Photoconductive imaging members with unsymmetrical squaraine compounds containing an hydroxyl group

Claim 2

An improved photoresponsive imaging member comprised of (1) a supporting substrate, (2) a photoconductive layer comprised of the unsymmertical squaraine compounds selected from the group consisting of (4-dimethylaminophenyl) (4-dimethylamino-2-hydroxyphenyl) squaraine; (4-dimethylaminophenyl) (2,6-dihydroxy-4-dimethylaminophenyl) squaraine; (4-dimethylaminophenyl) (9-(8-hydroxyjulolidinyl) squaraine; (4-dimethylamino-2-methylphenyl) (4-dimethylamino-2-hydroxyphenyl) squaraine; (4-dimethylamino-2-methylphenyl) (2,6-dihydroxy-4-dimethylaminophenyl) squaraine; (4-dimethylamino-2-fluorophenyl) (4-methylamino-2-hydroxyphenyl) squaraine; (4-dimethylamino-2-fluorophenyl) (2,6-dihydroxy-4-dimethylaminophenyl) squaraine; and (2,6-dihydroxy-4-dimethylaminophenyl) (4-dimethylamino-2-hydroxyphenyl) squaraine; and (3) a hole transport layer comprised of aryl amine molecules dispersed in a resinous binder.

Claim 3

An improved photoresponsive imaging member in accordance with claim 1 wherein the supporting substrate is comprised of a conductive material, or an organic polymeric composition.

Claim 4

An improved photoresponsive imaging member in accordance with claim 1 wherein the unsymmetrical squaraine is (4-dimethylaminophenyl) (4-dimethylamino-2-hydroxyphenyl) squaraine.

Claim 5

An improved photoresponsive imaging member in accordance with claim 1 wherein the unsymmetrical squaraine is (4-dimethylaminophenyl) (9-(8-hydroxyjulolidinyl) squaraine.

Claim 6

An improved photoresponsive imaging member in accordance with claim 1 wherein the unsymmetrical squaraine is (4-dimethylamino-2-methylphenyl) (2,6-dihydroxy-4-dimethylaminophenyl) squaraine.

Claim 7

An improved photoresponsive imaging member in accordance with claim 1 wherein the unsymmetrical squaraine is (4-dimethylamino-2-fluorophenyl) (4-dimethylamino-2-hydroxyphenyl) squaraine.

Claim 8

An improved photoresponsive imaging member in accordance with claim 1 wherein the unsymmetrical squaraine is (4-dimethylamino-2-fluorophenyl) (2,6-dihydroxy-4-dimethylaminophenyl) squaraine.

Claim 9

An improved photoresponsive imaging member in accordance with claim 1 wherein the unsymmetrical squaraine is (2,6-dihydroxy-4-dimethylaminophenyl) (4-dimethylamino-2-hydroxyphenyl) squaraine.

Claim 10

An improved photoresponsive imaging member in accordance with claim 1 wherein the unsymmetrical squaraine is dispersed in a resinous binder in an amount of from about 5 to about 95 percent by volume, and the aryl hole transport molecules are dispersed in a resinous binder in an amount of from about 10 percent by weight to about 75 percent by weight.

Claim 11

An improved photoresponsive imaging member in accordance with claim 9 wherein the resinous binder for the squaraine compound is a polyester, polyvinylbutyral, polyvinylcarbazole, or a phenoxy resin; and the resinous binder for the aryl hole transport molecules is a polycarbonate, a polyester, or a vinyl polymer.

Claim 12

An improved photoresponsive imaging member in accordance with claim 1 wherein the aryl amine comprises molecules of the formula: ##STR11## wherein X is selected from the group consisting of alkyl and halogen.

Claim 13

An improved photoresponsive imaging member in accordance with claim 11 wherein X is ortho (CH 3 ), meta (CH 3 ), para (CH 3 ), ortho (Cl), meta (Cl), or para (Cl).

Claim 14

An improved photoresponsive imaging member in accordance with claim 11 wherein the aryl amine is N,N'-diphenyl-N,N'-bis(3-methylphenyl) [1,1-biphenyl]-4,4'-diamine.

Claim 15

An improved photoresponsive imaging member in accordance with claim 1 wherein the unsymmetrical squaraine photoconductive layer is situated between the supporting substrate, and the aryl amine hole transport layer.

Claim 16

An improved photoresponsive imaging member in accordance with claim 1 wherein the aryl amine hole transport layer is situated between the unsymmetrical squaraine photoconductive layer, and the supporting substrate.

Claim 17

An improved photoresponsive imaging member comprised of (1) a supporting substrate, (2) a hole blocking layer, (3) an inorganic photogenerating layer, (4) a photoconductive layer comprised of the unsymmetrical squaraine compounds selected from the group consisting of (4-dimethylaminophenyl) (4-dimethylamino-2-hydroxyphenyl) squaraine; (4-dimethylaminophenyl) (2,6-dihydroxy-4-dimethylaminophenyl) squaraine; (4-dimethylaminophenyl) (9-(8-hydroxyjulolidinyl) squaraine; (4-dimethylamino-2-methylphenyl) (4-dimethylamino-2-hydroxyphenyl) squaraine; (4-dimethylamino-2-methylphenyl) (2,6-dihydroxy-4-dimethylaminophenyl) squaraine; (4-dimethylamino-2-fluorophenyl) (4-methylamino-2-hydroxyphenyl) squaraine; (4-dimethylamino-2-fluorophenyl) (2,6-dihydroxy-4-dimethylaminophenyl) squaraine; and (2,6-dihydroxy-4-dimethylaminophenyl) (4-dimethylamino-2-hydroxyphenyl) squaraine; and (5) a hole transport layer comprised of aryl amine molecules dispersed in a resinous binder.

Claim 18

An improved photoresponsive imaging member comprised of (1) a supporting substrate, (2) a hole blocking layer, (3) an inorganic photogenerating layer, (4) a photoconductive layer comprised of the unsymmetrical squaraine compounds selected from the group consisting of (4-dimethylaminophenyl) (4-dimethylamino-2-hydroxyphenyl) squaraine; (4-dimethylaminophenyl) (2,6-dihydroxy-4-dimethylaminophenyl) squaraine; (4-dimethylaminophenyl) (9-(8-hydroxyjulolidinyl) squaraine; (4-dimethylamino-2-methylphenyl) (4-dimethylamino-2-hydroxyphenyl) squaraine; (4-dimethylamino-2-methylphenyl) (2,6-dihydroxy-4-dimethylaminophenyl) squaraine; (4-dimethylamino-2-fluorophenyl) (4-methylamino-2-hydroxyphenyl) squaraine; (4-dimethylamino-2-fluorophenyl) (2,6-dihydroxy-4-dimethylaminophenyl) squaraine; and (2,6-dihydroxy-4-dimethylaminophenyl) (4-dimethylamino-2-hydroxyphenyl) squaraine; and (5) a hole transport layer comprised of aryl amine molecules dispersed in a resinous binder.

Claim 19

An improved photoresponsive imaging member comprised of (1) a supporting substrate, (2) a hole blocking layer, (3) a photoconductive layer comprised of the unsymmetrical squaraine compounds selected from the group consisting of (4-dimethylaminophenyl) (4-dimethylamino-2-hydroxyphenyl) squaraine; (4-dimethylaminophenyl) (2,6-dihydroxy-4-dimethylaminophenyl) squaraine; (4-dimethylaminophenyl (9-(8-hydroxyjulolidinyl) squaraine; (4-dimethylamino-2-methylphenyl) (4-dimethylamino-2-hydroxyphenyl) squaraine; (4-dimethylamino-2-methylphenyl) (2,6-dihydroxy-4-dimethylaminophenyl) squaraine; (4-dimethylamino-2-fluorophenyl) (4-methylamino-2-hydroxyphenyl) squaraine; (4-dimethylamino-2-fluorophenyl) (2,6-dihydroxy-4-dimethylaminophenyl) squaraine; and (2,6-dihydroxy-4-dimethylaminophenyl) (4-dimethylamino-2-hydroxyphenyl) squaraine; (4) an inorganic photogenerating layer, and (5) a diamine hole transport layer comprised of aryl amine molecules dispersed in a resinous binder.

Claim 20

An improved photoresponsive imaging member comprised of (1) a supporting substrate, (2) a hole blocking layer, (3) a photoconductive layer comprised of the unsymmetrical squaraine compounds selected from the group consisting of (4-dimethylaminophenyl) (4-dimethylamino-2-hydroxyphenyl) squaraine; (4-dimethylaminophenyl) (2,6-dihydroxy-4-dimethylaminophenyl) squaraine; (4-dimethylaminophenyl (9-(8-hydroxyjulolidinyl) squaraine; (4-dimethylamino-2-methylphenyl) (4-dimethylamino-2-hydroxyphenyl) squaraine; (4-dimethylamino-2-methylphenyl) (2,6-dihydroxy-4-dimethylaminophenyl) squaraine; (4-dimethylamino-2-fluorophenyl) (4-methylamino-2-hydroxyphenyl) squaraine; (4-dimethylamino-2-fluorophenyl) (2,6-dihydroxy-4-dimethylaminophenyl) squaraine; and (2,6-dihydroxy-4-dimethylaminophenyl) (4-dimethylamino-2-hydroxyphenyl) squaraine; (4) an inorganic photogenerating layer, and (5) a diamine hole transport layer comprised of aryl amine molecules dispersed in a resinous binder.

Claim 21

An improved photoresponsive imaging member in accordance with claim 16 wherein the fluorinated squaraine compound is (4-dimethylaminophenyl) (4-dimethylamino-2-hydroxyphenyl) squaraine.

Claim 22

An improved photoresponsive imaging member in accordance with claim 16 wherein the unsymmetrical squaraine compound is (4-dimethylaminophenyl) (9-(8-hydroxyjulolidinyl) squaraine.

Claim 23

An improved photoresponsive imaging member in accordance with claim 16 wherein the unsymmetrical squaraine compound is (4-dimethylamino-2-methylphenyl) (2,6-dihydroxy-4-dimethylaminophenyl) squaraine.

Claim 24

An improved photoresponsive imaging member in accordance with claim 16 wherein the unsymmetrical squaraine compound is (4-dimethylamino-2-fluorophenyl) (4-dimethylamino-2-hydroxyphenyl) squaraine.

Claim 25

An improved photoresponsive imaging member in accordance with claim 16 wherein the unsymmetrical squaraine is (4-dimethylamino-2-fluorophenyl) (2,6-dihydroxy-4-dimethylaminophenyl) squaraine.

Claim 26

An improved photoresponsive imaging member in accordance with claim 16 wherein the unsymmetrical squaraine is (2,6-dihydroxy-4-dimethylaminophenyl) (4-dimethylamino-2-hydroxyphenyl) squaraine.

Claim 27

An improved photoresponsive imaging member in accordance with claim 16 wherein the supporting substrate is comprised of a conductive metallic substance, or an insulating polymeric composition.

Claim 28

An improved photoresponsive imaging member in accordance with claim 17 wherein the supporting substrate is comprised of a conductive metallic substance, or an insulating polymeric composition.

Claim 29

An improved photoresponsive imaging member in accordance with claim 16 wherein the aryl amine comprises molecules of the formula: ##STR12## wherein X is selected from the group consisting of ortho (CH 3 ), meta (CH 3 ), para (CH 3 ), ortho) (Cl), meta (Cl), or para (Cl).

Claim 30

An improved photoresponsive imaging member in accordance with claim 17 wherein the aryl amine comprises molecules of the formula: ##STR13## wherein X is selected from the group consisting of ortho (CH 3 ), meta (CH 3 ), para (CH 3 ), ortho (Cl), meta (Cl), or para (Cl).

Claim 31

An improved photoresponsive imaging member in accordance with claim 26 wherein the resinous binder for the aryl amine transport molecules is a polycarbonate, a polyester, or a vinyl polymer.

Claim 32

An improved photoresponsive imaging member in accordance with claim 27 wherein the resinous binder for the aryl amine transport molecules is a polycarbonate, a polyester, or a vinyl polymer.

Claim 33

An improved photoresponsive imaging member in accordance with claim 26 wherein the aryl amine is N,N'-diphenyl-N,N'-bis(3-methylphenyl)-[1,1-biphenyl]-4,4'-diamine.

Claim 34

An improved photoresponsive imaging member in accordance with claim 27 wherein the aryl amine is N,N'-diphenyl-N,N'-bis(3-methylphenyl)-[1,1-biphenyl]-4,4'-diamine.

Claim 35

An improved photoresponsive imaging member in accordance with claim 26 wherein the photogenerating layer is selected from the group consisting of selenium, halogen doped selenium, selenium alloys, halogen doped selenium alloys.

Claim 36

An improved photoresponsive imaging member in accordance with claim 27 wherein the photogenerating layer is selected from the group consisting of selenium, halogen doped selenium, selenium alloys, and halogen doped selenium alloys.

Claim 37

An improved photoresponsive imaging member in accordance with claim 32 wherein the selenium alloy is selected from the group consisting of selenium tellurium, selenium, arsenic, and selenium tellurium arsenic.

Claim 38

An improved photoresponsive imaging member in accordance with claim 33 wherein the selenium alloy is selected from the group consisting of selenium tellurium, selenium arsenic, and selenium tellurium arsenic.

Claim 39

An improved photoresponsive imaging member in accordance with claim 26 wherein the photogenerating layer is trigonal selenium.

Claim 40

An improved photoresponsive imaging member in accordance with claim 27 wherein the photogenerating layer is trigonal selenium.

Claim 41

An improved photoresponsive imaging member in accordance with claim 26 wherein the photogenerating layer is comprised of trigonal selenium doped with Na 2 SeO 3 and Na 2 CO 3 .

Claim 42

An improved photoresponsive imaging member in accordance with claim 26 wherein the photogenerating layer is comprised of trigonal selenium doped with Na 2 SeO 3 and Na 2 CO 3 .

Claim 43

An improved photoresponsive imaging member in accordance with claim 1 further including a hole blocking layer.

Claim 44

An improved photoresponsive imaging member in accordance with claim 40 wherein the hole blocking layer is comprised of a silane.

Claim 45

A method of imaging which comprises formulating an electrostatic image on the photoreceptor member of claim 1; affecting development thereof; and subsequently transfering the developed image to a suitable substrate.

Claim 46

A method of imaging which comprises formulating an electrostatic image on the photoreceptor of claim 16; affecting development thereof; and subsequently transfering the developed image to a suitable substrate.

Claim 47

A method of imaging which comprises formulating an electrostatic image on the photoreceptor of claim 17; affecting development thereof; and subsequently transfering the developed image to a suitable substrate.

Claim 48

A photoresponsive imaging member consisting essentially of (1) a supporting substrate; (2) a photoconductive layer containing an unsymmetrical squaraine compound selected from the group consisting of (4-dimethylaminophenyl) (4-dimethylamino-2-hydroxyphenyl) squaraine; (4-dimethylaminophenyl) (2,6-dihydroxy-4-dimethylaminophenyl) squaraine; (4-dimethylaminophenyl) (9-(8-hydroxyjulolidinyl) squaraine; (4-dimethylamino-2-methylphenyl) (4-dimethylamino-2-hydroxyphenyl) squaraine; (4-dimethylamino-2-methylphenyl) (2,6-dihydroxy-4-dimethylaminophenyl) squaraine; (4-dimethylamino-2-fluorophenyl) (4-methylamino-2-hydroxyphenyl) squaraine; (4-dimethylamino-2-fluorophenyl) (2,6-dihydroxy-4-dimethylaminophenyl) squaraine, and (2,6-dihydroxy-4-dimethylaminophenyl) (4-dimethylamino-2-hydroxyphenyl) squaraine; and (3) a hole transport layer comprised of aryl amine molecules dispersed in a resinous binder.

Claim 49

A photoresponsive imaging member consisting essentially of (1) a supporting substrate; (2) a photoconductive layer containing an unsymmetrical squaraine compound selected from the group consisting of (4-dimethylaminophenyl) (4-dimethylamino-2-hydroxyphenyl) squaraine; (4-dimethylaminophenyl) (2,6-dihydroxy-4-dimethylaminophenyl) squaraine; (4-dimethylaminophenyl) (9-(8-hydroxyjulolidinyl) squaraine; (4-dimethylamino-2-methylphenyl) (4-dimethylamino-2-hydroxyphenyl) squaraine; (4-dimethylamino-2-methylphenyl) (2,6-dihydroxy-4-dimethylaminophenyl) squaraine; (4-dimethylamino-2-fluorophenyl) (4-methylamino-2-hydroxyphenyl) squaraine; (4-dimethylamino-2-fluorophenyl) (2,6-dihydroxy-4-dimethylaminophenyl) squaraine, and (2,6-dihydroxy-4-dimethylaminophenyl) (4-dimethylamino-2-hydroxyphenyl) squaraine; and (3) a hole transport layer comprised of aryl amine molecules dispersed in a resinous binder.

Claim 50

An improved photoresponsive device in accordance with claim 16 further including an adhesive layer situated between the hole blocking layer and the inorganic photogenerating layer.

Claim 51

An improved photoresponsive device in accordance with claim 17 further including an adhesive layer situated between the hole blocking layer and the photogenerating layer.

Claim 52

An improved photoresponsive device in accordance with claim 24 further including a semiconductive material present on the surface of the substrate.

Claim 53

An improved photoresponsive imaging member in accordance with claim 25 further including a semiconductive material present on the substrate.