Triazine 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-2023337532-A1
Application number	US-202118027785-A
Country	US
Kind code	A1
Filing date	Oct 1, 2021
Priority date	Oct 5, 2020
Publication date	Oct 19, 2023
Grant date	—

Abstract

A triazine compound represented by formula (1) is provided. In the formula (1),

A and B each independently represent an aryl group having 6 to 20 carbon atoms;
L represents a phenyl group or a naphthyl group;
n is 0 or 1; and
C represents any one of groups X, Y, and Z below,

wherein Ar 1 and Ar 2 each independently represent an aromatic hydrocarbon group or a pyridyl group.

First claim

1 . A triazine compound represented by formula (1):

wherein in the formula (1),
A and B each independently represent an aryl group having 6 to 20 carbon atoms;
L represents a phenyl group or a naphthyl group;
n is 0 or 1; and
C represents any one of groups X, Y, and Z below,

wherein Ar 1 and Ar 2 each independently represent an aromatic hydrocarbon group or a pyridyl group.

2 . A triazine compound represented by formula X(1):

wherein in the formula X(1), A represents any one group selected from formulas X(A-1) to X(A-9):

B represents any one group selected from formulas X(B-1) to X(B-15):

Ar 1 represents: an aryl group having 6 to 30 carbon atoms, optionally substituted with one or more selected from the group consisting of an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a cyano group, a diarylboryl group, and a phosphine oxide group, or a pyridyl group optionally substituted with a methyl group or a phenyl group; and Ar 2 represents: an aryl group having 6 to 30 carbon atoms, optionally substituted with one or more selected from the group consisting of an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a cyano group, a diarylboryl group, and a phosphine oxide group, or a pyridyl group optionally substituted with a methyl group or a phenyl group.

3 . The triazine compound according to claim 2 , wherein
A represents any one group selected from the formulas X(A-1) to X(A-9), Ar 1 represents an aryl group having 6 to 30 carbon atoms, optionally substituted with one or more selected from the group consisting of an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a cyano group, a diarylboryl group, and a phosphine oxide group, and Ar 2 represents an aryl group having 6 to 30 carbon atoms, optionally substituted with one or more selected from the group consisting of an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a cyano group, a diarylboryl group, and a phosphine oxide group.

4 . The triazine compound according to claim 2 , wherein
A represents any one group selected from the formulas X(A-1) to X(A-4), and B represents any one group selected from the formulas X(B-1) to X(B-4), X(B-7) to X(B-8), and X(B-10) to X(B-11).

5 . The triazine compound according to claim 2 , wherein
A represents any one group selected from the formulas X(A-1) to X(A-4), B represents a group selected from the formulas X(B-1) to X(B-4), X(B-7) to X(B-8), and X(B-10) to X(B-11), Ar 1 represents an aryl group having 6 to 30 carbon atoms, optionally substituted with one or more selected from the group consisting of an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a cyano group, a diarylboryl group, and a phosphine oxide group, and Ar 2 represents an aryl group having 6 to 30 carbon atoms, optionally substituted with one or more selected from the group consisting of an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a cyano group, a diarylboryl group, and a phosphine oxide group.

6 . The triazine compound according to claim 2 , wherein
Ar 1 represents a phenyl group, a 1-naphthalenyl group, a 2-naphthalenyl group, a 2-biphenylyl group, a 3-biphenylyl group, a 4-biphenylyl group, a 2-(1-naphthalenyl)phenyl group, a 3-(1-naphthalenyl)phenyl group, a 4-(1-naphthalenyl)phenyl group, a 2-(2-naphthalenyl)phenyl group, a 3-(2-naphthalenyl)phenyl group, a 4-(2-naphthalenyl)phenyl group, a 4-phenylnaphthalen-1-yl group, a 5-phenylnaphthalen-1-yl group, a 6-phenylnaphthalen-2-yl group, a 7-phenylnaphthalen-2-yl group, a 2-phenanthrenyl group, a 3-phenanthrenyl group, a 9-phenanthrenyl group, a 9-anthracenyl group, a p-terphenyl group, or a 2-triphenylenyl group, each optionally substituted with one or more selected from the group consisting of an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a cyano group, a diarylboryl group, and a phosphine oxide group, and Ar 2 represents a phenyl group, a 1-naphthalenyl group, a 2-naphthalenyl group, a 2-biphenylyl group, a 3-biphenylyl group, a 4-biphenylyl group, a 2-(1-naphthalenyl)phenyl group, a 3-(1-naphthalenyl)phenyl group, a 4-(1-naphthalenyl)phenyl group, a 2-(2-naphthalenyl)phenyl group, a 3-(2-naphthalenyl)phenyl group, a 4-(2-naphthalenyl)phenyl group, a 4-phenylnaphthalen-1-yl group, a 5-phenylnaphthalen-1-yl group, a 6-phenylnaphthalen-2-yl group, a 7-phenylnaphthalen-2-yl group, a 2-phenanthrenyl group, a 3-phenanthrenyl group, a 9-phenanthrenyl group, a 9-anthracenyl group, a p-terphenyl group, or a 2-triphenylenyl group, each optionally substituted with one or more selected from the group consisting of an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a cyano group, a diarylboryl group, and a phosphine oxide group.

7 . The triazine compound according to claim 2 , wherein
Ar 1 represents a phenyl group, a 1-naphthalenyl group, a 2-naphthalenyl group, a 2-biphenylyl group, a 3-biphenylyl group, or a 4-biphenylyl group, each optionally substituted with one or more selected from the group consisting of an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a cyano group, a diarylboryl group, and a phosphine oxide group, and Ar 2 represents a phenyl group, a 1-naphthalenyl group, a 2-naphthalenyl group, a 2-biphenylyl group, a 3-biphenylyl group, or a 4-biphenylyl group, each optionally substituted with one or more selected from the group consisting of an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a cyano group, a diarylboryl group, and a phosphine oxide group.

8 . The triazine compound according to claim 2 , wherein
A represents any one group selected from the formulas X(A-1) to X(A-4), B represents any one group selected from the formulas X(B-1) to X(B-4), Ar 1 represents a phenyl group, a 1-naphthalenyl group, a 2-naphthalenyl group, a 2-biphenylyl group, a 3-biphenylyl group, or a 4-biphenylyl group, and Ar 2 represents a phenyl group, a 1-naphthalenyl group, a 2-naphthalenyl group, a 2-biphenylyl group, a 3-biphenylyl group, or a 4-biphenylyl group.

9 . The triazine compound according to claim 2 , wherein
A represents a group represented by the formula X(A-1), B represents a group represented by the formula X(B-1), Ar 1 represents a phenyl group, a 1-naphthalenyl group, a 2-naphthalenyl group, a 2-biphenylyl group, a 3-biphenylyl group, or a 4-biphenylyl group, and Ar 2 represents a phenyl group, a 1-naphthalenyl group, a 2-naphthalenyl group, a 2-biphenylyl group, a 3-biphenylyl group, or a 4-biphenylyl group.

10 . A triazine compound represented by the formula Y(1):

wherein in the formula Y(1), A

Assignees

• Tosoh Corp

Inventors

• Ono Youhei
• Oike Kana
• Uehara Fuminari
• Hattori Kazuki
• Takahashi Yasuhiro
• Shono Tomohiro
• Uchida Naoki

Classifications

• H10K85/654 Primary

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

• C07D251/24 Primary

  to three ring carbon atoms · CPC title

• H10K85/6574

  comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes · CPC title

• H10K85/626

  containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene · CPC title

• H10K85/615

  Polycyclic condensed aromatic hydrocarbons, e.g. anthracene · CPC title