Organic electroluminescent material and organic optoelectronic device

Patent metadata

Field	Value
Publication number	US-10535824-B2
Application number	US-201715599009-A
Country	US
Kind code	B2
Filing date	May 18, 2017
Priority date	Dec 30, 2016
Publication date	Jan 14, 2020
Grant date	Jan 14, 2020

Abstract

A compound and an organic optoelectronic device are provided. The compound has the chemical formula (I):

wherein: X 1 to X 5 are independently selected from C and N, when N is selected, a substituent may not be included; R 1 to R 9 are independently selected nom hydrogen, deuterium, C 1 to C 30 alkyl, C 1 to C 30 heteroatom-substituted alkyl, C 6 to C 30 aryl, C 2 to C 30 heteroaryl, and a chemical group A represented by the following chemical formula (II):

and at least one of R 1 to R 9 is selected from the chemical group A. In the chemical formula (II), R 10 to R 17 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, and Y is selected from O, S, substituted or unsubstituted imino, substituted or unsubstituted methylene, and substituted or unsubstituted silylene.

First claim

What is claimed is:

1. A compound of the following chemical formula (I):

wherein:
in the chemical formula (I), X 1 to X 5 are independently selected from the group consisting of C and N, and at least one of X 1 to X 5 are selected from N, and when N is selected, a substituent is not included;
R 1 to R 9 are independently selected from the group consisting of hydrogen, deuterium, C 1 to C 30 alkyl, C 1 to C 30 heteroatom-substituted alkyl, C 6 to C 30 aryl, C 2 to C 30 heteroaryl, and a chemical group A represented by the following chemical formula (II):

and
at least one of R 5 to R 9 is selected from the chemical group A,
wherein in the chemical formula (II),
R 10 to R 17 are independently selected from the group consisting of 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; and
Y is selected from the group consisting of O, S, substituted or unsubstituted imino, substituted or unsubstituted methylene, and substituted or unsubstituted silylene, and a substituent is selected from the group consisting of 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.

2. The compound according to claim 1 has the following chemical formula (IV):

the chemical formula (IV),
wherein X 6 to X 10 are independently selected from the group consisting of C and N, and at least three of X 6 to X 10 are selected from C;
when N is selected, a substituent is not included;
R 23 to R 26 are independently selected from the group consisting of 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;
the chemical group A is connected to a number m of C of X 6 to X 10 , m is a positive integer, and 1≤m≤4; and
for a remaining C of X 6 to X 10 , a substituent selected from the group consisting of 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.

3. The compound according to claim 1 , wherein:
the heteroatom-substituted alkyl is selected from alkoxy groups.

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

5. The compound according to claim 1 , wherein:
the C 2 to C 30 heteroaryl is selected from heteroaryl containing one or more N.

6. The compound according to claim 1 , wherein:
the chemical group A is selected from the group consisting of:

7. The compound according to claim 1 , comprising a compound selected from the group consisting of:

8. 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 ΔE st ≤0.30 eV.

9. The compound according to claim 8 , wherein:
the energy difference between the lowest singlet excited state S 1 and the lowest triplet excited state T 1 of the compound is configured to be ΔE st ≤0.02 eV.

10. 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):

wherein:
in the chemical formula (I), X 1 to X 5 are independently selected from the group consisting of C and N, and at least one of X 1 to X 5 are selected from N, and when N is selected, a substituent is not included;
R 1 to R 9 are independently selected from the group consisting of hydrogen, deuterium, C 1 to C 30 alkyl, C 1 to C 30 heteroatom-substituted alkyl, C 6 to C 30 aryl, C 2 to C 30 heteroaryl, and a chemical group A represented by the following chemical formula (II):

and
at least one of R 5 to R 9 is selected from the chemical group A, wherein in the chemical formula (II),
R 10 to R 17 are independently selected from the group consisting of 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; and
Y is selected from the group consisting of O, S, substituted or unsubstituted imino, substituted or unsubstituted methylene, and substituted or unsubstituted silylene, and a substituent is selected from the group consisting of 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.

11. The organic optoelectronic device according to claim 10 , wherein:
the one or more compounds are heat activated delayed fluorescence (TADF) materials.

12. The organic optoelectronic device according to claim 10 , 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.

13. The organic optoelectronic device according to claim 12 , 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.

14. The organic optoelectronic device according to claim 10 , wherein:
the one or more organic thin film layers further include at least one layer selected from the group consisting 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.

15. The organic optoelectronic device according to claim 14 , wherein:
the at least one layer selected from the group 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.

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

17. The organic optoelectronic device according to claim 14 , wherein:
the one or more organic thin film layers further include the hole transport layer and the 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.

18. The organic optoelectronic device according to claim 14 , wherein:
the one

Assignees

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

Inventors

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

Classifications

• C07D413/04

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

• C07D401/10

  linked by a carbon chain containing aromatic rings · CPC title

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title

• C07D413/14

  containing three or more hetero rings · CPC title

• C09K2211/1007

  Non-condensed systems · CPC title