Organometallic complexes and organic electroluminescence device using the same

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;
• CyN is selected from the group consisting of a substituted C3-C60 heterocyclic group containing nitrogen bonded to said M, an unsubstituted C3-C60 heterocyclic group containing nitrogen bonded to said M, a substituted C3-C60 heteroaryl group containing nitrogen bonded to said M, and an unsubstituted C3-C60 heteroaryl group containing nitrogen bonded to said M;
• CyC is selected from the group consisting of an unsubstituted C4-C60 carbocyclic group containing carbon bonded to said M, a substituted C4-C60 carbocyclic group containing carbon bonded to said M, an unsubstituted C3-C60 heterocyclic group containing carbon bonded to said M, a substituted C3-C60 heterocyclic group containing carbon bonded to said M, an unsubstituted C6-C60 aryl containing carbon bonded to said M, a substituted C6-C60 aryl containing carbon bonded to said M, an unsubstituted C3-C60 heteroaryl containing carbon bonded to said M, and a substituted C3-C60 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, —PO2R, —PO3R, —SR, —Si(R)(R′)(R″), —B(R)(R′), —B(OR)(OR′), —C(O)R, —C(O)OR, —C(O)N(R), —CN, —NO2, —SO2, —SOR, —SO2R, —SO3R, substituted or unsubstituted C1-C20 alkyl, and substituted or unsubstituted C6-C20 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 C1-C70 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C6-C40 aryl, substituted or unsubstituted C7-C40 arylalkyl, substituted or unsubstituted C7-C40 alkylaryl, substituted or unsubstituted C2-C40 heteroaryl, and substituted or unsubstituted C3-C40 heteroarylalkyl;
• alternatively, the CyN-CyC is represented by the Formula 1a:
• wherein R1, R2, R3, and R4 are independently selected from the group consisting of hydrogen, halogen atom, —ORa, —N(Ra)2, —P(Ra)2, —PORa, —PO2Ra, —PO3Ra, —SRa, —Si(Ra)3, —B(Ra)2, —B(ORa)2, —C(O)Ra, —C(O)ORa, —C(O)N(Ra), —CN, —NO2—SO2, —SORa, —SO2Ra, —SO3Ra, C1-C20 alkyl, and C6-C20 aryl, and Ra is selected from the group consisting of hydrogen, a substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C6-C40 aryl, substituted or unsubstituted C7-C40 arylalkyl, substituted or unsubstituted C7-C40 alkylaryl, substituted or unsubstituted C2-C40 heteroaryl, and substituted or unsubstituted C3-C40 heteroarylalkyl;
• R6 and R7 are independently selected from the group consisting of hydrogen, halogen atom, —ORc, —N(Rc)2, —P(Rc)2, —PORc, —PO2Rc, —PO3Rc, SRc, —Si(Rc)3, —B(Rc)2, —B(ORc)2, —C(O)Rc, —C(O)ORc, —C(O)N(Rc), —CN, —NO2, —SO2, —SOW, —SO2Rc, —SO3Rc, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C20 aryl or substituted or unsubstituted C2-C20 heteroaryl group, and Rc is selected from the group consisting of hydrogen, a substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C6-C40 aryl, substituted or unsubstituted C7-C40 arylalkyl, substituted or unsubstituted C7-C40 alkylaryl, substituted or unsubstituted C2-C40 heteroaryl, and substituted or unsubstituted C3-C40 heteroarylalkyl;
• substituents of R6 and R7, which are substituted at different positions, are alternatively interconnected to form a substituted or unsubstituted fused 4-7 atom ring;
• R8, R9, and R10 are independently a substituted or unsubstituted C1-C20 alkyl, a substituted or unsubstituted C6-C20 aryl or substituted or unsubstituted C2-C20 heteroaryl group;
• X is selected from the group consisting of F, Cl, Br, I, CN, CN(R11), SCN or OCN, R11 is selected from the group consisting of hydrogen, a substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C6-C40 aryl, substituted or unsubstituted C7-C40 arylalkyl, substituted or unsubstituted C7-C40 alkylaryl, substituted or unsubstituted C2-C40 heteroaryl, and substituted or unsubstituted C3-C40 heteroarylalkyl;
• and
• n is one of 1 and 2.

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;
• CyN is selected from the group consisting of a substituted C3-C60 heterocyclic group containing nitrogen bonded to said M, an unsubstituted C3-C60 heterocyclic group containing nitrogen bonded to said M, a substituted C3-C60 heteroaryl group containing nitrogen bonded to said M, and an unsubstituted C3-C60 heteroaryl group containing nitrogen bonded to said M;
• CyC is selected from the group consisting of an unsubstituted C4-C60 carbocyclic group containing carbon bonded to said M, a substituted C4-C60 carbocyclic group containing carbon bonded to said M, an unsubstituted C3-C60 heterocyclic group containing carbon bonded to said M, a substituted C3-C60 heterocyclic group containing carbon bonded to said M, an unsubstituted C6-C60 aryl containing carbon bonded to said M, a substituted C6-C60 aryl containing carbon bonded to said M, an unsubstituted C3-C60 heteroaryl containing carbon bonded to said M, and a substituted C3-C60 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, —PO2R, —PO3R, —SR, —Si(R)(R′)(R″), —B(R)(R′), —B(OR)(OR′), —C(O)R, —C(O)OR, —C(O)N(R), —CN, —NO2, —SO2, —SOR, —SO2R, —SO3R, substituted or unsubstituted C1-C20 alkyl, and substituted or unsubstituted C6-C20 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 C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C6-C40 aryl, substituted or unsubstituted C7-C40 arylalkyl, substituted or unsubstituted C7-C40 alkylaryl, substituted or unsubstituted C2-C40 heteroaryl, and substituted or unsubstituted C3-C40 heteroarylalkyl;
• alternatively, the CyN-CyC is represented by the Formula 1a:
• wherein R1, R2, R3, and R4 are independently selected from the group consisting of hydrogen, halogen atom, —ORa, —N(Ra)2, —P(Ra)2, —PORa, —PO2Ra, —PO3Ra, —SRa, —Si(Ra)3, —B(Ra)2, —B(ORa)2, —C(O)Ra, —C(O)ORa, —C(O)N(Ra), —CN, —NO2, —SO2, —SORa, —SO2Ra, —SO3Ra, C1-C20 alkyl, and C6-C20 aryl, and Ra is selected from the group consisting of hydrogen, a substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C6-C40 aryl, substituted or unsubstituted C7-C40 arylalkyl, substituted or unsubstituted C7-C40 alkylaryl, substituted or unsubstituted C2-C40 heteroaryl, and substituted or unsubstituted C3-C40 heteroarylalkyl;
• 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.

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;
• CyN is selected from the group consisting of a substituted C3-C60 heterocyclic group containing nitrogen bonded to said M, an unsubstituted C3-C60 heterocyclic group containing nitrogen bonded to said M, a substituted C3-C60 heteroaryl group containing nitrogen bonded to said M, and an unsubstituted C3-C60 heteroaryl group containing nitrogen bonded to said M;
• CyC is selected from the group consisting of an unsubstituted C4-C60 carbocyclic group containing carbon bonded to said M, a substituted C4-C60 carbocyclic group containing carbon bonded to said M, an unsubstituted C3-C60 heterocyclic group containing carbon bonded to said M, a substituted C3-C60 heterocyclic group containing carbon bonded to said M, an unsubstituted C6-C60 aryl containing carbon bonded to said M, a substituted C6-C60 aryl containing carbon bonded to said M, an unsubstituted C3-C60 heteroaryl containing carbon bonded to said M, and a substituted C3-C60 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, —PO2R, —PO3R, —SR, —Si(R)(R′)(R″), —B(R)(R′), —B(OR)(OR′), —C(O)R, —C(O)OR, —C(O)N(R), —CN, —NO2, —SO2, —SOR, —SO2R, —SO3R, substituted or unsubstituted C1-C20 alkyl, and substituted or unsubstituted C6-C20 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 C1-C70 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C6-C40 aryl, substituted or unsubstituted C7-C40 arylalkyl, substituted or unsubstituted C7-C40 alkylaryl, substituted or unsubstituted C2-C40 heteroaryl, and substituted or unsubstituted C3-C40 heteroarylalkyl;
• alternatively, the CyN-CyC is represented by the Formula 1a:
• wherein R1, R2, R3, and R4 are independently selected from the group consisting of hydrogen, halogen atom, —ORa, —N(Ra)2, —P(Ra)2, —PORa, —PO2Ra—PO3Ra, —SRa, —Si(Ra)3, —B(Ra)2—, —B(ORa)2, —C(O)Ra, —C(O)ORa, —C(O)N(Ra), —CN, —NO2—SO2, —SORa, —SO2Ra—SO3Ra, C1-C20 alkyl, and C6-C20 aryl, and Ra is selected from the group consisting of hydrogen, a substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C6-C40 aryl, substituted or unsubstituted C7-C40 arylalkyl, substituted or unsubstituted C7-C40 alkylaryl, substituted or unsubstituted C2-C40 heteroaryl, and substituted or unsubstituted C3-C40 heteroarylalkyl;
• R6 and R7 are independently selected from the group consisting of hydrogen, halogen atom, —ORc, —N(Rc)2, —P(Rc)2, —PORc, —PO2Rc, —PO3Rc, —SRc, —Si(Rc)3, —B(Rc)2, —B(ORc)2, —C(O)Rc, —C(O)ORc, —C(O)N(Rc), —CN, —NO2, —SO2, —SOW, —SO2Rc, —SO3Rc, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C20 aryl or substituted or unsubstituted C2-C20 heteroaryl group, and Rc is selected from the group consisting of hydrogen, a substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C6-C40 aryl, substituted or unsubstituted C7-C40 arylalkyl, substituted or unsubstituted C7-C40 alkylaryl, substituted or unsubstituted C2-C40 heteroaryl, and substituted or unsubstituted C3-C40 heteroarylalkyl;
• substituents of R6 and R7, which are substituted at different positions, are alternatively interconnected to form a substituted or unsubstituted fused 4-7 atom ring;
• R8, R9, and R10 are independently a substituted or unsubstituted C1-C20 alkyl, a substituted or unsubstituted C6-C20 aryl or substituted or unsubstituted C2-C20 heteroaryl group;
• X is selected from the group consisting of F, Cl, Br, I, CN, CN(R11), SCN or OCN, R11 is selected from the group consisting of hydrogen, a substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C6-C40 aryl, substituted or unsubstituted C7-C40 arylalkyl, substituted or unsubstituted C7-C40 alkylaryl, substituted or unsubstituted C2-C40 heteroaryl, and substituted or unsubstituted C3-C40 heteroarylalkyl;
• and
• n is one of 1 and 2.

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;
• CyN is selected from the group consisting of a substituted C3-C60 heterocyclic group containing nitrogen bonded to said M, an unsubstituted C3-C60 heterocyclic group containing nitrogen bonded to said M, a substituted C3-C60 heteroaryl group containing nitrogen bonded to said M, and an unsubstituted C3-C60 heteroaryl group containing nitrogen bonded to said M;
• CyC is selected from the group consisting of an unsubstituted C4-C60 carbocyclic group containing carbon bonded to said M, a substituted C4-C60 carbocyclic group containing carbon bonded to said M, an unsubstituted C3-C60 heterocyclic group containing carbon bonded to said M, a substituted C3-C60 heterocyclic group containing carbon bonded to said M, an unsubstituted C6-C60 aryl containing carbon bonded to said M, a substituted C6-C60 aryl containing carbon bonded to said M, an unsubstituted C3-C60 heteroaryl containing carbon bonded to said M, and a substituted C3-C60 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, —PO2R, —PO3R, —SR, —Si(R)(R′)(R″), —B(R)(R′), —B(OR)(OR′), —C(O)R, —C(O)OR, —C(O)N(R), —CN, —NO2, —SO2, —SOR, —SO2R, —SO3R, substituted or unsubstituted C1-C20 alkyl, and substituted or unsubstituted C6-C20 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 C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C6-C40 aryl, substituted or unsubstituted C7-C40 arylalkyl, substituted or unsubstituted C7-C40 alkylaryl, substituted or unsubstituted C2-C40 heteroaryl, and substituted or unsubstituted C3-C40 heteroarylalkyl;
• alternatively, the CyN-CyC is represented by the Formula 1a:
• wherein R1, R2, R3, and R4 are independently selected from the group consisting of hydrogen, halogen atom, —ORa, —N(Ra)2, —P(Ra)2, —PORa, —PO2Ra, —PO3Ra, —SRa, —Si(Ra)3, —B(Ra)2, —B(ORa)2, —C(O)Ra, —C(O)ORa, —C(O)N(Ra), —CN, —NO2, —SO2, —SORa, —SO2Ra, —SO3Ra, C1-C20 alkyl, and C6-C20 aryl, and Ra is selected from the group consisting of hydrogen, a substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C6-C40 aryl, substituted or unsubstituted C7-C40 arylalkyl, substituted or unsubstituted C7-C40 alkylaryl, substituted or unsubstituted C2-C40 heteroaryl, and substituted or unsubstituted C3-C40 heteroarylalkyl;
• R6 is selected from the group consisting of hydrogen, halogen atom, —ORc, —N(Rc)2, —P(Rc)2, —PORc, —PO2Rc, —PO3Rc, —SRc, —Si(Rc)3, —B(Rc)2, —B(ORc)2, —C(O)Rc, —C(O)ORc, —C(O)N(Rc), —CN, —NO2, —SO2, —SORc, —SO2Rc, —SO3Rc, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C20 aryl or substituted or unsubstituted C2-C20 heteroaryl group, and Rc is selected from the group consisting of hydrogen, a substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C6-C40 aryl, substituted or unsubstituted C7-C40 arylalkyl, substituted or unsubstituted C7-C40 alkylaryl, substituted or unsubstituted C2-C40 heteroaryl, and substituted or unsubstituted C3-C40 heteroarylalkyl;
• R7 is selected from the group consisting of hydrogen, halogen atom, —ORc, —N(Rc)2, —P(Rc)2, —PORc, —PO2Rc, —PO3Rc, —SRc, —Si(Rc)3, —B(Rc)2, —B(ORc)2, —C(O)Rc, —C(O)ORc, —C(O)N(Rc), —CN, —NO2, —SO2, —SOW, —SO2Rc, —SO3Rc, substituted or unsubstituted C2-C20 alkyl, substituted or unsubstituted C6-C20 aryl or substituted or unsubstituted C2-C20 heteroaryl group, and Rc is selected from the group consisting of hydrogen, a substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C6-C40 aryl, substituted or unsubstituted C7-C40 arylalkyl, substituted or unsubstituted C7-C40 alkylaryl, substituted or unsubstituted C2-C40 heteroaryl, and substituted or unsubstituted C3-C40 heteroarylalkyl;
• substituents of R6 and R7, which are substituted at different positions, are alternatively interconnected to form a substituted or unsubstituted fused 4-7 atom ring;
• and R6 and R7 are not hydrogen at the same time;
• X is selected from the group consisting of F, Br, I, CN, CN(R11), SCN or OCN, R11 is selected from the group consisting of hydrogen, a substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C6-C40 aryl, substituted or unsubstituted C7-C40 arylalkyl, substituted or unsubstituted C7-C40 alkylaryl, substituted or unsubstituted C2-C40 heteroaryl, and substituted or unsubstituted C3-C40 heteroarylalkyl;
• and
• n is one of 1 and 2.

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 C3-C60 heterocyclic group containing nitrogen bonded to said M, an unsubstituted C3-C60 heterocyclic group containing nitrogen bonded to said M, a substituted C3-C60 heteroaryl group containing nitrogen bonded to said M, and an unsubstituted C3-C60 heteroaryl group containing nitrogen bonded to said M;
• CyC is selected from the group consisting of an unsubstituted C4-C60 carbocyclic group containing carbon bonded to said M, a substituted C4-C60 carbocyclic group containing carbon bonded to said M, an unsubstituted C3-C60 heterocyclic group containing carbon bonded to said M, a substituted C3-C60 heterocyclic group containing carbon bonded to said M, an unsubstituted C6-C60 aryl containing carbon bonded to said M, a substituted C6-C60 aryl containing carbon bonded to said M, an unsubstituted C3-C60 heteroaryl containing carbon bonded to said M, and a substituted C3-C60 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, —PO2R, —PO3R, —SR, —Si(R)(R′)(R″), —B(R)(R′), —B(OR)(OR′), —C(O)R, —C(O)OR, —C(O)N(R), —CN, —NO2, —SO2, —SOR, —SO2R, —SO3R, substituted or unsubstituted C1-C20 alkyl, and substituted or unsubstituted C6-C20 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 C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C6-C40 aryl, substituted or unsubstituted C7-C40 arylalkyl, substituted or unsubstituted C7-C40 alkylaryl, substituted or unsubstituted C2-C40 heteroaryl, and substituted or unsubstituted C3-C40 heteroarylalkyl;
• alternatively, the CyN-CyC is represented by the Formula 1a:
• wherein R1, R2, R3, and R4 are independently selected from the group consisting of hydrogen, halogen atom, —ORa, —N(Ra)2, —P(Ra)2, —PORa, —PO2Ra, —PO3Ra, —SRa, —Si(Ra)3, —B(Ra)2, —B(ORa)2, —C(O)Ra, —C(O)ORa, —C(O)N(Ra), —CN, —NO2, —SO2, —SORa, —SO2Ra, —SO3Ra, C1-C20 alkyl, and C6-C20 aryl, and Ra is selected from the group consisting of hydrogen, a substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C6-C40 aryl, substituted or unsubstituted C7-C40 arylalkyl, substituted or unsubstituted C7-C40 alkylaryl, substituted or unsubstituted C2-C40 heteroaryl, and substituted or unsubstituted C3-C40 heteroarylalkyl;
• 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.

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;
• CyN is selected from the group consisting of a substituted C3-C60 heterocyclic group containing nitrogen bonded to said M, an unsubstituted C3-C60 heterocyclic group containing nitrogen bonded to said M, a substituted C3-C60 heteroaryl group containing nitrogen bonded to said M, and an unsubstituted C3-C60 heteroaryl group containing nitrogen bonded to said M;
• CyC is selected from the group consisting of an unsubstituted C4-C60 carbocyclic group containing carbon bonded to said M, a substituted C4-C60 carbocyclic group containing carbon bonded to said M, an unsubstituted C3-C60 heterocyclic group containing carbon bonded to said M, a substituted C3-C60 heterocyclic group containing carbon bonded to said M, an unsubstituted C6-C60 aryl containing carbon bonded to said M, a substituted C6-C60 aryl containing carbon bonded to said M, an unsubstituted C3-C60 heteroaryl containing carbon bonded to said M, and a substituted C3-C60 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, —PO2R, —PO3R, —SR, —Si(R)(R′)(R″), —B(R)(R′), —B(OR)(OR′), —C(O)R, —C(O)OR, —C(O)N(R), —CN, —NO2, —SO2, —SOR, —SO2R, —SO3R, substituted or unsubstituted C1-C20 alkyl, and substituted or unsubstituted C6-C20 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 C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C6-C40 aryl, substituted or unsubstituted C7-C40 arylalkyl, substituted or unsubstituted C7-C40 alkylaryl, substituted or unsubstituted C2-C40 heteroaryl, and substituted or unsubstituted C3-C40 heteroarylalkyl;
• alternatively, the CyN-CyC is represented by the Formula 1a:
• wherein R1, R2, R3, and R4 are independently selected from the group consisting of hydrogen, halogen atom, —ORa, —N(Ra)2, —P(Ra)2, —PORa, —PO2Ra, —PO3Ra, —SRa, —Si(Ra)3, —B(Ra)2, —B(ORa)2, —C(O)Ra, —C(O)ORa, —C(O)N(Ra), —CN, —NO2, —SO2, —SORa, —SO2Ra, —SO3Ra, C1-C20 alkyl, and C6-C20 aryl, and Ra is selected from the group consisting of hydrogen, a substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C6-C40 aryl, substituted or unsubstituted C7-C40 arylalkyl, substituted or unsubstituted C7-C40 alkylaryl, substituted or unsubstituted C2-C40 heteroaryl, and substituted or unsubstituted C3-C40 heteroarylalkyl;
• 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.

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;
• CyN is selected from the group consisting of a substituted C3-C60 heterocyclic group containing nitrogen bonded to said M, an unsubstituted C3-C60 heterocyclic group containing nitrogen bonded to said M, a substituted C3-C60 heteroaryl group containing nitrogen bonded to said M, and an unsubstituted C3-C60 heteroaryl group containing nitrogen bonded to said M;
• CyC is selected from the group consisting of an unsubstituted C4-C60 carbocyclic group containing carbon bonded to said M, a substituted C4-C60 carbocyclic group containing carbon bonded to said M, an unsubstituted C3-C60 heterocyclic group containing carbon bonded to said M, a substituted C3-C60 heterocyclic group containing carbon bonded to said M, an unsubstituted C6-C60 aryl containing carbon bonded to said M, a substituted C6-C60 aryl containing carbon bonded to said M, an unsubstituted C3-C60 heteroaryl containing carbon bonded to said M, and a substituted C3-C60 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, —PO2R, —PO3R, —SR, —Si(R)(R′)(R″), —B(R)(R′), —B(OR)(OR′), —C(O)R, —C(O)OR, —C(O)N(R), —CN, —NO2, —SO2, —SOR, —SO2R, —SO3R, substituted or unsubstituted C1-C20 alkyl, and substituted or unsubstituted C6-C20 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 C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C6-C40 aryl, substituted or unsubstituted C7-C40 arylalkyl, substituted or unsubstituted C7-C40 alkylaryl, substituted or unsubstituted C2-C40 heteroaryl, and substituted or unsubstituted C3-C40 heteroarylalkyl;
• alternatively, the CyN-CyC is represented by the Formula 1a:
• wherein R1, R2, R3, and R4 are independently selected from the group consisting of hydrogen, halogen atom, —ORa, —N(Ra)2, —P(Ra)2, —PORa, —PO2Ra, —PO3Ra, —SRa, —Si(Ra)3, —B(Ra)2, —B(ORa)2, —C(O)Ra, —C(O)ORa, —C(O)N(Ra), —CN, —NO2, —SO2, —SORa, —SO2Ra, —SO3Ra, C1-C20 alkyl, and C6-C20 aryl, and Ra is selected from the group consisting of hydrogen, a substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C6-C40 aryl, substituted or unsubstituted C7-C40 arylalkyl, substituted or unsubstituted C7-C40 alkylaryl, substituted or unsubstituted C2-C40 heteroaryl, and substituted or unsubstituted C3-C40 heteroarylalkyl;
• R6 is selected from the group consisting of hydrogen, halogen atom, —ORc, —N(Rc)2, —P(Rc)2, —PORc, —PO2Rc, —PO3Rc, —SRc, —Si(Rc)3, —B(Rc)2, —B(ORc)2, —C(O)Rc, —C(O)ORc, —C(O)N(Rc), —CN, —NO2, —SO2, —SORc, —SO2Rc, —SO3Rc, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C20 aryl or substituted or unsubstituted C2-C20 heteroaryl group, and Rc is selected from the group consisting of hydrogen, a substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C6-C40 aryl, substituted or unsubstituted C7-C40 arylalkyl, substituted or unsubstituted C7-C40 alkylaryl, substituted or unsubstituted C2-C40 heteroaryl, and substituted or unsubstituted C3-C40 heteroarylalkyl;
• R7 is selected from the group consisting of hydrogen, halogen atom, —ORc, —N(Rc)2, —P(Rc)2, —PORc, —PO2Rc, —PO3Rc, —SRc, —Si(Rc)3, —B(Rc)2, —B(ORc)2, —C(O)Rc, —C(O)ORc, —C(O)N(Rc), —CN, —NO2, —SO2, —SORc, —SO2Rc, —SO3Rc, substituted or unsubstituted C2-C20 alkyl, substituted or unsubstituted C6-C20 aryl or substituted or unsubstituted C2-C20 heteroaryl group, and Rc is selected from the group consisting of hydrogen, a substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C6-C40 aryl, substituted or unsubstituted C7-C40 arylalkyl, substituted or unsubstituted C7-C40 alkylaryl, substituted or unsubstituted C2-C40 heteroaryl, and substituted or unsubstituted C3-C40 heteroarylalkyl;
• substituents of R6 and R7, which are substituted at different positions, are alternatively interconnected to form a substituted or unsubstituted fused 4-7 atom ring;
• and R6 and R7 are not hydrogen at the same time;
• X is a monoanionic monodentate ligand;
• and
• n is one of 1 and 2.