Organic compound, light-emitting element, light-emitting device, electronic appliance, and lighting device

Patent metadata

Field	Value
Publication number	US-9586924-B2
Application number	US-201514809427-A
Country	US
Kind code	B2
Filing date	Jul 27, 2015
Priority date	Jul 26, 2013
Publication date	Mar 7, 2017
Grant date	Mar 7, 2017

Abstract

An organic compound that emits blue light with high color purity and has a long lifetime is provided as a novel substance. The organic compound is a fluorescent organic compound having a structure in which benzonaphthofuranylamine is bonded to the 1-position and the 6-position of a pyrene skeleton.

First claim

The invention claimed is:

1. A compound represented by the following formula:

wherein:
Ar 1 and Ar 2 independently represent a substituted or unsubstituted aryl group having 6 to 13 carbon atoms;
R 1 to R 8 independently represent hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, a cyano group, halogen, a substituted or unsubstituted haloalkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms; and
the substituted aryl group is selected from an ortho-tolyl group, a meta-tolyl group, a para-tolyl group, an ortho-biphenyl group, a meta-biphenyl group, a para-biphenyl group, a 9,9-dimethyl-9H-fluoren-2-yl group, a 9,9-diphenyl-9H-fluoren-2-yl group, a 9H-fluoren-2-yl group, a para-t-butylphenyl group, and mesityl group.

2. The compound according to claim 1 ,
wherein R 1 to R 8 independently represent 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.

3. The compound according to claim 1 ,
wherein Ar 1 and Ar 2 are the same as each other.

4. A method for preparing a compound, the method comprising:
performing a reaction of a first compound with two compounds represented by the following formulae using a palladium catalyst,

wherein:
X 1 and X 2 each separately represents a substituted or unsubstituted benzo[b]naphtha[1,2-d]furanyl group;
X 5 and X 6 each separately represents halogen or a triflate group;
the first compound is represented by the following formula:

Ar 1 and Ar 2 independently represent a substituted or unsubstituted aryl group having 6 to 13 carbon atoms;
R 1 to R 8 independently represent hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, a cyano group, halogen, a substituted or unsubstituted haloalkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms;
the substituted aryl group is selected from an ortho-tolyl group, a meta-tolyl group, a para-tolyl group, an ortho-biphenyl group, a meta-biphenyl group, a para-biphenyl group, a 9,9-dimethyl-9H-fluoren-2-yl group, a 9,9-diphenyl-9H-fluoren-2-yl group, a 9H-fluoren-2-yl group, a para-t-butylphenyl group, and mesityl group;
wherein the halogen or the triflate group of the X 5 is reacted with the top N in the first compound; and
wherein the halogen or the triflate group of the X 6 is reacted with the bottom N in the first compound.

5. The method according to claim 4 ,
wherein R 1 to R 8 independently represent 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.

6. The method according to claim 4 ,
wherein Ar 1 and Ar 2 are the same as each other.

7. The method according to claim 4 ,
wherein the each of the two compounds is represented by any one of the following formulae:

8. A compound represented by any one of the following formulae:

9. The compound according to claim 8 ,
wherein the compound is represented by the following formula:

10. The compound according to claim 8 ,
wherein the compound is represented by the following formula:

11. The method according to claim 4 ,
wherein the palladium catalyst is any of bis(dibenzylideneacetone)palladium(0) or palladium(II) acetate and a ligand selected from tri(tert-butyl)phosphine, tri(n-hexyl)phosphine, tricyclohexylphosphine, di(1-adamantyl)-n-butylphosphine, or 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl.

Assignees

• Semiconductor Energy Lab

Inventors

• Kawakami Sachiko
• Hashimoto Naoaki
• Suzuki Tsunenori
• Seo Satoshi

Classifications

• C09K11/06

  containing organic luminescent materials · CPC title

• C09K2211/1088

  containing oxygen as the only heteroatom · CPC title

• C09K2211/1022

  bridged by heteroatoms, e.g. N, P, Si or B · CPC title

• C09K2211/1011

  Condensed systems · CPC title

• C07D307/77 Primary

  ortho- or peri-condensed with carbocyclic rings or ring systems · CPC title