Compound having benzotriazole ring structure and organic electroluminescent element

Patent metadata

Field	Value
Publication number	US-9005776-B2
Application number	US-201013257142-A
Country	US
Kind code	B2
Filing date	Mar 17, 2010
Priority date	Mar 18, 2009
Publication date	Apr 14, 2015
Grant date	Apr 14, 2015

Abstract

A compound having a benzotriazole ring structure and a formula (1):

wherein Ar is a substituted or unsubstituted aromatic hydrocarbon group, aromatic heterocyclic group, or condensed polycyclic aromatic group; A and B are the same as or different from each other and each represent a hydrogen atom or a monovalent group of formula (2), provided that A and B are not simultaneously hydrogen atoms:

wherein R 1 to R 8 are the same as or different and each represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, a linear or branched alkyl group having 1 to 6 carbon atoms, aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or condensed polycyclic aromatic group; m is an integer of 0, 1 or 2; X represents a carbon atom or a nitrogen atom; when X is a nitrogen atom, the nitrogen atom does not have substituents or bonding groups of R 1 , R 2 , R 3 and R 4 ; and when m is 2, a plurality of R 1 , R 2 , R 3 , R 4 and X each are the same or different.

First claim

The invention claimed is:

1. A compound having a benzotriazole ring structure represented by formula (1):

wherein
Ar represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group; and
A and B are the same as or different from each other and each represent a hydrogen atom or a monovalent group of formula (2) provided that A and B are not simultaneously hydrogen atoms:

wherein
R 1 to R 8 are the same as or different from each other and each represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, a linear alkyl group having 1 to 6 carbon atoms, a branched alkyl group having 3 to 6 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group;
m is an integer of 1 or 2,
X represents a carbon atom or a nitrogen atom,
wherein when X is a nitrogen atom, the nitrogen atom does not have substituents or bonding groups of R 1 , R 2 , and R 3 , and there is no R 4 ; and
wherein when m is 2, a plurality of R 1 , R 2 , R 3 , R 4 , and X each are the same or different.

2. The compound of claim 1 , wherein m is 1 in formula (2).

3. The compound of claim 1 , wherein m is 1 and X is a nitrogen atom in formula (2).

4. The compound of claim 1 , wherein m is 2 in formula (2).

5. The compound of claim 1 , wherein m is 2 and all X′s are nitrogen atoms in formula (2).

6. An organic electroluminescence device, comprising:
a pair of electrodes; and
at least one organic layer sandwiched therebetween,
wherein the device comprises a compound having a benzotriazole ring structure represented by formula (1), as a constituent material of at least one organic layer:

wherein
Ar represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group;
A and B are the same as or different from each other and each represent a hydrogen atom or a monovalent group of formula (2), provided that A and B are not simultaneously hydrogen atoms:

wherein
R 1 to R 8 are the same as or different from each other and each represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, a linear alkyl group having 1 to 6 carbon atoms, a branched alkyl group having 3 to 6 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group,
m is an integer of 1 or 2,
X represents a carbon atom or a nitrogen atom,
wherein when X is a nitrogen atom, the nitrogen atom does not have substituents or bonding groups of R 1 , R 2 , and R 3 , and there is no R 4 ; and
wherein when m is 2, a plurality of R 1 , R 2 , R 3 , and R 4 , and X each are the same or different.

7. The device of claim 6 , wherein the organic layer is an electron-transport layer, and the compound of formula (1) is at least one constituent material in the electron-transport layer.

8. The device of claim 6 , wherein the organic layer is a hole-blocking layer, and the compound of formula (1) is at least one constituent material in the hole-blocking layer.

9. The device of claim 6 , wherein the organic layer is a luminescent layer, and the compound of formula (1) is at least one constituent material in the luminescent layer.

10. The device of claim 6 , wherein the organic layer is an electron-injection layer, and the compound of formula (1) is at least one constituent material in the electron-injection layer.

11. The compound of claim 1 , wherein both A and B are a monovalent group of formula (2), and in the monovalent group of at least one of A and B, m is 1.

12. The compound of claim 1 , wherein both A and B are a monovalent group of formula (2), and in the monovalent group of at least one of A and B, m is 1 and X is a nitrogen atom.

13. The compound of claim 1 , wherein both A and B are a monovalent group of formula (2), and in the monovalent group of at least one of A and B, m is 2.

14. The compound of claim 4 , wherein both A and B are a monovalent group of formula (2), and in the monovalent group of at least one of A and B, X's are nitrogen atoms.

15. The compound of claim 1 , wherein both A and B are the monovalent group of formula (2), and wherein m is 1.

Assignees

• Yokoyama Norimasa
• Hayashi Shuichi
• Kabasawa Naoaki
• Taniguchi Yoshio
• Ichikawa Musubu
• Mochiduki Shunji
• Hodogaya Chemical Co Ltd
• Univ Shinshu

Inventors

• Yokoyama Norimasa
• Hayashi Shuichi
• Kabasawa Naoaki
• Taniguchi Yoshio
• Ichikawa Musubu
• Mochiduki Shunji

Classifications

• H10K85/615

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

• H10K85/654

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

• H10K50/18

  Carrier blocking layers · CPC title

• H10K85/6572

  comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole · CPC title

• C07D401/04 Primary

  directly linked by a ring-member-to-ring-member bond · CPC title