Organometallic iridium complex, light-emitting element, light-emitting device, electronic device, and lighting device

Patent metadata

Field	Value
Publication number	US-9412956-B2
Application number	US-201414482536-A
Country	US
Kind code	B2
Filing date	Sep 10, 2014
Priority date	Sep 12, 2013
Publication date	Aug 9, 2016
Grant date	Aug 9, 2016

Abstract

An organometallic iridium complex has high emission efficiency and a long lifetime. The iridium complex includes the structure represented by Formula (G1). In the formula, Ar represents a substituted or unsubstituted arylene group having 6 to 13 carbon atoms. R 1 to R 6 independently represent any one of hydrogen and a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, and one of R 2 and R 6 represents the alkyl group. X represents a carbon atom or a nitrogen atom, and when X represents a carbon atom, hydrogen or an alkyl group having 1 to 6 carbon atoms is bonded to the carbon atom. A dihedral angle between a ring bonded to R 1 and a phenyl group bonded to R 2 to R 6 is 30° or more and 90° or less. An interior angle of the pyridine/pyrimidine ring facing R 1 is within a range of 118° to 122°.

First claim

The invention claimed is:

1. A compound represented by Formula (G5):

wherein:
R 1 to R 9 independently represent hydrogen or an unsubstituted alkyl group having 1 to 6carbon atoms;
at least one of R 2 and R 6 represents a tert-butyl group;
X represents a nitrogen atom;
L represents a monoanionic ligand;
the monoanionic ligand is represented by any one of Formulae (L1) to (L7):

R 71 to R 109 independently represent any one of hydrogen, an alkyl group having 1 to 6carbon atoms, a halogen, a vinyl group, a haloalkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, and an alkylthio group having 1 to 6 carbon atoms;
A 1 to A 3 independently represent any one of nitrogen and carbon bonded to hydrogen or to a substituent R;
the substituent R is any one of an alkyl group having 1 to 6 carbon atoms, a halogen, a haloalkyl group having 1 to 6 carbon atoms, and a phenyl group;
when X represents the nitrogen atom, the other of R 2 and R 6 represents hydrogen, or one of R 1 , R 3 to R 5 and R 7 to R 9 represents an unsubstituted alkyl group having 1 to 6 carbon atoms,
a dihedral angle between a ring bonded to R 1 and a phenyl group bonded to R 2 to R 6 is greater than or equal to 30° and less than or equal to 90°;
a dihedral angle between the ring bonded to R 7 to R 9 is greater than or equal to 0° and less than 2°; and
a bond angle denoted by α is greater than or equal to 120° and less than 129°.

2. The compound according to claim 1 , wherein R 3 to R 5 represent hydrogen.

3. The compound according to claim 1 , wherein R l represents hydrogen.

4. The compound according to claim 1 , wherein one of R 2 and R 6 represents hydrogen.

5. A compound represented by Formula (G6):

wherein:
R 1 , R 2 and R 6 to R 9 independently represent hydrogen or an unsubstituted alkyl group having 1 to 6 carbon atoms;
one of R 2 and R 6 represents an alkyl group having 1 to 6 carbon atoms;
the other one of R 2 and R 6 represents hydrogen;
X represents a nitrogen atom;
the monoanionic ligand is represented by any one of Formulae (L1) to (L7):

R 71 to R 109 independently represent any one of hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a halogen, a vinyl group, a substituted or unsubstituted haloalkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkoxy group having 1to 6 carbon atoms, and a substituted or unsubstituted alkylthio group having 1 to 6 carbon atoms;
A 1 to A 3 independently represent any one of nitrogen and carbon bonded to hydrogen or to a substituent R;
the substituent R is any one of an alkyl group having 1 to 6 carbon atoms, a halogen, a haloalkyl group having 1 to 6 carbon atoms, and a phenyl group;
L represents a monoanionic ligand,
wherein a dihedral angle between a ring bonded to R 1 and a phenyl group bonded to R 2 to R 6 is greater than or equal to 30° and less than or equal to 90° ;
wherein a dihedral angle between the ring bonded to R 1 and a phenyl group bonded to R 7 to R 9 is greater than or equal to 0° and less than 2° ; and
a bond angle denoted by α is greater than or equal to 120° and less than 129°.

6. The compound according to claim 5 , wherein the compound is represented by Formula (134):

7. A light-emitting device comprising the compound according to claim 5 .

8. A lighting device comprising the compound according to claim 5 .

9. An electronic device comprising the light-emitting device according to claim 7 .

Assignees

• Semiconductor Energy Lab

Inventors

• Ohsawa Nobuharu
• Inoue Hideko
• Seo Satoshi
• Kanamoto Miki

Classifications

• H05B33/14

  characterised by the chemical or physical composition or the arrangement of the electroluminescent material {, or by the simultaneous addition of the electroluminescent material in or onto the light source} · CPC title

• C09K2211/185

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

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title

• C09K2211/1007

  Non-condensed systems · CPC title

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title