Heterocyclic compound, light-emitting element, light-emitting device, electronic device, and lighting device

Patent metadata

Field	Value
Publication number	US-9309223-B2
Application number	US-201213537763-A
Country	US
Kind code	B2
Filing date	Jun 29, 2012
Priority date	Jul 8, 2011
Publication date	Apr 12, 2016
Grant date	Apr 12, 2016

Abstract

Provided is a novel heterocyclic compound which can be used as a host material for dispersing a light-emitting material in a light-emitting layer of a light-emitting element. Further provided is a light-emitting element which is driven at a low voltage and has high current efficiency. By including the light-emitting element, a light-emitting device, an electronic device, and a lighting device each with reduced power consumption are provided. The light-emitting element contains a compound in which a dibenzo[f,h]quinoline ring and a hole-transport skeleton are bonded through an arylene group. The light-emitting device, the electronic device, and the lighting device each including the light-emitting element are provided. The light-emitting element contains a heterocyclic compound having a structure represented by the following general formula (G1).

First claim

What is claimed is:

1. A compound comprising the following structure:

wherein:
X 2 represents halogen or a triflate group,
Ar represents an arylene group having 6 to 13 carbon atoms,
R 11 to R 20 separately represent any of hydrogen, an alkyl group having 1 to 4 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.

2. The compound according to claim 1 , wherein the halogen is iodine or bromine.

3. A compound comprising the following structure:

wherein:
X 2 represents halogen or a triflate group,
Ar represents an arylene group having 6 to 13 carbon atoms, and
R 11 to R 20 separately represent hydrogen.

4. The compound according to claim 3 , wherein X 2 represents the triflate group.

5. The compound according to claim 3 , wherein Ar represents a phenylene group.

6. The compound according to claim 3 , wherein Ar represents a biphenyldiyl group.

7. A method for synthesizing a compound represented by a formula (G1), the method including:
performing a reaction according to the following scheme:

wherein:
X 2 represents halogen or a triflate group,
Ar represents an arylene group having 6 to 13 carbon atoms,
R 11 to R 20 separately represent any of hydrogen, an alkyl group having 1 to 4 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 13 carbon atoms,
R 52 and R 53 separately represent any of hydrogen and an alkyl group having 1 to 6 carbon atoms,
A represents any of a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzothiophenyl group, and a substituted or unsubstituted dibenzofuranyl group, and
B represents boron.

8. The method according to claim 7 , wherein the halogen is iodine or bromine.

9. The method according to claim 7 , wherein X 2 represents the triflate group.

10. The method according to claim 7 , wherein R 11 to R 20 separately represent hydrogen.

11. The method according to claim 7 , wherein Ar represents a phenylene group.

12. The method according to claim 7 , wherein Ar represents a biphenyldiyl group.

13. The method according to claim 7 , wherein A represents the unsubstituted dibenzothiophenyl group.

14. The method according to claim 7 , wherein a palladium catalyst is used in the reaction.

15. The method according to claim 14 , wherein the palladium catalyst is selected from the group of palladium(II) acetate, tetrakis(triphenylphosphine)palladium(0), and bis(triphenylphosphine)palladium(II) dichloride.

16. The method according to claim 14 , wherein a ligand of the palladium catalyst is selected from the group of tri(ortho-tolyl)phosphine, triphenylphosphine, and tricyclohexylphosphine.

17. A method of fabricating a light-emitting device comprising:
forming a light-emitting layer using the compound represented by the formula (G1) obtained by the method according to claim 7 over a first electrode, and
forming a second electrode over the light-emitting layer.

Assignees

• Kadoma Hiroshi
• Ogita Kaori
• Shitagaki Satoko
• Ohsawa Nobuharu
• Seo Satoshi
• Semiconductor Energy Lab

Inventors

• Kadoma Hiroshi
• Ogita Kaori
• Shitagaki Satoko
• Ohsawa Nobuharu
• Seo Satoshi

Classifications

• C09K11/06

  containing organic luminescent materials · CPC title

• H05B33/20

  characterised by the chemical or physical composition or the arrangement of the material in which the electroluminescent material is embedded · CPC title

• C07D409/10

  linked by a carbon chain containing aromatic rings · CPC title

• C07D401/10 Primary

  linked by a carbon chain containing aromatic rings · CPC title

• C09K2211/1088

  containing oxygen as the only heteroatom · CPC title