DE2047338A1 - Electrophotographic recording material - Google Patents

Description

LIektrop .iot o ^ r aphis ehe s recording material

Die iirfiuduri ;: nauriffc c-iii e.LektrophotO £ ra _t > hi shy recording material, uo.3 from a 3 chi ent carrier and a piiotoleit-filled ocnicate applied to it, ulo tin i'Olyiaareo ^ iacejittei una an organic photoconductor verbincurii .; contains.

In the xero ^ raphiochen method known from UoA-I atentachrifL 2 297 ö9i, an electrophoto ^ rciphisclied recording was made, since: 5 au;.; one. ¹ "" layer support and one ociiicht of a normally insulating material, üery.iQn clekti-i.iciier .jiueraLanu .iich je nacci "ien ^ je der v / ährena der Bildrr.li ^: .i; ei: L-cllciitunc aur-hitting electromagnetic .vti-ahlun ;; changes. , '. ". In uolc-iu.j Aufzeichnun ^ swaterial, the?; Eu"hniich:'. I.-i, hot oil it capable π .iufzei chnun ._, 3: ".;ateri; jl denotes v / ird, is first - in; generally in the dark after a suitable dark adaptation period - with a uniform surface -I distribute, ariociilie ^ end it is through a .Jild: iotively active-

trahlun, exposed, which the virkun ^ aat, dai.> da ^ ui uGi · ji'v _; x'fl>'. chenlaau: i ^ corresponding to the In den vernou TeJ-i-jη de :; iJild:.! ütlvj enthaitonon reiati '/ en i.net' ^ ie rt I. ·! v: r> ■ Inside vjii-d. That on the eleUtroi-h

BADOBJÖINÄL

Recording material remaining electrostatic charge image or different ie He surface charge is then made sieht- iar, by contacting the surface with suitable eineia electroscopic toner material in contact. Such a toner or marking material can then be applied either to the charged areas or to the discharged areas of the exposed surface, regardless of whether it is contained in an insulating liquid or applied to a dry carrier material. The deposited toner material can then either be permanently fixed on the surface of the sensitive recording material by known methods, for example using heat, pressure or solvent vapor, or transferred to a second recording material which can be fixed in a corresponding manner. However, the latent electrostatic image can also be transferred to a second recording material and developed there.

For the production of electrophotographic recording materials A wide variety of photoconductive insulating materials have already been used. So have for example vapors of selenium and selenium alloys deposited on a suitable substrate and of a resinous, a film-forming binder contained photoconductive Zinc oxide particles found in modern document copying processes used worldwide.

Since the introduction of electrophotography, there has been a very large one Number of organic compounds on their photoconductive Properties examined. It was found clafe a very large number of organic compounds a certain amount Has photoconductivity. Many organic compounds were found that have sufficient photoconductivity

10 9015/1771

ability and in the photoconductive layers of incorporated electrophotographiaerien recording materials ivei * aen can.

Typical examples of such organic photoconductor compounds are the triphenylamines and the triarylraethane leucobocr ... Particularly suitable for electrophotography are the optically clear recording materials containing photoconductor compounds with good electrophotographic properties The structure of the device can be made unusually flexible, if such photoconductive layers are applied in the form of a film or in the form of a layer to a suitable substrate, the result is a recording material that is reusable solder »Α.η., Which, after the removal of the toner remaining from the previous images by transfer and / or cancellation, is then used to generate v. ^r more pictures before; -; ends i-; earth-u can. So far, the various compounds that are suitable for incorporation into photoconductive coating materials for the production of electrophotographic recording materials have been selected. by trying out every single connection. In spite of the large number of different photoconductive oubotaises already investigated, it was not possible to date; fl - *. It was important to make any reliable predictions about their photoconductive properties, and therefore the respective compounds had to exhibit many different electrophotographic properties individually selected v; earth.

- •: ui \ ai> e the invention is therefore to an electropliotographiacaco Recording file must be specified that a new iQasse

1 f;

ι ν-

: / - 1-77

■ m ^ n ^ r- BAD ORIGINAL

of photoconductor connections in a high electrical sensitivity and high photosensitivity after electrification.

It has now been found, surprisingly, that this object can be achieved by inserting into the photoconductive layer an electropnotographic recording material as a photoconductor compound tetrasubstituted methane incorporated,

The invention relates to an electrophotographic recording material, which consists of a substrate and at least one photoconductive layer applied to it, which is a polymeric binder and an organic photoconductor compound contains, which is characterized in that the photoconductive layer (s) as a photoconductor compound at least contains a bis (dialkylaminoaryl) alkanol of the general formula:

where mean:

R., Rp, R, and Rj, each one optionally substituted short-chain aliphatic alkyl radical with 1 to 8 carbon atoms, e.g. B. a Methyl, propyl, ethyl, pentyl, hexyl, Isobutyl, 3-methylpentyl and octyl radical; and

one of the following residues: 1ÖS; ri 5/177 1

BATH ORIGINAL

2U47338

1. an optionally substituted aliphatic alkyl radical having 1 to 1b carbon atoms, in particular an optionally substituted short-chain aliphatic alkyl radical having 1 to 8 carbon atoms, ζ. B. a methyl, ethyl, propyl, butyl, isobutyl, octyl, dodecyl radical, an alkoxy alkyl radical, z. ii. an ethoxypropyl, methoxybutyl and propoxymethyl radicalj an aryloxyalkyl radical, e.g. B. a phenoxyethyl, uaphthoxymethyl and phenoxypentyl radical, an aminoalkyl radical, e.g. B, an aminobutyl, arainoethyl and aminopropyl radical, a hydroxyalkyl radical, see e.g. an hydroxypropyl, hydroxyoctyl and hydroxyraethyl radical, an aralkyl radical, e.g. B. a benzyl and phenethyl radical, an alkylaninoalkyl radical, z. B. a Methylamlnopropyl- and Hethylaminoäthylrest, and a dialkylaminoalkylrest, z. B. a Dläthylaminoäthyl-, Dimethylaminopropyl- and Dipropylaniinooctylrest, an arylaminoalkylrest, z. ii. a phenylarninoalkyl, diphenylarainoalkyl, M-phenyl-N-ethylaminopentyl, li-phenyl-N-ethylarainohexyl and naphthylaminomethyl radical, a nitroalkyl radical, e.g. B. a riitrobutyl, nitroethyl and nitropentyl radical, a cyanoalkyl radical, z. B. a cyanopropyl, cyanobutyl and cyanoethyl radical, a haloalkyl radical, z. B. a chloromethyl, bromopentyl, chlorooctyl and trifluoromethyl radical, one through an acyl group

of the formula | j

-C-R substituted alkyl radical,

in which R is a hydroxyl group, a hydrogen atom, an Ary! group, ζ. B. a Phenylocier .'iaphthylgruppe, a short-chain alkyl group with 1 to 8 carbon atoms, ζ. Ii. "

^{10 / Tr} / 71

2ÜA73-38

a methyl, ethyl or propyl group, an optionally substituted amino group, z. B, a di-lower alkylamino group, a short-chain alkoxy group with 1 to 8 carbon atoms, e.g. B. a butoxy and methoxy group or an aryloxy group, z. B. a phenoxy or liaphtnoxy group means;

an optionally substituted cycloalkyl radical with 4 to S carbon atoms, in your ring, e.g. B. a cyclobutyl, cyclohexyl, Cycloperityl radical, an alkoxycycloalkyl radical, z. B. an ethoxycyclohexyl, methoxycyclobutyl and propoxycyclohexyl radical, an aryloxycycloalkyl radical, &. B. a phenoxycyclohexyl, naphthoxycyclohexyl and phenoxycyclopentyl radical, an axninocycloalkyl radical, e.g. an aminocyclobutyl, Aminocyclohexyl and aminocyclopentyl radical, a hydroxycycloalkyl radical, z. B. an aminocyclohexyl, hydroxycyclopentyl and hydroxycyclobutylreat, an arylcycloalkyl radical, e.g. B. a phenylcyclohexyl and phenylcyclobutyl radical, a Alkylair.inocycloalkylrest, e.g. B. a! -! Ethylamino cyclone xy L- and l'Jethylaminocyclopentylrest, and a dialkylaminocycloalkyl radical, e.g. B. a diethylarainocyclohexyl, Dimethylaminocyclobutyl and Dipropylaminocyclooctylrest, an arylaminocycloalkylrest, z. B, a phenylaminocyclohexyl, diphenylarainocyclohexyl, IJ-phenyl-iI-ethylaminocyclopentyl, N-phenyl-M-methylaminocyclohexyl- and waphthylaminocyclopentyl, nitrocycloalkyl, e.g. B, one

177 1 "baD

t '' - ■ ι r ~, <"ϊ. η. Q

ijitrocyciobutyl, nitrocyclohexyl and nitrocyclopentyl radical, a cyanocycloalkyl radical, e.g. B. a Cyanocyclohexyl-, Cyanocyclobutyl- unct Cyanocyclopentylrest, a ^T Ialosenc./cloalkylrest, z. B. a Ciilorcyclohexyl-, Dromcyclopentyl- and Chlorcyolooctylrest, one by an acyl

f-, rupx-.e of the formula #

-C-R substituted

Cyeloalkylrest, in egg R is a hydroxyl group, a hydrogen atom, an aryl group, e.g. As a phenyl or Haphthy! Group, a ^ e be substituted Amiriogruppe such. B. a Dlniedri ^ alkylamino group, a kurzketti ^ e alkoxy group with 1 to 8 carbon atoms, z. 3. a butoxy or methoxy group, an aryloxy group, s * B. a phenoxy or iJ-aphthoxy group »a short-chain alkyl group with 1 to 8 carbon atoms» z. B. a, ethyl, ethyl, propyl or ßutylgi'uppe, means; or

an optionally substituted heterocyclic radical having 5 to 6 atoms in the hetero ring which contains at least one sulfur, selenium, oxygen or nitrogen atom, e.g. B. a thienyl radical, for example a benzthienyl radical, a pyrrolyl radical, e.g. B. a Mitropyrrolylrest, a Pyrrolidinylrest, z. B. a Prolylrest, a PyrrοlinyIrest, a Benzpyrrolylrest, z. B, an inciolyl radical, a carbazolyl radical, a furyl radical _# z. B. a furfuryl and Benzfurylrest, a pyridylrest, z. B.

BATH ORIGINAL

a halopyridyl, aniinopyridyl, hydroxypyridyl, alkylpyridyl and nitropyridyl radical, a piperidyl radical, a quinolyl radical, an acridinyl radical »a Pyranyl radical, a benzpyranyl radical, a pyrazolyl radical, an oxazolyl radical or a thiazolyl radical; or

4. an optionally substituted diphenylenemethane radical ", e.g. a fluorenyl radical, an alkylfluorenyl radical, e.g. a 2-methylfluorenyl-, Z-ethyl-y-methylfluorenyl-, 2,7-diraethylfluorenyl-, 2,7-I) iäthylfluorenyl-, 2-propylfluorenyl-, 2-butyl-luorenyl-, 2,7-propylfluorenyl-, 2,7-dibutylfluorenyl-, 2-propyl-7-bujt-ylilitOTemyl- 2rJMe-t4iyl-7-prtrpyj, - ¹ : fluorenyl-, 2-methyl-7-blltyl £ luorenyl- _> 2-

Ätliyl-7- »propylfluorenyl-V 2-ethyl-7-butylfluorenyl-, 2-pentylfluorenyl-, 2,7-dipentylfluorenyl-, 2-pentyl-7-methylfluorenyl-, 2-pentyl-7-ethyl luorenyl-, 2-pentyl-7-propylfluorenyl-, 2-pentyl-7-butylfluorenyl radical, an Ilalogenfluorenylrest, for example a 2,7-dibromofluorenyl-, 2,7-dichlorofluorenyl- and 2-chloro-7-methylfluürenyl radical.

Examples of particularly suitable compounds for the I class of rioto-conductor connection described above are the following:

T a b e 1 1 e A

■ I. Bis (4-di) iiethylaminophenyl) benzyl),! Ethanul

II. Bis (4-diithylaminophenyl) benzylinethanol

III. Bis (4-dipropylaminophenyl) benzylmethanol

IV. Bis (4-dimethylaminophenyl) fluorenylmethanol

V. Lis (4-dirίiethylaminophenyl) triflurl! ^ Etil} 'll _! ιetjlaHol

VI. 1,1-bis (4-i'iijfiethylamiiiopiicnyl) -1-aydroxyatJian

bap C

j-7338

jj, "I-Bis (4-di.:!etiiyIa:.ii.iuMiienyl)- i -Iiydroxypropane 1,1-3is (4-dimethylaminophenyl) -1-hydroxybutane bis (4-dioethylaminophenylJ cyclohexylmethanol bis (4-diiiietiiylaminopricnyl) cyclo _i ; eiitylinet! irruol 3is (4-uir.ietiiylar.iinophenyl) trichloromethylmethanol iiis (4-diethyla> ninophenyl) difluorr: ietnylmethanol j3is (4 ~ clia'tliylaminophenyl) cyclonexylmct.aanol oleoethlaminopnenyl3 (4-dia thy laKiinophenyl) fluorenylmethanol Lis (4 ~ diethylaniinophenyl) pyrrolylniethaiiol bis (4-diiiiothylaKiinophenyl) pyridinylmethanol ι'Λά (l-diHtaylajniiiopIianyl);

i) ic electro-photographic recording materials of the Lrfiiiduu ,; küiincn by working on the above described ;! iiiotoleitorverbiiidungen nac.i übliclien '/ experienced her ^ estc; lll. be, indon raaa for example- depending on .uiisch or jiach Lriordoriiis cine DiS ₁ CrSiOn or oixie Losiui., eirur Paotoleitervsr- "J-LiUUn ₁ PJ: tit a: Bindeiiittel i.iisciit and: ius this die!" • uutoleiterveruindun, i . üntüaltGiidon üasse manufactures a self-supporting splint over to / i or oijiC. Mixtures of the photoconductor compound described above can also be grounded. The crfindungs, .femaio ve rv; End photoconductor towers also in combination with other known ones

indun ^ on, », 'iu they boispiclst / eise are described in the bdjisciicn I.-i-tentsci-rift 7o5 117, used u ^r erüen. / vui-urde: ..]; ünnen the photoconductive layer of the eiektroj. aütu "· ri _r. üischen-Aufzeiciinun ^ sriitorials the invention i / urther eve .. tzo to .luderun ;, the spectral Jinipfindlichkeit or Llektropiiotjsonsibilitcit _zu2ö; be jo> jen, v / hen the ciiaraktax'istisc.icn .. ir] vun ', Oji soiciier Ziis: itze erv.' are desired.

10:, s / 177 j

"ί ORIQiNAL

The pliotoleitfahige layer of the electrophotographic ^ rapiiischen on ze ichnun ^ 's material of the invention can aucSi by adding iienscn effective to sensdbilisierenden compounds sensitized to improve tlcktropnotoempfindlichkeit. The most diverse compounds can be used as sensitizing compounds together with the photoconductor connections used according to the invention, for example the pyrylium, thiapyrylium and selonapyrylium dye salts known from US Pat. No. 3,250,615, the fluorenes. Γ>. 7, I 2-L) ioxo-13-dibenzo ^ "a, li7fluoren, 5, lo-Dioxo-4a, 11-diazabenzo- ^" ij7 £ luoren, 3,1 S-dioxo-y-oxadibenzo ^ ü, g7 Fluors, the Ag <; re, C4at sensitizers described in Belgian patent specification 705 117, the aromatic nitro compounds described in US Pat are, the quinones known from US Pat. No. 2,670,286, the benzo ^ iienones known from US Pat. No. 2,670,287, the yaiazoles known from US Pat. b. Maleic acid, dichloroessi ^ acid and oalicylic acid, sulphonic and phosphoric acid and various dyes, v / ie z. B. the cyanine, carbocyanine, ierocyanine, jiaryliiiethan, thiazine, azine, oxazine, xanthene, phthalein, acridine, azo and anti-irachinone colors t-jffe, soiie, 'iisc.nmien thereof. Together with the inotoconductor compounds used according to the invention, the fyrylium, selenapyryliui, and tiiiar / yrylium salts as well as the cyanine and carbocyanine dyes are preferably used as sensitizer compounds.

Uean to work with άα-.ί ßindej.uttol and the organic T'.iotoleiterverbiitdttn · .; If a sensitizing compound is used to set up a sequenced electrophotographic recording material, a "cei / '. netc of sensitizing compound _o ;; ii t der i-ciiCüicutiiii; s- ;; oiuischt, so ciaf- nie scnsibilioicrua.le \ ^r u -rbin> iuii ^ nacn

1 0: ^ S / 1 7 7 1

BAD ORIOtNAt.

thorough mixing evenly within the photoconductive Layer is distributed. But there can also be other methods of incorporating the sensitizing compound or be used to raise awareness »

The use of a sensitizing compound in the photoconductive Layers are not required per se. However, since there are already relatively small amounts of sensitizing Compounds which bring about a substantial increase in the sensitivity of such layers are preferably sensitizers used. Their concentration in the photoconductive layer can vary widely. In individual cases optimal concentration depends on the photoconductor and sensitizing compound used. Appropriate the sensitizers are used in concentrations of 0.0001 to 30% by weight, preferably in concentrations of 0.005 to 5.0% by weight based on the weight of the photoconductive Layer, used.

To produce the photoconductive layers of the electrophotographic Recording materials of the invention can the usual known binders are used, i.e. film-forming, hydrophobic, polymeric binders with fairly high dielectric strength, which are good electrical represent insulating film-forming carriers. Examples

771

for materials of this type are styrene-butadiene copolymers, Silicone resins, styrene alkyd resins, silicone alkyd resins, soy alkyd resins, polyvinyl chloride, poly (vinylidene chloride), Vinylidene chloride-acrylonitrile copolymers, poly (vinyl acetate) , Vinyl acetate-vinyl chloride polymers, poly (vinyl acetals), z. B. Pdy (vinyl butyral), polyacrylic acid and polymethacrylic acid ester, z. B. poly (methylinethacrylate), poly (n-butyl methacrylate), Poly (isobutyl methacrylate), polystyrene, nitrated polystyrene, polymethylstyrene, isobutylene polymers, Polyester, e.g. B. Copoly / 'ethylene-co-alkylenebis (alkylenoxyaryl) phenylenedicarboxylate7 » Phenol-formaldehyde resins, ketone resins, polyamides, polycarbonates, polythiocarbonates, polyethylene co-isopropylidene-2, 2-ois (ätliylenoxyphenyl) terephthalate copolymers of vinyl haloarylates and vinyl acetate, e.g. P>. Poly (vinyl-ffi-broinbcnzoate-co-vinyl acetate). Methods for making such resins are known; for example can the styrene-alkyd resins according to the USA patents in dsn 2,361,019 and 2,258,423. For use in the photoconductive layer of the Liarze suitable for electrophotographic recording material of the invention are, for example, under the liandelsn.ii.ieji Vitel PIi-101, Cymac, Piccopale 100, Saran Γ-22Ο, Lexan 105 and Lexan 145 available commercially. Other examples of those used in the electrohhotographic recording materials of the invention Usable binders are those substances ./ic z. j>. Paraffin and mineral waxes.

As Lösungsiaittel a variety of organic solvents for the .bestandteile the can for the manufacturing of the l'hotolcitcr-containing compound ßescliichtungsi-Iassen ßcschici.-tungsiiiasse veriv ^r ends are. Examples of suitable solvents are benzene, toluene, acetone, 2-butane, chlorinated λοίι-len'wasserstoffc, z. I). liethylencalorid, ethylenechlorid and other solvents, z. B. tetrahydrofuran. For the production of the clektrophotographic recordings.

1 0 I r ·;. '.. / 1 7 7 1

BATH ORIGINAL

^ kouiica but auca: iischun,!. ien these solvents with Advantage can be used.

In the production of the photoconductive layers of the electrojliotu ^ raphiscrien recording materials of the invention using the above-described photoconductor connections, good results are obtained, especially when the pliotoconductor connection is present in an amount that is at least about 1 cuw. % Jcr coating mass. The upper limit of the existing photoconductor connection can be varied within a wide range depending on the practical requirements. The Puoto conductor connection should normally be in a range within the range of t; tx? A 1 to about 99, preferably within the range of about 10 to about 60 wt ^. o, based on the coating type, be present.

The thickness of the photoconductive layer on the substrate can also vary widely. Usually there is a suitable one iMaij layer thickness within the range of approx 0.0254 to about 0.254 mm (0.001 to 0.01 inches). The layered one is preferably from about 0.0500 to before drying about 0.1524 nm (0.002 to 0.006 inches) although the layer thickness depending on the intended use of the electrophoto recording material can vary greatly.

The substrate materials used for the production of the electrophotographic Recording materials of the invention die various electrically conductive substrates suitable » for example various types of electrically conductive paper, aluminum paper laminates, metal foils, e.g. B. aluminum and Zinc foils, metal plates, e.g. ß. Aluminum, copper, zinc, brass and, ", galvanized plates, on usual Schiclitträger-

7 7 1 ~~~

BATH

materials made of e.g. cellulose acetate, poly (ethylene terephthalate) and polystyrene vapor-deposited metal layers for example silver, nickel or aluminum and the like electrically conductive sckichtträgermateriaiien.

am a particularly suitable, electrically conductive substrate can be produced by using a transparent film support material, z. D. polyethylene terephthalate) coated with a layer that. one dispersed in a iiarz Contains semiconductors in a suitable electrically conductive coating can, for example, from the iatriuric salt of a carboxyester-1 ac tons of an i-ialeinic anhydride / vinyl acetate mixed polyyncrisate and copper (I) iodide, such electrically conductive ones Layers and methods for optimal manufacture and use are, for example, in the United States patents 3 007 901, 3 245 833 and 3 267 S07.

The electrophotographic recording material of the Irrfindun can be used in all known electrophotographic processes in which photoconductive layers are required. An example of such a method is the xerographic method, called this method. Type v, an electrophotographic rapaic recording material is kept in the dark with an electrostatic surface; by placing it under a corona discharge tube and applying a uniform charge to the surface of the photoconductive layer * and the same charge is retained in the layer, since the layer is not practically an insulator in the dark, that is, in the dark it is an insulator, ~ e has electrical conductivity. The on. The electrostatic charge generated on the surface of the conductive layer is then selectively diverted from the surface of the layer. Ί, ιη this with the help of a common üolicutun..sver fahrons, ζ. Γ>.

fcHRO 0A8

10 ·. / 1 77 1

BAD ORJQJNAL

n-ac.ii of a., jumtaktkoplerver drive or durcn. Lens projection cii.es ii-iluu3 or according to a reflex or bireflex process jildii.af.i: = Lelicitet, v.'odurcn in the photoconductive rail of the electro ^ uoto ^ raphiscLen \ ufzcichnun,; 5i-iatDrials a latent electrostatic is generated, ßci the exposure of the vVuerflciciio in this way and i.eise arises an electrostatic: ·; Charge image, since the licntenerjie impinging on the pliotoconductor connection causes the electrostatic charge in the areas affected by the light to be diverted from the surface, depending on the intensity of the P-estraulun * in the respective area.

to this "., else .erzeugte charge image is then developed abv transferred to another surface and developed there, inlei untv.eoer the jeladenen or uncharged areas visible ^ be eiracivt by being with eineüi" behanuclt ediun! that electrostatically Contains addressable particles with optical density. The electrostatically responsive developer particles can be in the form of a dust or a powder and they generally represent a pigment contained in a resinous carrier material, a so-called toner. A preferred method of applying such a toner to a latent electrostatic image for development: ; Roi-er Flacnen is carried out using a magnetic brush, for example. Processes for the production and use of an I-iasnctbdrs.te for applying a toner are examples in US Pat. Nos. 2,756,439, 2,736,440,

2 7il6 441, 2 311 465, 2 Ö74 063, 2 984 163, 3 040 704,

3,117,884 and in Reissue Patent 25,779. To develop the latent electrostatic image, you can also Liquid developers are used. During liquid development, the developer particles are applied to those carrying the image Surface in an electrically insulating liquid carrier material upset. Development processes of this type are

10 '/ ι 771

BATH ORIGINAL

known and in patent and other literature, for example in U.S. Patent 2,297,691 and Australian Patent 212,315.

In the most widely used dry development processes, permanent record is achieved by selecting a developer particle which contains a low melting point resin as one of its components. When the powder image is heated, the resin melts on or into the surface of the recording material. As a result, the powder is firmly adhered to the surface of the photoconductive layer r of the electrophotographic recording material. In other cases, the charge image or powder image produced on the photoconductive layer can be applied to a second layer support, ζ. B. paper, are transferred, which then after the development and after melting or after melting the bndkopie represents. Such methods are known and are described, for example, in US ^{Patents 2,297,691 and 1,551,582 and in 11} RCA Review ", Volume 15 (1954), pages 469-484.

The electrophotographic recording materials of the invention can have the most varied of structures. For example the photoconductive cream in 1 · Όιτι a single layer or in the form of multiple layers on a suitable opaque or transparent one electrically conductive substrate are applied. The layers can adjoin one another or be made up of layers an insulating material or some other photoconductive material Be separate from each other or the photoconductive layer or the sensitizing rail and the material electrically conductive layers can be coated with such layers or arranged between such layers.

1.OiU; 1 H / 1771

The mutual position of the substrate and the electrical leitfaliijüii layer can be changed by clicking on a. Layer carrier applies a pliotoleitfahige layer and the free side of the layer support or the free or coated Side of the photoconductive layer with an electrically conductive layer Scaicnt covers. However, arrangements similar to those described in the examples below can also be used Arrangements are different for the same or different uses of the electrophotographic recording material be suitable or even preferred.

The following examples are intended to explain the invention in more detail.

example 1

On a poly (ethylene trephthalate) film backing with a electrically conductive layer made from the sodium salt of a carboxy ester lactone resin became a coating material in the form of a paste of the following composition in a wet layer thickness of 0.1016 mm (0.004 inch) applied:

Photoconductor compound 0.25 g polymeric binder 1.00 g

/ "a poly (4,4'-isopropylidenebisphenoxyethyl-co-ethylene-

terephthalate7 ~ polyester resin of the Goodyear Tire and Rubber Company, known under the Ilandel name Vitel 101_ /

Rhodanine B sensitizer 0.01 g dichloromethane 9.60 g

108 ;; 15/1771

BADORiGlNAt

In a darkened room, the surface of the photo-capable Layer of the electrophotographic produced in this way Recording material under a corona discharge source charged to a potential of about +600 volts. Then a transparent one was applied to the photoconductive layer Foil laid, which had a pattern of opaque and translucent surfaces, and with light from one Incandescent lamp with a light intensity of about 75 lux exposed for 12 seconds. The resulting latent electrostatic Image was developed by going over the surface of the negative charged layer let black thermoplastic toner particles trickle on glass bead carriers. The quality of the The image obtained while avoiding the various photoconductor compounds given below is the following Given in the table. ■

Table B.

Photo conductor connection , image quality

no picture

I good

II good

III good

IV ■ '.-. '■. · ■, ■ ■.:, " 'Good ■ ■; ■

V _ ^ good ■ .VI:; ^ good

-. VII; . good ': o

VIII good

IX good

■ X. . Well- . . ν:;

XI good

XII 'good

XIII good

XIV well XV

109: 1 1 5/1771
ΟΑβ "

Example 2

The procedure of Example 1 was repeated, but this time using 4- (p-dimethylaininophenyl) -2 _> 6-diphenylthiapyryryl perchlorate as the sensitizer and a polycarbonate resin (Lexan 145 from General Electric Co.) as the binder. In each case, a good reproduction was obtained. If the riotoconductor connection was omitted, poorer image quality was obtained.

Example 3

The procedure of Example 1 was repeated, this time together with the photoconductor compound I various sensitizers were used. The sensitizers used are given in the table below.

TabolleC

Get sensitizer pictures

6-chloro-1'-ethyl-i, 2 *, 3-triphenyliniidazo- / 4,5-b7cninoxalirt-3'-indolocarbocyanine-ptoluenesulfonate Yes

G, 6'-Jichlur-1, 1 ', 3,3 · -tetraphenylimidazo- I 1, S-bychiiioxali

sulfonate yes

2- (4-r: ethoxypaenyl) -4- (N-butylamino) benzo - / "b7i: yryliuir.perchlorate yes

6-Cp-n-amyloxystyryl) -2 _f 4-bis (p-ethoxyphenyl) pyrylium tetrafluoroborate yes

2,4-bis (4-ethylphenyl) -6- (4-styrylstyryl) pyrylium perchlorate Yes

15/1771

⁴ ^ OfilGINAL

- 2nd year -

Table C (Furt.se t ζ uuf.)

2, <\, (· -Tripiieny lpyry 1 iuir «tctr; i fluoruorat 'yes

t.iiol iuMpere.vLorat: yes

); Example 4

ij.is method of the iloi game 3 luirde uioderho.lt, uü.H \ i Ji. jedocii die VerL'iiiduiipn Il to XV of the table Λ ver \> ejulet In jedci ': I ^: .i lic became a ;; ute liildqual i tat crhallMt, ■;

'1 Ί 7

0A8

Claims (5)

!! "! Il! I ι" ^ι: » ¹ S (I - 2 1 - at CiIt α ti 5 tr α c η ο I.) i.lc -. ^ Tro · _l4 o to 'να ·· *! Laciio »Aui'zeicanun; svateriul, liuJtuaonJ ^ - ^ Mis oi.io ,: *> c, iiciit t ra; tr utiJ iuiiiUes t jjis oinoi 'on it- -, ^". ■> ν : ic; .tuu. «Ο tj Loit Γ ■ .i ; eu ^ caicht, the oin _t ⁱ v> lyuures '..i.ivivv-.ittoi u.k'. Cine jr /, aniscae t'JiotoloitorverbiadUii ^ oat-.u; It, ν - .. ulurci: ^ oküim-eichnet, Λλ> \ die pnotoioit due (a) .-> c.iICIt (OTi) Us Fiu) toloiterverbiadu! ii iriiiKlostens oin IU-S - (. Jialivv la: "iiuoaryl) alUaiiol which contains all ^ u ^ a formula: Iiedeutoa each one optionally substituted short-chain aliphatic alkyl radical with 1 to ο iCarbon atoms «un4 a possibly substituted aliphatic alkyl radical with 1 to 18 carbons stoffatoineK »an if necessary subst!> tuierten Cycloaikylrest, one optionally substituted Mphenylenmetaanresi ,, or a ^ e -tobiotically substituted uöterocyclic «residue with 5 to 6 atoms in hetero rings. BATH ORIGINAL 2. Electrophotographic recording material according to claim 1, characterized in that the photoconductive layer (s) additionally contains a sensitizer for the photoconductor compounds. 3. Electrophotographic recording material according to Claims 1 and 2, characterized in that the photoconductive layer (s) ate Bis (4-dimethylaminophenyl) benzylmethanol, "Bis (4-diraethylaminophenyl) fluorenylmethanol, Bis (4-dimethylaminophenyl) trifluoromethylmethanol or 1,1-bis (4-dimethylaminophenyl) -1-hydroxyethane as a photoconductor connection contains (contain). 4. Electrophotographic recording material according to claims 1 to 3, characterized in that the photoconductive layer (s) contains the photoconductor compound in a concentration amount * of 10 to 60% by weight. 5. Electrophotographic recording material according to the Proverbs 1 to 4, characterized in that the photoconductive capable layer (s) the sensitizer for the photoconductor compound in a concentration of 0.005 to 5 wt. contains (contain). 1 I - 'J 7 1