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

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

Abstract

There is disclosed squaraine compounds of formula I: ##STR00001## wherein each of Y.sub.1 and Y.sub.2 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.

Inventors:: Thompson, Mark E.; Forrest, Stephen R.; Wei, Guodan; Wang, Siyi; Hall, Lincoln; Diev, Viacheslav V.; Xiao, Xin

Issue Date:: 2019-06-25

Research Org.:: Univ. of Southern California, Los Angeles, CA (United States); Univ. of Michigan, Ann Arbor, MI (United States)

Sponsoring Org.:: USDOE

OSTI Identifier:: 1568536

Patent Number(s):: 10333079

Application Number:: 14/853,256

Assignee:: University of Southern California (Los Angeles, CA); The Regents of the University of Michigan (Ann Arbor, MI)

Patent Classifications (CPCs):: C - CHEMISTRY C09 - DYES C09K - MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

H - ELECTRICITY H01 - BASIC ELECTRIC ELEMENTS H01L - SEMICONDUCTOR DEVICES

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C - CHEMISTRY C09 - DYES C09K - MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
C09K2211/1014 - bridged by heteroatoms, e.g. N, P, Si or B

H - ELECTRICITY H01 - BASIC ELECTRIC ELEMENTS H01L - SEMICONDUCTOR DEVICES
H01L51/0046 - {Fullerenes, e.g. C60, C70}

Y - NEW / CROSS SECTIONAL TECHNOLOGIES Y02 - TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE Y02E - REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
Y02E10/542 - Dye sensitized solar cells
Y02E10/549 - organic PV cells

H - ELECTRICITY H01 - BASIC ELECTRIC ELEMENTS H01L - SEMICONDUCTOR DEVICES
H01L51/0071 - {Polycyclic condensed heteroaromatic hydrocarbons}

C - CHEMISTRY C09 - DYES C09B - ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES {, e.g. PIGMENTS},
C09B57/007 - {Squaraine dyes}

C - CHEMISTRY C09 - DYES C09K - MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
C09K2211/1011 - Condensed systems

H - ELECTRICITY H01 - BASIC ELECTRIC ELEMENTS H01L - SEMICONDUCTOR DEVICES
H01L51/4246 - {comprising multi-junctions, e.g. double hetero-junctions}

C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07C - ACYCLIC OR CARBOCYCLIC COMPOUNDS
C07C2601/04 - with a four-membered ring

H - ELECTRICITY H01 - BASIC ELECTRIC ELEMENTS H01L - SEMICONDUCTOR DEVICES
H01L51/0059 - {Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
H01L51/006 - {comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom}

B - PERFORMING OPERATIONS B82 - NANOTECHNOLOGY B82Y - SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES
B82Y10/00 - Nanotechnology for information processing, storage or transmission, e.g. quantum computing or single electron logic

C - CHEMISTRY C09 - DYES C09K - MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
C09K11/06 - containing organic luminescent materials

C - CHEMISTRY C09 - DYES C09B - ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES {, e.g. PIGMENTS},
C09B57/008 - {Triarylamine dyes containing no other chromophores}

C - CHEMISTRY C09 - DYES C09K - MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
C09K2211/1007 - Non-condensed systems
C09K2211/1029 - containing one nitrogen atom as the heteroatom

H - ELECTRICITY H01 - BASIC ELECTRIC ELEMENTS H01L - SEMICONDUCTOR DEVICES
H01L51/0058 - {containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene}

H - ELECTRICITY H01 - BASIC ELECTRIC ELEMENTS H01G - CAPACITORS
H01G9/2059 - {comprising an organic dye as the active light absorbing material, e.g. adsorbed on an electrode or dissolved in solution}

H - ELECTRICITY H01 - BASIC ELECTRIC ELEMENTS H01L - SEMICONDUCTOR DEVICES
H01L51/0072 - {comprising only nitrogen in the heteroaromatic polycondensed ringsystem, e.g. phenanthroline, carbazole}

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DOE Contract Number:: FG36-08GO18022; SC0000957; SC0001013

Resource Type:: Patent

Resource Relation:: Patent File Date: 09/14/2015

Country of Publication:: United States

Language:: English

Citation Formats


                    Thompson, Mark E., Forrest, Stephen R., Wei, Guodan, Wang, Siyi, Hall, Lincoln, Diev, Viacheslav V., and Xiao, Xin. Organic photosensitive devices comprising aryl squaraines and methods of making the same.  United States: N. p., 2019. 
        Web.

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                    Thompson, Mark E., Forrest, Stephen R., Wei, Guodan, Wang, Siyi, Hall, Lincoln, Diev, Viacheslav V., & Xiao, Xin. Organic photosensitive devices comprising aryl squaraines and methods of making the same.  United States.

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                    Thompson, Mark E., Forrest, Stephen R., Wei, Guodan, Wang, Siyi, Hall, Lincoln, Diev, Viacheslav V., and Xiao, Xin. Tue .  
        "Organic photosensitive devices comprising aryl squaraines and methods of making the same".  United States.  https://www.osti.gov/servlets/purl/1568536.

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@article{osti_1568536,

  title        = {Organic photosensitive devices comprising aryl squaraines and methods of making the same},

  author       = {Thompson, Mark E. and Forrest, Stephen R. and Wei, Guodan and Wang, Siyi and Hall, Lincoln and Diev, Viacheslav V. and Xiao, Xin},

  abstractNote = {There is disclosed squaraine compounds of formula I: ##STR00001## wherein each of Y.sub.1 and Y.sub.2 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.},

  doi          = {},

  journal      = {},
number       = ,

  volume       = ,

  place        = {United States},

  year         = {2019},

  month        = {6}

}

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Works referenced in this record:

Diphenylsquarylium compound and filter for display containing the same
patent, December 2004

Ozawa, Tetsuo; Haraguchi, Yukinari; Nakano, Tomomi
US Patent Document 6,836,383
URL: http://patft.uspto.gov/netacgi/nph-Parser?patentnumber=6836383

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

Abstract

Citation Formats

Diphenylsquarylium compound and filter for display containing the same patent, December 2004

Diphenylsquarylium compound and filter for display containing the same
patent, December 2004