Organic electroluminescent material and organic optoelectronic device

Patent metadata

Field	Value
Publication number	US-10385059-B2
Application number	US-201715600987-A
Country	US
Kind code	B2
Filing date	May 22, 2017
Priority date	Dec 30, 2016
Publication date	Aug 20, 2019
Grant date	Aug 20, 2019

Abstract

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

wherein: in the chemical formula (I), R 1 to R 10 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, X 1 to X 6 are independently selected from C and N, when N is selected, N does not include a substituent, and when C is selected, C includes 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, at least one of X 1 to X 3 and at least one of X 4 to X 6 are selected as C and, meanwhile, connected to A 1 and A 2 , respectively, and A 1 and A 2 are chemical groups independently represented by the following chemical formula (II):

First claim

What is claimed is:

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

wherein: in the chemical formula (I),
R 1 to R 10 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,
X 1 to X 6 are independently selected from C and N, when N is selected, N does not include a substituent, and when C is selected, C includes 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,
at least one of X 1 to X 3 and at least one of X 4 to X 6 are selected as C and, meanwhile, connected to A 1 and A 2 , respectively, and
A 1 and A 2 are chemical groups independently represented by the following chemical formula (II):

wherein: in the chemical formula (II),
R 5 to R 12 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, 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,
m represents 0 or 1, and n represents 0 or 1, and
n in A 1 and n in A 2 are not zero at the same time.

2. The compound according to claim 1 , wherein:
the compound is represented by the following chemical formula (III):

3. The compound according to claim 2 , wherein:
Y is selected from 0, S, —C(CH 3 ) 2 —, —C(Ph) 2 -, and —Si(CH 3 ) 2 —.

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

5. The compound according to claim 1 , wherein:
m in A 1 and m in A 2 are 1 at the same time; and
n in A 1 and n in A 2 are 1 at the same time.

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. The compound according to claim 7 , 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 ΔEst, wherein ΔEst≤0.02 eV.

9. The compound according to claim 1 is configured to emit light by absorbing energy generated by an electron-hole recombination.

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),
R 1 to R 10 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,
X 1 to X 6 are independently selected from C and N, when N is selected, N does not include a substituent, and when C is selected, C includes 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 , at least one of X 1 to X 3 and at least one of X 4 to X 6 are selected as C and, meanwhile, connected to A 1 and A 2 , respectively, and
A 1 and A 2 are chemical groups independently represented by the following chemical formula (II):

wherein: in the chemical formula (II),
R 5 to R 12 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, 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,
m represents 0 or 1, and n represents 0 or 1, and
n in A 1 and n in A 2 are not zero at the same time.

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 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:
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.

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 lig

Assignees

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

Inventors

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

Classifications

• C09K2211/1011

  Condensed systems · CPC title

• C07D487/14 Primary

  Ortho-condensed systems · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title

• C09K2211/1037

  with sulfur · CPC title