DE1943387A1 - Electrophotographic recording material - Google Patents

Description

Eastman Kodak Company, 343 State Street, Rochester, New York State, United States of America

Electrophotographic recording material

The invention relates to an electrophotographic recording material, consisting of an organic photoconductor, optionally applied to a layer support and optionally a film-forming binder and a sensitizer for the photoconductive one comprising the photoconductor Layer and optionally intermediate and / or top layers.

There are already electrophotographic recording materials of the most diverse composition known. So there is z. B. that known from US Pat. No. 2,297,691 for xerography determined electrophotographic. Recording material composed of a layer support and one applied to it Layer of a normally insulating compound, the electrical resistance of which increases with the amount of during the image-wise exposure to incident electromagnetic radiation changes. For use is one such in the Usually "photoconductive material"!

009812/1492

'- • 2 -; ... ■ _ ■■■ - ■. ■. ■ ■ .-

material initially, usually in the dark after a sufficient long adaptation to conceit, with a uniform surface charge Mistake. After that, the charged recording material becomes exposed to an exposure pattern of actinic radiation, which results in the potential of the surface charge is reduced to different degrees in accordance with the relative radiation energy present in the various parts of the exposure pattern. Those on the exposed electrophotographic Differentiated surface tension remaining on the recording material, d. H. thus the formed electrostatic latent image, is then made visible by adding the Surface of the recording material with a suitable one electroscopic marking substance or toner in con? clock is brought. One such, enti / eder in an insulating Liquid or toner on a dry carrier can be either according to the charge pattern or according to the non-charge pattern on the surface of the exposed recording material are deposited. The seasoned one Toner can then either by conventional known methods, e.g. B. with the help of heat, pressure or solvent vapors, permanently fixed on the surface of the radiation-sensitive recording material or on a receiving material be transferred, on which it can then be fixed in a corresponding P manner. If necessary, this can be done in the exposed Electrostatic latent image formed on the recording material also on a second photographic material transferred and then developed in it.

The photoconductive, insulating layers of such, electrophotographic recording materials can be made of consist of a wide variety of substances. So find z. B. for Document copying currently used in photographic recording materials a widespread application consisting of a substrate as well as one deposited on it in the form of fumes Selenium or selenium alloy layer or one on!

12/1492 OBlQiNAL INSPECTED

- 3 -. ■■ - * ■

a layer applied to a layer of resin-like, film-forming agents dispersed ■ photoconductive zinc * oxide particles exist.

Electrophotographic processes have been used since they became known already the most diverse organic compounds for their Suitability as photo conductor tested »It turned out that one very large number of organizational connections, more or less strong photoconductive is «Many © rgahische compounds turned out to be so strongly photoconductive that it can be used as a photoconductor for electrophotographic Recording materials appeared suitable. Typical suitable such organic photoconductors are known, e.g. the triphenylamines and the triarylmethane leuco bases.

Particularly suitable for electropiiotographic processes are op- ' table-top recording materials containing clear photoconductors, there Such recording materials may be replaced by transparent ones Substrate can be exposed - so that the copier can be designed very flexibly. Such photoconductors containing recording materials also offer the advantage of that they can be used multiple times, that is, they can after removing the toner from previous images by transferring and / or cleaning again to record Images are used.

It has not yet succeeded out of the large number of To find out photoconductive compounds of the most varied of structure characteristics which allow a prediction of the suitability of certain compounds as photoconductors, so that to choose from and finding new ones for incorporation into photoconductive ones Layers of electrophotographic recording

ORIGINALINSPECTED

009812 / U92

materials suitable photoconductors the "'in question. Connections must be tested individually ».

The object of the invention is to provide an electrophotographic Recording material with high photosensitivity electrical charge as well as high electrical sensitivity to indicate »that both positively and negatively chargeable and for the electrophotographic production of images suitable for so-called reflex or bireflex processes lsi: and which is also in the form of a transparent eiektrophotographi * ) look like recording material with high sensitivity ! can be designed.- Γ

The invention is based on the surprising finding that the specified task in a particularly advantageous manner can be solved when the photoconductive layer of the electrophotographic recording material a new one Organometallic compounds with a precisely defined structure that represent a class of photoconductors are incorporated.

; The invention is an electrophotographic recording

\ Drawing material, consisting of an organic photo-

W ladder and optionally a film-forming binder and a sensitizer for the photoconductive layer containing the photoconductor, and optionally intermediate and /

^: or cover layers, which is characterized in that the organic photoconductor consists of an organometallic compound with at least one aminoaryl radical bound to a metal atom of group IHa of the periodic table.

The present in the organic photoconductor of elektrophptographischen recording material according to the invention MetaJLlatome Group IIIA of the Periodic Table _# as in the "Handbook of Chemistry and Physics", is reproduced 38th edition, pages 594-395, boron, aluminum, gallium can * Indium or thallium atoms. These metal atoms can be of the most varied

009812/149 ^

:. OBtGiNALfNSPECTED

Carry substituents, but must, as already mentioned, at least one of these substituents can be an aminoaryl radical. In this aminoaryl radical, the amino group can be in any Position of the aromatic nucleus sit, but have aminoaryl radicals that are in the 4- or para-position by a Phenyl radicals substituted by amino groups have been found to be particularly advantageous.

Typical suitable ones at the metal atom of the group IHa of the organometallic Substituents bound to the compound are, for. B ,:

a) a hydrogen atom;

b) an optionally substituted alkyl radical, ζ. B. an aralkyl radical, for example a benzyl radical, a halogen-substituted alkyl radical, for example a chloromethylene radical, or an aminoalkyl radical, for example a radical of the formula -CH.-Nö & fctex * C ^C 2 ^H 5

a

c) optionally substituted aryl radical, for example a

Phenyl or naphthyl radical, or an aminoaryl radical of the general formula

in which R ₁ and R _{9 are} hydrogen atoms, optionally substituted alkyl radicals, e.g. B * aralkyl radicals, or optionally substituted aryl radicals, for example alkaryl radicals or halogen-substituted aryl radicals;

d) a "" oxygen-containing * residue, e.g. a ** alkoxy or aryloxy radical;

e) an optionally substituted amino radical, for example a dialkylamino, diphenylamino, alkylamino or Phenylamino radical as well

009812/1492 originally inspected

f) an organometallic radical, with a metal atom of Group Ilia of the periodic table, ζ. B. a remainder of the general formula

in which M denotes a metal atom of group IIJa and R ₉ and R | Q have the meaning of the radicals given under a) to e).

Electrophotographic recording materials according to the invention have proven to be particularly advantageous which contain an organometallic compound of the following general formula as the organic photoconductor:

N - Ar-]

D and E

in which:

a) hydrogen atoms;

b) optionally substituted aryl radicals, ζ. Β. Phenyl,

Naphthyl, dialkylaminophenyl or dialkylamino - _o njaphthylreste;

^ c) alkyl radicals having 1 to 8 carbon atoms; - * d) alkoxy radicals having 1 to 8 carbon atoms; ^. e) aryloxy, z "B. Phenyloxyreste oäet ^ f) Aaiaoreste, z · B, those of the general formula

to - - '. "." - ■ '■■■■■

ro ^^ R-z

, in which R and R _{4 are} hydrogen atoms _s I. alkyl or aryl radicals;

INSPECTED

Ar is an optionally substituted arylene radical,

ζ. B. a phenylene or alkylphenylene radical, or a halagensübs.tituierten phenylene radical;

M is a metal atom from group IHa of the periodic table;

R.J and R2

a) water to ff atoms,

b) AlkyIreste with 1 to "8 carbon atoms or

c) aryl radicals of the phenyl or naphthyl series, e.g. B. Phenyl or naphthyl radicals

Organic photoconductors have proven to be particularly advantageous proven by the following general formula:

wherein

attached M, D, H, R ^ and R ^ have the meaning given and T _t X and Z have the following meaning:

a) hydrogen atoms,

b) alkyl radicals with 1 to 8 carbon atoms,

c) optionally substituted aryl radicals, e.g. B. phenyl, naphthyl, tolyl, aminophenyl or halogen-substituted phenyl radicals,

d) Alkoxy res te "-mif 1 to 5 carbon atoms,

e) aryloxy residues, e.g. phenyloxy residues,

f) halogen atoms, ζ, B. chlorine, bromine or Iodine atoms or

009612/1492 _Λ -

ORIGINAL INSPECTED

J943387

- 8 -g) amino radicals, e.g. B. those of the general formula,

^V 7 —N ', in which R ₇ and R _g V / ass first ff atoms,

^ * R ₈ alkyl radicals with 1 to 8 carbon atoms or aryl radicals, e.g. B. mean phenyl or naphthyl radicals,

where X, T and Z ₉ , which are radicals with the same or different meaning, can be bonded in the 2-, 3-, 5- or 6-position of the phenylene ring *

Typical for the electrophotographic recording material According to the invention suitable photoconductors are, for. B. the organometallic compounds listed in Table I below

Table I.

1. Tri-p-diethyiaminophenyiborane

2. Tri-p-diphenylaminophenylborane

3. Tri-p-methylaminophenylgallium

4. Methylphenyl-p-diethylaminophenylborane 5 x 2-naphthy1-p-dimethylaminophenylborane

6. p-Dipropylaminophenylborane

7. Di-p-diethylaminophenylborane

8. Ethoxy-p-dimethylaminophenylaluminium hydride

9. Diphenoxy-p-dibutylaminophenylaluKinium

10, tri- (2,6-dimethyl-4 * diethylaBilnophenyl) indium

11. 2-Chloro-4-dimethylaminophenylgalliurahydride

Ö098t2 / U92

ORiGINALINSPECTEQ

VV If fc

It C t *

- 9- ■■ - ""

12. Tri- (2,6-diphenoxy-4-diethylaminophenyl) thallium

13. Tri- (2,6-dimethoxy-4-dimethylaminophenyl) thallium

14. Diphenylamino-p-diethylaminophenylborane

15. Dimesityl-4-dimethylaminonaphthylborane

16. Dimesity1-4-dimethylaminophenylborane

17. Dimesityl-4-diphenylaminophenylborane

18. 1,2-bis (p-diethylaminophenyl) diborane

To produce such photoconductors, as a rule usual known methods can be used. So z. B. in a conventional manner, initially as an intermediate the desired substituents carrying Grignard or lithium compound are prepared, whereupon for the preparation of the end product, the intermediate product obtained with stoichiometric Amounts of a metal halide having a metal atom of the group IHa or of a metal atom of the group lilac, as well as metal halides having the desired substituents is implemented.

The electrophotographic recording materials according to the invention comprising the organic photoconductors specified can be prepared by conventional methods, e.g. B. by coating a substrate with one of the Photoconductor-containing dispersion or solution, which, if appropriate, if this proves to be expedient, a binder can be incorporated, .or by producing a self-supporting layer from a mass containing the photoconductor, | ür In addition, mixtures of the specified photoconductors and mixtures of the specified photoconductors and known photoconductors can also be used to produce the electrophotographic recording media according to the invention

r * if

-. to -

can use the electrophotographic recording materials known additives which are customary according to the invention and which influence the spectral sensitivity or electrophotosensitivity included if their addition is expedient or proves advantageous *

Typical suitable sensitizers of this type are, for example, pyrylium salts, e.g. B. Thiapyrylium- and Selenapyryliumsalze, as they are z. B, in US Pat. No. 3,250,615, and fluorenes, e.g. B. 7,12-Dioxo-13-dibenzo (a, h) fluorene, 5,10-Dioxo-4a, 11-diazabenzo (b) fluorene, 3,13-Dioxo-7-oxadibenzo- (b _# g) - fluorene, trinitrofluorenone and tetranitrofluorenon, also the aromatic nitro compounds known from US Pat. No. 2,610,120, the anthrones known from US Pat. No. 2,670,285, the quinones known from US Pat. No. 2,670,286, those from US Pat 2,670,287 known benzophenones and the thiazoles known from US Pat. No. 2,732,301; also maleic acids, carboxylic acids, ζ. B. maleic acid, dichloroacetic acid and salicylic acid, sulfonic and phosphoric acids; as well as various dyes, e.g. ■ & ■ · triphenylmethane, diarylmethane, thiazine, azine, oxazine, xanthene, phthalein, acridine, azo and anthraquinone dyes.

As particularly advantageous sensitizers for the electrophotographic recording materials according to the invention have pyrylium salts, e.g. B. selenapyrylium and thiapyrylium salts, also fluorene, carboxylic acids and triphenyl ^ methanfarbstpffe proved. ~;

Should such a sensitizer be the photoconductive layer an electrophotographic recording material according to Invention are incorporated, this is usually done by intimately mixing an appropriate amount of the

OB-SQiNAL 8NSPECTED

· F -C

- 11 -

with the sealing compound, so that the layer formed from the compound contains the sensitizer in a uniform distribution contains. The photoconductive layers of the electrophotographic recording materials according to the invention need to Developing their photoconductivity not to contain a sensitizer »d. H. the lower limit of the required sensitizer concentration is c ■ 0. However, it has been found to be It has been shown to be advantageous to add sensitizers in low concentrations, since the addition of comparatively small amounts of sensitizer already significantly increases the electrophotographic sensitivity of the recording materials is improved. To effectively increase the sensitivity, the sensitizer can be incorporated into the photoconductive layer in various concentrations. The optimal one Concentration depends on * various factors, e.g. B. on the respective type of photoconductor and sensitizer used.

- Rttnf ι till 2 4 imi

To achieve a unique Bwnctkeitserhöhung it has proven to be advantageous as a rule, the sensitizer in concentrations of approximately 0 _# 0001 to 30 wt .- *, based on the weight of the film-forming Beschichtungsraasse to use "In general, the sensitizer of the coating composition incorporated in a concentration of about O ₉ OOS to 5.0 wt.

The photoconductive layers of electrophotography see Recording materials according to the invention can particularly advantageously contain film-forming, hydrophobic polymeric binders with fairly high dielectric strengths as well contain good electrical insulation properties. Typical suitable binders of this type are e.g. styrene-butadiene copolymer, silicone resins »styrene-alkyd resins, silicone alkyd resins, StJ «alkyd resins, polyvinyl chloride, polyvinylidene chloride, vinylidene chloride-acrylonitrile copolymers, polyvinyl acetate, vinyl »Citat vinyl chloride miscopolymers, polyvinyl acetals, e.g. Polyvinyl butyral, polyacrylic and methacrylic acid esters, e.g. B. Polymethyl methacrylate, poly-n-butyl methacrylate and polyiobutyl

0Ö9812 / U92

ORIGINAL / NSPECTED

methacrylate also polystyrene, nitrated polystyrene, ^ methyl styrene, isobutylene polymers, polyester, ζ. B. Poly-. ethylene alkaryloxyalkylene terephthalate, phenol formaldehyde resins, Ketone resins, polyamides, polycarbonates, polythiocarbonates, polyethylene glycol-co-bishydroxyethoxyphenylpropane terephthalate and copolymers of vinyl halide arylates and vinyl acetate ,, ζ * B. polyvinyl m-bromobenzoate-covinylacetate.

Processes for making resins of the type indicated are known. So z. B. styrene alkyd resins according to the US patents 2,361,019 and 2,258,423 processes described. For the production of photoconductive Layers of the electrophotographic recording materials Resins of the specified type suitable according to the invention are e.g. B. under the trade names "Vitel PE-IOI", ä'Cymac "," Piecopale 100'Y "Saran F-220", "Lexan 105" and "Lexan 145" on sale Other binding agents have also proven to be suitable, ζ ... B. Paraffin or mineral waxes "

A wide variety of solvents can be used to produce the coating composition containing the photoconductor. As a particularly advantageous solvent z. B ₀ benzene, toluene, acetone, 2-butanone, chlorinated hydrocarbons, such as methylene chloride and ethylene chloride, and also ether, e.g. B. Tetrahydrofuran, as well as mixtures of these solvents have been proven «

It has proven to be expedient for the production of the feed masses proved the organic photoconductor in one concentration of at least about 1 weight percent based on weight the coating compound to be used. The upper limit of the Photoconductor concentration can vary widely. If a binder is used, it has generally proven to be expedient to use the photoconductor in a concentration of about

009812/1492

1 to 99 wt. T, based on the weight of the coating compound, to use. It has proven to be particularly advantageous proven to use the photoconductor in the coating compound in a concentration of about 10 to 60 wt.

The layer thickness of the coating applied to a substrate photoconductive layer may be very different "In - general, it has proved advantageous to apply the coating in such a thickness on the support, that the layer thickness before drying about O ₁ OZS to 0.25 mm (0.001 to 0.01 inch), preferably about 0.05 to 0.15 mm (0.002 to 0.006 inch).

The electrophotographic recording materials according to the invention can contain a wide variety of conventionally known electrically conductive supports. Typical suitable substrates of this type are e.g. B, paper support (at a relative humidity above 201). Multi-layer support made up of aluminum * and paper layers, as well as support made of metal foils, e.g. B, aluminum or zinc foils, from metal plates, e.g. B. aluminum, copper, zinc _t brass and galvanized plates, as well as layer supports with metal layers deposited in the form of vapors, e.g. silver or aluminum layers.

For the production of a particularly advantageous layer carrier can, for example, be a suitable carrier material, ζ. B, a polyethylene terephthalate film, with a * a semiconductor. in dispersed Resin layer containing mold Electrically conductive layers of the specified type, including those that additionally contain insulating barrier layers, are ζ. B. in the USA patent specification S 245 833 described. To produce such a conductive layer, it is also possible to use; Sodium salt from a carboxy ester octone

194338?

,. 14 -

of maleic anhydride and a vinyl acetate polymer used will. Supports of this type and processes for their manufacture are z. B. in U.S. Patents 3,007,90t and 3,267,807. .

The electrophotographic recording materials of the invention can be used to carry out conventionally known electrophotographic processes requiring the presence of a photoconductive layer, e.g. B-. to carry out the specified xerographic process. To carry out such a process, as already mentioned, the electrophotographic recording material is exposed to a corona discharge so that the surface of the conductive layer is given a uniform electrostatic charge electrical conductivity in the dark, retained. Thereafter, the electrostatic charge present on the surface of the photoconductive layer is selectively dissipated with the formation of a latent image in the photoconductive layer by exposing the electrically charged recording material, e.g. B. by a slide carrying the image to be copied according to the usual known exposure rivets ^ z. B-. according to the Koataktkopiertechnik or by lens projection of the to be copied. Image. The charge eiuster representing the latent image arises in such a way that the incident light depends on the light intensity prevailing in the individual districts; different strong dissipation d @ r on the Gbesflacke the tsitota-Ieitfähigen betiimct layer -befindlichen elektrisclien charge ^ The LadungsmusteT formed by the exposure can then _f / gemaciit be developed that is visible "by using a. entftaltenden electrostatically attractable ,, optically dense particles Means are treated * Qie for the elimination: electrostatic development; Attractable particles can be in var ^ liegjem _A '.z _m B% in the form © ines StaÄes _ft sS

Q098I2 / 14S-2. ORIGINAL h «» * jecied

a pigment in a resinous vehicle; d. H. Toner, or in the form of a developer liquid that contains the developer particles in an electrically insulating liquid acting as a carrier. Development process of the specified Type are known from the patent literature, e.g. B. from the USA patent 2,297,691 and Australian patent 212 315.

Is used in such electrophotographic reproduction processes, z. B. in the so-called. Xerographic process, a developer with developer particles, one component of which consists of a low-melting resin, is used, so lets the development on the surface of the photoconductive Layer of deposited developer powder by heating of the developed electrophotographic recording material are permanently fixed on the image surface.

Optionally, as already mentioned, that in the photoconductive Layer generated image also transferred to a second carrier material and then on this as the final Copy to be fixed. Such methods are known from the technical literature and are z. B. in the United States patents 2,297,691 and 2,551,582 and in "RCA Review", Volume 15 (1954), Pages 469-484.

The electrophotographic recording materials according to Invention can be used for a wide variety of purposes and exposed, developed and processed in a wide variety of ways be, d. H. the processes used for exposure, charging, possibly image transfer, development and fixing and materials can be very different and adapted to the respective purpose.

So z. B. the electrophotographic recording materials be used according to the invention for carrying out photographic reproduction processes according to which the

00981-2 / 1492.

OR (GJNAl INSPECTED

Recording material radiation of various types expor is ned, d. H. both electromagnetic radiation and also nuclear radiation. It must therefore be stated that, although the electrophotographic recording material after of the invention primarily for carrying out an exposure comprehensive process is used, the term "electrophotographic" to express that the electrophotographic Recording material according to the invention both for carrying out so-called xerographic and so-called xeroradiographic processes can be used in an advantageous manner.

The following production example is intended to produce a as a photoconductor for the electrophotographic recording materials suitable organometallic compound typical of the invention having at least one on the metal atom Aminoaryl radical bound to group IIIa of the periodic table, the amino group of which is substituted by alkyl radicals having 1 to 8 carbon atoms.

Manufacturing example

For the preparation of tri-p-diäthylaminophenylboran 17.2 g (0.72 moles) were combined in a reaction flask magnesium befindliches 1 hour heated to 100 ⁰ C, after which it is cooled to a temperature of less than 60 ^Q C and then 25 ml of a A solution containing 55.2 g (0.24 moles) of distilled p-bromo-NjN-diethylaniline in 240 ml of dry tetrahydrofuran distilled over calcium hydride was added. The reaction began as soon as the reaction mixture obtained was heated to reflux temperature. The remainder of the solution was added at such a rate that the reaction mixture was kept at reflux temperature. The dark brown reaction mixture formed was heated to reflux temperature for a further hour, whereupon a solution of 11.4 g (0.08 mol) of boron trifluoride ethyl ether in 100 ml of dry tetrahydrofuran was added dropwise

0098127U92

- 17 -

* The resulting mixture was then heated to reflux temperature for 2 hours * The resulting solution was separated from the unreacted magnesium, whereupon it was treated with ice and a dilute ammonium chloride solution. The solid which precipitated out was separated off, then dried in air at room temperature and then purified by recrystallization from boiling acetonitrile * The solid obtained was dried in air at room temperature. There were 1.79 g of tri-p-diäthylaminophenylboran obtained in the form of a white crystalline solid having a melting point of F = 242-273 ⁰ C.

analysis for C ₃₀ H ₄₂ N, 5 ^B C. 79. U H 9. 2; B. 2. 4; N 9 .21 calculated; C. 79. Oj H 9 * 1; B. 2. 5; N 9 .31 found?

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

example 1

It was first made using tri-p-diethylaminophenylborane prepared a photoconductive coating composition of the following composition;

a) 0.25 g under the name "Lexan 145" known poly (4,4 * -isopropylidenediphenyl carbonate) as a binder;

b) 0.25 g of tri-p-diethylaminophenylborane as photoconductor j

c) 4.5 g of a 0.0029 g / "4-Cp-dimethylaminophenyl) -2,6-diphenylthiapyrylium perchlorate 7 per ml of solution containing methylene chloride as a sensitizer for the photoconductor as

ORIGINAL INSPECTED

0 & 9t8127149 2

d) 7.7 g of a mixture prepared by the process described in Belgian patent specification 705 117 from 3.92 g of the specified poly (4.4 * "• isopropylidenediphenyl carbonate), 0.008 g £ "4- (p ~ Dijnethylaminophenyl) T 2,6-diphenylthiapyrylium perchlorate and 26.8 ml of methylene chloride.

The coating compound obtained was then applied by hand to an electrically conductive layer of the sodium salt of a carboxy ester lactone, as described in US Pat. No. 3,120,028, on a cellulose acetate film so that the layer thickness in the moist state was 0.15 mm (0.006 inch). The coating blot
held.

processing blocks were at a temperature of about 30 ° C (90 ⁰ F)

Samples of the electrophographic recording material obtained were then given a positive or negative! Corona discharge exposed until the surface charge measured with the help of an electrometer probe had reached a potential of around 600 volts. The charged samples were then exposed through a stepped gray wedge of a violam light source of 3000 ° K. The exposure caused a decrease in the surface potential from the original potential V _o to a lower potential V, the exact value of which, from the -Exposure in meters «candle-seconds to which the individual districts were exposed depended;

The results obtained for the individual stages were; evaluated graphically, i.e. the surface potential V found was plotted against the logarithm of the exposure. The so-called "shoulder sensitivity" is the numerical value that results when IQ with the reciprocal value of the exposure in meters «candle-seconds, the ₇ for the reduction of 600 volts

009112 / H92 oraotNÄL inspected

- 19 -

multiplied by 100 volts is required, Kj & xitCK becomes.

Hit 'toe speed' becomes the numeric see value which results when 10 is the reciprocal value of the exposure in meter-core-seconds, which is required to reduce the original 600 volt surface potential to 100 ¥ olt, multiplied will.

It was found that the tested samples had the elektrophotogaphischen Aufzeichnungssaterials according to the invention, a positive school terempfindliclikeit of 2500, a negative shoulder speed VOA 54OQ _t is a positive slack sensitivity of 250 and a negative toe speed of 900th

example Ϊ

The procedure described in Example 1 was repeated with the exception that 2,6-bis (4-ethylphenyl) -4- (amyloxyphene ^ l ') -thiaprvlium percolorate was used as the sensitizer was used. The results of the evaluation of the obtained electrophotographic recording material showed that thereby the positive and negative shoulder and sag sensitivities remained practically unchanged.

Correspondingly advantageous results have been obtained when as a sensitizer 2,4 »bis (4-ethylphenyl) -6- (4-styrylstyryl) -pyryliumperciilorat was used"

Example 3

Following the procedure described in Example 1 were under Use of photoconductors No. 1-18 listed in Table I.

ORIGINAL INSPECTED 009812 / T492

electrophotographic recording materials prepared. Then, in the dark, the surfaces of the obtained electrophotographic Recording materials are charged to a potential of about +600 volts with the aid of a corona discharge. The photoconductive layers then became the charged Recording materials each with a transparent, a pattern of opaque and translucent Covered areas exhibiting foil, whereupon they each 12 seconds larfg emitted by an incandescent lamp Radiation with an illumination intensity of about 75) meter candles were exposed.

The thus formed electrostatic latent BiI-der were then developed in a conventional manner by acting on the surfaces of the latent image bearing pho'to · »ι conductive layers, a mixture of negatively charged black thermoplastic toner particles and the toner particles as a carrier medium Glass beads were scattered. In all cases, good reproductions of the template used were obtained.

Correspondingly advantageous results have been obtained when a liquid is used to develop the latent images formed Form of the present developer was used.

ORIGINAL IKiSPECTEQ 009812/1 492>

Claims (1)

*, 21 - Patent claims e Electrophotographic recording material consisting of from a possibly on a layer support; " brought an organic photoconductor and optionally a film-forming binder and a sensitizer for the photoconductive j-layer comprising the photoconductor, and optionally intermediate and / or top layers, characterized in that the organic Photoconductor made from an organometallic compound with at least one to a metal atom of group IIIa des; Aminoaryl radical bound in the periodic table. I. Electrophotographic recording material according to claim! 1, characterized in that the organic photoconductor j consists of an organometallic compound which is attached to the j Metal a torn of group IHa of the periodic table in addition to min at least one aminoaryl radical still has at least one hydrogen * atom or an alkyl, aryl, alkoxy, aryloxy or Amino radical or the radical of an organometallic compound with a metal atom from group IHa of the periodic table contains bound. 3. Electrophotographic recording material according to claim 1, characterized in that the organic Photoconductor made from an organometallic compound of the general formula: N —Ar —M 008812714 in which: D and £ and consists. an optionally substituted arylene radical; Hydrogen atoms, optionally substituted Aryl radicals of the phenyl or naphthyl series, alkyl radicals with 1 to 8 carbon atoms, Alkoxy radicals with 1 to 8 carbon atoms, Aryloxy radicals or optionally substituted amino radicals; a metal atom of group HIa of the periodic table and Hydrogen atoms, alkyl radicals with 1 to 8 Carbon atoms or aryl radicals of the phenyl or naphthyl series, 4. The electrophotographic recording material according to claim 3, characterized in that the organic photoconductor is made from an organometallic compound of the general formula:; N- ORiQiHAL INSPECTED- 009812 / T492 in which M, D, E, R. and R have the meaning given and T, X and Z are hydrogen or halogen atoms and alkyl radicals with 1 to 8 carbon atoms, optionally substituted aryl radicals of the phenyl or naphthyl series, alkoxy radicals with 1 to 8 carbon atoms, aryloxy radicals or optionally substituted by alkyl radicals with 1 to δ carbon atoms or aryl radicals of the phenyl · »or naphthyl series Amino radicals mean consists. 5 · Electrophotographic recording material according to claims 1 to 4, characterized in that the organic photoconductor consists of a metailorganfehen compound with boron as Consists of metal atom of group purple of the periodic table * 6 »Electrophotographic recording material according to claims 1 to S, characterized in that the organic photoconductor consists of a »p-dialkylaminophenylborane. 7. Electrophotographic recording material according to claim 6, characterized in _{that B} that the organic photoconductor · ■ * ■ consists of a p-diethylaminophenylborane. . 8. Electrophotographic recording material according to claims T to 7, characterized in that the organic photoconductor consists of tri-p-, diathylafiinophenylborane. 9. Electrophotographic recording material according to claims 1 to 8, characterized in that the sensitizer for the photoconductor consists of a pyrylium salt. 009812/1492 10. Electrophotographic recording material according to claim 9, characterized in that the sensitizer for the photoconductor consists of _< /"4-(p-Diäthylaminophenyl)-2,6-diphenylthia.pyryliumperchlorat7. 11. Electrophotographic recording material according to claims 8 to 10, characterized in that the photoconductor in a concentration of about 10 to 60% by weight and the sensitizer for the photoconductor in a concentration from about 0.005 to 5.0 weight percent. 0098 1 2 / 1J, y 2