Organic photosensitive devices comprising aryl squaraines and methods of making the same

a technology of organic photosensitive devices and aryl squaraines, which is applied in the field of new squaraine compounds, can solve the problems of difficult and expensive production of efficient crystalline-based devices, low stability of high-efficiency amorphous silicon devices, and inability to provide power to circuits, devices or equipmen

Inactive Publication Date: 2012-10-04
UNIV OF SOUTHERN CALIFORNIA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

A photodetector or photoconductor provides a signal or current to control detection circuitry, or the output of information from the detection circuitry but does not provide power to the circuitry, device or equipment.
However, efficient crystalline-based devices, especially of large surface area, are difficult and expensive to produce due to the problems inherent in producing large crystals without significant efficiency-degrading defects.
On the other hand, high efficiency amorphous silicon devices still suffer from problems with stability.
The maximum total power generated by

Method used

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  • Organic photosensitive devices comprising aryl squaraines and methods of making the same
  • Organic photosensitive devices comprising aryl squaraines and methods of making the same
  • Organic photosensitive devices comprising aryl squaraines and methods of making the same

Examples

Experimental program
Comparison scheme
Effect test

example 1

CBZSQ: 2,4-bis[4-N-carbazolo-2,6-dihydroxyphenyl] squaraine

[0156]

[0157]1H-NMR (CDCl3, 500 MHz):8.51 (s, 2H), 7.99 (d, 2H), 7.53 (d, 1H), 7.32 (m, 2H), 7.21 (m, 2H), 7.01 (m, 2H), 6.67 (s, 2H)

example 2

DPSQ: 2,4-bis[4-(N,N-diphenylamino)-2,6-dihydroxyphenyl] squaraine

[0158]

[0159]1H-NMR (CDCl3, 500 MHz): 10.1 (s, 1H), 7.41 (t, 2H, J=7.5 Hz), 7.29 (t, 1H, J=5 Hz), 7.23 (d, 2H, J=5 Hz), 5.87 (s, 1H)

[0160]13C-NMR (CDCl3, 500 MHz): 31.29, 50.78, 98.75, 104.96, 127.57, 129.81, 144.08, 159.51, 163.06, 181.36

[0161]MS: m / z 632.2 (MH+).

example 3

1NPSQ:2,4-bis[4-(N-Phenyl-1-naphthylamino)-2,6-dihydroxyphenyl] squaraine

[0162]

[0163]1H-NMR (CDCl3, 400 MHz): 10.90 (s, 2H), 7.81-7.88 (, 3H), 7.44-7.48 (m, 3H), 7.26-7.29 (m, 4H), 5.71 (s, 2H). MS: m / z 732.2 (M+—CH3).

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Abstract

There is disclosed squaraine compounds of formula I:
wherein each of Y1 and Y2 is independently chosen from an optionally substituted amino group and an optionally substituted aryl group. Also described are organic optoelectronic devices comprising a Donor-Acceptor heterojunction that is formed from one or more of the squaraine compounds. A method of making the disclosed device, which may include one or more sublimation step for depositing said squaraine compound, is also disclosed.

Description

CROSS-REFERENCE TO RELATED APPLICATIONS[0001]This application claims priority to U.S. Provisional Application Nos. 61 / 441,153, filed on Feb. 9, 2011, and 61 / 479,231, filed on Apr. 26, 2011, both of which are incorporated herein by reference in their entirety.STATEMENT REGARDING FEDERALLY SPONSORED RESEARCH[0002]The subject matter of this application was prepared with U.S. Government support under Contract No. DE-FG36-08GO18022 awarded by U.S. Department of Energy, Center for Energy Nanoscience, and Contract Nos. DE-SC0001013 and DE-SC0000957. The government has certain rights in the subject matter of this application.JOINT RESEARCH AGREEMENT[0003]The subject matter of this application was made by, on behalf of, and / or in connection with one or more of the following parties to a joint university-corporation research agreement: University of Michigan, University of Southern California, and Global Photonic Energy Corporation. The agreement was in effect on and before the date the claim...

Claims

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Application Information

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IPC IPC(8): C07C211/55H01L51/40H01L51/54C07D209/86C07C211/58
CPCB82Y10/00C09B57/007H01L51/0046Y02E10/549H01L51/4246C09B57/008H01L51/0059C07C215/44C07C215/78C07C215/82C07D209/86C07D279/22H10K85/615H10K85/631H10K85/633H10K85/657H10K85/6572C07C2601/04C09K11/06Y02E10/542H10K85/211H10K30/211C09B23/00C09B57/00H10K99/00H10K85/626C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1029H01G9/2059
Inventor THOMPSON, MARKWANG, SIYIHALL, LINCOLNDIEV, VIACHESLAV V.FORREST, STEPHEN R.WEI, GUODANXIAO, XIN
Owner UNIV OF SOUTHERN CALIFORNIA
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