Organic electroluminescent material and organic optoelectronic device

Patent metadata

Field	Value
Publication number	US-9911932-B2
Application number	US-201715598891-A
Country	US
Kind code	B2
Filing date	May 18, 2017
Priority date	Dec 30, 2016
Publication date	Mar 6, 2018
Grant date	Mar 6, 2018

Abstract

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

chemical formula (I). In the chemical formula (I), X 1 to X 2 are independently selected from O, S,

and substituted or unsubstituted methylene, 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. X 3 is selected from O, S, substituted or unsubstituted methylene, substituted or unsubstituted methylene, and substituted or unsubstituted silylene, and a substituent is selected 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. R 1 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.

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 2 are independently selected from O, S,

 and substituted or unsubstituted methylene, 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;
X 3 is selected from O, S, substituted or unsubstituted methylene, substituted or unsubstituted methylene, and substituted or unsubstituted silylene, and a substituent is selected 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
R 1 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.

2. The compound according to claim 1 has the following chemical structure (II):

3. The compound according to claim 1 , wherein:
X 3 is selected from

4. The compound according to claim 2 , wherein:
X 3 is selected from

5. The compound according to claim 1 , wherein:
X 1 is selected from

 and
X 2 is selected from O, S, and dimethyl-substituted methylene (—C(CH 3 ) 2 —).

6. The compound according to claim 2 , wherein:
X 1 is selected from

 and
X 2 is selected from O, S, and dimethyl-substituted methylene (—C(CH 3 ) 2 —).

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

8. The compound according to claim 2 , wherein:
C 6 to C 30 aryl is selected from phenyl and naphthyl.

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

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

11. The compound according to claim 10 , wherein:
the energy difference between the lowest singlet excited state S 1 and the lowest triplet excited state T 1 of the organic electroluminescent compound is configured to be ΔEst, wherein ΔEst≦0.02 eV.

12. 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 organic electroluminescent compounds each having the following chemical formula (I):

wherein; in the chemical formula (I),
X 1 to X 2 are independently selected from O, S,

 and substituted or unsubstituted methylene, 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;
X 3 is selected from O, S, substituted or unsubstituted methylene, substituted or unsubstituted methylene, and substituted or unsubstituted silylene, and a substituent is selected 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
R 1 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.

13. The organic optoelectronic device according to claim 12 , wherein:
the one or more organic electroluminescent compounds are heat activated delayed fluorescence (TADF) materials.

14. The organic optoelectronic device according to claim 12 , 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 organic electroluminescent compounds.

15. The organic optoelectronic device according to claim 14 , wherein:
the one or more organic electroluminescent compounds are used as a dopant material, a co-doping material, and a host material in the light-emitting layer.

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

17. The organic optoelectronic device according to claim 16 , 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 organic electroluminescent compounds.

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

19. The organic optoelectronic device according to claim 16 , 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.

20. The organic optoelectronic device according to claim 16 , wherein:
the one or more organic thin film layers further include the hole transport layer, the electron transport layer, the electron injection layer, the hole injection layer, the electron blocking layer, and the hole blocking layer,

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 Primary

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

• C09K2211/185

  of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd · CPC title

• C07D265/38

  [b, e]-condensed with two six-membered rings · CPC title

• C09K2211/1007

  Non-condensed systems · CPC title

• C07F7/0816

  said ring comprising Si as a ring atom · CPC title