Metal complex and device using the metal complex

Patent metadata

Field	Value
Publication number	US-9287514-B2
Application number	US-201113822867-A
Country	US
Kind code	B2
Filing date	Sep 12, 2011
Priority date	Sep 15, 2010
Publication date	Mar 15, 2016
Grant date	Mar 15, 2016

Abstract

Disclosed is an device having high light-emitting efficiency. A metal complex represented by the following formula (1).

In the formula (1), n represents an integer of 1 to 3. L A and L B each independently represent the moiety of a group bonded to an iridium atom, except for coordinating atoms. When n is 3, a metal complex represented by the following formula (1-3):

wherein Me represents a methyl group) is excluded.

First claim

The invention claimed is:

1. A metal complex represented by formula (1):

wherein:
in formula (1), n is 1 or 2; L A and L B each independently represent a moiety of a group bonded to an iridium atom except for coordinating atoms; a group represented by formula (1-1):

means a group represented by formula (L1):

wherein, in formula (L1), R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 each independently represent a hydrogen atom, an alkyl group, an aryl group, a monovalent aromatic heterocyclic group, an alkoxy group, an aryloxy group, an aralkyl group, an arylalkoxy group, a substituted amino group, a substituted carbonyl group, a substituted carboxyl group, an alkenyl group, an alkynyl group, a halogen atom, or a cyano group; Ar 1 and Ar 2 each independently represent an aryl group optionally having a substituent or a monovalent aromatic heterocyclic group optionally having a substituent; X 1 represents a bivalent group in which two or more groups selected from among the group consisting of an arylene group, a bivalent aromatic heterocyclic group, and an ethynylene group are directly bonded to each other, an arylene group, a bivalent aromatic heterocyclic group, an ethynylene group, or a direct bond;
a group represented by formula (1-2):

is different from the group represented by the formula (1-1) and means a group represented by a formula (L2):

wherein, in formula (L2), R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 and R 15 each independently represent a hydrogen atom, an alkyl group, an aryl group, a monovalent aromatic heterocyclic group, an alkoxy group, an aryloxy group, an aralkyl group, an arylalkoxy group, a substituted amino group, a substituted carbonyl group, a substituted carboxyl group, an alkenyl group, an alkynyl group, a halogen atom, or a cyano group; and
when two groups represented by the formula (1-1) are present, the groups represented by the formula (1-1) may be the same as or different from each other; and when two groups represented by the formula (1-2) are present, the groups represented by the formula (1-2) may be the same as or different from each other.

2. The metal complex according to claim 1 , wherein the group represented by the formula (L1) is a group represented by formula (L1-1):

wherein, in formula (L1-1), R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and X 1 are as defined above; R 16 , R 17 , R 18 , R 19 , R 20 , and R 21 each independently represent a hydrogen atom, an alkyl group, an aryl group, a monovalent aromatic heterocyclic group, an alkoxy group, an aryloxy group, an aralkyl group, an arylalkoxy group, a substituted amino group, a substituted carbonyl group, a substituted carboxyl group, an alkenyl group, an alkynyl group, a halogen atom, or a cyano group; S 1 , S 2 , S 3 , and S 4 each independently represent an alkyl group, an alkoxy group, an aryl group, an aralkyl group, a substituted amino group, or a monovalent aromatic heterocyclic group; and these groups may have a substituent.

3. The metal complex according to claim 2 , wherein S 1 , S 2 , S 3 , and S 4 are each independently an alkyl group, an aryl group, a substituted amino group, or a monovalent aromatic heterocyclic group.

4. The metal complex according to claim 2 , wherein S 1 , S 2 , S 3 , and S 4 are each independently an alkyl group or an aryl group.

5. The metal complex according to claim 2 , wherein S 1 , S 2 , S 3 , and S 4 are an alkyl group.

6. The metal complex according to claim 1 , wherein X 1 is a direct bond.

7. The metal complex according to claim 2 , wherein at least one of R 16 , R 17 , R 18 , R 19 , R 20 , and R 21 is an alkyl group.

8. A composition comprising:
a charge transporting material; and
a metal complex represented by formula (1):

wherein:
in formula (1), n is 1 or 2: L A and L B each independently represent a moiety of a group bonded to an iridium atom except for coordinating atoms; a group represented by formula (1-1):

means a group represented by formula (L1):

wherein, in formula (L1), R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 each independently represent a hydrogen atom, an alkyl group, an aryl group, a monovalent aromatic heterocyclic group, an alkoxy group, an aryloxy group, an aralkyl group, an arylalkoxy group, a substituted amino group, a substituted carbonyl group, a substituted carboxyl group, an alkenyl group, an alkynyl group, a halogen atom, or a cyano group; Ar 1 and Ar 2 each independently represent an aryl group optionally having a substituent or a monovalent aromatic heterocyclic group optionally having a substituent; X 1 represents a bivalent group in which two or more groups selected from among the group consisting of an arylene group, a bivalent aromatic heterocyclic group, and an ethynylene group are directly bonded to each other, an arylene group, a bivalent aromatic heterocyclic group, an ethynylene group, or a direct bond;
a group represented by formula (1-2):

is different from the group represented by the formula (1-1) and means a group represented by formula (L2):

wherein, in formula (L2), R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 and R 15 each independently represent a hydrogen atom, an alkyl group, an aryl group, a monovalent aromatic heterocyclic group, an alkoxy group, an aryloxy group, an aralkyl group, an arylalkoxy group, a substituted amino group, a substituted carbonyl group, a substituted carboxyl group, an alkenyl group, an alkynyl group, a halogen atom, or a cyano group; and
when two groups represented by the formula (1-1) are present, the groups represented by the formula (1-1) may be the same as or different from each other; and when two groups represented by the formula (1-2) are present, the groups represented by the formula (1-2) may be the same as or different each other.

9. The composition according to claim 8 , wherein the charge transporting material is a polymer compound.

10. The composition according to claim 8 , wherein the charge transporting material is a polymer compound having, as a structural unit, at least one group selected from among the group consisting of a bivalent aromatic amine residue, an arylene group, and a bivalent aromatic heterocyclic group.

11. The composition according to claim 8 , wherein the charge transporting material is a polymer compound having, as structural units, at least two groups selected from among the group consisting of a bivalent aromatic amine residue, an arylene group, and a bivalent aromatic hete

Assignees

• Kitamura Noboru
• Sakuda Eri
• Ito Akitaka
• Hirokawa Takeo
• Sekine Chizu
• Ishii Yusuke
• Sumitomo Chemical Co
• Univ Hokkaido Nat Univ Corp

Inventors

• Kitamura Noboru
• Sakuda Eri
• Ito Akitaka
• Hirokawa Takeo
• Sekine Chizu
• Ishii Yusuke

Classifications

• H10K85/658

  Organoboranes · CPC title

• H10K85/342

  comprising iridium · CPC title

• C07F15/0033 Primary

  Iridium compounds · CPC title

• H01L51/008

  Electricity · mapped topic

• C09K2211/1014

  bridged by heteroatoms, e.g. N, P, Si or B · CPC title