EP0161005B1 - "Squarium"-Verbindungen, Verfahren zu deren Herstellung und elekatrophotographische Photorezeptoren, die jene enthalten - Google Patents

"Squarium"-Verbindungen, Verfahren zu deren Herstellung und elekatrophotographische Photorezeptoren, die jene enthalten Download PDF

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Publication number
EP0161005B1
EP0161005B1 EP19850105887 EP85105887A EP0161005B1 EP 0161005 B1 EP0161005 B1 EP 0161005B1 EP 19850105887 EP19850105887 EP 19850105887 EP 85105887 A EP85105887 A EP 85105887A EP 0161005 B1 EP0161005 B1 EP 0161005B1
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EP
European Patent Office
Prior art keywords
photoreceptor
group
charge generation
layer
generation layer
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
Application number
EP19850105887
Other languages
English (en)
French (fr)
Other versions
EP0161005A3 (en
EP0161005A2 (de
Inventor
Satoshi Fuji Xerox Co. Ltd. Saeki
Seki Fuji Xerox Co. Ltd. Kin
Kaoru Fuji Xerox Co. Ltd. Torikoshi
Hiroyuki Fuji Xerox Co. Ltd. Tanaka
Lyong Fuji Xerox Co. Ltd. Sun Pu
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.)
Fujifilm Business Innovation Corp
Original Assignee
Fuji Xerox Co Ltd
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
Priority claimed from JP59092771A external-priority patent/JPS60258556A/ja
Priority claimed from JP59092769A external-priority patent/JPS60260547A/ja
Application filed by Fuji Xerox Co Ltd filed Critical Fuji Xerox Co Ltd
Publication of EP0161005A2 publication Critical patent/EP0161005A2/de
Publication of EP0161005A3 publication Critical patent/EP0161005A3/en
Application granted granted Critical
Publication of EP0161005B1 publication Critical patent/EP0161005B1/de
Expired legal-status Critical Current

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    • 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
    • G03G5/0609—Acyclic or carbocyclic compounds containing oxygen
    • G03G5/0611—Squaric acid
    • 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
    • G03G5/0618—Acyclic or carbocyclic compounds containing oxygen and nitrogen

Definitions

  • This invention relates to novel squarium compounds having a flat photosensitivity in the wide range from visible ray region to the near infrared ray region as a charge generator, a process for preparing them and electrophotographic photoreceptors containing the squarium compounds.
  • inorganic photographic materials such as amorphous selenium, selenium alloys, cadmium sulfide and zinc oxide and organic photographic materials represented by polyvinylcarbazole and polyvinylcarbazole derivatives are widely known as electrophotographic photoreceptors.
  • Examples of the squarium compounds of formula (1) above of this invention include the following compounds.
  • a solvent coating method and a vacuum evaporation method can be used to prepare the charge generation layer with the squarium compound of this invention without using a binder resin.

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  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Photoreceptors In Electrophotography (AREA)

Claims (16)

1. Eine Squariumverbindung der allgemeinen Formel
Figure imgb0021
worin X ein Halogenatom, eine Nitrogruppe, eine Cyanogruppe, eine Formylgruppe, eine Acylgruppe, eine Carboxylgruppe oder eine Alkoxycarbonylgruppe darstellt, n = 0 oder eine ganze Zahl von 1 bis 5 ist und R ein Wasserstoffatom oder eine Methylgruppe darstellt.
2. Squariumverbindung nach Anspruch 1, der allgemeinen Formel
Figure imgb0022
worin X' ein Fluoratom oder ein Chloratom und Y ein Wasserstoffatom oder ein Fluoratom bedeuten.
3. Verfahren zur Herstellung einer Squariumverbindung der allgemeinen Formel
Figure imgb0023
worin X, n und R die vorstehend angegebenen Bedeutungen besitzen, bei dem man 3,4-Dihydroxy-3-cyclo- buten-1,2-dion der allgemeinen Formel
Figure imgb0024
mit einem Anilinderivat der allgemeinen Formel
Figure imgb0025
umsetzt, worin X, n und R die vorstehend angegebenen Bedeutungen besitzen.
4. Elektrophotografischer Photorezeptor mit einem elektrisch leitenden Träger und einer lichtsensitiven Schicht mit einer Squariumverbindung der Formel
Figure imgb0026
worin X ein Halogenatom, eine Nitrogruppe, eine Cyanogruppe, eine Formylgruppe, eine Acylgruppe, eine Carboxylgruppe oder eine Alkoxycarbonylgruppe bedeutet, n = 0 oder eine ganze Zahl von 1 bis 5 ist und R ein Wasserstoffatom oder eine Methylgruppe bedeutet.
5. Photorezeptor nach Anspruch 4, bei dem die lichtempfindliche Schicht eine Ladungstransportschicht und eine Ladungserzeugungsschicht mit einem Gahalt an der Squariumverbindung umfaßt.
6. Photorezeptor nach Anspruch 5, bei dem die Ladungstransportschicht ein photoleitendes Polymeres aus der aus Poly-(vinyldibenzothiophen), Poly-(vinylpyren), Poly-(vinylanthracen) und Poly-(vinylcarbazol) gebildeten Gruppe umfaßt.
7. Photorezeptor nach Anspruch 5, bei dem die Ladungstransportschicht Triallylpyrazolin, Triphenylmethan, Oxadiazol, Tetraphenylbenziden oder Trinitrofluorenon und ein Bindemittelharz umfaßt.
8. Photorezeptor nach Anspruch 5, bei dem die Ladungserzegungsschicht im wesentlichen aus der Squariumverbindung besteht.
9. Photorezeptor nach Anspruch 5, bei dem die Ladungserzeuzeugungsschicht die Squariumverbindung in einer Menge von etwa 10 bis 90 Gew.-% auf Basis des Gewichts der Ladungserzeugungsschicht umfaßt.
10. Photorezeptor nach Anspruch 9, bei dem die Squariumverbindung in einer Menge von etwa 10 bis 50 Gew-% auf Basis der Gewichts der Ladungserzeugungsschicht vorliegt.
11. Photorezeptor nach Anspruch 5, bei dem die Ladungserzeugungsschicht etwa 0,1 bis 3 um dick ist.
12. Photorezeptor nach Anspruch 11, bei dem das Dickenverhältnis der Ladungserzeugungsschicht zur Ladungstransportschicht etwa 1/2 bis etwa 1/200 beträgt.
13. Photorezeptor nach Anspruch 5, bei dem die Ladungserzeugungsschicht zwischen dem Träger und der Ladungstransportschicht angeordnet ist.
14. Photorezeptor nach Anspruch 7, bei dem die Ladungstransportschicht zwischen dem Träger und der Ladungserzeugungsschicht angeordnet ist.
15. Photorezeptor nach Anspruch 4, bei dem die lichtempfindliche Schicht eine Schicht umfaßt, die die Squariumverbindung und ein Ladungstransportmaterial enthält.
16. Photorezeptor nach Anspruch 5, bei dem die Squariumverbindung in Form von Teilchen in der Ladungserzeugungsschicht dispergiert ist.
EP19850105887 1984-05-11 1985-05-13 "Squarium"-Verbindungen, Verfahren zu deren Herstellung und elekatrophotographische Photorezeptoren, die jene enthalten Expired EP0161005B1 (de)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP92771/84 1984-05-11
JP59092771A JPS60258556A (ja) 1984-05-11 1984-05-11 電子写真用感光体
JP92769/84 1984-05-11
JP59092769A JPS60260547A (ja) 1984-05-11 1984-05-11 新規なスクエアリウム化合物およびその製造方法

Publications (3)

Publication Number Publication Date
EP0161005A2 EP0161005A2 (de) 1985-11-13
EP0161005A3 EP0161005A3 (en) 1986-12-10
EP0161005B1 true EP0161005B1 (de) 1989-12-20

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
EP19850105887 Expired EP0161005B1 (de) 1984-05-11 1985-05-13 "Squarium"-Verbindungen, Verfahren zu deren Herstellung und elekatrophotographische Photorezeptoren, die jene enthalten

Country Status (2)

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EP (1) EP0161005B1 (de)
DE (1) DE3574866D1 (de)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US12055851B2 (en) 2020-09-29 2024-08-06 Samsung Sdi Co., Ltd. Core-shell compound, photosensitive resin composition including the same, photosensitive resin layer, color filter and CMOS image sensor

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4508803A (en) * 1983-12-05 1985-04-02 Xerox Corporation Photoconductive devices containing novel benzyl fluorinated squaraine compositions
US4521621A (en) * 1983-12-05 1985-06-04 Xerox Corporation Novel squarine systems

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US12055851B2 (en) 2020-09-29 2024-08-06 Samsung Sdi Co., Ltd. Core-shell compound, photosensitive resin composition including the same, photosensitive resin layer, color filter and CMOS image sensor

Also Published As

Publication number Publication date
EP0161005A3 (en) 1986-12-10
DE3574866D1 (de) 1990-01-25
EP0161005A2 (de) 1985-11-13

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