Organic electroluminescent material and organic optoelectronic device

Patent metadata

Field	Value
Publication number	US-10629822-B2
Application number	US-201715599244-A
Country	US
Kind code	B2
Filing date	May 18, 2017
Priority date	Dec 30, 2016
Publication date	Apr 21, 2020
Grant date	Apr 21, 2020

Abstract

A compound and an organic optoelectronic device are provided. The compound has the chemical formula (I): A B] n chemical formula (I). In the chemical formula (I): n denotes a positive integer and 1≤n≤5; a chemical group B has the following chemical formula (II):

and a chemical group A has the following chemical formula (III) or (IV):

In the chemical formula (II): R 1 to R 8 are independently selected from hydrogen, deuterium, C 1 to C 30 alkyl, C 1 to C 30 heteroatom-substituted alkyl, C 6 to C 30 aryl, and C 2 to C 30 heteroaryl. Y is selected from O, S, substituted or unsubstituted imino, substituted or unsubstituted methylene, and substituted or unsubstituted silylene, and a substituent is selected from hydrogen, deuterium, C 1 to C 30 alkyl, C 1 to C 30 heteroatom-substituted alkyl, C 6 to C 30 aryl, and C 2 to C 30 heteroaryl. Ar is selected from C 6 to C 30 aryl, and C 2 to C 30 heteroaryl.

First claim

What is claimed is:

1. A compound of the following chemical formula (I):
A B] n   chemical formula (I),

wherein in the chemical formula (I):
n denotes a positive integer and 1≤n≤5;
a chemical group B has the following chemical formula (II):

chemical formula (II),
wherein each chemical group B has a same or different structure when n>1, and in the chemical formula (II):
R 1 to R 8 are independently selected from hydrogen, deuterium, C 1 to C 30 alkyl, C 1 to C 30 heteroatom-substituted alkyl, C 6 to C 30 aryl, and C 2 to C 30 heteroaryl,
Y is selected from O, S, substituted or unsubstituted imino, and substituted or unsubstituted silylene, and a substituent is selected from hydrogen, deuterium, C 1 to C 30 alkyl, C 1 to C 30 heteroatom-substituted alkyl, C 6 to C 30 aryl, and C 2 to C 30 heteroaryl,
Ar is selected from C 6 to C 30 aryl, and C 2 to C 30 heteroaryl, and
q is an integer and 1≤q≤3; and

a chemical group A has the following chemical formula (IV):

chemical formula (IV),
wherein in the chemical formula (IV):
X 15 and X 17 are selected from N while X 9 to X 14 , X 16 and X 18 are selected from C, or X 10 and X 12 are selected from N while X 9 , X 11 and X 13 to X 18 are selected from C, when N is selected, a substituent is not included, while when C is selected, a substituent selected from hydrogen, deuterium, C 1 to C 30 alkyl, C 1 to C 30 heteroatom-substituted alkyl, C 6 to C 30 aryl, and C 2 to C 30 heteroaryl is included, and
the chemical group B is connected to C.

2. The compound according to claim 1 , wherein:
the chemical formula (IV) is

3. The compound according to claim 1 , wherein:
the C 6 to C 30 aryl is selected from phenyl and naphthyl.

4. The compound according to claim 1 , wherein:
R 1 to R 8 are selected from hydrogen, and Y is selected from O, S, and dimethyl substituted Si(—Si(CH 3 ) 2 —).

5. The compound according to claim 1 , wherein:
q represents an integer of 1.

6. The compound according to claim 1 , comprising a compound selected from the following:

7. The compound according to claim 1 , wherein:
an energy difference between a lowest singlet excited state S 1 and a lowest triplet excited state T 1 of the compound is configured to be ΔEst, wherein ΔEst≤0.30 eV.

8. An organic optoelectronic device, comprising:
an anode;
a cathode; and
one or more organic thin film layers disposed between the anode and the cathode,
wherein at least one of the one or more organic thin film layers includes one or more compounds each having the following chemical formula (I):
A B] n   chemical formula (I),

wherein in the chemical formula (I):
n denotes a positive integer and 1≤n≤5;
a chemical group B has the following chemical formula (II):

chemical formula (II),
wherein each chemical group B has a same or different structure when n>1, and in the chemical formula (II):
R 1 to R 8 are independently selected from hydrogen, deuterium, C 1 to C 30 alkyl, C 1 to C 30 heteroatom-substituted alkyl, C 6 to C 30 aryl, and C 2 to C 30 heteroaryl,
Y is selected from O, S, substituted or unsubstituted imino, and substituted or unsubstituted silylene, and a substituent is selected from hydrogen, deuterium, C 1 to C 30 alkyl, C 1 to C 30 heteroatom-substituted alkyl, C 6 to C 30 aryl, and C 2 to C 30 heteroaryl,
Ar is selected from C 6 to C 30 aryl, and C 2 to C 30 heteroaryl, and
q is an integer and 1≤q≤3; and

a chemical group A has the following chemical formula (IV):

chemical formula (IV),
wherein in the chemical formula (IV):
X 15 and X 17 are selected from N while X 9 to X 14 , X 16 and X 18 are selected from C, or X 10 and X 12 are selected from N while X 9 , X 11 and X 13 to X 18 are selected from C, when N is selected, a substituent is not included, while when C is selected, a substituent selected from hydrogen, deuterium, C 1 to C 30 alkyl, C 1 to C 30 heteroatom-substituted alkyl, C 6 to C 30 aryl, and C 2 to C 30 heteroaryl is included, and
the chemical group B is connected to C.

9. The organic optoelectronic device according to claim 8 , wherein:
the one or more compounds are heat activated delayed fluorescence (TADF) materials.

10. The organic optoelectronic device according to claim 8 , wherein:
the at least one of the one or more organic thin film layers disposed between the anode and the cathode is a light-emitting layer, wherein the light-emitting layer includes the one or more compounds.

11. The organic optoelectronic device according to claim 10 , wherein:
the one or more compounds are used as a dopant material, a co-doping material, or a host material in the light-emitting layer.

12. The organic optoelectronic device according to claim 8 , wherein:
the one or more organic thin film layers further include at least one of a hole transport layer, a hole injection layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer.

13. The organic optoelectronic device according to claim 12 , wherein:
at least one of the hole transport layer, the hole injection layer, the electron blocking layer, the hole blocking layer, the electron transport layer, and the electron injection layer includes the one or more compounds.

14. The organic optoelectronic device according to claim 10 , wherein:
the one or more organic thin film layers further include a hole transport layer disposed between the light-emitting layer and the anode.

15. The organic optoelectronic device according to claim 10 , wherein:
the one or more organic thin film layers further include a hole transport layer and an electron transport layer,
wherein the hole transport layer is disposed between the light-emitting layer and the anode, and
the electron transport layer is disposed between the light-emitting layer and the cathode.

16. The organic optoelectronic device according to claim 10 , wherein:
the one or more organic thin film layers further include a hole transport layer, an electron transport layer, an electron injection layer and a hole injection layer,
wherein the hole transport layer and the hole injection layer are disposed between the light-emitting layer and the anode, and
the electron transport layer and the electron injection layer are disposed between the light-emitting layer and the cathode.

17. The compound according to claim 1 , wherein n=2 and Y in each of two chemical groups B is different from each other.

18. A compound of the following chemical formula (I):
A B] n   chemical formula (I),

wherein in the chemical formula (I):
n deno

Assignees

• Shanghai Tianma Am Oled Co Ltd
• Tianma Micro Electronics Co Ltd

Inventors

• Wang Xiangcheng
• Liu Ying
• Ren Hongyang
• He Wei
• Liu Chen

Classifications

• C07D401/10

  linked by a carbon chain containing aromatic rings · CPC title

• C07D413/10

  linked by a carbon chain containing aromatic rings · CPC title

• C09K2211/1007

  Non-condensed systems · CPC title

• C09K2211/1011

  Condensed systems · CPC title

• C09K2211/1033

  with oxygen · CPC title