Metal complex and light emitting device using the same

Patent metadata

Field	Value
Publication number	US-10128449-B2
Application number	US-201415109959-A
Country	US
Kind code	B2
Filing date	Dec 18, 2014
Priority date	Jan 8, 2014
Publication date	Nov 13, 2018
Grant date	Nov 13, 2018

Abstract

In formula (1), M represents an iridium atom or a platinum atom; n1 represents 1, 2 or 3. n2 represents 0, 1 or 2; E1 to E4 represent a nitrogen atom or a carbon atom; R1 to R10 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; Xa and Xb represent a direct bond, an oxygen atom, a sulfur atom, —C(═O)—, —CRXa2— or —NRXa—; A1-G1-A2 represents an anionic bidentate ligand; and G1 represents an atomic group constituting a bidentate ligand together with A1 and A2.

First claim

The invention claimed is:

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

wherein
M represents an iridium atom or a platinum atom,
n 1 represents 1, 2 or 3, n 2 represents 0, 1 or 2, 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,
E 1 , E 2 , E 3 and E 4 each independently represent a nitrogen atom or a carbon atom, and when a plurality of E 1 , E 2 , E 3 and E 4 are present, they may be the same or different at each occurrence, and R 1 is not present when E 1 is a nitrogen atom, R 2 is not present when E 2 is a nitrogen atom, R 3 is not present when E 3 is a nitrogen atom, and R 4 is not present when E 4 is a nitrogen atom,
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 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, and these groups optionally have a substituent, and when a plurality of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 are present, they may be the same or different at each occurrence, and R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 6 and R 7 , R 7 and R 8 , and R 8 and R 9 each may be combined together to form a ring together with the atoms to which they are attached, and at least one selected from the group consisting of R 1 , R 2 , R 3 and R 4 is a group represented by the following formula (D-A) or (D-B),
X a and X b each independently represent a direct bond, an oxygen atom, a sulfur atom, —C(═O)—, —CR Xa 2 — or —NR Xa —, R Xa represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups optionally have a substituent, and when a plurality of R Xa are present, they may be the same or different and may be combined together to form a ring together with the carbon atoms to which they are attached, and when a plurality of X a and X b are present, they may be the same or different at each occurrence, and at least one of X a and X b is an oxygen atom, a sulfur atom, —C(═O)—, —CR Xa 2 — or —NR Xa —, and
A 1 -G 1 -A 2 represents an anionic bidentate ligand, G 1 represents an atomic group constituting a bidentate ligand together with A 1 and A 2 , A 1 and A 2 each independently represent a carbon atom, an oxygen atom or a nitrogen atom, and these atoms each may be an atom constituting a ring, and when a plurality of A 1 -G 1 -A 2 are present, they may be the same or different,

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

2. The metal complex according to claim 1 , wherein the R 2 is the group represented by the formula (D-A).

3. The metal complex according to claim 1 , wherein the group represented by the formula (D-A) is a group represented by the following formula (D-A1), (D-A2) or (D-A3):

wherein
R p1 , R p2 and R p3 each independently represent an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group or a halogen atom, and a plurality of R p1 and R p2 are present, they may be the same or different at each occurrence, and
np1 represents an integer of 0 to 5, np2 represents an integer of 0 to 3, and np3 represents 0 or 1, and the plurality of np1 may be the same or different.

4. The metal complex according to claim 3 , wherein the group represented by the formula (D-A) is the group represented by the formula (D-A3).

5. The metal complex according to claim 1 , wherein X a is —CR Xa 2 —, and X b is a direct bond.

6. The metal complex according to claim 1 , wherein the E 1 , E 2 , E 3 and E 4 are each a carbon atom.

7. The metal complex according to claim 1 , wherein M is an iridium atom, n 1 is 3, and n 2 is 0.

8. A metal complex represented by the following formula (2):

wherein
M represents an iridium atom or a platinum atom,
n 1 represents 1, 2 or 3, n 2 represents 0, 1 or 2, 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,
E 1 , E 2 , E 3 and E 4 each independently represent a nitrogen atom or a carbon atom, when a plurality of E 1 , E 2 , E 3 and E 4 are present, they may be the same or different at each occurrence, and R 11 is not present when E 1 is a nitrogen atom, R 12 is not present when E 2 is a nitrogen atom, R 13 is not present when E 3 is a nitrogen atom, and R 14 is not present when E 4 is a nitrogen atom,
R 11 , R 12 , R 13 , R 14 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 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, and these groups optionally have a substituent, and when a plurality of R 11 , R 12 , R 13 , R 14 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 are present, they may be the same or different at each occurrence, and R 11 and R 12 , R 12 and R 13 , R 13 and R 14 , R 14 and R 5 , R 6 and R 7 , R 7 and R 8 , and R 8 and R 9 each may be combined together to form a ring together with the atoms to which they are attached,
Y a and Y b each independently represent a direct bond, an oxygen atom, a sulfur atom, —C(═O)—, —CR Ya R Yb — or —NR Yc —, R Ya represents an alkyl group or a cycloalkyl group, and these groups optionally have an aryl group or a monovalent heterocyclic group as a substituent, R Yb represents an aryl group having an alkyl group as a substituent or a monovalent heterocyclic group having an alkyl group as a substituent, and these groups optionally further have a substituent, R Yc represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups optionally have a substituent, an

Assignees

• Sumitomo Chemical Co

Inventors

• Saito Takakazu
• Ishii Yusuke
• Ohuchi Kazuei
• Asada Kohei
• Akino Nobuhiko

Classifications

• C09K2211/1007

  Non-condensed systems · CPC title

• C09K2211/1059

  containing three nitrogen atoms as heteroatoms · CPC title

• C09K2211/1011

  Condensed systems · CPC title

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title