Organometallic Complex, Light-Emitting Element, Light-Emitting Device, Electronic Device, and Lighting Device

Patent metadata

Field	Value
Publication number	US-2016181550-A1
Application number	US-201514974142-A
Country	US
Kind code	A1
Filing date	Dec 18, 2015
Priority date	Dec 19, 2014
Publication date	Jun 23, 2016
Grant date	—

Abstract

To provide an organometallic complex with high emission efficiency and high heat resistance, which emits yellow green light. The organometallic complex includes a metal and a ligand which is a benzo[h]quinazoline skeleton including a condensed ring bonded to benzo[h]quinazoline through a carbon-carbon bond between the 5-position and the 6-position. The organometallic complex has a structure represented by General Formula (G1). In General Formula (G1), M represents a metal belonging to Group 9 or 10; each of R 1 to R 4 independently represents hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms; and R 5 represents hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted phenyl group. A ring X represents a substituted or unsubstituted six-membered aromatic ring formed with carbon or both carbon and nitrogen.

First claim

What is claimed is:

1 . An organometallic complex comprising:
a metal belonging to Group 9 or 10; and a benzo[h]quinazoline skeleton, wherein the benzo[h]quinazoline skeleton comprises a condensed ring sharing a carbon-carbon bond between a 5-position and a 6-position with a benzo[h]quinazoline, and wherein the benzo[h]quinazoline skeleton is bonded to the metal.

2 . The organometallic complex according to claim 1 ,
wherein the organometallic complex further comprises a ligand selected from a monoanionic bidentate chelate ligand having a β-diketone structure, a monoanionic bidentate chelate ligand having a carboxyl group, a monoanionic bidentate chelate ligand having a phenolic hydroxyl group, and a monoanionic bidentate chelate ligand in which two coordinating elements are both nitrogen, and wherein the ligand is bonded to the metal.

3 . The organometallic complex according to claim 1 ,
wherein the condensed ring is a substituted or unsubstituted six-membered aromatic ring formed with carbon or both carbon and nitrogen.

4 . An organometallic complex comprising a structure represented by Formula (G1),

wherein M represents a metal belonging to Group 9 or 10,
wherein each of R 1 to R 4 independently represents hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms,
wherein R 5 represents hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted phenyl group, and
wherein a ring X represents a substituted or unsubstituted six-membered aromatic ring formed with carbon or both carbon and nitrogen.

5 . The organometallic complex according to claim 4 ,
wherein the organometallic complex is represented by Formula (G2),

wherein M represents a metal belonging to Group 9 or 10,
wherein L represents a monoanionic ligand,
wherein each of R 1 to R 4 independently represents hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms,
wherein R 5 represents hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted phenyl group,
wherein a ring X represents a substituted or unsubstituted six-membered aromatic ring formed with carbon or both carbon and nitrogen,
wherein in is 3 and n is 1, 2, or 3, when the metal belongs to Group 9, and
wherein in is 2 and n is 1 or 2, when the metal belongs to Group 10.

6 . The organometallic complex according to claim 5 ,
wherein the monoanionic ligand is a monoanionic bidentate chelate ligand having a β-diketone structure, a monoanionic bidentate chelate ligand having a carboxyl group, a monoanionic bidentate chelate ligand having a phenolic hydroxyl group, or a monoanionic bidentate chelate ligand in which two coordinating elements are both nitrogen.

7 . The organometallic complex according to claim 5 ,
wherein the monoanionic ligand is represented by any of Formulae (L1) to (L7),

wherein each of R 71 to R 109 independently represents hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a halogen group, a vinyl group, a substituted or unsubstituted haloalkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, or a substituted or unsubstituted alkylthio group having 1 to 6 carbon atoms, and
wherein each of A 1 to A 3 independently represents nitrogen, sp 2 hybridized carbon bonded to hydrogen, or sp 2 hybridized carbon having a substituent, the substituent being an alkyl group having 1 to 6 carbon atoms, a halogen group, a haloalkyl group having 1 to 6 carbon atoms, or a phenyl group.

8 . The organometallic complex according to claim 4 ,
wherein the organometallic complex is represented by Formula (G3),

wherein each of R 1 to R 4 independently represents hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms,
wherein R 5 represents hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted phenyl group,
wherein each of R 6 and R 7 independently represents hydrogen or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, and
wherein a ring X represents a substituted or unsubstituted six-membered aromatic ring formed with carbon or both carbon and nitrogen.

9 . The organometallic complex according to claim 4 ,
wherein the organometallic complex is represented by Formula (G4),

wherein each of R 1 to R 4 independently represents hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms,
wherein R 5 represents hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted phenyl group, and
wherein a ring X represents a substituted or unsubstituted six-membered aromatic ring formed with carbon or both carbon and nitrogen.

10 . The organometallic complex according to claim 4 ,
wherein the organometallic complex is represented by any one of Formulae (100), (101), (104), and (114),

11 . A light-emitting element comprising an EL layer between a pair of electrodes, the EL layer comprising the organometallic complex according to claim 4 .

12 . A light-emitting device comprising:
the light-emitting element according to claim 11 ; and at least one of a transistor and a substrate.

13 . An electronic device comprising:
the light-emitting device according to claim 12 ; and at least one of a microphone, a camera, an operation button, an external connection portion, and a speaker.

14 . A lighting device comprising:
the light-emitting device according to claim 12 ; and a housing.

Assignees

• Semiconductor Energy Lab

Inventors

• Yamada Yui
• Inoue Hideko
• Seo Hiromi
• Takahashi Tatsuyoshi

Classifications

• C07F15/0086

  Platinum compounds · CPC title

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title

• F21K9/00

  Light sources using semiconductor devices as light-generating elements, e.g. using light-emitting diodes [LED] or lasers · CPC title

• C09K2211/185

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

• C09K11/06

  containing organic luminescent materials · CPC title