted or unsubstituted C 7 -C 40 arylalkyl, substituted or unsubstituted C 7 -C 40 alkylaryl, substituted or unsubstituted C 2 -C 40 heteroaryl, and substituted or unsubstituted C 3 -C 40 heteroarylalkyl;

substituents of R 6 and R 7 , which are substituted at different positions, are alternatively interconnected to form a substituted or unsubstituted fused 4-7 atom ring;

R 8 , R 9 , and R 10 are independently a substituted or unsubstituted C 1 -C 20 alkyl, a substituted or unsubstituted C 6 -C 20 aryl or substituted or unsubstituted C 2 -C 20 heteroaryl group;

n is one of 1 and 2.

11. The organic electroluminescent device of claim 6 , wherein the organometallic complex represented by Formula 1 is doped to at least one selected from the group consisting of a polymer host, a mixture of a polymer host and a small molecular host, a small molecular host, and non-luminous polymer matrix.

12. An organometallic complex represented by Formula 4:

wherein M is a metal selected from the group consisting of Ir, Os, Pt, Pb, Re, Ru, and Pd;

the CyN-CyC formed by said CyN and said CyC is a cyclometalating ligand bonded to said M through nitrogen (N) of said CyN and carbon (C) of said CyC;

alternatively, the CyN-CyC is represented by the Formula 1a:

wherein R 1 , R 2 , R 3 , and R 4 are independently selected from the group consisting of hydrogen, halogen atom, —OR a , —N(R a ) 2 , —P(R a ) 2 , —POR a , —PO 2 R a , —PO 3 R a , —SR a , —Si(R a ) 3 , —B(R a ) 2 , —B(OR a ) 2 , —C(O)R a , —C(O)ORa, —C(O)N(R a ), —CN, —NO 2 , —SO 2 , —SOR a , —SO 2 R a , —SO 3 R a , C 1 -C 20 alkyl, and C 6 -C 20 aryl, and R a is selected from the group consisting of hydrogen, a substituted or unsubstituted C 1 -C 20 alkyl, substituted or unsubstituted C 1 -C 20 alkoxy, substituted or unsubstituted C 2 -C 20 alkenyl, substituted or unsubstituted C 2 -C 20 alkynyl, substituted or unsubstituted C 1 -C 20 heteroalkyl, substituted or unsubstituted C 6 -C 40 aryl, substituted or unsubstituted C 7 -C 40 arylalkyl, substituted or unsubstituted C 7 -C 40 alkylaryl, substituted or unsubstituted C 2 -C 40 heteroaryl, and substituted or unsubstituted C 3 -C 40 heteroarylalkyl;

R 6 is selected from the group consisting of hydrogen, halogen atom, —OR c , —N(R c ) 2 , —P(R c ) 2 , —POR c , —PO 2 R c , —PO 3 R c , —SR c , —Si(R c ) 3 , —B(R c ) 2 , —B(OR c ) 2 , —C(O)R c , —C(O)OR c , —C(O)N(R c ), —CN, —NO 2 , —SO 2 , —SOR c , —SO 2 R c , —SO 3 R c , substituted or unsubstituted C 1 -C 20 alkyl, substituted or unsubstituted C 6 -C 20 aryl or substituted or unsubstituted C 2 -C 20 heteroaryl group, and R c is selected from the group consisting of hydrogen, a substituted or unsubstituted C 1 -C 20 alkyl, substituted or unsubstituted C 1 -C 20 alkoxy, substituted or unsubstituted C 2 -C 20 alkenyl, substituted or unsubstituted C 2 -C 20 alkynyl, substituted or unsubstituted C 1 -C 20 heteroalkyl, substituted or unsubstituted C 6 -C 40 aryl, substituted or unsubstituted C 7 -C 40 arylalkyl, substituted or unsubstituted C 7 -C 40 alkylaryl, substituted or unsubstituted C 2 -C 40 heteroaryl, and substituted or unsubstituted C 3 -C 40 heteroarylalkyl;

R 7 is selected from the group consisting of hydrogen, halogen atom, —OR c , —N(R c ) 2 , —P(R c ) 2 , —POR c , —PO 2 R c , —PO 3 R c , —SR c , —Si(R c ) 3 , —B(R c ) 2 , —B(OR c ) 2 , —C(O)R c , —C(O)OR c , —C(O)N(R c ), —CN, —NO 2 , —SO 2 , —SOW, —SO 2 R c , —SO 3 R c , substituted or unsubstituted C 2 -C 20 alkyl, substituted or unsubstituted C 6 -C 20 aryl or substituted or unsubstituted C 2 -C 20 heteroaryl group, and R c is selected from the group consisting of hydrogen, a substituted or unsubstituted C 1 -C 20 alkyl, substituted or unsubstituted C 1 -C 20 alkoxy, substituted or unsubstituted C 2 -C 20 alkenyl, substituted or unsubstituted C 2 -C 20 alkynyl, substituted or unsubstituted C 1 -C 20 heteroalkyl, substituted or unsubstituted C 6 -C 40 aryl, substituted or unsubstituted C 7 -C 40 arylalkyl, substituted or unsubstituted C 7 -C 40 alkylaryl, substituted or unsubstituted C 2 -C 40 heteroaryl, and substituted or unsubstituted C 3 -C 40 heteroarylalkyl;

substituents of R 6 and R 7 , which are substituted at different positions, are alternatively interconnected to form a substituted or unsubstituted fused 4-7 atom ring; and R 6 and R 7 are not hydrogen at the same time;

X is selected from the group consisting of F, Br, I, CN, CN(R 11 ), SCN or OCN, R 11 is selected from the group consisting of hydrogen, a substituted or unsubstituted C 1 -C 20 alkyl, substituted or unsubstituted C 1 -C 20 alkoxy, substituted or unsubstituted C 2 -C 20 alkenyl, substituted or unsubstituted C 2 -C 20 alkynyl, substituted or unsubstituted C 1 -C 20 heteroalkyl, substituted or unsubstituted C 6 -C 40 aryl, substituted or unsubstituted C 7 -C 40 arylalkyl, substituted or unsubstituted C 7 -C 40 alkylaryl, substituted or unsubstituted C 2 -C 40 heteroaryl, and substituted or unsubstituted C 3 -C 40 heteroarylalkyl; and

n is one of 1 and 2.

13. An organometallic complex represented by Formula 1:

wherein M is a metal selected from the group consisting of Ir, Os, Pt, Pb, Re, Ru, and Pd;

the CyN-CyC formed by said CyN and said CyC is a cyclometalating ligand bonded to said M through nitrogen (N) of said CyN and carbon (C) of said CyC;

alternatively, the CyN-CyC is represented by the Formula 1a:

A is one containing nitrogen bonded to said M selected from the group consisting of unsubstituted pyrimidine, unsubstituted pyrazole, and unsubstituted pyrazine;

X is —OCN; and

n is one of 1 and 2.

14. An organic electroluminescent device, comprising:

a first electrode;

a second electrode; and

an organic layer between said first electrode and said second electrode, said organic layer comprising an organometallic complex represented by Formula 1:

wherein M is a metal selected from the group consisting of Ir, Os, Pt, Pb, Re, Ru, and Pd;

the CyN-CyC formed by said CyN and said CyC is a cyclometalating ligand bonded to said M through nitrogen (N) of said CyN and carbon (C) of said CyC;

alternatively, the CyN-CyC is represented by the Formula 1a:

A is one containing nitrogen bonded to said M selected from the group consisting of unsubstituted pyrimidine, unsubstituted pyrazole, and unsubstituted pyrazine;

X is —OCN; and

n is one of 1 and 2.

15. An organic electroluminescent device, comprising:

a first electrode;

a second electrode; and

an organic layer between said first electrode and said second electrode, said organic layer comprising an organometallic complex represented by Formula 4:

wherein M is a metal selected from the group consisting of Ir, Os, Pt, Pb, Re, Ru, and Pd;

the CyN-CyC formed by said CyN and said CyC is a cyclometalating ligand bonded to said M through nitrogen (N) of said CyN and carbon (C) of said CyC;

alternatively, the CyN-CyC is represented by the Formula 1a:

R 7 is selected from the group consisting of hydrogen, halogen atom, —OR c , —N(R c ) 2 , —P(R c ) 2 , —POR c , —PO 2 R c , —PO 3 R c , —SR c , —Si(R c ) 3 , —B(R c ) 2 , —B(OR c ) 2 , —C(O)R c , —C(O)OR c , —C(O)N(R c ), —CN, —NO 2 , —SO 2 , —SOR c , —SO 2 R c , —SO 3 R c , substituted or unsubstituted C 2 -C 20 alkyl, substituted or unsubstituted C 6 -C 20 aryl or substituted or unsubstituted C 2 -C 20 heteroaryl group, and R c is selected from the group consisting of hydrogen, a substituted or unsubstituted C 1 -C 20 alkyl, substituted or unsubstituted C 1 -C 20 alkoxy, substituted or unsubstituted C 2 -C 20 alkenyl, substituted or unsubstituted C 2 -C 20 alkynyl, substituted or unsubstituted C 1 -C 20 heteroalkyl, substituted or unsubstituted C 6 -C 40 aryl, substituted or unsubstituted C 7 -C 40 arylalkyl, substituted or unsubstituted C 7 -C 40 alkylaryl, substituted or unsubstituted C 2 -C 40 heteroaryl, and substituted or unsubstituted C 3 -C 40 heteroarylalkyl;

X is a monoanionic monodentate ligand; and

n is one of 1 and 2.

Assignments (2)

MERGER Recorded Sep 21, 2012

From: SAMSUNG MOBILE DISPLAY CO., LTD.

To: SAMSUNG DISPLAY CO., LTD.

Reel/Frame 029241/0599 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 18, 2008

From: SAMSUNG SDI CO., LTD.

To: SAMSUNG MOBILE DISPLAY CO., LTD.

Reel/Frame 022034/0001 →