Search Images Maps Play YouTube News Gmail Drive More »
Sign in
Screen reader users: click this link for accessible mode. Accessible mode has the same essential features but works better with your reader.

Patents

  1. Advanced Patent Search
Publication numberUS3658520 A
Publication typeGrant
Publication dateApr 25, 1972
Filing dateFeb 20, 1968
Priority dateFeb 20, 1968
Also published asDE1908345A1, DE1908345B2
Publication numberUS 3658520 A, US 3658520A, US-A-3658520, US3658520 A, US3658520A
InventorsBrantly Thomas B, Contois Lawrence E, Fox Charles J
Original AssigneeEastman Kodak Co
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Photoconductive elements containing as photoconductors triarylamines substituted by active hydrogen-containing groups
US 3658520 A
Abstract
Triarylamines having at least one of the aryl radicals substituted by an active hydrogen-containing group are good organic photoconductors in electrophotographic systems.
Images(6)
Previous page
Next page
Description  (OCR text may contain errors)

United States Patent Brantly et al.

[ 51 Apr. 25, 1972 PHOTOCONDUCTIVE ELEMENTS CONTAINING AS PHOTOCONDUCTORS TRIARYLAMINES SUBSTITUTED BY ACTIVE HYDROGEN-CONTAINING GROUPS Thomas B. Brantly; Lawrence E. Contois; Charles J. Fox, all of Rochester, NY.

Eastman Kodak Company, Rochester, NY.

Filed: Feb. 20, 1968 Appl. No.: 706,780

Inventors:

Assignee:

US. Cl ..96/l.6, 96/15, 260/576,

252/501 Int. Cl. ..G03g 5/00, 603g 7/00 Field of Search ..96/1.5; 252/501 Primary ExaminerGeorge F. Lesmes Assistant Examiner-John R. Miller AnomeyWilliam H. J. Kline, James R. Frederick and Fred L. Denson [57] ABSTRACT Triarylamines having at least one of the aryl radicals substituted by an active hydrogen-containing group are good organic photoconductors in electrophotographic systems.

18 Claims, No Drawings PHOTOCONDUCTIVE ELEMENTS CONTAINING AS PHOTOCONDUCTORS TRIARYLAMINES SUBSTITUTED BY ACTIVE HYDROGEN-CONTAINING GROUPS This invention relates to electrophotography, and in particular to photoconductive compositions and elements.

The process of xerography, as disclosed by Carlson in US. Pat. No. 2,297,691, employs an electrophotographic element comprising a support material bearing a coating of a normally insulating material whose electrical resistance varies with the amount of incident actinic radiation it receives during an imagewise exposure. The element, commonly termed a photoconductive element, is first given a uniform surface charge, generally in the dark after a suitable period of dark adaptation. It is then exposed to a pattern of actinic radiation which has the effect of differentially reducing the potential of the surface charge in accordance with the relative energy contained in various parts of the radiation pattern. The differential surface charge or electrostatic latent image remaining on the electrophotographic element is then made visible bycontacting the surface with a suitable electroscopic marking material. Such marking material or toner, whether contained in an insulating liquid or on a dry carrier, can be deposited on the exposed surface in accordance with either the charge pattern or the discharge pattern as desired. The deposited marking material can then be either permanently fixed to the surface of the sensitive element by known means such as heat, pressure, solvent vapor, or the like, ortransferred to a second element to which it can be similarly be fixed. Likewise, the electrostatic latent image can be transferred to a second element and developed there.

Various photoconductive insulating materials have been employed in the manufacture of electrophotographic elements. For example, vapors of selenium and vapors of selenium alloys deposited on a suitable support and particles of photoconductive zinc oxide held in a resinous, film-forming binder have found wide application in present-day document copying applications.

Since the introduction of electrophotography, a great many organic compounds have also been screened for their photoconductive properties. As a result, a very large number of organic compounds are known to possess some degree of photoconductivity. Many organic compounds have revealed a useful level of photoconduction and have been incorporated into photoconductive compositions. Optically clear organic photoconductorcontaining elements having desirable electrophotographic properties can be especially useful in electrophotography. Such electrophotographic elements can be exposed through a transparent base if desired, thereby providing unusual flexibility in equipment design. Such compositions, when coated as a film or layer on a suitable support also yield an element which is reusable; that is, it can be used to form subsequent images after residual toner from prior images has been removed by transfer and/or cleaning. Thus far, the selection of organic compounds for incorporation into photoconductive compositions to form electrophotographic layers has proceeded on a compound-by-compound basis. Nothing has yet been discovered from the large number of dif ferent photoconductive substances tested which permits effective prediction and therefore selection of particular compounds exhibiting the desired electrophotographic properties.

It is, therefore, an object of this invention to provide photoconductive elements for use in electrophotography containing a novel class of organic photoconductors having enhanced photosensitivity when electrically charged.

It is also an object to provide electrophotographic elements having a layer of a novel photoconductive composition which can be positively or negatively charged.

It is another object to provide novel transparent electrophotographic elements having high speed characteristics.

It is a further object of this invention to provide novel electrophotographic elements useful for producing images electrophotographically by reflex or bireflex processes.

These and other objects of this invention are accomplished with electrophotographic elements having coated thereon organic photoconductive compositions containing a tiarylamine photoconductor wherein at least one of the aryl radicals is substituted by an active hydrogen-containing group and a sensitizer for the photoconductor. Groups which contain active hydrogen are well known in the art, the definitionof this term being set forth in several textbooks such as Advanced Organic Chemistry, R. C. Fuson, pp. 154-157, John Wiley & Sons, 1950. The term active hydrogen-containing group as used herein includes those compounds encompassed by the discussion in the textbook cited above and in addition include those compounds which contain groups which are hydrolyzable to active hydrogen-containing groups. Typical active hydrogen-containing groups which are sub stituted on an aryl radical of the triarylamine according to this invention include:

a. carboxy radicals; b. hydroxy radicals; c. ethynyl radicals including substituted ethynyl radicals such as hydroxy ethynyl radicals, aryl ethynyl radicals and alkyl ethynyl radicals;

O l d) ester radicals (e.g. i10 R wherein R is an alkyl oran aryl group) e. lower alkylene hydroxy radicals (e.g., having one to eight carbon atoms);

f. carboxylic acid anhydride radicals;

g. lower alkylene carboxy radicals (e.g., having two to eight carbon atoms);

h. Acyl halide radicals (e.g.,

O H CCl etc.);

i. Arnido radicals (e.g.,

0 R ll C-N wherein R is a hydrogen atom, an alkyl group or an aryl group) j. Lower alkylidyne oxirnido radicals having 1-8 carbon atoms including substituted alkylidyne oxirnido radicals (e.g., C NOH wherein R is hydrogen or a lower alkyl radical); and

k. semicarbazono radicals; and

l. Arylene carboxy radicals including substituted arylene carboxy radicals leg,

wherein D and E are phenyl or lower alkyl radicals.

The preferred photoconductors of this invention are represented by the following structure:

carboxylic acid anhydride radical, an ester radical, a cyano radical, a semicarbazono radical, a hydroxy radical, an ethynyl radical, a methylidyne oximido radical or a phenylene carboxy radical.

The organic photoconductors of this invention exhibit substantial improvements in speed over comparable photoconductors which do not have an active hydrogen-containing group (including groups hydrolyzable to active hydrogen-containing groups). Also, those compounds in which Ar and Ar in the above formula are phenyl radicals generally have improved photoconducting properties over those which are substituted by one or two alkyl radicals. Thus, p-diphenylaminobenzoic acid generally displays higher electrical speeds than p-diethylaminobenzoic acid of p-N-methyl-N- phenylaminobenzoic acid.

Some typical photoconductors of this invention are:

TABLE I l methyl p-diphenylaminobenzoate,

ll N,N-diphenylanthranilic acid,

Ill 3-p-diphenylaminophenyl-l-propanol lV 4-acetyltriphenylamine semicarbazone,

V ethyl-2,6-diphenyl-4-(pdiphenylaminophenyl)benzoate,

VI l-(p-diphenylaminophenyl)-1-hydroxy-3- butyne,

VII 4-hydroxymethyltriphenylamine.

Vlll l-(p-diphenylaminophenyl)ethanol,

IX 4-hydroxytriphenylamine,

X Z-hydroxytriphenylamine,

ylaminobenzoic acid, XIX p-diphenylaminobenzoyl chloride,

3-p-diphenylaminophenylpropionic acid, and 4 formyltriphcnylnmine semicarbazone.

These compounds can be prepared by the methods set forth in a copending application, Ser. No. 706,799 filed concurrently herewith entitled Novel Substituted Triarylamines.

Electrophotographic elements of the invention can be prepared with these photoconducting compounds in the usual manner, i.e., by blending a dispersion or solution of a photoconductive compound together with a binder, when necessary or desirable, and coating or forming a self-supporting layer with the photoconductor-containing material. Mixtures of the photoconductors described herein can be employed. Likewise, other photoconductors known in the art can be combined with the present photoconductors. In addition, supplemental materials useful for changing the spectral sensitivity or electrophotosensitivity of the element can be added to the composition of the element when it is desirable to produce the characteristic effect of such materials.

Generally, the photoconducting compounds of this invention are not sensitive to light unless a sensitizing compound is present. While a wide variety of such substances impart spectral sensitivity to the photoconductors of this invention, it has been found that pyrylium salts, that is the pyrylium, thiapyrylium and selenapyrylium salts of U.S. Pat. No. 3,250,615, are particularly useful for sensitizing these compounds to the extent that they exhibit relatively high electrical speeds compared to those compounds which do not have an active hydrogen-containing group. Other sensitizing compounds useful with the photoconductors of the invention include tluorenes, such as 7. l 2-dioxol 3-dibenzo(a,h)-fluorene, 5,10- dioxo-4u,l ldiazodenzo(b)fluorene, 3,13-dioxo-7-oxndibcnzotb.g)fluorene, trinitrofluorenone, tetranitroflurenone and the like; aromatic nitro compounds of U.S. Pat. No. 2,610,120; anthrones of U.S. Pat. No. 2,670,285; quinones of U.S. Pat. No. 2,670,286; benzophenones of U.S. Pat. No. 2,670,287; thiazoles of U.S. Pat. No. 2,732,301; mineral acids; carboxylic acids, such as maleic acid, dichloroacetic acid, and salicylic acid; sulfonic and phosphoric acids; and various dyes such as triphenylmethane, diarylmethane, thiazine, azine, oxazine, xanthene, phthalein, acridine, azo, anthraquinone dyes.

In preparing the photoconducting layers disclosed herein, it is conventional practice to mix a suitable amount of the sensitizing compounds with the coating composition so that, after thorough mixing, the sensitizing compound is uniformly distributed throughout the desired layer of the coated element. The amount of sensitizer that can be added to a photoconductor-incorporating layer to give effective increases in speed can vary widely. The optimum concentration in any given case will vary with the specific photoconductor and sensitizing compound used. In general, substantial speed gains can be obtained where an appropriate sensitizer is added in a concentration range from about 0.0001 to about 30 percent by weight based on the weight of the film-forming coating composition. Generally, a sensitizer is added to the coating composition in an amount by weight from about 0.005 to about 5.0 percent by weight of the total coating composition.

Preferred binders for use in preparing the present photoconductive layers are film-forming polymeric binders having fairly high dielectric strength which are good electrically insulating film-forming vehicles. Materials of this type comprise styrene-butadiene copolymers; silicone resins; styrene-alkyd resins; silicone-alkyd resins; soya-alkyd resins; poly (vinyl chloride); poly(vinylidene chloride); vinylidene chloride-acrylonitrile copolymers; poly(vinyl acetate); vinyl acetate-vinyl chloride copolymers; poly(vinyl acetals), such as poly (vinyl butyral); polyacrylic and methacrylic esters, such as poly(methylmethacrylate), poly(n-butylmethacrylate), poly (isobutyl methacrylate), etc.; polystyrene; nitrated polystyrene; polymethylstyrene; isobutylene polymers; polyesters, such as poly(ethylenealkaryloxyalkylene terephthalate); phenol-formaldehyde resins; ketone resins; polyamides; polycarbonates; polythiocarbonates; poly(ethyleneglycol-co-bishydroxyethoxy phenyl propane terephthalate); nuclear substituted vinyl haloarylates such as poly(vinyl meta-bromobenzoate-co-vinyl acetate; etc. Methods of making resins of this type have been described in the prior art, for example, styrene-alkyd resins can be prepared according to the method described in U.S. Pat. Nos. 2,361,019 and 2,258,423. Suitable resins of the type contemplated for use in the photoconductive layers of the invention are sold under such trade names as Vitel PE-lO l Cymac, Piccopale 100, Saran F-220 and Lexan 105. Other types of binders which can be used in the photoconductive layers of the invention include such materials as paraffin, mineral waxes, etc.

Solvents of choice for preparing coating compositions of the present invention can include a number of solvents such as benzene, toluene, acetone, 2-butanone, chlorinated hydrocarbons, e.g., methylene chloride, ethylene chloride, etc., ethers, e.g., tetrahydrofuran, or mixtures of these solvents, etc.

In preparing the coating composition useful results are obtained where the photoconductor substance is present in an amount equal to at least about 1 weight percent ofthe coating composition. The upper limit in the amount of photoconductor substance present can be widely varied in accordance with usual practice. In those cases where a binder is employed, it is normally required that the photoconductor substance be present in an amount from about 1 weight percent ofthe coating composition to about 99 weight percent of the coating composition. A preferred weight range for the photoconductor substance in the coating composition is from about 10 weight percent to about 60 weight percent.

Coating thicknesses of the photoconductive composition on a support can vary widely. Normally, a coating in the range of about 0.001 inch to about 0.01 inch before drying is useful for the practice of this invention. The preferred range of coating thicknesses was found to be in the range from about 0.002 inch to about 0.006 inch before drying although useful results can be obtained outside of this range.

Suitable supporting materials for coating the photoconductive layers of the present invention can include any of a wide variety of electrically conducting supports, for example, paper (at a relative humidity above 20 percent); aluminum-paper laminates; metal foils such as aluminum foil, zinc foil, etc.; metal plates, such as aluminum, copper, zinc, brass, and galvanized plates; vapor deposited metal layers such as silver, nickel, or aluminum and the like. Metal (e.g., nickel, etc.) conducting layers deposited by high vacuum deposition techniques can be coated at low coverages so as to be substantially transparent to facilitate image exposure through the support. An especially useful conducting support can be prepared by coating a support material such as polyethylene terephthalate with a layer containing a semiconductor dispersed in a resin. Suitable conducting layers both with and without insulating barrier layers are described in U.S. Pat. No. 3,245,833. Other suitable conducting layers are described in U.S. Pat. No. 3,120,028. Likewise, a suitable conducting coating can be prepared from the sodium salt of a carboxyester lactone of maleic anhydride and a vinyl acetate polymer. Such kinds of conducting layers and methods for their optimum preparation and use are disclosed in U.S. Pat. Nos. 3,007,901 and 3,267,807.

The elements of the present invention can be employed in any of the well-known electrophotographic processes which require photoconductive layers. One such process is the aforementioned xerographic process. As previously explained, in a process of this type the electrophotographic element is given a blanket electrostatic charge by placing the same under a corona discharge which serves to give a uniformchargeto the surface of the photoconductive layer. This charge is retained by the layer owing to the substantial insulating property of the layer, i.e., the low conductivity of the layer in the dark. The electrostatic charge formed on the surface of the photoconducting layer is then selectively dissipated from the surface of the layer by exposure to light through an image-bearing transparency by a conventional exposure operation such as, for example, by contact-printing technique, or by lens projection of an image, etc., to form a latent image in the photoconducting layer. By exposure of the surface in this manner, a charge pattern is created by virtue of the fact that light causes the charge to be conducted away in proportion to the intensity of the illumination in a particular area. The'charge pattern remaining after exposure is then developed, i.e., rendered visible, by treatment with a medium comprising electrostatically attractable particles having optical density. The developing electrostatically attractable particles can be in the form of a dust, e.g., powder, pigment in a resinous carrier, i.e., toner, or a liquid developer may be used in which the developing particles are carried in an electrically insulating liquid carrier. Methods of development of this type are widely known and have been described in the patent literature in such patents, for example, as U.S. Pat. No. 2,297,691 and in Australian Pat. No. 212,315. In processes of electrophotographic reproduction such as in xerography, by selecting a developing particle which has as one of its components, a low-melting resin, it is possible to treat the developed photoconductive material with heat to cause the powder to adhere permanently to the surface of the photoconductive layer. in other cases, a transfer of the image formed on the photoconductive layer can be made to a second support, which would then become the final print. Techniques of the type indicated are well known in'the art and have been described in a number of U.S. and foreign patents,

such as U.S. Pat. Nos. 2,297,691 and 2,551,582, and in RCA Review," vol. (1954), page 469-484. j

The present invention is not limited to any particular mode of use of the new electrophotographic materials, and the expo sure technique, the charging method, the transfer (if any), the

developing method, and the fixing method as well as the materials used in these methods can be selected and adapted to the requirements of any particular technique.

Electrophotographic materials according to the present invention can be applied to reproduction techniques wherein different kinds of radiations, i.e., electromagnetic radiations as well as nuclear radiations, can be used. For this reason, it is pointed out herein that although materials according to the invention are mainly intended for use in connection with methods comprising an exposure, the term electrophotography wherever appearing in the description and the claims, is to be interpreted broadly and understood to comprise both xerography and xeroradiography.

The following examples are included for a further understanding of the invention.

EXAMPLE 1 Organic photoconductor 0.

5 g. Polymeric binder 1.5 g. Sensitizer 0.02 g. Methylene chloride 1 1.7 ml.

The resulting compositions are handcoated at a wet thickness of 0.004 inch on a conducting layer comprising the sodium salt ofa carboxyester lactone, such as described in U.S. Pat. No. 3,120,028 which in turn is coated on a cellulose acetate film base. The coating blocks are maintained at a temperature of F. These electrophotographic elements are charged under a positive or negative corona source until the surface potentials, as measured by an electrometer probe, reach between about 500 and 600 volts. They are then subjected to exposure from behind a stepped density gray scale to a 3,000 K. tungsten source. The exposure causes reduction of the surface potentials of the elements under each step of the gray scale from their initial potential V,,, to some lower potential V, whose exact value depends on the actual amount of exposure in metencandle-seconds received by the areas. The results of the measurements are plotted on a graph of surface potential V vs. log exposure for each step. The speed is the numerical expression of 10* multiplied by the reciprocal of the exposure in meter-candle-seconds required to reduce the 500 to 600 volt charged surface potentials to l00 volts above 0 volts. The

reduction of the surface potential to volts or below is significant in that it represents a requirement for suitable broad area development of a latent image. This speed at 100 volts is a measure of the ability to produce and henceforth to develop or otherwise utilize the latent image, higher speeds requiring less illumination to produce a latent image. When the photoconductor is absent from the coating, the surface potential does not drop to-or below 100 volts and no speed value can be assigned. This is also the case when a compound is present in the composition but is ineffective as a photoconductor. The sensitizers used are referred to below as follows:

A no sensitizer added C 2,4,7-trinitrofluorenone D crystal violet E rhodamine B F 2,4-bis(4-ethyoxyphenyl)-6-(4-n-amyloxystyryl)-pyrylium fluoborate 2,6-bis(4-ethyoxyphenyl)-4-(4-n-amyloxyphenyl)- thiapyrylium perchlorate The data in the following Table 11 represents the positive speeds at 100 volts of various compositions prepared as described above containing some of the organic photoconductors set forth in Table l. Included for comparison purposes is triphenylamine which has no active hydrogen-containing group. In each case it is noted that the photoconductive compounds of this invention show substantial improvements in speed compared to'triphenylamine. The binder employed is poly(vinyl meta-bromobenzoate-co-vinyl acetate).

TABLE ll Speed at I Volts for Sensitizer Photoconductor F H V 160 200 \'ll 200 130 ix 200 120 Triphenylamine I23 103 EXAMPLE 2 Example 1 is repeated except the photoconductive coating has the following composition:

Organic photoconductor:

p-diphenylaminobenzoic acid Binder poly(vinyl meta-bromobenzoateco-vinyl-acetate) acetate) l Sensitizer F 0. Methylene chloride 1 The 100 volt positive speed is 250. When the organic photoconductor is replaced by triphenylamine, the 100 volt positive speed is 71.

EXAMPLE 3 In order to show the ineffectiveness of sensitizing compounds other than the pyrylium, thiapyrylium and selenapyrylium salts, Example 1 is repeated using the following composition:

Photoconductor:

p-diphenylaminobenzoic acid 0.15 g. Binder:

Vitel 101* 0.50 g. Sensitizer (see Table III) 0.002 g. Dichloromethane 5.0 ml.

' A polyester of tcrephthalic acid and a mixture of ethylene glycol (1 part by weight) and 2,2-bisl4-( B-hydroxyethoxy)phenyl] propane (9 parts by weight).

The lOO volt positive speeds are set forth in Table II]. It is apparent that while some of these sensitizers impart light sensitivity to the organic photoconductor, the speed is so trivial as to have no practical effect.

TABLE III Sensitizer 100 Volt Positive Speed A C 5 D 0 E 8 EXAMPLE 4 Coating dopes prepared in the manner set forth in Example 1 containing the compounds in Table l are coated in the manner described in Example 1. In a darkened room, the surface of each of the photoconductive layers so prepared is charged to a potential of about +600 volts under a corona charger. The layer is then covered with a transparent sheet bearing a pattern of opaque and light transmitting areas and exposed to the radiation from an incandescent lamp with an illumination intensity of about 75 meter-candles for 12 seconds. The resulting electrostatic latent image is developed by conventional electrophotographic liquid developers (e.g., US. Pat. No. 2,907,674) and also by cascading over the surface of the layer a mixture of negatively charged black thermoplastic toner particles and glass beads. A good reproduction of the pattern results in each instance,

The invention has been described in detail with particular reference to preferred embodiments thereof, but it will be understood that variations and modifications can be effected within the spirit and scope of the invention as described hereinbefore and as defined in the appended claims.

We claim:

' 1. An electrophotographic element comprising an electrically conductive support having coated thereon a photoconductive composition comprising an electrically insulating polymeric binder, a photoconductor and a sensitizing amount of a pyrylium salt, said photoconductor having the structure:

wherein:

a. Ar, and Ar are phenyl radicals; b. Ar is an arylene radical selected from the group consisting of: l. a phenylene radical and 2. a naphthylene radical; and X is an active hydrogen-containing group selected from the group consisting of:

. a carboxy radical, an ester radical, a hydroxy radical, an alkylene hydroxy radical, an acid anhydride radical, an alkylene carboxy radical, and an acyl halide radical.

2. A photoconductive element as described in claim 1 wherein said pyrylium salt is present in an amount from about 0.005 to 5.0 percent by weight based on said photoconductive composition and said active hydrogen-containing group is a carboxy radical.

3. A photoconductive element as described in claim 1 wherein said pyrylium salt is present in an amount from about 0.005 to 5.0 percent by weight based on said photoconductive composition and said active hydrogen-containing group is an alkylene carboxy radical.

4. A photoconductive element as described in claim 1 wherein said pyrylium salt is present in an amount from about 0.005 to 5.0 percent by weight based on said photoconductive composition and said active hydrogen-containing group is an acyl halide radical.

5. A photoconductive element as described in claim I wherein said pyrylium salt is present in an amount from about 0.005 to 5.0 percent by weight based on said photoconductive composition and said active hydrogen-containing group is an ester radical.

6. An electrophotographic element comprising a conducting support having coated thereon a photoconductive composition comprising a sensitizer which is a pyrylium salt, a polymeric binder and a photoconductor selected from the group consisting of:

methyl p-diphenylaminobenzoate,

N,N-diphenylanthranilic acid,

ethyl 2,6-diphenyl-4-(p-diphenylaminophenyl)benzoate,

l-(p-diphenylaminophenyl)- l -hydroxy-3-butyne,

4-hydroxymethyltriphenylamine,

l -(p-dipheny1aminophenyl)ethanol,

3-p-diphenylaminophenylpropionic acid,

3-p-diphenylaminophenyll -propanol, 4-hydroxytriphenylamine,

2-hydroxytriphenylamine,

l-(p-diphenylaminophenyl)hexanol,

l-(p-diphenylaminophenyl)dodeconal, p-diphenylaminobenzoic acid anhydride, p-diphenylaminobenzoic acid N,N-diphenylamide, and p-diphenylaminobenzoic acid.

7. A photoconductive element for use in electrophotography comprising a conducting support having coated thereon a photoconductive composition comprising:

a. about 10 to 60 percent, by weight, based on said photoconductive composition of methyl p-diphenylaminobenzoate,

b. about 0.005 to 5.0 percent, by weight, based on said photoconductive composition of a pyrylium salt as a sensitizer, and

c. a film-forming polymeric binder for said photoconductor.

8. A photoconductive element for use in electrophotography comprising a conducting support having coated thereon a photoconductive composition comprising:

a. about 10 to 60 percent by weight based on said photoconductive composition of ethyl 2,6-diphenyl-4-(p-diphenylaminophenyl)benzoate,

b. about 0.005 to 5.0 percent by weight based on said photoconductive composition of a pyrylium salt as a sensitizer and c. a film-forming polymeric binder for said photoconductor.

9. A photoconductive element for use in electrophotography comprising a conducting support having coated thereon a photoconductive composition comprising:

a. about 10 to 60 percent by weight based on said photoconductive composition of l-(p-diphenylamino-phenyl)-lhydroxy-B-butyne,

b. about 0.005 to 5.0 percent by weight based on said photoconductive composition of a pyrylium salt at a sensitizer and c. a film-forming polymeric binder for said photoconductor.

10. A photoconductive element for use in electrophotography comprising a conducting support having coated thereon a photoconductive composition comprising:

a. about 10 to 60 percent by weight based on said photoconductive composition of 4-hydroxymethyltriphenylamine,

b. about 0.005 to 5.0 percent by weight based on said photoconductive composition of a pyrylium salt as a sensitizer and i c. a film-forming polymeric binder for said photoconductor.

11. A photoconductive element for use in electrophotography comprising a conducting support having coated thereon a photoconductive composition comprising:

a. about 10 to 60 percent by weight based on said photoconductive composition of 1-(p-diphenylaminophenyl) ethanol,

b. about 0.005 to 5.0 percent by weight based on said photoconductive composition of a pyrylium salt as a sensitizer and a film-forming polymeric binder for said photoconductor.

12. A photoconductive element for use in electrophotography comprising a conducting support having coated thereon a photoconductive composition comprising:

a. about 10 to 60 percent by weight based on said photoconductive composition of p-diphenylaminobenzoic acid,

b. about 0.005 to 5.0'percent by weight based on said photoconductive composition of a pyrylium salt as a sensitizer and I c. a film-forming polymeric binder for said photoconductor.

13. The photoconductive element of claim 7 wherein the film-forming polymeric binder is poly(vinyl metabromobenzoate-co-vinyl acetate).

14. The photoconductive element of claim 8 wherein the film-forming polymeric binder is poly( vinyl metabromobenzoate-co-vinyl acetate).

15. The photoconductive element of claim 9 wherein the film-forming polymeric binder is poly(vinyl metabromobenzoate-co-vinyl acetate).

16. The photoconductive element of claim 10 wherein the film-forming polymeric binder is poly(vinyl metaboromobenzoate-co-vinyl acetate).

17. The photoconductive element of claim 11 wherein the film-forming polymeric binder is poly(vinyl metabromobenzoate-co-vinyl acetate).

18. The photoconductive element of claim 12 wherein the film-forming polymeric binder is poly(vinyl metabromobenzoate-co-vinyl acetate).

Patent Citations
Cited PatentFiling datePublication dateApplicantTitle
US3141770 *Dec 29, 1961Jul 21, 1964Eastman Kodak CoElectrophotographic layers and sensitizers for same
US3180730 *Apr 7, 1960Apr 27, 1965Azoplate CorpMaterial for electrophotographic purposes
US3274000 *Jan 19, 1965Sep 20, 1966Gevaert Photo Prod NvElectrophotographic material and method
Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US4105447 *Jul 14, 1975Aug 8, 1978Eastman Kodak CompanyPhotoconductive insulating compositions including polyaryl hydrocarbon photoconductors
US4218247 *Aug 14, 1978Aug 19, 1980Teijin LimitedPhotoconductive resin containing tertiary amino groups for electrophotography
US4402573 *Jun 18, 1981Sep 6, 1983International Business Machines CorporationMaterials for electrochromic display devices
US4801517 *Jun 10, 1987Jan 31, 1989Xerox CorporationPolyarylamine compounds and systems utilizing polyarylamine compounds
US4818650 *Jun 10, 1987Apr 4, 1989Xerox CorporationArylamine containing polyhydroxy ether resins and system utilizing arylamine containing polyhydroxyl ether resins
US4871634 *May 24, 1988Oct 3, 1989Xerox CorporationElectrophotographic elements using hydroxy functionalized arylamine compounds
US4937165 *Apr 3, 1989Jun 26, 1990Xerox CorporationPhotoconductive imaging members with N,N-bis(biarylyl)aniline charge transport polymers
US4959288 *Apr 3, 1989Sep 25, 1990Xerox CorporationPhotoconductive imaging members with diaryl biarylylamine copolymer charge transport layers
US5028687 *Jul 12, 1990Jul 2, 1991Xerox CorporationFrom hydroxy arylamines and bis-chloroformates, improved charge transport layer for electrographic use
US5061569 *Jul 26, 1990Oct 29, 1991Eastman Kodak CompanySuperior stability
US5108859 *Apr 16, 1990Apr 28, 1992Eastman Kodak CompanyPhotoelectrographic elements and imaging method
US5409783 *Feb 24, 1994Apr 25, 1995Eastman Kodak CompanyRed-emitting organic electroluminescent device
US5443922 *Oct 28, 1992Aug 22, 1995Konica CorporationOrganic thin film electroluminescence element
US5468583 *Dec 28, 1994Nov 21, 1995Eastman Kodak CompanyPhotoconductor element
US5484922 *Feb 14, 1994Jan 16, 1996Eastman Kodak CompanyInternal junction organic electroluminescent device with a novel composition
US5500568 *Jul 22, 1993Mar 19, 1996Idemitsu Kosan Co., Ltd.Electroluminescence device
US5552678 *Sep 23, 1994Sep 3, 1996Eastman Kodak CompanyIn an organic light emitting device
US5554450 *Mar 8, 1995Sep 10, 1996Eastman Kodak CompanyOrganic electroluminescent devices with high thermal stability
US5585483 *Oct 20, 1995Dec 17, 1996Fuji Electric., Ltd.Metal-free phythalocyanine, process for preparing the same, and electrophotographic photoconductor using the same
US5591555 *Jan 10, 1995Jan 7, 1997Fuji Electric Co., Ltd.Electrophotographic photoconductor including a metal-free phthalocyanine
US5780194 *Apr 9, 1996Jul 14, 1998Mita Industrial Co., Ltd.Electrophotosensitive material
US5824800 *Jun 21, 1996Oct 20, 1998Fuji Electric Co., Ltd.Heating phthalonitrile, alkali metal or alkali metal compound, hydrogen donor compound in organic solvent, then dealkalizing; used as charge-generating substance to produce an electrophotographic photoconductor
US5834100 *Jun 25, 1996Nov 10, 1998Northwestern UniversityOrganic light-emitting dioddes and methods for assembly and emission control
US5935721 *Mar 20, 1998Aug 10, 1999Eastman Kodak CompanyOrganic electroluminescent elements for stable electroluminescent
US5972247 *Mar 20, 1998Oct 26, 1999Eastman Kodak CompanyOrganic electroluminescent elements for stable blue electroluminescent devices
US6020078 *Dec 18, 1998Feb 1, 2000Eastman Kodak CompanyGreen organic electroluminescent devices
US6127004 *Jan 29, 1999Oct 3, 2000Eastman Kodak CompanyProviding substrate having top surface coating with material including anode having indium-tin-oxide; forming amorphous conductive layer over anode by applying radio frequency field across fluorocarbon gas to deposit fluorocarbon polymer layer
US6187493Feb 10, 1998Feb 13, 2001Kyocera Mita CorporationElectrophotosensitive material
US6208077Nov 5, 1998Mar 27, 2001Eastman Kodak CompanyOrganic electroluminescent device with a non-conductive fluorocarbon polymer layer
US6399221Nov 6, 1998Jun 4, 2002Northwestern UniversityOrganic light-emitting diodes and methods for assembly and emission control
US6428912Sep 30, 1998Aug 6, 2002Agere Systems Guardian Corp.Electron transport material and light emitting diode that contains the electron transport material
US6444333 *Oct 12, 1999Sep 3, 2002Fuji Photo Film Co., Ltd.Organic luminescent device material, organic luminescent device using the same, and tetraarylmethane compound
US6610455Jan 30, 2002Aug 26, 2003Eastman Kodak CompanyFocusing and scanning a laser beam on the radiation-absorbing layer
US6765349 *Sep 30, 2002Jul 20, 2004Eastman Kodak CompanyHigh work function metal alloy cathode used in organic electroluminescent devices
US6770502 *Apr 4, 2002Aug 3, 2004Eastman Kodak CompanyMethod of manufacturing a top-emitting OLED display device with desiccant structures
US6835953Apr 8, 2003Dec 28, 2004Eastman Kodak CompanyDesiccant structures for OLED displays
US6872472Feb 15, 2002Mar 29, 2005Eastman Kodak CompanyProviding an organic electroluminescent device having stacked electroluminescent units
US6890627Aug 2, 2002May 10, 2005Eastman Kodak CompanyLaser thermal transfer from a donor element containing a hole-transporting layer
US6939625Mar 15, 2002Sep 6, 2005N˘rthwestern UniversityOrganic light-emitting diodes and methods for assembly and enhanced charge injection
US6939660Aug 2, 2002Sep 6, 2005Eastman Kodak CompanyLaser thermal transfer donor including a separate dopant layer
US7094121Jul 1, 2003Aug 22, 2006Northwestern UniversityOrganic light-emitting diodes and methods for assembly and emission control
US7221332Dec 19, 2003May 22, 2007Eastman Kodak Company3D stereo OLED display
US7390601Jun 16, 2005Jun 24, 2008Xerox CorporationTetrapolymers, terpolymers or copolymers of 2-hydroxypropyl acrylate, maleic acid, vinyl acetate, vinyl chloride, vinyl butyral, and cyanoethyl vinyl alcohol chemically bound to the charge transfer compound, preferably N,N'-diphenyl-N,N-bis(3-methyl phenyl)-1,1'-biphenyl-4,4'-diamine
US7414188 *Jan 24, 2003Aug 19, 2008Konarka Technologies, Inc.Increase efficiency of photovoltaic cells by improving charge transfer efficiency and reducing back transfer of electrons from interconnected semiconductor oxide nanoparticle material to sensitizing dye
US7449268May 27, 2005Nov 11, 2008Xerox CorporationPolycarbonates, polyesters and polyimides from the dimers exhibit properties of both binders and an electron-transporting materials; electrographic and photoconductor elements
US7544450Mar 19, 2008Jun 9, 2009Xerox CorporationFor use in active layer of an imaging member and exhibit properties of binder and electron-transporting material; photoconductivity; electrophotography; xerography
US7820780Jun 5, 2009Oct 26, 2010Xerox Corporationas monomer for polycarbonates, polyesters, polyethers and polyimides, exhibit properties of both binders and an electron-transporting materials; electrographic and photoconductor elements
US7911133May 10, 2007Mar 22, 2011Global Oled Technology LlcElectroluminescent device having improved light output
US7931975Nov 7, 2008Apr 26, 2011Global Oled Technology LlcElectroluminescent device containing a flouranthene compound
US7947974Mar 25, 2008May 24, 2011Global Oled Technology LlcOLED device with hole-transport and electron-transport materials
US7968215Dec 9, 2008Jun 28, 2011Global Oled Technology LlcOLED device with cyclobutene electron injection materials
US7969088May 4, 2009Jun 28, 2011Northwestern UniversityMethod of using silicon molecular components for controlling charge migration and light emission of organic light-emitting diodes
US7990058May 13, 2010Aug 2, 2011Global Oled Technology LlcTop-emitting OLED device with light-scattering layer and color-conversion
US8016631Nov 16, 2007Sep 13, 2011Global Oled Technology LlcDesiccant sealing arrangement for OLED devices
US8034465Jun 20, 2007Oct 11, 2011Global Oled Technology LlcPhosphorescent oled having double exciton-blocking layers
US8053094Jul 2, 2009Nov 8, 2011Northwestern UniversityOrganic light-emitting diodes and methods for assembly and enhanced charge injection
US8057916Apr 20, 2005Nov 15, 2011Global Oled Technology, Llc.OLED device with improved performance
US8076009Oct 26, 2007Dec 13, 2011Global Oled Technology, Llc.OLED device with fluoranthene electron transport materials
US8088500Nov 12, 2008Jan 3, 2012Global Oled Technology LlcOLED device with fluoranthene electron injection materials
US8102114Feb 27, 2009Jan 24, 2012Global Oled Technology, Llc.Method of manufacturing an inverted bottom-emitting OLED device
US8129039Oct 26, 2007Mar 6, 2012Global Oled Technology, LlcPhosphorescent OLED device with certain fluoranthene host
US8147989Feb 27, 2009Apr 3, 2012Global Oled Technology LlcOLED device with stabilized green light-emitting layer
US8202674Oct 11, 2010Jun 19, 2012Xerox CorporationPolymers of napthalene tetracarboxylic diimide dimers
US8206842Apr 6, 2009Jun 26, 2012Global Oled Technology LlcOrganic element for electroluminescent devices
US8216697Feb 13, 2009Jul 10, 2012Global Oled Technology LlcOLED with fluoranthene-macrocyclic materials
US8247088Aug 28, 2008Aug 21, 2012Global Oled Technology LlcEmitting complex for electroluminescent devices
US8253126Oct 31, 2006Aug 28, 2012Lg Chem. Ltd.Organic electronic device
US8258693Jun 22, 2011Sep 4, 2012Global Oled Technology LlcTop-emitting OLED device with integrated light-scattering and color-conversion layer
US8268457Dec 5, 2008Sep 18, 2012Idemitsu Kosan Co., Ltd.Organic electroluminescent device and material for organic electroluminescent device
US8324800Jun 12, 2008Dec 4, 2012Global Oled Technology LlcPhosphorescent OLED device with mixed hosts
US8420229Oct 26, 2007Apr 16, 2013Global OLED Technologies LLCOLED device with certain fluoranthene light-emitting dopants
US8431242Oct 26, 2007Apr 30, 2013Global Oled Technology, Llc.OLED device with certain fluoranthene host
US8628862Sep 10, 2008Jan 14, 2014Basf SeElectroluminescent device
US8653279Apr 16, 2007Feb 18, 2014Samsung Sdi Co., Ltd.Dye for dye-sensitized solar cell, and solar cell prepared from same
US8680693Jan 17, 2007Mar 25, 2014Lg Chem. Ltd.OLED having stacked organic light-emitting units
DE102010006280A1Jan 30, 2010Aug 4, 2011Merck Patent GmbH, 64293Farbkonvertierung
DE102011117422A1Oct 28, 2011May 2, 2013Merck Patent GmbhHyperverzweigte Polymere, Verfahren zu deren Herstellung sowie deren Verwendung in elektronischen Vorrichtungen
EP0067942A1 *Apr 27, 1982Dec 29, 1982International Business Machines CorporationAn electrochromic display device
EP0295115A2 *Jun 10, 1988Dec 14, 1988Xerox CorporationArylamine compounds
EP0534510A1Aug 1, 1992Mar 31, 1993Eastman Kodak CompanyImproved blue emitting internal junction organic electroluminescent device
EP0616020A1Mar 14, 1990Sep 21, 1994Idemitsu Kosan Company LimitedAromatic dimethylidyne compounds and process for preparation thereof
EP0715216A1Nov 23, 1995Jun 5, 1996Fuji Electric Co., Ltd.Titanyloxyphthalocyanine crystals, methods for preparing the same, and electrophotographic photoreceptors using such crystals
EP0786925A2Jan 13, 1997Jul 30, 1997Eastman Kodak CompanyWhite light-emitting electroluminescent devices
EP2161272A1Sep 5, 2008Mar 10, 2010Basf SePhenanthrolines
EP2229039A1Jun 16, 2004Sep 15, 2010Idemitsu Kosan Co., Ltd.Organic electroluminescent device and display using same
EP2239352A2Sep 16, 2005Oct 13, 2010Global OLED Technology LLCDelivering particulate material to a vaporization zone
EP2262032A2Apr 4, 2000Dec 15, 2010Idemitsu Kosan Co., Ltd.Organic electroluminescence device and its manufacturing method
EP2270117A2Dec 22, 1999Jan 5, 2011Idemitsu Kosan Co., Ltd.Organic electroluminescence device
EP2276089A2Jul 13, 2005Jan 19, 2011Global OLED Technology LLCMethod for reducing moisture contamination in a top-emitting oled using a dessicant
EP2355198A1May 8, 2006Aug 10, 2011Global OLED Technology LLCOLED electron-injecting layer
EP2371810A1Dec 20, 2005Oct 5, 2011Idemitsu Kosan Co., Ltd.Aromatic amine derivative and organic electroluminescent device using same
EP2448374A2Nov 30, 2004May 2, 2012Idemitsu Kosan Co., Ltd.Asymmetric monoanthracene derivative, material for organic electroluminescent device and organic electroluminescent device utilizing the same
EP2498317A2Jul 23, 2008Sep 12, 2012Global OLED Technology LLCPreventing stress transfer in OLED display components
EP2518045A1Oct 26, 2007Oct 31, 2012Idemitsu Kosan Co., Ltd.Aromatic amine derivative and organic electroluminescent element using the same
EP2568515A1Oct 16, 2008Mar 13, 2013Global OLED Technology LLCOLED device with fluoranthene electron transport materials
EP2713415A1Dec 22, 2009Apr 2, 2014Idemitsu Kosan Co., LtdMaterial for organic electroluminescent element, and organic electroluminescent element
WO2000041443A1Dec 22, 1999Jul 13, 2000Idemitsu Kosan CoOrganic electroluminescence device
WO2006034028A2Sep 16, 2005Mar 30, 2006Eastman Kodak CoDelivering particulate material to a vaporization source
WO2006073054A1Dec 20, 2005Jul 13, 2006Idemitsu Kosan CoAromatic amine derivative and organic electroluminescent device using same
WO2007007553A1Jun 28, 2006Jan 18, 2007Idemitsu Kosan CoBiphenyl derivatives, organic electroluminescent materials, and organic electroluminescent devices made by using the same
WO2007017995A1Jun 30, 2006Feb 15, 2007Masakazu FunahashiAromatic amine derivative and organic electroluminescence device making use of the same
WO2007029410A1Jul 5, 2006Mar 15, 2007Idemitsu Kosan CoOrganic electroluminescent element using polyarylamine
WO2007032161A1Aug 8, 2006Mar 22, 2007Masakazu FunahashiAsymmetric fluorene derivative and organic electroluminescent element containing the same
WO2007032162A1Aug 8, 2006Mar 22, 2007Idemitsu Kosan CoPyrene derivative and organic electroluminescence device making use of the same
WO2007052759A1Nov 2, 2006May 10, 2007Arakane TakashiOrganic electroluminescent element
WO2007058044A1Oct 18, 2006May 24, 2007Idemitsu Kosan CoAromatic amine derivative and organic electroluminescent element employing the same
WO2007058127A1Nov 10, 2006May 24, 2007Idemitsu Kosan CoAromatic amine derivative and organic electroluminescent element using the same
WO2007058172A1Nov 14, 2006May 24, 2007Arai HiromasaOrganic electroluminescent device
WO2007060795A1Oct 17, 2006May 31, 2007Idemitsu Kosan CoAmine compound and organic electroluminescent element employing the same
WO2007061063A1Nov 24, 2006May 31, 2007Arakane TakashiOrganic electroluminescent device
WO2007063993A1Dec 1, 2006Jun 7, 2007Idemitsu Kosan CoNitrogenous heterocyclic derivative and organic electroluminescence device making use of the same
WO2007077766A1Dec 22, 2006Jul 12, 2007Chishio HosokawaMaterial for organic electroluminescent device and organic electroluminescent device
WO2007080704A1Nov 15, 2006Jul 19, 2007Idemitsu Kosan CoAromatic amine derivatives and organic electroluminescent devices made by using the same
WO2007097178A1Feb 2, 2007Aug 30, 2007Idemitsu Kosan CoMaterial for organic electroluminescent device, method for producing same and organic electroluminescent device
WO2007099983A1Feb 28, 2007Sep 7, 2007Takashi ArakaneOrganic electroluminescent device using fluoranthene derivative and indenoperylene derivative
WO2007100010A1Feb 28, 2007Sep 7, 2007Idemitsu Kosan CoOrganic electroluminescent device
WO2007102361A1Feb 28, 2007Sep 13, 2007Idemitsu Kosan CoAromatic amine derivative and organic electroluminescent device using same
WO2007105448A1Feb 22, 2007Sep 20, 2007Takashi ArakaneNaphthacene derivative and organic electroluminescent device using same
WO2007111262A1Mar 23, 2007Oct 4, 2007Idemitsu Kosan CoNitrogen-containing heterocyclic derivative and organic electroluminescent device using same
WO2007111263A1Mar 23, 2007Oct 4, 2007Takashi ArakaneNitrogen-containing heterocyclic derivative and organic electroluminescent device using same
WO2007114358A1Mar 30, 2007Oct 11, 2007Idemitsu Kosan CoBenzanthracene derivative and organic electroluminescent device using the same
WO2007116750A1Mar 27, 2007Oct 18, 2007Chishio HosokawaMaterial for organic electroluminescent device and organic electroluminescent device using the same
WO2007116828A1Mar 30, 2007Oct 18, 2007Idemitsu Kosan CoBisanthracene derivative and organic electroluminescent device using the same
WO2007125714A1Mar 28, 2007Nov 8, 2007Idemitsu Kosan CoAromatic amine derivative, and organic electroluminescence element using the same
WO2007132678A1May 2, 2007Nov 22, 2007Idemitsu Kosan CoOrganic electroluminescent device
WO2007132704A1May 9, 2007Nov 22, 2007Chishio HosokawaOrganic electroluminescence element
WO2007138906A1May 21, 2007Dec 6, 2007Idemitsu Kosan CoOrganic electroluminescent device and full color light-emitting device
WO2007148660A1Jun 19, 2007Dec 27, 2007Idemitsu Kosan CoOrganic electroluminescent device employing heterocycle-containing arylamine derivative
WO2008001551A1May 10, 2007Jan 3, 2008Idemitsu Kosan CoAromatic amine derivative, and organic electroluminescence device using the same
WO2008015949A1Jul 26, 2007Feb 7, 2008Hiromasa AraiOrganic electroluminescence device
WO2008023549A1Aug 1, 2007Feb 28, 2008Idemitsu Kosan CoAromatic amine derivatives and organic electroluminescent devices made by using the same
WO2008023623A1Aug 15, 2007Feb 28, 2008Idemitsu Kosan CoOrganic electroluminescent device
WO2008023759A1Aug 23, 2007Feb 28, 2008Idemitsu Kosan CoAromatic amine derivatives and organic electroluminescence devices using the same
WO2008056652A1Nov 6, 2007May 15, 2008Idemitsu Kosan CoOrganic el material-containing solution, method for synthesizing organic el material, compound synthesized by the synthesizing method, method for forming thin film of organic el material, thin film of organic el material, and organic el device
WO2008056722A1Nov 8, 2007May 15, 2008Idemitsu Kosan CoOrganic el material-containing solution, method for forming thin film of organic el material, thin film of organic el material, and organic el device
WO2008056723A1Nov 8, 2007May 15, 2008Chishio HosokawaOrganic el material-containing solution, method for forming thin film of organic el material, thin film of organic el material, and organic el device
WO2008059713A1Oct 30, 2007May 22, 2008Idemitsu Kosan CoFluoranthene compound, organic electroluminescent device using the fluoranthene compound, and organic electroluminescent material-containing solution
WO2008062636A1Oct 26, 2007May 29, 2008Idemitsu Kosan CoAromatic amine derivative and organic electroluminescent element using the same
WO2008081823A1Dec 26, 2007Jul 10, 2008Idemitsu Kosan CoSolution containing organic el material, method for synthesis of organic el material, compound synthesized by the synthesis method, method for formation of thin film of organic el material, thin film of organic el material, organic el element
WO2008102740A1Feb 19, 2008Aug 28, 2008Takashi ArakaneOrganic electroluminescent device
WO2008111554A1Mar 10, 2008Sep 18, 2008Chishio HosokawaOrganic el device and display
WO2008123178A1Mar 24, 2008Oct 16, 2008Idemitsu Kosan CoOrganic el device
WO2008126802A1Apr 4, 2008Oct 23, 2008Idemitsu Kosan CoOrganic electroluminescent element
WO2009011327A1Jul 14, 2008Jan 22, 2009Idemitsu Kosan CoOrganic electroluminescent device material and organic electroluminescent device
WO2009020095A1Aug 4, 2008Feb 12, 2009Idemitsu Kosan CoAromatic amine derivative and organic electroluminescent device using the same
WO2009066778A1Nov 21, 2008May 28, 2009Idemitsu Kosan CoOrganic el element and solution containing organic el material
WO2009069717A1Nov 27, 2008Jun 4, 2009Idemitsu Kosan CoAzaindenofluorenedione derivative, organic electroluminescent device material, and organic electroluminescent device
WO2009081857A1Dec 19, 2008Jul 2, 2009Idemitsu Kosan CoOrganic electroluminescent device
WO2009145016A1Apr 21, 2009Dec 3, 2009Idemitsu Kosan Co., Ltd.Aromatic amine derivative and organic electroluminescent device using the same
WO2010074087A1Dec 22, 2009Jul 1, 2010Idemitsu Kosan Co.,Ltd.Material for organic electroluminescent element, and organic electroluminescent element
WO2010074181A1Dec 24, 2009Jul 1, 2010Idemitsu Kosan Co.,Ltd.Organic electroluminescence element and compound
WO2010076878A1Dec 25, 2009Jul 8, 2010Idemitsu Kosan Co.,Ltd.Organic electroluminescent element material and organic electroluminescent element comprising same
WO2010114749A1Mar 24, 2010Oct 7, 2010Global Oled Technology LlcTandem white oled with efficient electron transfer
WO2010116970A1Apr 5, 2010Oct 14, 2010Idemitsu Kosan Co., Ltd.Organic electroluminescent element and material for organic electroluminescent element
WO2011032686A1Sep 15, 2010Mar 24, 2011Merck Patent GmbhFormulas for producing electronic devices
WO2011046182A1Oct 14, 2010Apr 21, 2011Idemitsu Kosan Co.,Ltd.Fluorene-containing aromatic compound, material for organic electroluminescent element, and organic electroluminescent element using same
WO2011091946A1Jan 3, 2011Aug 4, 2011Merck Patent GmbhOrganic electroluminescent device comprising an integrated layer for colour conversion
WO2011137922A1Nov 26, 2010Nov 10, 2011Merck Patent GmbhFormulations and electronic devices
WO2012014841A1Jul 25, 2011Feb 2, 2012Idemitsu Kosan Co.,Ltd.Organic electroluminescence element
WO2012084114A1Nov 24, 2011Jun 28, 2012Merck Patent GmbhOrganic electroluminescent device
WO2012157211A1May 9, 2012Nov 22, 2012Idemitsu Kosan Co.,Ltd.Organic el multi-color light-emitting device
WO2013035275A1Aug 29, 2012Mar 14, 2013Idemitsu Kosan Co.,Ltd.Nitrogen-containing heteroaromatic ring compound
WO2013046635A1Sep 25, 2012Apr 4, 2013Idemitsu Kosan Co.,Ltd.Material for organic electroluminescent element, and organic electroluminescent element produced using same
WO2013060411A1Oct 1, 2012May 2, 2013Merck Patent GmbhHyperbranched polymers, methods for producing same, and use of same in electronic devices
WO2013069242A1Nov 2, 2012May 16, 2013Idemitsu Kosan Co.,Ltd.Material for organic electroluminescent elements, and organic electroluminescent element using same
Classifications
U.S. Classification430/73, 430/83
International ClassificationG03G5/06
Cooperative ClassificationG03G5/0618
European ClassificationG03G5/06B7