Non-fullerene acceptor compound containing benzoselenadiazole and organic optoelectronic device including the same

Patent metadata

Field	Value
Publication number	US-12139465-B2
Application number	US-202017105673-A
Country	US
Kind code	B2
Filing date	Nov 27, 2020
Priority date	Jan 17, 2020
Publication date	Nov 12, 2024
Grant date	Nov 12, 2024

Abstract

The present invention relates to a non-fullerene acceptor compound containing benzoselenadiazole, and organic optoelectronic devices comprising the same.

First claim

What is claimed is:

1. A non-fullerene acceptor compound containing benzoselenadiazole having the following formula:

wherein Ar 1 is a five-membered heterocyclic ring;
Ar 2 is a monocyclic or polycyclic, C5, C6, C8, C9, or C10 heteroaromatic derivative;
π is a monocyclic or polycyclic, C5, C6, C7, C8 or C9 heteroaromatic derivative, wherein
m=0-5; and
EG is a monocyclic or polycyclic derivative containing a ketone group and electron-withdrawing group.

2. The non-fullerene acceptor compound containing benzoselenadiazole according to claim 1 , wherein Ar 1 is selected from the group consisting of

which the substituent R 1 of Ar 1 is selected from the group consisting of C1-C30 linear alkyl, C1-C30 branched alkyl, C1-C30 silyl, C1-C30 ester, C1-C30 alkoxy, C1-C30 alkylthio, C1-C30 haloalkyl, C1-C30 alkyl substituted with alkene groups or alkyne groups, C1-C30 cyanoalkyl, C1-C30 nitroalkyl, C1-C30 hydroxyalkyl, C1-C30 keto-alkyl, and halogen.

3. The non-fullerene acceptor compound containing benzoselenadiazole according to claim 1 , wherein Ar 2 is selected from the group consisting of

which the substituent R 2 of Ar 2 is selected from the group consisting of C1-C30 linear alkyl, C1-C30 branched alkyl, C1-C30 silyl, C1-C30 ester, C1-C30 alkoxy, C1-C30 alkylthio, C1-C30 haloalkyl, C1-C30 alkyl substituted with alkene groups or alkyne groups, C1-C30 cyanoalkyl, C1-C30 nitroalkyl, C1-C30 hydroxyalkyl, C1-C30 keto-alkyl, halogen, benzene ring containing R 1 , five-membered heterocycle containing R 1 , and six-membered heterocycle containing R 1 ,
R 1 is selected from the group consisting of C1-C30 linear alkyl, C1-C30 branched alkyl, C1-C30 silyl, C1-C30 ester, C1-C30 alkoxy, C1-C30 alkylthio, C1-C30 haloalkyl, C1-C30 alkyl substituted with alkene groups or alkyne groups, C1-C30 cyanoalkyl, C1-C30 nitroalkyl, C1-C30 hydroxyalkyl, C1-C30 keto-alkyl, and halogen.

4. The non-fullerene acceptor compound containing benzoselenadiazole according to claim 1 , wherein the π is selected from the group consisting of

which the substituent R 3 of π is selected from the consisting of C1-C30 linear alkyl, C1-C30 branched alkyl, C1-C30 silyl, C1-C30 ester, C1-C30 alkoxy, C1-C30 alkylthio, C1-C30 haloalkyl, C1-C30 alkyl substituted with alkene groups or alkyne groups, C1-C30 cyanoalkyl, C1-C30 nitroalkyl, C1-C30 hydroxyalkyl, C1-C30 keto-alkyl, and halogen.

5. The non-fullerene acceptor compound containing benzoselenadiazole according to claim 1 , wherein the EG is selected from the group consisting of

which the substituent R 4 of EG is selected from the group consisting of hydrogen atom, halogen, C1-C20 alkyl, C1-C20 alkoxy, C1-C20 carbonyl, C1-C20 ester, and C1-C20 cyano.

6. An organic optoelectronic device comprising:
a substrate;
a bottom electrode disposed on the substrate;
a top electrode arranged opposite to the bottom electrode; and
an intermediate layer which is mounted between the bottom electrode and the top electrode and including a first carrier transport layer comprising molybdenum trioxide (MoO 3 ), a second carrier transport layer comprising zinc oxide (ZnO), and an active layer which is arranged between the first carrier transport layer and the second carrier transport layer and including a polymer donor and a non-fullerene acceptor compound containing benzoselenadiazole having the following structural formula

wherein Ar 1 is a five-membered heterocyclic ring;
Ar 2 is a monocyclic or polycyclic, C5, C6, C8, C9, or C10 heteroaromatic derivative;
π is a monocyclic or polycyclic, C5, C6, C7, C8 or C9 heteroaromatic derivative, wherein
m=0-5; and
EG is a monocyclic or polycyclic derivative containing a ketone group and electron-withdrawing group.

7. The organic optoelectronic device according to claim 6 , wherein the active layer is arranged over the first carrier transport layer and the second carrier transport layer is disposed over the active layer.

8. The organic optoelectronic device according to claim 6 , wherein the active layer is arranged over the second carrier transport layer and the first carrier transport layer is disposed over the active layer.

9. The organic optoelectronic device according to claim 6 , wherein the Ar 1 is selected from the group consisting of

which the substituent R 1 of Ar 1 is selected from the group consisting of C1-C30 linear alkyl, C1-C30 branched alkyl, C1-C30 silyl, C1-C30 ester, C1-C30 alkoxy, C1-C30 alkylthio, C1-C30 haloalkyl, C1-C30 alkyl substituted with alkene groups or alkyne groups, C1-C30 cyanoalkyl, C1-C30 nitroalkyl, C1-C30 hydroxyalkyl, C1-C30 keto-alkyl, and halogen.

10. The organic optoelectronic device according to claim 6 , wherein the Ar 2 is selected from the group consisting of:

which the substituent R 2 of Ar 2 is selected from the group consisting of C1-C30 linear alkyl, C1-C30 branched alkyl, C1-C30 silyl, C1-C30 ester, C1-C30 alkoxy, C1-C30 alkylthio, C1-C30 haloalkyl, C1-C30 alkyl substituted with alkene groups or alkyne groups, C1-C30 cyanoalkyl, C1-C30 nitroalkyl, C1-C30 hydroxyalkyl, C1-C30 keto-alkyl, halogen, benzene ring containing R 1 , five-membered heterocycle containing R 1 , and six-membered heterocycle containing R 1 ,
R 1 is selected from the group consisting of C1-C30 linear alkyl, C1-C30 branched alkyl, C1-C30 silyl, C1-C30 ester, C1-C30 alkoxy, C1-C30 alkylthio, C1-C30 haloalkyl, C1-C30 alkyl substituted with alkene groups or alkyne groups, C1-C30 cyanoalkyl, C1-C30 nitroalkyl, C1-C30 hydroxyalkyl, C1-C30 keto-alkyl, and halogen.

11. The organic optoelectronic device according to claim 6 , wherein the π is selected from the group consisting of

which the substituent R 3 of the π is selected from the consisting of C1-C30 linear alkyl, C1-C30 branched alkyl, C1-C30 silyl, C1-C30 ester, C1-C30 alkoxy, C1-C30 alkylthio, C1-C30 haloalkyl, C1-C30 alkyl substituted with alkene groups or alkyne groups, C1-C30 cyanoalkyl, C1-C30 nitroalkyl, C1-C30 hydroxyalkyl, C1-C30 keto-alkyl, and halogen.

12. The organic optoelectronic device according to claim 6 , wherein the EG is selected from the group consis

Assignees

• Raynergy Tek Inc

Inventors

• Hsiao Yu-Tang
• Lee Chia-Hao
• Liao Chuang-Yi
• Lee Chun-Chieh
• Li Chia-Hua
• Ho Hsiuan-Ling
• Chang Yi-Ming

Classifications

• H10K30/50

  Photovoltaic [PV] devices · CPC title

• H10K50/166

  comprising a multilayered structure · CPC title

• H10K85/1135

  Polyethylene dioxythiophene [PEDOT]; Derivatives thereof · CPC title

• H10K85/151

  Copolymers · CPC title

• H10K85/113

  Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene · CPC title