CA2832613C - Fluoroacylated arylamines - Google Patents

Fluoroacylated arylamines Download PDF

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Publication number
CA2832613C
CA2832613C CA2832613A CA2832613A CA2832613C CA 2832613 C CA2832613 C CA 2832613C CA 2832613 A CA2832613 A CA 2832613A CA 2832613 A CA2832613 A CA 2832613A CA 2832613 C CA2832613 C CA 2832613C
Authority
CA
Canada
Prior art keywords
fluoroacyl
arylamine
alkyl
reaction
light
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Fee Related
Application number
CA2832613A
Other languages
English (en)
French (fr)
Other versions
CA2832613A1 (en
Inventor
Adrien P. Cote
Richard A. Klenkler
Amanda L. Bongers
Gregory M. Mcguire
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Xerox Corp
Original Assignee
Xerox Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Xerox Corp filed Critical Xerox Corp
Publication of CA2832613A1 publication Critical patent/CA2832613A1/en
Application granted granted Critical
Publication of CA2832613C publication Critical patent/CA2832613C/en
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
    • C07C225/22—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording-members for original recording by exposure, e.g. to light, to heat or to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02—Charge-receiving layers
    • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0601—Acyclic or carbocyclic compounds
    • G03G5/0603—Acyclic or carbocyclic compounds containing halogens
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording-members for original recording by exposure, e.g. to light, to heat or to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02—Charge-receiving layers
    • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0601—Acyclic or carbocyclic compounds
    • G03G5/0612—Acyclic or carbocyclic compounds containing nitrogen
    • G03G5/0614—Amines
    • G03G5/06142—Amines arylamine
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording-members for original recording by exposure, e.g. to light, to heat or to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02—Charge-receiving layers
    • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0601—Acyclic or carbocyclic compounds
    • G03G5/0612—Acyclic or carbocyclic compounds containing nitrogen
    • G03G5/0614—Amines
    • G03G5/06142—Amines arylamine
    • G03G5/06144—Amines arylamine diamine
    • G03G5/061443—Amines arylamine diamine benzidine
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording-members for original recording by exposure, e.g. to light, to heat or to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02—Charge-receiving layers
    • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0601—Acyclic or carbocyclic compounds
    • G03G5/0612—Acyclic or carbocyclic compounds containing nitrogen
    • G03G5/0614—Amines
    • G03G5/06142—Amines arylamine
    • G03G5/06144—Amines arylamine diamine
    • G03G5/061446—Amines arylamine diamine terphenyl-diamine
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers

Landscapes

  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Photoreceptors In Electrophotography (AREA)
  • Electroluminescent Light Sources (AREA)
CA2832613A 2012-11-21 2013-11-05 Fluoroacylated arylamines Expired - Fee Related CA2832613C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US13/682764 2012-11-21
US13/682,764 US9196840B2 (en) 2012-11-21 2012-11-21 Fluoroacylated arylamines

Publications (2)

Publication Number Publication Date
CA2832613A1 CA2832613A1 (en) 2014-05-21
CA2832613C true CA2832613C (en) 2017-04-25

Family

ID=50728562

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2832613A Expired - Fee Related CA2832613C (en) 2012-11-21 2013-11-05 Fluoroacylated arylamines

Country Status (4)

Country Link
US (1) US9196840B2 (https=)
JP (1) JP6182053B2 (https=)
CA (1) CA2832613C (https=)
DE (1) DE102013222787B4 (https=)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20230153510A (ko) * 2017-04-18 2023-11-06 더 유니버서티 오브 시카고 광활성인 무기 리간드-캐핑된 무기 나노결정

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0475676B1 (en) 1990-09-04 1996-04-03 Hitachi Chemical Co., Ltd. Electrophotographic member
US5202408A (en) 1991-11-25 1993-04-13 Xerox Corporation Arylamine containing terpolymers with CF3 substituted moieties
JP2000319236A (ja) * 1999-05-07 2000-11-21 Daiden Co Ltd 新規蛍光性化合物及びその錯体
JP5135777B2 (ja) * 2006-11-27 2013-02-06 コニカミノルタビジネステクノロジーズ株式会社 色素増感型光電変換素子及び色素増感型太陽電池
US7652148B1 (en) 2008-08-29 2010-01-26 Xerox Corporation Electrophilic aromatic substitution with diacyl imidazolium
JP2010229279A (ja) * 2009-03-27 2010-10-14 Toyo Ink Mfg Co Ltd 光機能材料
JP2011001474A (ja) * 2009-06-19 2011-01-06 Toyo Ink Mfg Co Ltd 光機能材料
US8883383B2 (en) * 2012-11-21 2014-11-11 Xerox Corporation Charge transport layer comprising fluoroacyl arylamine
US8754260B2 (en) * 2012-11-21 2014-06-17 Xerox Corporation Method for preparing fluoroacylated arylamine
US9070886B2 (en) * 2012-11-21 2015-06-30 Xerox Corporation Electroactive fluoroacylated arylamines

Also Published As

Publication number Publication date
JP2014101364A (ja) 2014-06-05
JP6182053B2 (ja) 2017-08-16
US20140142340A1 (en) 2014-05-22
DE102013222787A1 (de) 2014-05-22
US9196840B2 (en) 2015-11-24
CA2832613A1 (en) 2014-05-21
DE102013222787B4 (de) 2022-06-09

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