Metal complex and light emitting device using the same

Patent metadata

Field	Value
Publication number	US-10529934-B2
Application number	US-201515511553-A
Country	US
Kind code	B2
Filing date	Sep 9, 2015
Priority date	Sep 17, 2014
Publication date	Jan 7, 2020
Grant date	Jan 7, 2020

Abstract

Provided is a metal complex which is excellent in quantum yield and full width at half maximum of a light emission spectrum. The metal complex is represented by the following formula (1):

wherein M represents an iridium atom or the like, n 1 represents 1 to 3, n 2 represents 0 to 2, X 1 to X 8 represent a carbon atom or the like, R 1 to R 8 represent a hydrogen atom or the like, one of X a and X b is a single bond, and the other is a group represented by —CR 11 R 12 —CR 13 R 14 —, R 11 to R 14 represent an alkyl group or the like, ring A represents a heteroaromatic ring, and A 1 -G 1 -A 2 represents an anionic bidentate ligand.

First claim

The invention claimed is:

1. A metal complex represented by one of the following formulae (1), (2) or (3):

wherein
M represents an iridium atom or a platinum atom,
n 1 represents 1, 2 or 3 and n 2 represents 0, 1 or 2, provided that n 1 +n 2 is 3 when M is an iridium atom and n 1 +n 2 is 2 when M is a platinum atom,
X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 and X 8 each independently represent a nitrogen atom or a carbon atom, provided that at least two selected from the group consisting of X 5 , X 6 , X 7 and X 8 are carbon atoms, and when there are a plurality of X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 or X 8 , they may be the same or different at each occurrence, provided that R 1 is not present when X 1 is a nitrogen atom, R 2 is not present when X 2 is a nitrogen atom, R 3 is not present when X 3 is a nitrogen atom, R 4 is not present when X 4 is a nitrogen atom, R 5 is not present when X 5 is a nitrogen atom, R 6 is not present when X 6 is a nitrogen atom, R 7 is not present when X 7 is a nitrogen atom, and R 8 is not present when X 8 is a nitrogen atom,
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group or a halogen atom, the foregoing groups each optionally having a substituent, provided that R 1 and R 2 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 , and R 7 and R 8 each may be combined together to form a ring together with the atoms to which they are attached, and when there are a plurality of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 or R 8 , they may be the same or different at each occurrence,
X a and X b each represent a single bond or a group represented by —CR 11 R 12 —CR 13 R 14 —, provided that one of X a and X b is a single bond, and the other is a group represented by —CR 11 R 12 —CR 13 R 14 —, wherein R 11 , R 12 , R 13 and R 14 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group or a halogen atom, the foregoing groups each optionally having a substituent, provided that R 11 and R 12 , R 13 and R 14 , R 11 and R 13 , and R 12 and R 14 each may be combined together to form a ring together with the atoms to which they are attached, and when there are a plurality of R 11 , R 12 , R 13 or R 14 , they may be the same or different at each occurrence, provided that at least one selected from the group consisting of R 11 , R 12 , R 13 and R 14 is an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group or a halogen atom,
ring A represents a heteroaromatic ring, the heteroaromatic ring optionally having a substituent, and when there are a plurality of ring A, they may be the same or different, and
A 1 -G 1 -A 2 represents an anionic bidentate ligand, wherein A 1 and A 2 each independently represent a carbon atom, an oxygen atom or a nitrogen atom, the foregoing atoms each optionally being an atom constituting a ring, G 1 represents a single bond or an atomic group constituting the bidentate ligand together with A 1 and A 2 , and when there are a plurality of A 1 -G 1 -A 2 , they may be the same or different,

wherein ring A has a group represented by the following formula (D-A) or (D-B) as a substituent:

wherein
m DA1 , m DA2 and m DA3 each independently represent an integer of 0 or more,
G DA represents a nitrogen atom, an aromatic hydrocarbon group or a heterocyclic group, the foregoing groups each optionally having a substituent,
Ar DA1 , Ar DA2 and Ar DA3 each independently represent an arylene group or a divalent heterocyclic group, the foregoing groups each optionally having a substituent, and when there are a plurality of Ar DA1 , Ar DA2 or Ar DA3 , they may be the same or different at each occurrence, and
T DA represents an aryl group or a monovalent heterocyclic group, the foregoing groups each optionally having a substituent, and the plurality of T DA may be the same or different:

wherein
m DA1 , m DA2 , m DA3 , m DA4 , m DA5 , m DA6 and m DA7 each independently represents an integer of 0 or more,
G DA1 , G DA2 , and G DA3 each independently represents a nitrogen atom, an aromatic hydrocarbon group or a heterocyclic group, the foregoing groups each optionally having a substituent,
m DA2 is an integer of 1 or more when G DA1 and G DA2 are each a nitrogen atom, m DA3 is an integer of 1 or more when G DA1 and G DA3 are each a nitrogen atom,
Ar DA1 , Ar DA2 , Ar DA3 , Ar DA4 , Ar DA5 , Ar DA6 and Ar DA7 each independently represent an arylene group or a divalent heterocyclic group, the foregoing groups each optionally having a substituent, and when there are a plurality of Ar DA1 , Ar DA2 , Ar DA3 , Ar DA4 , Ar DA5 , Ar DA6 or Ar DA7 , they may be the same or different at each occurrence, and
T DA represents an aryl group or a monovalent heterocyclic group, the foregoing groups each optionally having a substituent, and the plurality of T DA may be the same or different.

2. The metal complex according to claim 1 represented by one of the following formulae (1-1), (1-2) or (2-1):

wherein M, n 1 , n 2 , X 1 , X 3 , X 4 , X 5 , X 6 , X 7 , X 8 , R 1 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 11 , R 12 , R 13 , R 14 , ring A and A 1 -G 1 -A 2 are as defined above.

3. The metal complex according to claim 1 , wherein R 11 , R 12 , R 13 and R 14 are each an alkyl group optionally having a substituent.

4. The metal complex according to claim 3 , wherein R 11 and R 13 are combined to form a ring together with the atoms to which they are attached, and R 12 and R 14 are combined to form a ring together with the atoms to which they are attached.

5. The metal complex according to claim 4 represented by one of the following formulae (1-3), (1-4) or (2-3):

wherein
M, n 1 , n 2 , X 1 , X 3 , X 4 , X 5 , X 6 , X 7 , X 8 , R 1 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , ring A and A 1 -G 1 -A 2 are as defined above,
m 1 and m 2 each independently represent an integer of 1 to 5, and when there are a plurality of m 1 or m 2 , they may be the same or different at each occurrence, and
R 15 , R 16 , R 17 and R 18 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group or a halogen atom, the foregoing groups each optionally having a substituent, and when there are a plurality of R 15 , R 16 , R 17 or R 18 , they may be the same or different at each occurrence.

6. The metal complex according to claim 5 , wherein m 1 and m 2 are each 3 or 4.

7. The metal complex according to claim 1 , wherein X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 and X 8 are each a carbon atom.

8. The metal complex according to claim 1 , wherein ring A is a pyridine ring optionally having a substituent, a pyrimidine ring optionally having a substituent, a quinoline ring optionally having a substituent, an isoquinoline ring option

Assignees

• Sumitomo Chemical Co

Inventors

• Saito Takakazu
• Ishii Yusuke
• Ohuchi Kazuei
• Akino Nobuhiko
• Ishikawa Rui

Classifications

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title

• C08G2261/95

  Use in organic luminescent diodes · CPC title

• C09K2211/1074

  containing more than three nitrogen atoms as heteroatoms · CPC title

• C09K2211/1059

  containing three nitrogen atoms as heteroatoms · CPC title

• C09K2211/185

  of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd · CPC title