Hydrazone-based charge transport compounds

Details Hydrazone-based charge transport compounds Hydrazone-based charge transport compounds

2003-03-06

2004-12-28

Chapman, Mark A. (Department: 1756)

Radiation imagery chemistry: process, composition, or product th

Electric or magnetic imagery, e.g., xerography,...

Radiation-sensitive composition or product

C430S058400, C430S058500, C548S416000

Reexamination Certificate

active

06835514

ABSTRACT:

FIELD OF THE INVENTION
This invention relates to organophotoreceptors suitable for use in electrophotography and, more specifically, to flexible organophotoreceptors having an improved charge transport compound comprising a hydrazone group.
BACKGROUND
In electrophotography, an organophotoreceptor in the form of a plate, disk, sheet, belt, drum or the like having an electrically insulating photoconductive element on an electrically conductive substrate is imaged by first uniformly electrostatically charging the surface of the photoconductive layer, and then exposing the charged surface to a pattern of light. The light exposure selectively dissipates the charge in the illuminated areas, thereby forming a pattern of charged and uncharged areas. A liquid or solid toner is then deposited in either the charged or uncharged areas depending on the properties of the toner to create a toner image on the surface of the photoconductive layer. The resulting toner image can be transferred to a suitable receiving surface such as paper. The imaging process can be repeated many times to complete a single image and/or to reproduce additional images.
Both single layer and multilayer photoconductive elements have been used. In single layer embodiments, a charge transport material and charge generating material are combined with a polymeric binder and then deposited on the electrically conductive substrate. In multilayer embodiments, the charge transport material and charge generating material are in the form of separate layers, each of which can optionally be combined with a polymeric binder, deposited on the electrically conductive substrate. Two arrangements are possible. In one arrangement (the “dual layer” arrangement), the charge generating layer is deposited on the electrically conductive substrate and the charge transport layer is deposited on top of the charge generating layer. In an alternate arrangement (the “inverted dual layer” arrangement), the order of the charge transport layer and charge generating layer is reversed.
In both the single and multilayer photoconductive elements, the purpose of the charge generating material is to generate charge carriers (i.e., holes and/or electrons) upon exposure to light. The purpose of the charge transport compound is to accept at least one type of these charge carriers, generally holes, and transport them through the charge transport layer in order to facilitate discharge of a surface charge on the photoconductive element.
SUMMARY OF THE INVENTION
In a first aspect, the invention features an organophotoreceptor that includes:
(a) a charge transport compound having the formula
where R
1
has a structure of:
in which Ar is selected form the group consisting of;
R
4
is a hydrogen or an aromatic group and R
2
and R
3
are, independently, an (N,N-disubstituted) arylamine group;
(b) a charge generating compound; and
(c) an electrically conductive substrate over which the charge transport compound and the charge generating compound are located.
In a second aspect, the invention features an electrophotographic imaging apparatus that includes (a) a plurality of support rollers; and (b) the above-described organophotoreceptor operably coupled to the support rollers with motion of the support rollers resulting in motion of the organophotoreceptor. The apparatus can further comprise a liquid or solid toner dispenser.
In a third aspect, the invention features an electrophotographic imaging process that includes (a) applying an electrical charge to a surface of the above-described organophotoreceptor; (b) imagewise exposing the surface of the organophotoreceptor to radiation to dissipate charge in selected areas and thereby form a pattern of charged and uncharged areas on the surface; (c) contacting the surface with a liquid or dry toner to create a toned image; and (d) transferring the toned image to a substrate.
In a fourth aspect, the invention features an improved charge transport compound having the formula
where R
1
has a structure of:
in which Ar is selected form the group consisting of;
R
4
is a hydrogen or an aromatic group and R
2
and R
3
are, independently, an (N,N-disubstituted) arylamine group.
In another aspect, the invention features a charge transport compound having the formula
where R
1
has a structure of
and R
2
is a julolidene group or a carbazole group. These charge transport compounds can further be used in the formation of organophotoreceptors as well as corresponding electrophotographic imaging apparatuses and electrophotographic imaging processes.
These photoreceptors can be used successfully with liquid toners to produce high quality images. The high quality of the images can be maintained after repeated cycling.
Other features and advantages of the invention will be apparent from the following description of the preferred embodiments thereof, and from the claims.


REFERENCES:
patent: 3932455 (1976-01-01), Bilofsky et al.
patent: 3943108 (1976-03-01), Teuscher
patent: 4072519 (1978-02-01), Pearson et al.
patent: 4297426 (1981-10-01), Sakai et al.
patent: 4322487 (1982-03-01), Merrill et al.
patent: 4426327 (1984-01-01), Hashimoto et al.
patent: 4476137 (1984-10-01), Haviv et al.
patent: 4786571 (1988-11-01), Ueda
patent: 4957838 (1990-09-01), Aruga et al.
patent: 5128227 (1992-07-01), Monbaliu et al.
patent: 5274116 (1993-12-01), Martin et al.
patent: 5932384 (1999-08-01), Mitsumori et al.
patent: 6001522 (1999-12-01), Woo et al.
patent: 6020096 (2000-02-01), Fuller et al.
patent: 6030734 (2000-02-01), Mitsumori
patent: 6066426 (2000-05-01), Mott et al.
patent: 6099996 (2000-08-01), Yanus et al.
patent: 6140004 (2000-10-01), Mott et al.
patent: 6214503 (2001-04-01), Gaidelis et al.
patent: 6340548 (2002-01-01), Jubran et al.
patent: 6670085 (2003-12-01), Jubran et al.
patent: 2002/0064397 (2002-05-01), Kellie et al.
patent: 2002/0122997 (2002-09-01), Lee et al.
patent: 1 202 120 (2002-05-01), None
patent: 1047525 (1966-11-01), None
Boyd et al., “The Dimerisation of 5-Methylene-2-1,3,4-oxadiazolines,” J. Chem. Soc., C, Organic 12, pp. 2314-2317, 1971.
Atherton et al., “Synthesis of 3(S)-Acylamino-1-[(Phenyl)(1H-Tetrazol-5-yl)Amino]-2-Azetidinones,” Tetrahedron, vol. 39, No. 15, pp. 2599-2608, 1983.
Murakami et al., “An Efficient Synthesis of 1,1-Disubstituted Hydrazines,” Chem. Pharm. Bull., 31(2), pp. 423-428, 1983.

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