Method of synthesizing pyrazine derivative, and light-emitting element, light-emitting device, electronic device, and lighting device

Patent metadata

Field	Value
Publication number	US-9196844-B2
Application number	US-201313905829-A
Country	US
Kind code	B2
Filing date	May 30, 2013
Priority date	Jun 1, 2012
Publication date	Nov 24, 2015
Grant date	Nov 24, 2015

Abstract

A novel method includes a synthetic pathway in which α-diketone and a 1-(haloaryl)ethane-1,2-diamine derivative are cyclized to each other to form a 2-(haloaryl)pyrazine derivative. Further, a 2-arylpyrazine derivative having an aryl group or a heteroaryl group as a substituent is synthesized by coupling the 2-(haloaryl)pyrazine derivative obtained by the above synthetic pathway and an arylboronic acid or a heteroarylboronic acid. The 2-arylpyrazine derivative obtained by the novel method is useful for a light-emitting element, a light-emitting device, an electronic device, or a lighting device with high emission efficiency.

First claim

What is claimed is:

1. A method comprising the step of cyclizing an α-diketone and a 1-(haloaryl)ethane-1,2-diamine derivative to form a 2-(haloaryl)pyrazine derivative,
wherein the α-diketone is any one of glyoxal, 1-phenyl glyoxal, benzil, and 9,10-phenanthrenequinone in which phenyl groups of benzil are bonded to each other at the ortho position,
wherein the 1-(haloaryl)ethane-1,2-diamine derivative is represented by a formula (A1),

wherein α represents an aryl group,
wherein X represents halogen, and
wherein n is any of 1 to 3.

2. The method according to claim 1 , wherein the 2-(haloaryl)pyrazine derivative is represented by a formula (G0),

wherein α represents an aryl group,
wherein X represents halogen,

wherein n is any of 1 to 3, and
wherein R 1 and R 2 each independently represent hydrogen or a phenyl group.

3. The method according to claim 1 ,
wherein the 2-(haloaryl)pyrazine derivative is represented by a formula (G0),

wherein α represents an aryl group,
wherein X represents halogen,

wherein n is any of 1 to 3, and
wherein R 1 and R 2 are bonded to each other to form a phenanthrene ring.

4. The method according to claim 1 , wherein the α-diketone is represented by a formula (A2),

wherein R 1 and R 2 each independently represent hydrogen or a phenyl group.

5. A method comprising the steps of:
cyclizing an α-diketone and a 1-(haloaryl)ethane-1,2-diamine derivative to form a 2-(haloaryl)pyrazine derivative; and
coupling the 2-(haloaryl)pyrazine derivative and an arylboronic acid or a heteroarylboronic acid to form a 2-arylpyrazine derivative comprising an aryl group or a heteroaryl group,
wherein the α-diketone is any one of glyoxal, 1-phenyl glyoxal, benzil, and 9,10-phenanthrenequinone in which phenyl groups of benzil are bonded to each other at the ortho position,
wherein the 1-(haloaryl)ethane-1,2-diamine derivative is represented by a formula (A1),

wherein α represents an aryl group,
wherein X represents halogen, and
wherein n is any of 1 to 3.

6. The method according to claim 5 , wherein the 2-arylpyrazine derivative is represented by a formula (G1),

wherein α represents an aryl group,
wherein X represents halogen,
wherein n is any of 1 to 3, and
wherein R 1 and R 2 each independently represent hydrogen, an alkyl group, or a phenyl group.

7. The method according to claim 5 ,
wherein the 2-(haloaryl)pyrazine derivative is represented by a formula (G0),

wherein α represents an aryl group,
wherein X represents halogen,

wherein n is any of 1 to 3, and
wherein R 1 and R 2 are bonded to each other to form a phenanthrene ring.

8. The method according to claim 5 , wherein the 2-arylpyrazine derivative is represented by a formula (101),

9. The method according to claim 1 , wherein the α-diketone is 9,10-phenanthrenequinone.

10. The method according to claim 5 , wherein the α-diketone is 9,10-phenanthrenequinone.

Assignees

• Semiconductor Energy Lab

Inventors

• Inoue Hideko
• Yamaguchi Tomoya
• Kitano Yasushi
• Seo Hiromi
• Seo Satoshi

Classifications

• C07D241/42

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring · CPC title

• C07D409/10 Primary

  linked by a carbon chain containing aromatic rings · CPC title

• H10K59/876

  comprising a resonant cavity structure, e.g. Bragg reflector pair · CPC title

• H10K85/657

  Polycyclic condensed heteroaromatic hydrocarbons · CPC title

• H01L51/0071 Primary

  Electricity · mapped topic