IP Library Granted Patent US 7,670,692
Granted Patent B2
US 7,670,692 · App. 11/347,242 · Granted Mar 2, 2010

Cyclometalated transition metal complex and organic electroluminescent device using the same

Assignee: Samsung Mobile Display Co., Ltd.
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Quick Facts
Patent No.
US 7,670,692
App. No.
11/347,242
Granted
Mar 2, 2010
Kind
B2
Abstract

A cyclometalated transition metal complex very efficiently emits phosphorescent light and an organic electroluminescent device using the same. The transition metal complex is suitable for an organic layer of an organic electroluminescent device, can emit light with a wavelength of 400 to 650 nm, and can emit white light when used with a red emissive material or a green emissive material.

Claims (59)

1. A transition metal complex represented by Formula 1:

where M is a transition metal;

X is one of N and C;

L is a neutral ligand;

CY1 and CY2 are each independently an aromatic or aliphatic ring system, and CY1 contains a nitrogen atom that is bonded to M, and CY2 contains X that is bonded to M;

m is 1 or 2; and

A 1 , A 2 , A 3 , and A 4 are each independently imidazole, pyrazole, a derivative of the imidazole, or a derivative of pyrazole.

2. The transition metal complex of claim 1 , wherein the compound represented by Formula 1 is represented by one of Formulae 2 and 3:

where M is a transition metal;

X is one of N and C;

L is a neutral ligand;

CY1 and CY2 are each independently an aromatic or aliphatic ring system;

m is 1 or 2;

R 1 , R 2 , R 3 , and R 4 are each independently a substituent or H; and

n is 1, 2, or 3.

3. The transition metal complex of claim 1 , wherein A 1 , A 2 , A 3 , and A 4 are each independently substituted with one substituent selected from the group consisting of a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, an amino group, an alkoxy group, an aryloxy group, a heterocyclicoxy group, an acyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an acyloxy group, an acylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfonylamino group, a sulfamoyl group, a carbamoyl group, an alkylthio group, an arylthio group, a heterocyclicthio group, a sulfonyl group, a sulfynyl group, an ureido group, a phosphoric acid amid group, a hydroxyl group, a mercapto group, a halogen atom, a cyano group, a sulfo group, a carboxyl group, a nitro group, a hydroxamine acid group, a sulfino group, a hydrazino group, an imino group, a heterocyclic group a silyl group, and a silyloxy group.

4. The transition metal complex of claim 1 , wherein the compound represented by Formula 1 is represented by Formula 5:

where M is a transition metal;

L is a neutral ligand;

m is 1 or 2;

R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R, and R′ are each independently a substituent or a hydrogen atom where n is 1, 2, or 3; and

n 1 is 3.

5. The transition metal complex of claim 1 , wherein M is Ru, Rh, Os, Ir, Pt, Or Au.

6. The transition metal complex of claim 1 , wherein the compound represented by Formula 1 is represented by one of Formulae 6 through 16:

7. An organic electroluminescent device comprising an organic layer interposed between a pair of electrodes, the organic layer comprising the transition metal complex of claim 1 .

8. A transition metal complex represented by Formula 1:

where M is a transition metal;

CY1 contains a nitrogen atom that is bonded to M, and CY2 has X that is bonded to M;

X is one of N and C;

L is a neutral ligand;

m is 1 or 2; and

A 1 , A 2 , A 3 and A 4 are each independently imidazole, pyrazole, a derivative of the imidazole, or a derivative of pyrazole; and

CY1-CY2 formed by CY1 and CY2 is a cyclometalated ligand represented by one of Formulae 1-(i) to 1-(xxiii):

where R 1 , R 2 , R 3 , R 4 , and R 5 are single-substituted or multi-substituted functional groups, and R 1 , R 2 , R 3 , R 4 , and R 5 are each independently H, 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 C1-C20 alkyl group, or a C6-C20 aryl group, where R is a substituent or a hydrogen atom.

9. The transition metal complex of claim 8 , wherein L of Formula 1 is represented by one selected from the group consisting of Formulae 1-(xxix) to 1-(xxxx):

where R, R 1 , R 2 , and R 3 of Formulae 1-(xxix) to 1-(xxxx) are each independently an alkyl group, an alkoxy group, an aryl group, an aryloxy group, or a heteroaryl group.

10. An organic electroluminescent device comprising an organic layer interposed between a pair of electrodes, the organic layer composed of the transition metal complex of claim 8 .

11. An organic electroluminescent device, comprising:

a pair of electrodes; and

an organic layer interposed between the pair of electrodes, the organic layer comprising an emission layer composed of the transition metal complex represented by Formula 1:

where M is a transition metal;

X is one of N and C;

L is a neutral ligand;

CY1 and CY2 are each independently an aromatic or aliphatic ring system, and CY1 has a nitrogen atom that is bonded to M, and CY2 has X that is bonded to M;

m is 1 or 2; and

A 1 , A 2 , A 3 , and A 4 are each independently imidazole, pyrazole, a derivative of the imidazole, or a derivative of pyrazole.

12. The organic electroluminescent device of claim 11 , wherein the emission layer further comprises at least one host selected from the group consisting of at least one polymer host, a mixture of a polymer host and a low molecular weight host, a low molecular weight host, and a non-emissive polymer host.

13. The organic electroluminescent device of claim 11 , wherein the emission layer further comprises a green emissive material or a red emissive material.

14. The organic electroluminescent device of claim 11 , wherein the transition metal complex is represented by one of Formulae 2 and 3:

where R 1 , R 2 , R 3 , and R 4 are each independently a substituent or H; and

n is 1, 2, or 3.

15. The organic electroluminescent device of claim 11 , wherein A 1 , A 2 , A 3 , and A 4 are each independently substituted with one substituent selected from the group consisting of a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, an amino group, an alkoxy group, an aryloxy group, a heterocyclicoxy group, an acyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an acyloxy group, an acylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfonylamino group, a sulfamoyl group, a carbamoyl group, an alkylthio group, an arylthio group, a heterocyclicthio group, a sulfonyl group, a sulfynyl group, an ureido group, a phosphoric acid amid group, a hydroxyl group, a mercapto group, a halogen atom, a cyano group, a sulfo group, a carboxyl group, a nitro group, a hydroxamine acid group, a sulfino group, a hydrazino group, an imino group, a heterocyclic group a silyl group, and a silyloxy group.

16. The organic electroluminescent device of claim 11 , wherein the compound represented by Formula 1 is represented by Formula 5:

where R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R, and R′ are each independently a substituent or a hydrogen atom where n is 1, 2, or 3; and

n 1 is 3.

17. The organic electroluminescent device of claim 11 , wherein M is Ru, Rh, Os, Ir, Pt, or Au.

18. The organic electroluminescent device of claim 11 , wherein the transition metal complex is represented by one of Formulae 6 through 16:

19. The organic electroluminescent device of claim 18 , wherein the organic layer further comprises a green emissive material or a red emissive material.

20. The organic electroluminescent device of claim 11 , wherein the organic electroluminescent device emits light of 400 nm to 650 nm.

Assignments (3)
MERGER Recorded Jun 25, 2021
From: SAMSUNG MOBILE DISPLAY CO., LTD.
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 056695/0361 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 18, 2008
From: SAMSUNG SDI CO., LTD.
To: SAMSUNG MOBILE DISPLAY CO., LTD.
Reel/Frame 022034/0001 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 6, 2006
From: RAGINI, DAS RUPASREE; CHANG, SEOK; HAN, EUN-SIL; KIM, HEE-KYUNG; PU, LYONG-SUN; LEE, JONG-HYOUP
To: SAMSUNG SDI CO., LTD.,
Reel/Frame 017607/0647 →
Priority Claims (1)
KR 10-2005-0010857 · Feb 4, 2005 · national
Continuity (1)
Related Publication 20060177695A1 · Aug 10, 2006