Organic photoconductors sensitized by free radical liberators and organometallic compounds

Claim 2

AN ELECTROPHOTOGRAPHIC PHOTOSENSITIVE MEMBER WHICH COMPRISES A SUPPORT HAVING A COATED THEREON A SENSITIZED LAYER OF PHOTOCONDUCTIVE PHOTOSENSITIVE MATERIAL, SAID MATERIAL COMPRISING AN ORGANIC PHOTOCONDUCTIVE MATERIAL, A FREE RADICAL FORMER CAPABLE OF PRODUCING FREE RADICALS FOR SENSITIZING SAID ORGANIC PHOTOCONDUCTIVE MATERIAL WHEN UNIFORMLY EXCITED BY RADIATION ENERGY AND AN ORGANOMETALLIC COMPOUND INCAPABLE OF LIBERATING FREE RADICALS UNDER THE EXPOSURE USED TO XCITE SAID FREE RADICAL FORMER, BUT CAPABLE OF CATALYZING THE SENSITIZING ABILITY OF THE RADICAL FORMER, SAID PHOTOCONDUCTIVE PHOTOSENSITIVE MATERIAL HAVING BEEN SENSITIZED BY APPLYING SAID RADIATION ENERGY UNIFORMLY TO AT LEAST SAID FREE RADICAL FORMER AND SAID ORGANOMETALLIC COMPOUND.

Claim 3

A photosensitive material according to claim 1 in which the organometallic compound is at least one member selected from the group consisting of alkyl metallic compounds, aryl metallic compounds, and alkylaryl metallic compounds of a metal element of Group IV B or Group V B of the Periodic Table.

Claim 4

A photosensitive material according to claim 2 in which the metal element of Group IV B is a member selected from the group consisting of Ge, Sn and Pb.

Claim 5

A photosensitive material according to claim 2 in which the metal element of Group V B is a member selected from the group consisting of P, As, Sb and Bi.

Claim 6

A photosensitive material according to claim 2 in which the aryl metallic compound is one of triphenyl metallic compound and tetraphenyl metallic compound.

Claim 7

A photosensitive material according to claim 1 in which the organometallic compound is a cyclopentadienyl metallic compound of at least one transition metal element selected from the group consisting of Group III A, IV A, V A, VI A, VII A and VIII A of the Periodic Table.

Claim 8

A photosensitive material according to claim 6 in which the transition metal element of Group III A of the Periodic Table is a member selected from the group consisting of Sc, Y, La, Ce, Pr, Nd, Sm, Gd, Dy, Er and Yb.

Claim 9

A photosensitive material according to claim 6 in which the transition metal element of Group IV A of the Periodic Table is a member selected from the group consisting of Ti, Zr and Hf.

Claim 10

A photosensitive material according to claim 6 in which the transition metal element of Group V A of the Periodic Table is a member selected from the group consisting of V, Nd and Ta.

Claim 11

A photosensitive material according to claim 6 in which the transition metal element of Group VI A is a member selected from the group consisting of Cr, Mo, W and U.

Claim 12

A photosensitive material according to claim 6 in which the transition metal element of Group VII A is a member selected from the group consisting of Mn, Tc and Re.

Claim 13

A photosensitive material according to claim 6 in which the transition metal element of Group VIII A is a member selected from the group consisting of Fe, Co, Ni and Ru.

Claim 14

A photosensitive material according to claim 1 in which the content of the organometallic compound is 10 3 - 10 percent by weight based on the organic photoconductive material.

Claim 15

A photosensitive material according to claim 1 in which the content of the free radical former is 1 - 30 percent by weight based on the organic photoconductive material.

Claim 16

A photosensitive material according to claim 1 in which a sensitizing material is incorporated in a mixture of a free radical former and an organic photoconductive material reactively treated by a radiation energy.

Claim 17

A photosensitive material according to claim 15 in which the sensitizing material is Lewis acid.

Claim 18

A photosensitive material according to claim 15 in which the sensitizing material is a sensitizing dye.

Claim 19

A photosensitiVe material according to claim 15 in which the sensitizing material is a Lewis acid and a sensitizing dye.

Claim 20

A photosensitive member according to claim 1 wherein at least one organometallic compound is selected from the group consisting of triphenylbismuthine, triphenylphosphine, tetraphenylarsine, ferrocene and cobaltocene.

Claim 21

A photosensitive member according to claim 1 including at least one organic photosensitive material selected from the group consisting of vinyl carbazoles, aromatic amine derivatives, diphenylmethane compounds and triphenylmethane compounds.

Claim 22

A photosensitive material according to claim 20 in which the vinyl carbazole is at least one member selected from the group consisting of poly-9-vinylcarbazole, bromine substituted poly-9-vinylcarbazole and iodine substituted poly-9-vinylcarbazole.

Claim 23

A photosensitive material according to claim 20 in which the vinyl carbazole is a member selected from the group consisting of 9-vinylcarbazole copolymer, bromine substituted 9-vinylcarbazole copolymer and iodine substituted 9-vinyl-carbazole copolymer.

Claim 24

A photosensitive member according to claim 1 including at least one free radical former selected from the group consisting of polyhalogen containing compound, carbonyl compound, organic sulfur compound, peroxide, azo compound, and diazo compound.

Claim 25

A photosensitive material according to claim 23 in which the poly-halogen containing compound is a compound of the formula

Claim 26

A photosensitive material according to claim 24 in which the polyhalogen containing compound is carbon tetrabromide.

Claim 27

A photosensitive material according to claim 24 in which the polyhalogen containing compound is bromoform.

Claim 28

A photosensitive material according to claim 24 in which the polyhalogen containing compound is iodoform.

Claim 29

A photosensitive material according to claim 24 in which the polyhalogen containing compound is a halogenated organic sulfoxide.

Claim 30

A photosensitive material according to claim 24 in which the polyhalogen containing compound is a halogenated organic sulfone compound.

Claim 31

A photosensitive member according to claim 1 wherein said free radical former is a polyhalogen containing compound and said organic photoconductive material is a vinylcarbazole.

Claim 32

A photosensitive member according to claim 1 including a colorization component selected from the group consisting of a dye base or an organic colorization component capable of forming a coloring material by reaction with said free radical former upon radiation excitation.

Claim 33

A photosensitive material according to claim 31 in which the dye base compound is selected from the group consisting of leuco bases, carbinol bases, styryl dye bases, cyanine dye bases, merocyanine dye bases and leuco dihydroanthracenes.

Claim 34

A photosensitive material according to claim 32 in which the leuco base is a member selected from the group consisting of leuco bases of triphenylmethane dye and leuco bases of diphenylmethane dye.

Claim 35

A photosensitive material according to claim 32 in which the carbinol base is selected from the group consisting of carbinol bases of triphenylmethane dye and carbinol bases of diphenylmethane dye.

Claim 36

A photosensitive material according to claim 31 in which the organic colorization component is a member selected from the group consisting of arylamines, carbazoles, indoles, 1,3,4-oxadiazoles, 1,3,4-triazoles, imidazoles, pyrazolines, aminophenyl substituted oxazoles, benzidines, 1,3-diphenyl-tetrahydroimidazoles, pHenazines, acridines, acyl hydrazone derivatives, quinoxalines, N-di-substituted amino containing arylideneazines, pyridines, quinolines, ethylene derivatives, and spiropyran compounds.

Claim 37

A photosensitive material according to claim 35 in which the arylamine is a compound of the formula:

Claim 38

A photosensitive material according to claim 36 in which the carbazole is a compound of the formula:

Claim 39

A photosensitive material according to claim 36 in which the indole is a compound of the formula:

Claim 40

An electrophotographic photosensitive member which comprises a support having coated thereon a sensitized layer of photoconductive photosensitive material, said material comprising an organic photoconductive material, a free radical former capable of producing free radicals for sensitizing said organic photoconductive material when uniformly excited by radiation energy having ultraviolet radiation and an organometallic compound incapable of liberating free radicals under the exposure used to excite said free radical former, but capable of catalyzing the sensitizing ability of the radical former, said photoconductive photosensitive material having been sensitized by applying said radiation energy uniformly having ultraviolet radiation to at least said free radical former and said organometallic compound.

Claim 41

An electrophotographic photosensitive member which comprises a support having coated thereon a sensitized layer of photoconductive photosensitive material, said material comprising an organic photoconductive material, a free radical former capable of producing free radicals for sensitizing said organic photoconductive material when uniformly excited by radiation energy having ultraviolet radiation and an organometallic compound incapable of liberating free radicals under the exposure used to excite said free radical former, but capable of catalyzing the sensitizing ability of the radical former, said photoconductive photosensitive material having been sensitized by applying said radiation energy uniformly having ultraviolet radiation to at least said free radical former and said organometallic compound.

Claim 42

The member of claim 29 wherein said photoconductive photosensitive material is sensitized by applying said radiation energy to said organic photoconductive material, said free radical former and said organometallic compound.