Nitrogen annulated perylene diimides for use as electron transport materials in organic electronic devices

Patent metadata

Field	Value
Publication number	US-9865819-B2
Application number	US-201715615212-A
Country	US
Kind code	B2
Filing date	Jun 6, 2017
Priority date	Jun 6, 2016
Publication date	Jan 9, 2018
Grant date	Jan 9, 2018

Abstract

PDI derivatives useful as opto-electronically active materials or for the synthesis of such materials. Certain compounds herein function as efficient electron acceptors and are useful as electron active components of electronic devices.

First claim

The invention claimed is:

1. A compound of formula:

where p is 0 or 1;
n is 2, 3 or 4;
R 1 and R 2 are independently selected from a straight-chain alkyl having 1-30 carbon atoms and a branched alkyl having 3-30 carbon atoms;
R 3 is independently selected from a straight-chain alkyl having 1-30 carbon atoms and a branched alkyl group having 3-30 carbon atoms; and
M 1 is selected from an arylene (—Ar—), a heteroarylene (—HAr—), an alkynylene (-≡-), a dialkynylene (-≡-≡-), and an organic dye moiety.

2. The compound of claim 1 , wherein p is 0 and n is 2.

3. The compound of claim 1 , wherein p is 1 and n is 2.

4. The compound of claim 1 , wherein M 1 is an alkynylene or a dialkynylene.

5. The compound of claim 1 , wherein M 1 is an arylene.

6. The compound of claim 1 , wherein M 1 is heteroarylene.

7. The compound of claim 1 , wherein M 1 is a phenylene, a naphthylene or an anthracenylene.

8. The compound of claim 1 , wherein M 1 is selected from any one of:

wherein each R 3 is independently selected from alkyl groups having 1-30 carbon atoms.

9. The compound of claim 1 , wherein M 1 is selected from any one of:

where X 1 is O, S or Se and n=1-6;

where X 3 is O, S or Se;

where X 4 is F or CN;

where X 5 is F or CN;

wherein each R 3 is independently selected from alkyl groups having 1-30 carbon atoms and X11 is S or O.

10. The compound of claim 1 , wherein M 1 is selected from any one of:

where X 3 is O, S or Se;

where X 5 is CN or F;

where X 4 is CN or F;

and

where X 12 is C, Si or Ge, and
wherein each R 1 and each R 3 is independently selected from alkyl groups having 1-30 carbon atoms.

11. The compound of claim 1 , wherein M 1 is

wherein each R 3 is independently selected from alkyl groups having 1-30 carbon atoms.

12. The compound of claim 1 , wherein M 1 is

where each R 10 independently is a straight-chain alkyl having 1-30 carbon atoms or a branched alkyl group having 3 to 20 carbon atoms.

13. The compound of claim 12 , wherein each R 10 is a straight-chain alkyl group having 6-12 carbon atoms.

14. The compound of claim 1 having formula:

where R 1 and R 2 are independently selected from a straight-chain alkyl having 1-30 carbon atoms and a branched alkyl having 3-30 carbon atoms;
R 3 is independently selected from a straight-chain alkyl having 1-30 carbon atoms and a branched alkyl group having 3-30 carbon atoms; and
M is selected from an arylene (—Ar—), a heteroarylene (—HAr—), an alkynylene (-≡-), and a dialkynylene (-≡-≡-).

15. The compound of claim 14 , wherein M is an alkynylene (-≡-), or a dialkynylene (-≡-≡-).

16. An electronic device employing an electron acceptor wherein the electron acceptor is one or more compounds of claim 1 .

17. The electronic device of claim 16 which is an organic solar cell, an organic thin film transistor or a redox flow battery.

18. A compound of formula I:

where:
X is a halogen, triflyl, tosyl or mesyl group;
R 1 and R 2 are independently selected from a straight-chain alkyl having 1-30 carbon atoms or a branched alkyl having 3-30 carbon atoms and
R 3 is independently selected from a straight-chain alkyl having 1-30 carbon atoms or a branched alkyl group having 3-30 carbon atoms.

19. The compound of claim 18 , wherein X is Br, R 1 and R 2 are branched alkyl groups having 3-12 carbon atoms and R 3 is a straight-chain alkyl having 3-8 carbon atoms.

20. A method for making the compound of claim 18 , where X is bromine, which comprises the step of bromination of a compound of formula V:

in an organic solvent in which the compound of formula V is soluble at room temperature in a molar excess of Br 2 with respect to the compound of formula V.

Assignees

• Uti Lp

Inventors

• Hendsbee Arthur D
• Sun Jon-Paul
• Welch Gregory C
• Hill Ian G
• McAFEE Seth
• Cann Jonathan

Classifications

• H01L51/0071

  Electricity · mapped topic

• H01L51/4253

  Electricity · mapped topic

• C07D471/16 Primary

  Peri-condensed systems · CPC title

• H01L51/0053 Primary

  Electricity · mapped topic

• H01L51/0072

  Electricity · mapped topic