Metal coordination compound, luminescence device and display apparatus

• US 6,921,915 B2
• Filed: 03/06/2002
• Issued: 07/26/2005
• Est. Priority Date: 03/08/2001
• Status: Expired due to Term

• Current Assignee: Samsung Electronics Co. Ltd.
• Original Assignee: Canon Kabushiki Kaisha (Canon Inc.)
• Inventors: Furugori, Manabu, Tsuboyama, Akira, Moriyama, Takashi, Okada, Shinjiro, Miura, Seishi, Takiguchi, Takao, Kamatani, Jun
• Primary Examiner(s): CRANE, SARA W
• Application Number:
  US10/090,836
• Publication Number:
  US 20030068535A1
• Time in Patent Office: 1,238 Days
• Field of Search: 257/40, 257/103, 313/504, 252/519.3
• US Class Current: 257/40
• CPC Class Codes: C07F 15/0033 Iridium compounds
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 85/324 comprising aluminium, e.g. Alq3
• CPC Class Codes: H10K 85/342 comprising iridium
• CPC Class Codes: H10K 85/631 Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine

Abstract

An electroluminescence device having a layer containing a specific metal coordination compound is provided. The metal coordination compound is represented by formula (1) below:
ML_mL′_n  (1),
wherein M is a metal atom of Ir, Pt, Rh or Pd; L and L′ are mutually different bidentate ligands; m is 1, 2 or 3 and n is 0, 1 or 2 with the proviso that m+n is 2 or 3; a partial structure MLm is represented by formula (2) shown below and a partial structure ML′_n is represented by formula (3) or (4) shown below:
 

• • at least one of the optional substituent(s) of the cyclic groups, and the cyclic groups CyC₁ and CyC2 include an aromatic group capable of having a substituent represented by the following formula (5):
     

The metal coordination compound having the aromatic group is effective in providing high-efficiency luminescence and long-term high luminance.

Claims

1. A metal coordination compound represented by the following formula (6):

 

wherein X denotes CRR′

, O or S where R and R′

are independently a linear or branched alkyl group of formula;

C_nH_2n+1—

in which n is an integer of 1-20, the alkyl group can include one or non-neighboring two or more methylene groups that can be replaced with —

O— and

also can include a hydrogen atom that can be optionally replaced with a fluorine atom;

R2 denotes a hydrogen atom;

a fluorine atom;

a linear or branched alkyl group of formula;

C_nH_2n+1—

in which n is an integer of 1-20, the alkyl group can include one or non-neighboring two or more methylene groups that can be replaced with —

O— and

also can include a hydrogen atom that can be optionally replaced with a fluorine atom;

a phenyl group optionally having a substituent;

a 9,9-dialkylfluorenyl group (of which the alkyl groups are independently a linear or branched alkyl group of formula;

C_nH_2n+1—

in which n is an integer of 1-20, the alkyl group can include one or non-neighboring two or more methylene groups that can be replaced with —

O— and

also can include a hydrogen atom that can be optionally replaced with a fluorine atom);

a dibenzofuranyl group optionally having a substituent; and

a dibenzothienyl group optionally having a substituent; and

R1 and R4 independently denote a hydrogen atom;

a fluorine atom;

a phenyl group optionally having a substituent; and

a linear or branched alkyl group of formula;

C_nH_2n+1—

in which n is an integer of 1-20, the alkyl group can include one or non-neighboring two or more methylene groups that can be replaced with —

O— and

also can include a hydrogen atom that can be optionally replaced with a fluorine atom;

the said optional substituent of said phenyl group, said 9,9-dialkylfluorenyl group, said dibenzofuranyl group and said dibenzothienyl group is a fluorine atom or a linear or branched alkyl group of formula;

C_nH_2n+1—

in which n is an integer of 1-20, the alkyl group can include one or non-neighboring two or more methylene groups that can be replaced with —

O— and

also can include a hydrogen atom that can be optionally replaced with a fluorine atom.

2. An electroluminescence device, comprising:

a pair of electrodes disposed on a substrate, and a luminescence unit comprising at least one organic compound disposed between the electrodes, wherein the organic compound comprises a metal coordination compound represented by the formula (6) in claim 1.

3. An electroluminescence device according to claim 2, wherein a voltage is applied between the electrodes to emit light.

4. An electroluminescence device according to claim 2, wherein a voltage is applied between the electrodes to emit phosphorescense.

5. A picture display apparatus, comprising an electroluminescence device according to claim 2, and a means for supplying electric signals to the electroluminescence device.