Ortho-substituted thermally activated delayed fluorescence material and organic light-emitting device comprising same

Patent metadata

Field	Value
Publication number	US-11758808-B2
Application number	US-201515562415-A
Country	US
Kind code	B2
Filing date	Nov 25, 2015
Priority date	Mar 27, 2015
Publication date	Sep 12, 2023
Grant date	Sep 12, 2023

Abstract

A thermally activated delayed fluorescent (TADF) material is provided. The TADF material has a form in which an electron donating group and an electron withdrawing group are connected to benzene and the electron withdrawing group is position in an ortho position to the electron donating group.

First claim

The invention claimed is:

1. The light-emitting material represented by Chemical Formula 3:

wherein in Chemical Formulas 3;
R 3 and R 4 are combined together with the nitrogen to which they are attached to independently form a substituted or unsubstituted heteroaryl group represented by any one of Structural Formulas A9 or A24, and R 5 and R 6 are combined together with the nitrogen to which they are attached to independently form a substituted or unsubstituted heteroaryl group represented by any one of Structural Formulas A9 or A24:

wherein in Structural Formulas A9 and A24:
R 11 and R 12 are, each independently, hydrogen, deuterium, a substituted or unsubstituted C1-C2 alkyl group, or a substituted or unsubstituted C6-C30 aryl group
in Formula A9, Sub 1 and Sub 2 are, each independently, deuterium, a substituted or unsubstituted C5-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 alkylaryl group, a substituted or unsubstituted C6-C30 aralkyl group, a substituted or unsubstituted C3-C30 heteroaryl group, a substituted or unsubstituted C1-C9 alkyloxy group, or a substituted or unsubstituted C6-C30 aryloxy group,
in Formula A24, Sub 1 to Sub 3 are, each independently, hydrogen, deuterium, a substituted or unsubstituted C1-C9 alkyl group, a substituted or unsubstituted C5-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 alkylaryl group, a substituted or unsubstituted C6-C30 aralkyl group, a substituted or unsubstituted C3-C30 heteroaryl group, a substituted or unsubstituted C1-C9 alkyloxy group, or a substituted or unsubstituted C6-C30 aryloxy group,
R 19 is a substituted or unsubstituted C6 aryl group, and
R 26 to R 33 are, each independently, hydrogen, deuterium, a halogen group, a substituted or unsubstituted C4-C6 aryl group, or a substituted or unsubstituted C1-C3 alkyl group.

2. The light-emitting material of claim 1 ,
wherein the compound represented by Chemical Formula 3 is represented by the following Chemical Formula 6:

in Chemical Formula 6, R 3 , R 4 , R 5 , R 6 , R 26 to R 29 , and R 30 to R 33 are as defined in Chemical Formula 3,
Sub 5 is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted C1-C9 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group, a substituted or unsubstituted C1-C9 alkyloxy group, a substituted or unsubstituted —NR e R f , a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted thiol group, a substituted or unsubstituted sulfoxide group, a substituted or unsubstituted sulfone group, a substituted or unsubstituted C5-C30 arylthio group, a substituted or unsubstituted C5-C30 aryloxy group, a substituted or unsubstituted C5-C30 arylamine group, or a substituted or unsubstituted C5-C30 aralkyl group; Sub 5 is optionally fused to a main body to which it is bonded to form a substituted or unsubstituted cyclyl or a substituted or unsubstituted aryl,
R e and R f are independently selected from the group consisting of a substituted or unsubstituted C1-C9 alkyl group, a substituted or unsubstituted C5-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 alkylaryl group, a substituted or unsubstituted C6-C30 aralkyl group, and a substituted or unsubstituted C3-C30 heteroaryl group; R e and R f are optionally joined together with the nitrogen to which they are attached to form a substituted or unsubstituted heterocyclyl or a substituted or unsubstituted heteroaryl.

3. A light-emitting material represented by any one of the following Compounds 68, 69, 71, 72, and 74:

4. The light-emitting material of claim 1 ,
wherein the triazine group in Chemical Formula 3 is any one of the following Structural Formulas B34 to B40:

in Structural Formulas B34 to B40,
R 11 represents hydrogen, deuterium, or a substituted or unsubstituted C1-C2 alkyl group.

5. An organic light emitting diode comprising sequentially stacked an anode, a hole conduction layer, a light emitting layer, an electron conduction layer, and a cathode,
wherein the hole conduction layer comprises a hole transporting layer;
wherein the electron conduction layer comprises an electron transporting layer;
wherein one of the hole transporting layer, the light emitting layer and the electron transporting layer comprises the light-emitting material of claim 1 .

6. The organic light emitting diode of claim 5 ,
wherein the light emitting layer comprises a host material and a dopant material, and the dopant material comprises the light-emitting material.

7. The organic light emitting diode of claim 6 , wherein the dopant material is a delayed fluorescent light emitting material.

8. The light-emitting material of claim 1 , wherein in Formula A24, Sub 1 to Sub 3 are each hydrogen.

9. The light-emitting material of claim 2 , wherein Sub 5 is hydrogen.

10. The light-emitting material of claim 2 , wherein —NR 3 R 4 and —NR 5 R 6 are each independently A9.

Assignees

• Samsung Display Co Ltd

Inventors

• Lee Chilwon
• Gong Myoungseon
• Cha Jaeryung

Classifications

• H10K50/10

  OLEDs or polymer light-emitting diodes [PLED] · CPC title

• H10K2101/20

  Delayed fluorescence emission · CPC title

• H10K85/654 Primary

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

• C07D251/24 Primary

  to three ring carbon atoms · CPC title

• C07D403/10 Primary

  linked by a carbon chain containing aromatic rings · CPC title