Photoconductive imaging members with unsymmetrical squaraine compositions

Claim 2

A photoconductive imaging member comprised of a supporting substrate, a hole transport layer, and a photogenerating layer comprising the unsymmetrical squaraines of the formula ##STR3## wherein R 1 , R 2 and R 3 are independently selected from alkyl groups; X is hydrogen, hydroxy, alkyl, alkoxy, or halogen; n is a number of 1 to about 3; and m is a number of from 0 to about 2.

Claim 3

A photoconductive imaging member comprised of a supporting substrate, a hole transport layer, and a photogenerating layer comprising the squaraine selected from the group consisting of 4-dimethylaminophenyl-4'-methoxyphenyl squaraine; 2-hydroxy-4-dimethylaminophenyl-4'-methoxyphenyl squaraine; 2-methyl-4-dimethylaminophenyl-4'-methoxyphenyl squaraine; 2-fluoro-4-dimethylaminophenyl-4'-methoxyphenyl squaraine; 2-methoxy-4-dimethylaminophenyl-4'-methoxyphenyl squaraine; 4-benzylmethylaminophenyl-4'-methoxyphenyl squaraine; 4-dimethylaminophenyl-3',4'-dimethoxyphenyl squaraine; 2-hydroxy-4-dimethylaminophenyl-3',4'-dimethoxyphenyl squaraine; 2-methyl-4-dimethylaminophenyl-3',4'-dimethoxyphenyl squaraine; 2-fluoro-4-dimethylaminophenyl-3',4'-dimethoxyphenyl squaraine; 2-methoxy-4-dimethylaminophenyl-3',4'-dimethoxyphenyl squaraine; 4-dimethylaminophenyl-3',4',5'-trimethoxyphenyl squaraine; and 2-hydroxy-4-dimethylaminophenyl-3',4',5'-trimethoxyphenyl squaraine.

Claim 4

A photoconductive imaging member comprised of a supporting substrate, a hole transport layer, and a photogenerating layer comprising the squaraine selected from the group consisting of 4-dimethylaminophenyl-4'-methoxyphenyl squaraine; 2-hydroxy-4-dimethylaminophenyl-4'-methoxyphenyl squaraine; 2-methyl-4-dimethylaminophenyl-4'-methoxyphenyl squaraine; 2-fluoro-4-dimethylaminophenyl-4'-methoxyphenyl squaraine; 2-methoxy-4-dimethylaminophenyl-4'-methoxyphenyl squaraine; 4-benzylmethylaminophenyl-4'-methoxyphenyl squaraine; 4-dimethylaminophenyl-3',4'-dimethoxyphenyl squaraine; 2-hydroxy-4-dimethylaminophenyl-3',4'-dimethoxyphenyl squaraine; 2-methyl-4-dimethylaminophenyl-3',4'-dimethoxyphenyl squaraine; 2-fluoro-4-dimethylaminophenyl-3',4'-dimethoxyphenyl squaraine; 2-methoxy-4-dimethylaminophenyl-3',4'-dimethoxyphenyl squaraine; 4-dimethylaminophenyl-3',4',5'-trimethoxyphenyl squaraine; and 2-hydroxy-4-dimethylaminophenyl-3',4',5'-trimethoxyphenyl squaraine.

Claim 5

A photoconductive imaging member in accordance with claim 1 wherein the photogenerating layer is situated between the supporting substrate and the hole transport layer.

Claim 6

A photoconductive imaging member in accordance with claim 1 wherein the hole transport layer is situated between the supporting substrate and the photogenerating layer.

Claim 7

A photoconductive imaging member in accordance with claim 1 wherein the photoconductive imaging member includes therein a metal oxide hole blocking layer situated between the supporting substrate and the photogenerating layer.

Claim 8

A photoconductive imaging member in accordance with claim 5 wherein the metal oxide is aluminum oxide.

Claim 9

A photoconductive imaging member in accordance with claim 5 wherein the metal oxide hole blocking layer has a thickness of less than about 500 Angstroms.

Claim 10

A photoconductive imaging member in accordance with claim 1 wherein the photoconductive imaging member contains an adhesive interface layer situated between the supporting substrate and the metal oxide hole blocking layer.

Claim 11

A photoconductive imaging member in accordance with claim 8 wherein the adhesive interface layer comprises a polymeric material selected from the group consisting of polyester, polyvinylbutyral, and polyvinylpyrrolidone.

Claim 12

A photoconductive imaging member in accordance with claim 8 wherein the adhesive interface layer has a thickness of less than about 0.6 micron.

Claim 13

A photoconductive imaging member in accordance with claim 1 wherein the supporting substrate is a metal.

Claim 14

A photoconductive imaging member in accordance with claim 11 wherein the metal is aluminum, or titanium.

Claim 15

A photoconductive imaging member in accordance with claim 1 wherein the supporting substrate is an organic polymeric composition.

Claim 16

A photoconductive imaging member in accordance with claim 1 wherein the supporting substrate has a thickness of from about 3 to about 100 mils.

Claim 17

A photoconductive imaging member in accordance with claim 1 wherein the supporting substrate has a thickness of from about 3 to about 10 mils.

Claim 18

A photoconductive imaging member in accordance with claim 1 wherein the squaraine layer has a thickness of from about 0.05 to about 10 microns.

Claim 19

A photoconductive imaging member in accordance with claim 1 wherein the squaraine layer has a thickness of from about 0.1 to about 3 microns.

Claim 20

A photoconductive imaging member in accordance with claim 1 wherein the hole transport layer has a thickness of from about 5 to about 50 microns.

Claim 21

A photoconductive imaging member in accordance with claim 1 wherein the squaraine compound is dispersed in a resinous binder in an amount of from about 5 percent by weight to about 95 percent by weight.

Claim 22

A photoconductive imaging member in accordance with claim 19 wherein the resinous binder is a polyester, polyvinyl butyral, a polycarbonate, or polyvinyl formal.

Claim 23

A photoconductive imaging member in accordance with claim 1 wherein the hole transport layer comprises an aryl amine compound.

Claim 24

A photoconductive imaging member in accordance with claim 21 wherein the aryl amine comprises molecules of the formula: ##STR4## dispersed in a highly insulating and transparent organic resinous binder wherein X is selected from the group consisting of alkyl and halogen.

Claim 25

A photoconductive imaging member in accordance with claim 22 wherein X is selected from the group consisting of ortho (CH 3 ), meta (CH 3 ), para (CH 3 ), ortho (Cl), meta (Cl), and para (Cl).

Claim 26

A photoconductive imaging member in accordance with claim 22 wherein the resinous binder is a polyester, polyvinyl butyral, a polycarbonate, or polyvinyl formal.

Claim 27

A photoconductive imaging member in accordance with claim 1 wherein the imaging member exhibits a dark development potential of from about -500 to about -1,000 volts.

Claim 28

A photoconductive imaging member in accordance with claim 1 wherein the imaging member exhibits a dark decay of from about -5 to about -50 volts per second.

Claim 29

A photoconductive imaging member in accordance with claim 1 wherein the imaging member exhibits a residual potential of from about 1 to about 50 volts.

Claim 30

A photoconductive imaging member in accordance with claim 11 wherein the imaging member exhibits a photosensitivity of from about 2 to about 12 ergs/cm 2 at 600 nanometers.

Claim 31

A method of imaging which comprises the steps of: (a) generating an electrostatic image on the photoconductive imaging member of claim 1; (b) subsequently developing the electrostatic image; (c) transferring the developed electrostatic image to a suitable substrate; and (d) permanently affixing the transferred image to the substrate.

Claim 32

A method of imaging in accordance with claim 29 wherein the electrostatic image is developed by cascade, touchdown, powder cloud, or magnetic brush methods.

Claim 33

A method of imaging in accordance with claim 29 wherein the developed electrostatic image is transferred to a substrate by means of a corotron or a biased roll.

Claim 34

A method of imaging in accordance with claim 29 wherein the substrate is paper.

Claim 35

A method of imaging in accordance with claim 29 wherein the substrate is a transparency.

Claim 36

A photoconductive imaging member comprised of the squaraine ##STR5## wherein R 1 , R 2 and R 3 are independently selected from alkyl groups; X is hydrogen, hydroxy, alkyl, alkoxy, or halogen; n is a number of 1 to about 3; and m is a number of from 0 to about 2, and a hole transport layer.

Claim 37

A photoconductive imaging member comprised of the squaraine ##STR5## wherein R 1 , R 2 and R 3 are independently selected from alkyl groups; X is hydrogen, hydroxy, alkyl, alkoxy, or halogen; n is a number of 1 to about 3; and m is a number of from 0 to about 2, and a hole transport layer.

Claim 38

A photoconductive imaging member in accordance with claim 34 wherein n is 1,2 or 3.

Claim 39

A photoconductive imaging member in accordance with claim 34 wherein X is methoxy.

Claim 40

A photoconductive imaging member in accordance with claim 1 wherein the squaraine is selected from the group consisting of 4-dimethylaminophenyl-4'-methoxyphenyl squaraine; 2-hydroxy-4-dimethylaminophenyl-4'-methoxyphenyl squaraine; 2-methyl-4-dimethylaminophenyl-4'-methoxyphenyl squaraine; 2-fluoro-4-dimethylaminophenyl-4'-methoxyphenyl squaraine; 2-methoxy-4-dimethylaminophenyl-4'-methoxyphenyl squaraine; 4-benzylmethylaminophenyl-4'-methoxyphenyl squaraine; 4-dimethylaminophenyl-3',4'-dimethoxyphenyl squaraine; 2-hydroxy-4-dimethylaminophenyl-b 3',4'-dimethoxyphenyl squaraine; 2-methyl-4-dimethylaminophenyl-3',4'-dimethoxyphenyl squaraine; 2-methyl-4-dimethylaminophenyl-3',4'-dimethoxyphenyl squaraine; 2-fluoro-4-dimethylaminophenyl-3',4'-dimethoxyphenyl squaraine; 2-methoxy-4-dimethylaminophenyl-3',4'-dimethoxyphenyl squaraine; 4-dimethylaminophenyl-3',4',5'-trimethoxyphenyl squaraine; and 2-hydroxy-4-dimethylaminophenyl-3',4',5'-trimethoxyphenylsquaraine.

Claim 41

A photoconductive imaging member in accordance with claim 34 wherein the squaraine is selected from the group consisting of 4-dimethylaminophenyl-4'-methoxyphenyl squaraine; 2-hydroxy-4-dimethylaminophenyl-4'-methoxyphenyl squaraine; 2-methyl-4-dimethylaminophenyl-4'-methoxyphenyl squaraine; 2-fluoro-4-dimethylaminophenyl-4'-methoxyphenyl squaraine; 2-methoxy-4-dimethylaminophenyl-4'-methoxyphenyl squaraine; 4-benzylmethylaminophenyl-4'-methoxyphenyl squaraine; 4-dimethylaminophenyl-3',4'-dimethoxyphenyl squaraine; 2-hydroxy-4-dimethylaminophenyl-3',4'-dimethoxyphenyl squaraine; 2-methyl-4-dimethylaminophenyl-3',4'-dimethoxyphenyl squaraine; 2-fluoro-4-dimethylaminophenyl-3',4'-dimethoxyphenyl squaraine; 2-methoxy-4-dimethylaminophenyl-3',4'-dimethoxyphenyl squaraine; 4-dimethylaminophenyl-3',4',5'-trimethoxyphenyl squaraine; and 2-hydroxy-4-dimethylaminophenyl-3',4',5'-trimethoxyphenylsquaraine.

Claim 42

A photoconductive imaging member in accordance with claim 34 wherein the hole transport layer comprises an aryl amine compound.

Claim 43

A photoconductive imaging member in accordance with claim 39 wherein the aryl amine comprises molecules of the formula ##STR6## dispersed in a highly insulating and transparent organic resinous binder wherein X is selected from the group consisting of alkyl and halogen.

Claim 44

A photoconductive imaging member in accordance with claim 40 wherein X is selected from the group consisting of ortho (CH 3 ), meta (CH 3 ), para (CH 3 ), ortho (Cl), and meta (Cl).

Claim 45

A photoconductive imaging member in accordance with claim 34 containing a supporting substrate.

Claim 46

A photoconductive imaging member in accordance with claim 42 wherein the photoconductive imaging member contains an adhesive interfacial layer situated between the supporting substrate and the squaraine layer.

Claim 47

A photoconductive imaging member in accordance with claim 42 wherein the imaging member contains a metal oxide hole blocking layer.

Claim 48

A photoconductive imaging member comprised of a hole transport layer, and a photogenerating layer comprising the unsymmetrical squaraines of the formula ##STR7## wherein R 1 , R 2 and R 3 are independently selected from alkyl groups; X is hydrogen, hydroxy, alkyl, alkoxy, or halogen; n is a number of 1 to about 3; and m is a number of from 0 to about 2.

Claim 49

A photoconductive imaging member comprised of a hole transport layer, and a photogenerating layer comprising the unsymmetrical squaraines of the formula ##STR7## wherein R 1 , R 2 and R 3 are independently selected from alkyl groups; X is hydrogen, hydroxy, alkyl, alkoxy, or halogen; n is a number of 1 to about 3; and m is a number of from 0 to about 2.