Cyclic azine compound, material for organic light emitting diode, electron transport material for organic light emitting diode, and organic light emitting diode

Patent metadata

Field	Value
Publication number	US-2022274952-A1
Application number	US-202017630859-A
Country	US
Kind code	A1
Filing date	Jul 22, 2020
Priority date	Jul 30, 2019
Publication date	Sep 1, 2022
Grant date	—

Abstract

An object of the present invention is to provide a cyclic azine compound exhibiting both excellent driving voltage characteristics and excellent current efficiency characteristics. The desired cyclic azine compound has a specific structure represented by formula (1).

First claim

1 . A cyclic azine compound represented by formula (1):

wherein in the formula (1),
Ar 1 represents a phenyl group or a 4-biphenylyl group;
Ar 2 represents a group represented by any one of formulas (2-1) to (2-3):

and
Ar 3 represents a group represented by formula (3);

wherein in the formula (3),
Ar 31 represents:
a hydrogen atom, or
a group represented by any one of the formulas (2-1) to (2-3).

2 . The cyclic azine compound according to claim 1 , wherein Ar 2 represents a group represented by formula (2-1), (2-2a), (2-2b), (2-3a), or (2-3b).

3 . The cyclic azine compound according to claim 1 , wherein Ar 3 represents a group represented by any one of formulas (3-1) to (3-9).

4 . The cyclic azine compound according to claim 1 , which is a cyclic azine compound represented by formula (1-6), (1-15), (1-48), (1-49), (1-51), (1-52), (1-54), (1-64), (1-65), (1-66), (1-67), (1-71), (1-73) or (1-82).

5 . A material for an organic light emitting diode, the material comprising the cyclic azine compound of claim 1 .

6 . An electron transport material for an organic light emitting diode, the electron transport material comprising the cyclic azine compound of claim 1 .

7 . An organic light emitting diode comprising the cyclic azine compound of claim 1 .

8 . A method for producing a cyclic azine compound represented by formula (1), comprising:
reacting a compound represented by formula (4) with a compound represented by formula (5),

wherein in the formulas,
Ar 1 represents a phenyl group or a 4-biphenylyl group;
Ar 2 represents a group represented by any one of formulas (2-1) to (2-3):

and
Ar 3 represents a group represented by formula (3);

wherein Ar 1 represents:
a hydrogen atom, or
a group represented by any one of the formulas (2-1) to (2-3);
X 4 represents a leaving group; and
Y 4 represents a halogen atom, a metal-containing group, or a boron-containing group.

9 . A pyridine compound represented by formula (5):

wherein in the formula (5),
Ar 2 represents a group represented by any one of formulas (2-1) to (2-3):

and
Ar 3 represents a group represented by formula (3);

wherein Ar 31 represents:
a hydrogen atom, or
a group represented by any one of the formulas (2-1) to (2-3); and
Y 4 represents a halogen atom, a metal-containing group, or a boron-containing group.

10 . The pyridine compound according to claim 9 , which is represented by formula (5-1), (5-2) or (5-3):

wherein in the formulas,
Ar 2 and Y 4 are as defined in the formula (5); and
Ar 31 is as defined in the formula (3).

Assignees

• Tosoh Corp
• Sagami Chem Res Inst

Inventors

• Uchida Naoki
• Aihara Hidenori
• Yamagata Takuya
• Hayakawa Naoki
• NAKAJIMA Natsumi
• Hattori Kazuki
• Uehara Fuminari
• Ono Yohei
• Hirano Masaya
• Morinaka Yuta
• Nomura Keisuke
• Ohta Eriko
• Shono Tomohiro
• Oike Kana
• Hayashi Kazushi
• AOYAGI Keiya
• Sato Kosuke
• NISHIURA Toshiki

Classifications

• H10K50/16

  Electron transporting layers · CPC title

• H10K85/654

  comprising only nitrogen as heteroatom (H10K85/652 takes precedence) · CPC title

• C07D401/14

  containing three or more hetero rings · CPC title

• C07D213/16

  containing only one pyridine ring · CPC title

• C07D401/10 Primary

  linked by a carbon chain containing aromatic rings · CPC title