Disazo compounds, process for preparation of same and application of said disazo compounds and analogues thereof to electrophotographic sensitive materials

Claim 2

An electrophotographic material which comprises an electrically conductive support and a photosensitive layer formed thereon, said photosensitive layer consisting essentially of fine particles of a disazo compound having the formula A'--N═N--Z--N═N--A', wherein A' is a member selected from the group consisting of ##STR43## is a fused ring selected from the group consisting of benzene ring, bromobenzene ring, naphthalene ring, indole ring, carbazole ring and benzofuran ring; Ar 1 is a member selected from the group consisting of phenyl, methylphenyl, methoxyphenyl, chlorophenyl, nitrophenyl, ethoxyphenyl, dimethylphenyl, methylchlorophenyl, methoxychlorophenyl, methoxybromophenyl, ethoxychlorophenyl, methylmethoxyphenyl, dimethoxyphenyl, dimethoxychlorophenyl, dimethylaminophenyl, cyanophenyl, carboxyphenyl, benzenesulfonic acid sodium salt, tert-butoxyphenyl, naphthyl, methoxydibenzofuryl and carbazolyl; each of Ar 2 and Ar 3 is a member selected from the group consisting of phenyl, naphthyl, nitrophenyl, benzenesulfonamide, benzenesulfonic acid, trichlorobenzenesulfonic acid, methylphenyl, methoxyphenyl, chlorophenyl, dinitrophenyl, cyanophenyl, dimethylaminophenyl and acetylaminophenyl; each of R 1 and R 3 is a member selected from the group consisting of hydrogen, methyl, ethyl, phenyl and chlorophenyl; and R 2 is selected from the group consisting of methyl, carboxyl and COOC 2 H 5 ; and Z is a member selected from the group consisting of ##STR44## and a resinous binder.

Claim 3

An electrophotographic material according to claim 1, wherein the particle size of said disazo compound is less than 5 microns, the content of said disazo compound is in the range of from 30 to 70% based on the weight of the photosensitive layer and the thickness of said photosensitive layer is about 3 to 50 microns.

Claim 4

An electrophotographic material according to claim 1 in which A' is ##STR45##

Claim 5

An electrophotographic material according to claim 1 in which A' is ##STR46##

Claim 6

An electrophotographic material according to claim 1 in which Z is ##STR47##

Claim 7

An electrophotographic material according to claim 5 in which A' is ##STR48##

Claim 8

An electrophotographic material according to claim 5 in which A' is ##STR49##

Claim 9

An electrophotographic material according to claim 5 in which A' is ##STR50##

Claim 10

An electrophotographic material according to claim 5 in which A' is ##STR51##

Claim 11

An electrophotographic material according to claim 5 in which A' is ##STR52##

Claim 12

An electrophotographic material according to claim 5 in which A' is ##STR53##

Claim 13

An electrophotographic material according to claim 5 in which A' is ##STR54##

Claim 14

An electrophotographic material according to claim 5 in which A' is ##STR55##

Claim 15

An electrophotographic material according to claim 5 in which A' is ##STR56##

Claim 16

An electrophotographic material according to claim 5 in which A' is ##STR57##

Claim 17

An electrophotographic material according to claim 5 in which A' is ##STR58##

Claim 18

An electrophotographic material according to claim 5 in which A' is ##STR59##

Claim 19

An electrophotographic material according to claim 5 in which A' is ##STR60##

Claim 20

An electrophotographic material according to claim 5 in which A' is ##STR61##

Claim 21

An electrophotographic material according to claim 5 in which A' is ##STR62##

Claim 22

An electrophotographic material which comprises an electrically conductive support and a photosensitive layer formed thereon, said photosensitive layer consisting essentially of fine particles of a disazo compound having the formula A'--N═N--Z--N═N--A', wherein A' is a member selected from the group consisting of ##STR63## is a fused ring selected from the group consisting of benzene ring, bromobenzene ring, naphthalene ring, indole ring, carbazole ring and benzofuran ring; Ar 1 is a member selected from the group consisting of phenyl, methylphenyl, methoxyphenyl, chlorophenyl, nitrophenyl, ethoxyphenyl, dimethylphenyl, methylchlorophenyl, methoxychlorophenyl, methoxybromophenyl, ethoxychlorophenyl, methylmethoxyphenyl, dimethoxyphenyl, dimethoxychlorophenyl, dimethylaminophenyl, cyanophenyl, carboxyphenyl, benzenesulfonic acid sodium salt, tert-butoxyphenyl, naphthyl, methoxydibenzofuryl and carbazolyl; each of Ar 2 and Ar 3 is a member selected from the group consisting of phenyl, naphthyl, nitrophenyl, benzenesulfonamide, benzenesulfonic acid, trichlorobenzenesulfonic acid, methylphenyl, methoxyphenyl, chlorophenyl, dinitrophenyl, cyanophenyl, dimethylaminophenyl and acetylaminophenyl; each of R 1 and R 3 is a member selected from the group consisting of hydrogen, methyl, ethyl, phenyl and chlorophenyl; and R 2 is selected from the group consisting of methyl, carboxyl and COOC 2 H 5 ; and Z is a member selected from the group consisting of ##STR64## a charge-transfer substance and a resinous binder.

Claim 23

An electrophotographic material which comprises an electrically conductive support and a photosensitive layer formed thereon, said photosensitive layer consisting essentially of fine particles of a disazo compound having the formula A'--N═N--Z--N═N--A', wherein A' is a member selected from the group consisting of ##STR63## is a fused ring selected from the group consisting of benzene ring, bromobenzene ring, naphthalene ring, indole ring, carbazole ring and benzofuran ring; Ar 1 is a member selected from the group consisting of phenyl, methylphenyl, methoxyphenyl, chlorophenyl, nitrophenyl, ethoxyphenyl, dimethylphenyl, methylchlorophenyl, methoxychlorophenyl, methoxybromophenyl, ethoxychlorophenyl, methylmethoxyphenyl, dimethoxyphenyl, dimethoxychlorophenyl, dimethylaminophenyl, cyanophenyl, carboxyphenyl, benzenesulfonic acid sodium salt, tert-butoxyphenyl, naphthyl, methoxydibenzofuryl and carbazolyl; each of Ar 2 and Ar 3 is a member selected from the group consisting of phenyl, naphthyl, nitrophenyl, benzenesulfonamide, benzenesulfonic acid, trichlorobenzenesulfonic acid, methylphenyl, methoxyphenyl, chlorophenyl, dinitrophenyl, cyanophenyl, dimethylaminophenyl and acetylaminophenyl; each of R 1 and R 3 is a member selected from the group consisting of hydrogen, methyl, ethyl, phenyl and chlorophenyl; and R 2 is selected from the group consisting of methyl, carboxyl and COOC 2 H 5 ; and Z is a member selected from the group consisting of ##STR64## a charge-transfer substance and a resinous binder.

Claim 24

An electrophotographic material according to claim 21, wherein the particle size of said disazo compound is less than 5 microns, the content of said disazo compound and said charge-transfer substance are in the range of from 1 to 50% and from 10 to 90%, respectively, based on the weight of said photosensitive layer, and the thickness of said photosensitive layer is about 3 to 50 microns.

Claim 25

An electrophotographic material according to claim 21 in which A' is ##STR65##

Claim 26

An electrophotographic material according to claim 21 in which A' is ##STR66##

Claim 27

An electrophotographic material according to claim 21 in which Z is ##STR67##

Claim 28

An electrophotographic material according to claim 25 in which A' is ##STR68##

Claim 29

An electrophotographic material according to claim 25 in which A' is ##STR69##

Claim 30

An electrophotographic material according to claim 25 in which A' is ##STR70##

Claim 31

An electrophotographic material according to claim 25 in which A' is ##STR71##

Claim 32

An electrophotographic material according to claim 25 in which A' is ##STR72##

Claim 33

An electrophotographic material according to claim 25 in which A' is ##STR73##

Claim 34

An electrophotographic material according to claim 25 in which A' is ##STR74##

Claim 35

An electrophotographic material according to claim 25 in which A' is ##STR75##

Claim 36

An electrophotographic material according to claim 25 in which A' is ##STR76##

Claim 37

An electrophotographic material according to claim 25 in which A' is ##STR77##

Claim 38

An electrophotographic material according to claim 25 in which A' is ##STR78##

Claim 39

An electrophotographic material according to claim 25 in which A' is ##STR79##

Claim 40

An electrophotographic material according to claim 25 in which A' is ##STR80##

Claim 41

An electrophotographic material according to claim 25 in which A' is ##STR81##

Claim 42

An electrophotographic material according to claim 25 in which A' is ##STR82##

Claim 43

An electrophotographic sensitive material which comprises an electrically conductive support, a charge-carrier generating layer which consists essentially of fine particles of a disazo compound having the formula A'--N═N--Z--N═N--A', wherein A' is a member selected from the group consisting of ##STR83## is a fused ring selected from the group consisting of benzene ring, bromobenzene ring, naphthalene ring, indole ring, carbazole ring and benzofuran ring; Ar 1 is a member selected from the group consisting of phenyl, methylphenyl, methoxyphenyl, chlorophenyl, nitrophenyl, ethoxyphenyl, dimethylphenyl, methylchlorophenyl, methoxychlorophenyl, methoxybromophenyl, ethoxychlorophenyl, methylmethoxyphenyl, dimethoxyphenyl, dimethoxychlorophenyl, dimethylaminophenyl, cyanophenyl, carboxyphenyl, benzenesulfonic acid sodium salt, tert-butoxyphenyl, naphthyl, methoxydibenzofuryl and carbazolyl; each of Ar 2 and Ar 3 L is a member selected from the group consisting of phenyl, naphthyl, nitrophenyl, benzenesulfonamide, benzenesulfonic acid, trichlorobenzenesuflonic acid, methylphenyl, methoxyphenyl, chlorophenyl, dinitrophenyl, cyanophenyl, dimethylaminophenyl and acetylaminophenyl; each of R 1 and R 3 is a member selected from the group consisting of hydrogen, methyl, ethyl, phenyl and chlorophenyl; and R 2 is selected from the group consisting of methyl, carboxyl and COOC 2 H 5 ; and Z is a member selected from the group consisting of ##STR84## and a charge-transfer layer which consists essentially of a charge-transfer substance and a resinous binder, said two layers being formed on said conductive support.

Claim 44

An electrophotographic sensitive material which comprises an electrically conductive support, a charge-carrier generating layer which consists essentially of fine particles of a disazo compound having the formula A'--N═N--Z--N═N--A', wherein A' is a member selected from the group consisting of ##STR83## is a fused ring selected from the group consisting of benzene ring, bromobenzene ring, naphthalene ring, indole ring, carbazole ring and benzofuran ring; Ar 1 is a member selected from the group consisting of phenyl, methylphenyl, methoxyphenyl, chlorophenyl, nitrophenyl, ethoxyphenyl, dimethylphenyl, methylchlorophenyl, methoxychlorophenyl, methoxybromophenyl, ethoxychlorophenyl, methylmethoxyphenyl, dimethoxyphenyl, dimethoxychlorophenyl, dimethylaminophenyl, cyanophenyl, carboxyphenyl, benzenesulfonic acid sodium salt, tert-butoxyphenyl, naphthyl, methoxydibenzofuryl and carbazolyl; each of Ar 2 and Ar 3 L is a member selected from the group consisting of phenyl, naphthyl, nitrophenyl, benzenesulfonamide, benzenesulfonic acid, trichlorobenzenesuflonic acid, methylphenyl, methoxyphenyl, chlorophenyl, dinitrophenyl, cyanophenyl, dimethylaminophenyl and acetylaminophenyl; each of R 1 and R 3 is a member selected from the group consisting of hydrogen, methyl, ethyl, phenyl and chlorophenyl; and R 2 is selected from the group consisting of methyl, carboxyl and COOC 2 H 5 ; and Z is a member selected from the group consisting of ##STR84## and a charge-transfer layer which consists essentially of a charge-transfer substance and a resinous binder, said two layers being formed on said conductive support.

Claim 45

An electrophotographic material according to claim 41, wherein the particle size of said disazo compound is less than 5 microns, the content of said charge-transfer substance is in the range of from 10 to 95% based on the weight of the charge-transfer layer, the thickness of said charge-carrier generating layer is less than 5 microns and the thickness of said charge-transfer layer is about 3 to 50 microns.

Claim 46

An electrophotographic material according to claim 41 in which A' is ##STR85##

Claim 47

An electrophotographic material according to claim 41 in which A' is ##STR86##

Claim 48

An electrophotographic material according to claim 41 in which Z is ##STR87##

Claim 49

An electrophotographic material according to claim 45 in which A' is ##STR88##

Claim 50

An electrophotographic material according to claim 45 in which A' is ##STR89##

Claim 51

An electrophotographic material according to claim 45 in which A' is ##STR90##

Claim 52

An electrophotographic material according to claim 45 in which A' is ##STR91##

Claim 53

An electrophotographic material according to claim 45 in which A' is ##STR92##

Claim 54

An electrophotographic material according to claim 45 in which A' is ##STR93##

Claim 55

An electrophotographic material according to claim 45 in which A' is ##STR94##

Claim 56

An electrophotographic material according to claim 45 in which A' is ##STR95##

Claim 57

An electrophotographic material according to claim 45 in which A' is ##STR96##

Claim 58

An electrophotographic material according to claim 45 in which A' is ##STR97##

Claim 59

An electrophotographic material according to claim 45 in which A' is ##STR98##

Claim 60

An electrophotographic material according to claim 45 in which A' is ##STR99##

Claim 61

An electrophotographic material according to claim 45 in which A' is ##STR100##

Claim 62

An electrophotographic material according to claim 45 in which A' is ##STR101##

Claim 63

An electrophotographic material according to claim 45 in which A' is ##STR102##