Organometallic complex and organic electroluminescent device using the same
View Patent ↗Provided are a highly efficient phosphorescent organometallic complex and an organic electroluminescent (EL) device using the same. The organometallic complex can be used in the formation of an organic layer of the organic EL device, and can emit light in a red wavelength range as a highly efficient phosphorescent material. The organic EL device using the organometallic complex can exhibit high brightness and a low driving voltage.
1. An organometallic complex represented by Formula 2 below:
wherein,
M is Ir, Os, Pt, Pb, Re, Ru, or Pd;
CyN is a substituted or unsubstituted C3-C60 heterocyclic group comprising nitrogen bound to M or a substituted or unsubstituted C3-C60 heteroaryl group comprising nitrogen bound to M;
CyC is a substituted or unsubstituted C4-C60 carbocyclic group comprising carbon bound to M, a substituted or unsubstituted C3-C60 heterocyclic group comprising carbon bound to M, a substituted or unsubstituted C6-C60 aryl group comprising carbon bound to M, or a substituted or unsubstituted C3-C60 heteroaryl group comprising carbon bound to M;
CyN-CyC is a cyclometalating ligand bound to M via nitrogen (N) and carbon (C);
X is NR a , O, S, SiR b R c or CR d R e ;
R 1 , R 4 , R 5 , R 6 , R 7 , R 8 , R a , R b , R c , R d , and R e are each independently hydrogen, a hydroxyl group, a sulfo group, 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 group, 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 6 -C 30 aryloxy group, a substituted or unsubstituted C 2 -C 20 alkoxycarbonyl group, a substituted or unsubstituted C 1 -C 20 acyloxy group, a substituted or unsubstituted C 1 -C 20 acylamino group, a substituted or unsubstituted C2-C20 alkoxycarbonylamino group, a substituted or unsubstituted C 7 -C 30 aryloxycarbonylamino group, a sulfonylamino group, a sulfamoyl group, a carbamoyl group, a substituted or unsubstituted C 6 -C 30 arylthio group, a substituted or unsubstituted C3-C30 heteroarylthio group, a sulfonyl group, a sulfinyl group, an ureido group, a phosphoric acid amido group, a hydroxaminic group, a sulfino group, a hydrazine group, an imino group, a silyl group, a phosphino group, a phosphinyl a substituted or unsubstituted C4-C30 cycloalkyl group, a substituted or unsubstituted C 7 -C 30 arylalkyl group, a substituted or unsubstituted C 5 -C 30 heteroaryl group, or a substituted or unsubstituted C 3 -C 30 heteroarylalkyl group.
2. The organometallic complex of claim 1 , wherein the compound of Formula 2 is selected from compounds represented by Formulae 4 through 9 below:
3. The organometallic complex of claim 1 , wherein the cyclometalating ligand CyN-CyC is one of compounds represented by the following formulae:
wherein,
R 11 , R 12 , R 13 , R 14 , and R 15 are each independently a monosubstituted or polysubstituted functional group selected from 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 where R is selected from 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 group, 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 C1-C20 alkyl group.
4. The organometallic complex of claim 1 , wherein the ligand bound to the central metal via nitrogen and oxygen atoms is one of compounds represented by the following formulae:
wherein
R 21 , R 22 , and R 23 are each independently a monosubstituted or polysubstituted functional group selected from 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 where R is selected from 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 group, 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
X is oxygen or sulfur.
5. The organometallic complex of claim 1 , wherein M is Ir or Pt.
6. An organic electroluminescent (EL) device comprising an organic layer interposed between a pair of electrodes,
wherein the organic layer comprises the organometallic complex of claim 1 .
7. The organic EL device of claim 6 , wherein the organic layer is an emitting layer.
8. The organic EL device of claim 6 , wherein the content of the organometallic complex is 1 to 30 parts by weight based on the total weight (100 parts by weight) of an emitting layer forming material.