DE3202404A1 - Photoconductive organic substance and electrophotographic layer containing such a substance - Google Patents

Photoconductive organic substance and electrophotographic layer containing such a substance

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Publication number
DE3202404A1
DE3202404A1 DE19823202404 DE3202404A DE3202404A1 DE 3202404 A1 DE3202404 A1 DE 3202404A1 DE 19823202404 DE19823202404 DE 19823202404 DE 3202404 A DE3202404 A DE 3202404A DE 3202404 A1 DE3202404 A1 DE 3202404A1
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Germany
Prior art keywords
organic substance
substance
photoconductive organic
ferrocene
layer
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Granted
Application number
DE19823202404
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German (de)
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DE3202404C2 (en
Inventor
Max Prof.Dr.rer.nat. 8581 Weidenberg Herberhold
Klaus Rüdiger Dr.rer.nat. 8520 Erlangen Petrikat
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Alcatel Lucent Deutschland AG
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Standard Elektrik Lorenz AG
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Priority to DE19823202404 priority Critical patent/DE3202404C2/en
Publication of DE3202404A1 publication Critical patent/DE3202404A1/en
Application granted granted Critical
Publication of DE3202404C2 publication Critical patent/DE3202404C2/en
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, 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
    • G03G5/0662—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic containing metal elements

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Photoreceptors In Electrophotography (AREA)

Abstract

Photoconductive organic substance, in particular for electrophotography, containing a substance which is formed by replacing at least one phenyl group in the triphenylamine by ferrocene. The ferrocene derivative of triphenylamine is dissolved in polystyrene or polycarbonate. For electrophotographic layers, a layer composed of the photoconductive organic substance is situated on a layer which is composed at least partly of amorphous selenium or at least partly of amorphous silicon.

Description

Fotoleitende organische Substanz und elektrofoto- Photoconductive organic matter and electrophoto-

grafische Schicht mit einer solchen Substanz Die Erfindung bezieht sich auf fotoleitende organische Substand enthaltend eir Ferrocenderivat sowie auf eine elektrofotografische Schicht, die eine solche fotoleitende organische Substanz enthält. graphic layer containing such a substance The invention relates based on photoconductive organic substance containing eir ferrocene derivative and on an electrophotographic layer containing such a photoconductive organic substance contains.

Es ist bereits bekannt, daß Ferrocen fotoleitende Eigenschaften hat, welche diese Substanz zur Verwendung in elektrofotografischen Schichten geeignet macht.It is already known that ferrocene has photoconductive properties, which make this substance suitable for use in electrophotographic layers power.

Es sind weiter verschiedene Ferrocenderivate bekalint, die ebenfalls fotoleitende Eigenschaften haben und in elektrofotografischen Schichten verwendet werden können. Verschiedene solche Ferrocenderivate sind beispielsweise in der US-PS 3 711 280 beschrieben. Das Ferrocen bzw. die Ferrocenderivate sind hierbei in Polysterolschichten oder Polycarbonatschichten enthalten.There are also various ferrocene derivatives, which are also known have photoconductive properties and are used in electrophotographic layers can be. Various such ferrocene derivatives are described, for example, in U.S. Patent 3 711 280. The ferrocene or ferrocene derivatives are in this case in polystyrene layers or contain polycarbonate layers.

Die bekannten fotoleitenden organischen Substanzen mit Ferrocen oder Ferrocenderivaten haben den Nachteil, da;3 das Ferrocen bzw. die Ferrocenderivate bei Temperaturen von etwa 500C herausdampfen, so daß sich die elektrofotografiscilen Eigenschaften laufend verschlechtern.The known photoconductive organic substances with ferrocene or Ferrocene derivatives have the disadvantage that 3 ferrocene or ferrocene derivatives evaporate at temperatures of about 500C, so that the electrophotographscilen Properties continuously deteriorate.

Cm da Herausdampfen von Ferrocen bzw. Ierrocenderivaten aus elektrofotografischen Schichten zu verhindern, wurde bereits vorgeschlagen, als fotoleitende organische Substanz ein Co-Solymerisat eines Ferrocenderivats mit einer Phenylverbindung, ie z 13. Styrol zu verwenden. Hierdurch wird zwar das Ausdampfen des Ferrocenderivats aus der Schicht wesentlich vermin-Werte jedoch haften solche Schichten nur sehr schlecht an bestimmten Unterlagen, wie z.B. an amorphem Silizium.Cm da evaporation of ferrocene or ferrocene derivatives from electrophotographic Preventing layers has already been proposed as photoconductive organic Substance a co-solvent of a ferrocene derivative with a phenyl compound, ie z 13. Use styrene. This indeed causes the evaporation of the ferrocene derivative From the layer, however, substantially vermin values, such layers are only very adherent bad on certain substrates, such as amorphous silicon.

Eine weitere wesentliche Eigenschaft, die von fotoleitenden organischen Substanzen, insbesondere für die Elektrofotografie, gefordert wird, ist die Erzielung eines möglichst niedrien Rstpotentials nach Aufladung und Belichtung. Auch in dieer Beziehung befriedigen die bekannten fotoleitenden organischen Substanzen mit Ferrocen und Ferrocenderivaten nicht.Another essential property that of photoconductive organic Substances, in particular for electrophotography, are required, is to be achieved the lowest possible residual potential after charging and exposure. Even in them Relationship satisfy the known photoconductive organic substances with ferrocene and ferrocene derivatives do not.

Von einem guten organischen Fotoleiter wird weiter gefordert, daß er gute Transporteigenschaften für Elektronen oder Defektelektronen hat. Eine Substanz, die gute Transporteigenschafen fur Defektelektronen hat, ist das Triphenylamin. Die fotoelektrischen Eigenschaften dieser Substanz sind beschrieben ;n dem Aufsatz von P.W.Borsenberger, W.Mey und A.Chowdry in der Zeitschrift Journal of Applied Physics", Band 49, Nr.1, anuar 1978, Seite 273 bis 279. Die Entladung beim Triphenylmin st jedoch unbefriedigend, so daß ein verhältnismäßig hohes Restpotential nach Belichtung verbleibt.A good organic photoconductor also requires that it has good transport properties for electrons or holes. A substance Triphenylamine is the one that has good defect transport properties. The photoelectric properties of this substance are described; in the article by P.W.Borsenberger, W.Mey, and A.Chowdry in the Journal of Applied Physics ", Volume 49, No. 1, January 1978, pages 273 to 279. The discharge in triphenylmin However, it is unsatisfactory, so that there is a relatively high residual potential after exposure remains.

er Erfindung liegt die Aufgabe zugrunde, eine fotolei ende organische Substanz auf der Basis von Ferrocenderivatei zu schaften, bei der das Ferrocen so fest in der Substanz gebunden i t daß es nicht aus der Substanz herausdampft, die auf der Unterlage gut haftet und die ein niedriges Restpotential nach belichtung aufweist. he invention is based on the object of a photolei end organic Substance on the basis of Ferrocenderivatei to create, in which the ferrocene so firmly bound in the substance so that it does not evaporate from the substance adheres well to the substrate and has a low residual potential after exposure having.

kiese Aufgabe kird adurch gelöst, daß als errocnderivat ein Triphenylamin verwendet wird, bei dem m-ndestens eine Phenylgruppe durch Ferrocen ersetzt ist.This problem is solved by using a triphenylamine as the errocnderivat is used in which at least one phenyl group is replaced by ferrocene.

Die in Frage kommenden Substanzen sind also Diphenylferrocenylamin, Phenyldiferrocenylamin und Triferrocenylamia.The substances in question are diphenylferrocenylamine, Phenyldiferrocenylamine and triferrocenylamia.

Diese Substanzen werden in an sich bekannter Weis in Polystyrol oder Polycarbonat gelöst.These substances are in a known manner in polystyrene or Polycarbonate dissolved.

tur Erzielung geeigneter elektrofotografischer Schichten wird die fotoleitende organische Substanz gemäß @er Erfindulg in -orm einer Schicht Auf einer Schicht angeordnet, die m"ndestens teilweise aus amorphem Selen oder aus amorphem Silizium besteht.To achieve suitable electrophotographic layers, the photoconductive organic substance according to the invention in the form of a layer on a Layer arranged at least partially from amorphous selenium or from amorphous selenium Silicon is made of.

Die Haftfähigkeit der fotoleitenden organischen Substanz gemäß der Erfindung auf Schichten, die amorphes Selen oder -amorphes Silizium enthalten, ist sehr gut und das Ferrocenderivat wird in der Schicht jut festgehalten, so daß ein Herau-dampfen nicht stattfindet. Die Transporteigenschaften für Defektelekronen sind bei der fotoleitenden organischen Substanz gemäß der Erfindung wesentlich besser als bei den bekannten zotoleitenden organischen Substanzen mit Ferrocenderivaten.The adhesiveness of the photoconductive organic substance according to Invention on layers that contain amorphous selenium or amorphous silicon is very good and the ferrocene derivative is retained in the layer, so that a Steaming out does not take place. The transport properties for defective crowns are much better in the photoconductive organic substance according to the invention than with the known zotoconductive organic substances with ferrocene derivatives.

Das Restpotential der elektrofotografischen Schichten gemäB der Erfindung weist sehr gute Werte auf, die erheblich besser sind, als die Werte, die mit Triphenylamin erhalten werden. Während Schichten mit Triphenylamin auf einer Unterlage von Selen-Tellur Restpotentiale von etwa 300 V aufweisen, eigen Schichten mit der fotoleitenden organische: Substanz gemäß der Erfindung Restpotentiale von nur 40 V oder weniger.The residual potential of the electrophotographic layers according to the invention shows very good values that are considerably better than the values obtained with triphenylamine can be obtained. During layers with triphenylamine on a pad of selenium-tellurium Have residual potentials of about 300 V, own layers with the photoconductive organic: Substance according to the invention residual potentials of only 40 V or less.

Die Benetzung der fotoleitenden organischen Substanz auf amorphem Selen, auf amorphen Selenlegierungen und auf amorphem Silizium ist sehr gut, so daß eine sehr qute Haftung zwischen cen beiden Schichten vorhanden ist.The wetting of the photoconductive organic substance on amorphous Selenium, on amorphous selenium alloys and on amorphous Silicon is very good, so that there is very good adhesion between the two layers is.

Ausführungsbeispiel ts wurden je zwei Millimol von Triphenylamin (TPA), Diphenylferrocenylamin (DPFA), Phenyldiferrocenylamin (PDFA) und Triferrocenylamin (TFA) zusammen mit einem Gramm Polystyrol (Standard Polystyrol der Firma Norddeutsche Seekabelwerke) (der Polykarbonat (Lexan 135 der Firma General Electric) in 15 ml Dichlormetan gelöst und auf eine etwa 1/um starke ladungserzeugende Schicht aus einer amorphen Selenlegierung mit 7,5 % Teilur aufgetragen.Embodiment ts were two millimoles of triphenylamine (TPA), Diphenylferrocenylamine (DPFA), phenyldiferrocenylamine (PDFA) and triferrocenylamine (TFA) together with one gram of polystyrene (standard polystyrene from Norddeutsche Submarine cable works) (the polycarbonate (Lexan 135 from General Electric) in 15 ml Dissolved dichloromethane and applied to an approximately 1 / um thick charge-generating layer an amorphous selenium alloy with 7.5% partur applied.

Die sc erhaltenen elektrofotografischen Schichten wurden bei einem vorgegebenen Koronastrom aufgeladen und mit 50 lx.s (Wolframlampe mit einer Verteilungstemperatur von 2856° Kelvin) telichtet. Es wurden die Aufladung U0 und das Restpotential L nach Belichtung pro /um Schichtdicke verglichen. In der Tabelle 1 sind die Werte dargestellt, bei denen die fotoleiende organische Substanz in Polystyrol gelöst ist, während in Tabelle 2 die Werte dargestellt sind, bei denen die fotoeitende orqanische Substanz in PolZcarbonat gelöst ist. Aus den T bellen kann entnommen werden, daß das Restpotential gegenüber dem von Triphenylamin wesentlich vermindert is Tabelle 1 Schicht- Aufladung Restpotential dicke Ud(µm) U0 (V) U0/d (V/µm) UL (V) U/s (V/µm) TPA 6 1160 193 300 50 DPFA 5 600 120 40 8 PDFA 8 100 12 20 Z,S TFA 6 100 17 20 3,3 Tabelle 2 Schicht- Aufladung Restpotential dicke Ud (µm) U0 (V) U0/d (V/µm) UL (V) UL/d (V/µm) TPA 7 1200 170 300 43 DPFA 14 300 21 260 19 PDFA 6 160 27 50 TFA 8 150 19 100The electrophotographic layers obtained sc were at a given corona current and charged with 50 lx.s (tungsten lamp with a distribution temperature of 2856 ° Kelvin) illuminates. The charge U0 and the residual potential L after exposure per / µm layer thickness compared. In Table 1 are the values shown in which the photoconductive organic substance is dissolved in polystyrene is, while Table 2 shows the values at which the photoconductive organic substance is dissolved in PolZcarbonat. From the tables can be taken that the residual potential is significantly reduced compared to that of triphenylamine is table 1 layer charge residual potential thickness Ud (µm) U0 (V) U0 / d (V / µm) UL (V) U / s (V / µm) TPA 6 1160 193 300 50 DPFA 5 600 120 40 8 PDFA 8 100 12 20 Z, S TFA 6 100 17 20 3.3 Table 2 Layer charge residual potential thickness Ud (µm) U0 (V) U0 / d (V / µm) UL (V) UL / d (V / µm) TPA 7 1200 170 300 43 DPFA 14 300 21 260 19 PDFA 6 160 27 50 TFA 8 150 19 100

Claims (8)

Patentansprüche Fototeitende organische Substanz enthaltend ein Ferrocenderivat, d a d u r c h g e k e n n z e i c h n e t, daß das Ferrocenderivat dadurch gebildet ist, daß im Triphenylamin mindestens eine Phenylgruppe durch Ferrocen ersetzt ist. Claims Photo-conductive organic substance containing a ferrocene derivative, it is noted that the ferrocene derivative is thereby formed is that at least one phenyl group in the triphenylamine has been replaced by ferrocene. 2. Fotoleitende organische Substanz nach Anspruch 1, dadurch gekennzeichnet, daß sie Diphenylferrocenylamin enthält.2. Photoconductive organic substance according to claim 1, characterized in that that it contains diphenylferrocenylamine. 3. Fotoleitende organische Substanz nach Anspruch 1, dadurch gekennzeichnet, daß sie Phenyldiferrocenylamin enthält.3. Photoconductive organic substance according to claim 1, characterized in that that it contains phenyldiferrocenylamine. 4. Fotoleitende organische Substanz nach Anspruch 1, dadurch gekennzeichnet, daß sie Triferrocenylamin enthält 4. Photoconductive organic substance according to claim 1, characterized in that that it contains triferrocenylamine 5. Fotoleitende organische Substanz nach Anspruch 1 bis 4, dadurch gekennzeichnet, daß das Ferrocenderivat in Polystyrol gelöst ist.5. Photoconductive organic substance according to claim 1 to 4, characterized in that the ferrocene derivative is dissolved in polystyrene. 6. Fotoleitende organische Substanz nach Anspruch 1 bis 4, dadurch gekennzeichnet, daß das Ferrocenderivat i-i Polycarbonat gelöst ist.6. Photoconductive organic substance according to claim 1 to 4, characterized characterized in that the ferrocene derivative i-i polycarbonate is dissolved. 7. Elektrofotografische Schicht aus einer Schicht eines anorganischen Fotoleiters und einer darauf angeordneten Schicht aus einem organischen Fotoleiter nach einem der Ansprüche 1 bis 6, dadurch gekennzeichnet, daß der anorganische Fotoleiter mindestens teilweise aus amorphem Selen besteht.7. Electrophotographic layer composed of a layer of an inorganic one Photoconductor and a layer arranged thereon made of an organic photoconductor according to one of claims 1 to 6, characterized in that the inorganic photoconductor at least partially consists of amorphous selenium. 8. Elektrofotografische Schicht aus einer Schicht eines anorganischen Fotoleiters und einer darauf angeordneten Schicht eines organischen Fotoleiters nach einem der Ansprüche 1 bis 6, dadurch gekennzeichnet, daß der anorganische Fotoleiter mindestens teilweise aus amorphem Silizium besteht.8. Electrophotographic layer composed of a layer of an inorganic one Photoconductor and a layer of an organic photoconductor arranged thereon according to one of claims 1 to 6, characterized in that the inorganic photoconductor at least partially consists of amorphous silicon.
DE19823202404 1982-01-26 1982-01-26 Electrophotographic recording material Expired DE3202404C2 (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111018040A (en) * 2019-12-02 2020-04-17 天津科技大学 Photothermal performance material for degrading methylene blue and application

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3711280A (en) * 1971-02-17 1973-01-16 Eastman Kodak Co Metallocene photoconductors used in electrophotography
DE3016453A1 (en) * 1980-04-29 1981-11-05 Standard Elektrik Lorenz Ag, 7000 Stuttgart Electrophotographic recording carrier with charge transport layer - of solid soln. of ferrocene cpd. in polymer contg. benzene rings

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3711280A (en) * 1971-02-17 1973-01-16 Eastman Kodak Co Metallocene photoconductors used in electrophotography
DE3016453A1 (en) * 1980-04-29 1981-11-05 Standard Elektrik Lorenz Ag, 7000 Stuttgart Electrophotographic recording carrier with charge transport layer - of solid soln. of ferrocene cpd. in polymer contg. benzene rings

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111018040A (en) * 2019-12-02 2020-04-17 天津科技大学 Photothermal performance material for degrading methylene blue and application
CN111018040B (en) * 2019-12-02 2022-02-01 天津科技大学 Photothermal performance material for degrading methylene blue and application

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