Metal coordination compound, luminescence device and display apparatus

• US 20030054198A1
• Filed: 11/29/2001
• Published: 03/20/2003
• Est. Priority Date: 12/01/2000
• Status: Active Grant

• Current Assignee: Canon Kabushiki Kaisha (Canon Inc.)
• Original Assignee: Canon Kabushiki Kaisha (Canon Inc.)
• Inventors: Furugori, Manabu, Tsuboyama, Akira, Moriyama, Takashi, Igawa, Satoshi, Okada, Shinjiro, Mizutani, Hidemasa, Miura, Seishi, Takiguchi, Takao, Kamatani, Jun, Noguchi, Koji
• Granted Patent: US 6,991,857 B2
• Time in Patent Office: Days
• US Class Current: 428/690
• CPC Class Codes: C07F 15/0033 Iridium compounds
• CPC Class Codes: C07F 15/006 Palladium compounds
• CPC Class Codes: C07F 15/0073 Rhodium compounds
• CPC Class Codes: C07F 15/0086 Platinum compounds
• CPC Class Codes: H10K 2101/10 Triplet emission
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 85/146 poly N-vinylcarbazol; Derivatives thereof
• CPC Class Codes: H10K 85/342 comprising iridium
• CPC Class Codes: H10K 85/346 comprising platinum
• CPC Class Codes: H10K 85/361 Polynuclear complexes, i.e. complexes comprising two or more metal centers
• CPC Class Codes: Y10S 428/917 Electroluminescent

Abstract

An organic EL device includes a luminescence layer containing, as a luminescent material allowing a high-luminescence and high-efficiency luminescence for a long period of time, a metal coordination compound represented by the following formula (1): LmML′n, wherein M denotes Ir, Pt, Ph or Pd; L denotes a bidentate ligand; L′ denotes a bidentate ligand different from L; m is an integer of 1, 2 or 3; and n is an integer of 0, 1 or 2 with the proviso that the sum of m and n is 2 or 3. The partial structure MLm is represented by a formula (2) or a formula (3) shown below, and the partial structure ML′n is represented by a formula (4) or a formula (5) shown below:

wherein CyN1, CyN2 and CyN3 independently denote a substituted or unsubstituted cyclic group containing a nitrogen atom connected to M; CyN4 denotes a cyclic group containing 8-quinoline or its derivative having a nitrogen atom connected to M; CyC1, CyC2 and CyC3 independently denote a substituted or unsubstituted cyclic group containing a carbon atom connected to M, with the proviso that the metal coordination compound is represented by the formula (2) when n is 0.

Claims

1. A metal coordination compound represented by the following formula (1):

LmML′

n 

 

(1),

wherein M denotes Ir, Pt, Ph or Pd;

L denotes a bidentate ligand;

L′

denotes a bidentate ligand different from L;

m is an integer of 1, 2 or 3; and

n is an integer of 0, 1 or 2 with the proviso that the sum of m and n is 2 or 3,

the partial structure MLm being represented by a formula (2) or a formula (3) shown below, and the partial structure ML′

n being represented by a formula (4) or a formula (5) shown below;

wherein CyN1, CyN2 and CyN3 independently denote a substituted or unsubstituted cyclic group containing a nitrogen atom connected to M;

CyN4 denotes a cyclic group containing 8-quinoline or its derivative having a nitrogen atom connected to M;

CyC1, CyC2 and CyC3 independently denote a substituted or unsubstituted cyclic group containing a carbon atom connected to M,

each of substituents for CyN1, CyN2, CyN3, CyC1, CyC2 and CyC3 being selected from the group consisting of a halogen atom;

cyano group;

nitro group;

a trialkylsilyl group containing three linear or branched alkyl groups each independently having 1-8 carbon atoms;

a linear or branched alkyl group having 1-20 carbon atoms capable of including one or at least two non-neighboring methylene groups which can be replaced with —

O—

, —

S—

, —

CO—

, —

CO—

O—

, —

O—

CO—

, —

CH═

CH—

or —

C≡

C— and

capable of including a hydrogen atom which can be replaced with a fluorine atom; and

an aromatic ring group capable of having a substituent selected from the group consisting of a halogen atom;

cyano group;

nitro group; and

a linear or branched alkyl group having 1-20 carbon atoms capable of including one or at least two non-neighboring methylene groups which can be replaced with —

O—

, —

S—

, —

CO—

, —

CO—

O—

, —

O—

CO—

, —

CH═

CH—

or —

C≡

C— and

capable of including a hydrogen atom which can be replaced with a fluorine atom,

CyN1 and CyC1 being connected via a covalent group containing X which is represented by —

O—

, —

S—

, —

CO—

, —

C(R1)(R2)—

or —

NR—

where R1, R2 and R independently denote a hydrogen atom, a halogen atom, an alkyl group, an alkyl group substituted with a halogen atom, a phenyl group or a naphthyl group, and

CyN2 and CyC2, and CyN3 and CyC3 being independently connected via a covalent bond,

with the proviso that the metal coordination compound is represented by the formula (2) when n is 0.

2. A compound according to claim 1, wherein the partial structure MLm is represented by the formula (2).

3. A compound according to claim 2, wherein M is Ir.

4. A compound according to claim 2, wherein the metal coordination compound has another partial structure represented by the following formula (6):

5. A compound according to claim 1, which exhibits a phosphorescence at the time of energy transition from an excited state to a ground state.

6. A compound according to claim 1, wherein one of the ligands L and L′

is a luminescent ligand and the other ligand is a carrier transport ligand.

7. A compound according to claim 1, wherein at least one of the ligands L and L′

is in a metal to ligand charge transfer excited state.

8. A compound according to claim 1, wherein the ligands L and L′

includes a first ligand capable of providing a first maximum luminescence wavelength λ

1 based on an excited state thereof and a second ligand capable of providing a second maximum luminescence wavelength λ

2 shorter than λ

1, the number of the first ligand providing λ

1 being smaller than that of the second ligand providing λ

2.

9. A compound according to claim 1, wherein the ligands L and L′

includes a stronger luminescent ligand and a weaker luminescent ligand, the number of the stronger luminescent ligand is smaller than that of the weaker luminescent ligand.

10. An organic luminescence device, comprising:

a substrate, a pair of electrodes disposed on the substrate, and a luminescence function layer disposed between the pair of electrodes comprising at least one species of an organic compound,

wherein the organic compound comprises a metal coordination compound represented by the following formula (1);

LmML′

n 

 

(1),

wherein M denotes Ir, Pt, Ph or Pd;

L denotes a bidentate ligand;

L′

denotes a bidentate ligand different from L;

m is an integer of 1, 2 or 3; and

n is an integer of 0, 1 or 2 with the proviso that the sum of m and n is 2 or 3,

the partial structure MLm being represented by a formula (2) or a formula (3) shown below, and the partial structure ML′

n being represented by a formula (4) or a formula (5) shown below;

wherein CyN1, CyN2 and CyN3 independently denote a substituted or unsubstituted cyclic group containing a nitrogen atom connected to M;

CyN4 denotes a cyclic group containing 8-quinoline or its derivative having a nitrogen atom connected to M;

CyC1, CyC2 and CyC3 independently denote a substituted or unsubstituted cyclic group containing a carbon atom connected to M,

each of substituents for CyN1, CyN2, CyN3, CyC1, CyC2 and CyC3 being selected from the group consisting of a halogen atom;

cyano group;

nitro group;

a trialkylsilyl group containing three linear or branched alkyl groups each independently having 1-8 carbon atoms;

a linear or branched alkyl group having 1-20 carbon atoms capable of including one or at least two non-neighboring methylene groups which can be replaced with —

O—

, —

S—

, —

CO—

, —

CO—

O—

, —

O—

CO—

, —

CH═

CH—

or —

C≡

C— and

capable of including a hydrogen atom which can be replaced with a fluorine atom; and

an aromatic ring group capable of having a substituent selected from the group consisting of a halogen atom;

cyano group;

nitro group; and

a linear or branched alkyl group having 1-20 carbon atoms capable of including one or at least two non-neighboring methylene groups which can be replaced with —

O—

, —

S—

, —

CO—

, —

CO—

O—

, —

O—

CO—

, —

CH═

CH—

or —

C≡

C— and

capable of including a hydrogen atom which can be replaced with a fluorine atom,

CyN1 and CyC1 being connected via a covalent group containing X which is represented by —

O—

, —

S—

, —

CO—

, —

C(R1)(R2)—

or —

NR—

where R1, R2 and R independently denote a hydrogen atom, a halogen atom, an alkyl group, an alkyl group substituted with a halogen atom, a phenyl group or a naphthyl group, and

CyN2 and CyC2, and CyN3 and CyC3 being independently connected via a covalent bond,

with the proviso that the metal coordination compound is represented by the formula (2) when n is 0.

11. A device according to claim 10, wherein the partial structure MLm is represented by the formula (2).

12. A device according to claim 11, wherein M is Ir.

13. A device according to claim 10, wherein a voltage is applied between the pair of electrodes to cause phosphorescence from the luminescence function layer.

14. An image display device, comprising:

an organic luminescence device according to claim 10 and means for supplying electrical signals to the organic luminescence device.