IP Library Granted Patent US 10,385,059
Granted Patent B2
US 10,385,059 · App. 15/600,987 · Granted Aug 20, 2019

Organic electroluminescent material and organic optoelectronic device

Inventors: Xiangcheng Wang (Shanghai, CN); Ying Liu (Shanghai, CN); Hongyang Ren (Shanghai, CN); Wei He (Shanghai, CN); Chen Liu (Shanghai, CN)
Assignees: Shanghai Tianma AM-OLED Co., Ltd.; Tianma Micro-Electronics Co., Ltd.
C07D487/14C09K11/06H01L51/0071H01L51/0072H01L51/5012H01L51/5016
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Quick Facts
Patent No.
US 10,385,059
App. No.
15/600,987
Granted
Aug 20, 2019
Kind
B2
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):

Claims (66)

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 light-emitting layer and the cathode.

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

the one or more organic thin film layers further include the hole transport layer, the electron transport layer, the electron injection layer and the 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.

19. The organic optoelectronic device according to claim 14 , 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,

wherein the electron blocking layer, the hole transport layer and the hole injection layer are disposed between the light-emitting layer and the anode, and

the hole blocking layer, the electron transport layer and the electron injection layer are disposed between the light-emitting layer and the cathode.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 7, 2022
From: SHANGHAI TIANMA AM-OLED CO.,LTD.; TIANMA MICRO-ELECTRONICS CO., LTD.
To: WUHAN TIANMA MICRO-ELECTRONICS CO., LTD.; WUHAN TIANMA MICROELECTRONICS CO., LTD.SHANGHAI BRANCH; TIANMA MICRO-ELECTRONICS CO., LTD.
Reel/Frame 059619/0730 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 22, 2017
From: WANG, XIANGCHENG; LIU, YING; REN, HONGYANG; HE, WEI; LIU, CHEN
To: SHANGHAI TIANMA AM-OLED CO., LTD.; TIANMA MICRO-ELECTRONICS CO., LTD.
Reel/Frame 042451/0182 →
Priority Claims (1)
CN 2016 1 1264917 · Dec 30, 2016 · national
Continuity (1)
Related Publication 20170256716A1 · Sep 7, 2017