Photoconductive compositions and elements

Claim 2

An organic photoconductive insulating composition comprising an electrically insulating polymeric binder and an organic photoconductive compound having the formula ##STR34## wherein R 1 and R 2 , which may be the same or different, represent, when taken separately, (i) hydrogen, (ii) an unsubstituted alkyl group or substituted alkyl group having 1 to about 18 carbon atoms, said substituted alkyl having a substituent selected from the group consisting of alkoxy, aryloxy, amino, hydroxy, aryl, alkylamino, arylamino, nitro, cyano, halogen, and acyl or (iii) when taken together R 1 and R 2 represent the saturated carbon atoms necessary to complete a cycloalkyl ring having 3 to 10 carbon atoms in the cycloalkyl ring, R 3 , r 4 , r 5 and R 6 , which may be the same or different, each represent an unsubstituted or substituted aryl group having a substituent selected from the group consisting of alkyloxy, aryloxy, amino, hydroxy, alkylamino, arylamino, nitro, cyano, halogen, alkyl, and acyl; and A 1 and A 2 , which may be the same or different, represent an unsubstituted phenyl group or a substituted phenyl having the substituents defined for R 3 , R 4 , R 5 and R 6 above.

Claim 3

A photoconductive composition as described in claim 1 wherein said composition contains an amount of sensitizer effective to sensitize said composition.

Claim 4

An organic photoconductive insulating composition comprising an electrically insulating polymeric binder, an organic photoconductive compound, and an amount of sensitizer effective to sensitize said composition, said photoconductive compound having the formula ##STR35## wherein R 1 and R 2 , which may be the same or different, represent, when taken separately, (i) hydrogen, (ii) an unsubstituted alkyl group or substituted alkyl group having 1 to about 18 carbon atoms, said substituted alkyl having a substituent selected from the group consisting of alkoxy, aryloxy, amino, hydroxy, aryl, alkylamino, arylamino, nitro, cyano, halogen, and acyl or (iii) when taken together, R 1 and R 2 represent the saturated carbon atoms necessary to complete a cycloalkyl ring having 3 to 10 carbon atoms in the cycloalkyl ring, R 3 , r 4 , r 5 , and R 6 , which may be the same or different, each represent an unsubstituted or substituted aryl group having a substituent selected from the group consisting of alkyloxy, aryloxy, amino, hydroxy, alkylamino, arylamino, nitro, cyano, halogen, alkyl, and acyl; and A 1 and A 2 , which may be the same or different, represent an unsubstituted phenyl group or a substituted phenyl group having the substituents defined for R 3 , R 4 , R 5 and R 6 above.

Claim 5

An organic photoconductive insulating composition comprising an electrically insulating polymeric binder, an organic photoconductive compound, and an amount of sensitizer effective to sensitize said composition, said photoconductive compound having the formula ##STR35## wherein R 1 and R 2 , which may be the same or different, represent, when taken separately, (i) hydrogen, (ii) an unsubstituted alkyl group or substituted alkyl group having 1 to about 18 carbon atoms, said substituted alkyl having a substituent selected from the group consisting of alkoxy, aryloxy, amino, hydroxy, aryl, alkylamino, arylamino, nitro, cyano, halogen, and acyl or (iii) when taken together, R 1 and R 2 represent the saturated carbon atoms necessary to complete a cycloalkyl ring having 3 to 10 carbon atoms in the cycloalkyl ring, R 3 , r 4 , r 5 , and R 6 , which may be the same or different, each represent an unsubstituted or substituted aryl group having a substituent selected from the group consisting of alkyloxy, aryloxy, amino, hydroxy, alkylamino, arylamino, nitro, cyano, halogen, alkyl, and acyl; and A 1 and A 2 , which may be the same or different, represent an unsubstituted phenyl group or a substituted phenyl group having the substituents defined for R 3 , R 4 , R 5 and R 6 above.

Claim 6

A photoconductive composition as defined in claim 3 wherein R 1 and R 2 , taken together, represent the saturated carbon atoms necessary to complete a 6-member cycloalkyl ring and A 1 and A 2 represent unsubstituted phenyl groups.

Claim 7

A photoconductive composition as defined in claim 3 wherein R 3 , R 4 , R 5 , and R 6 each represent unsubstituted phenyl groups or alkyl substituted phenyl groups and A 1 and A 2 represent unsubstituted phenyl groups.

Claim 8

A photoconductive composition as defined in claim 3 wherein said sensitizer is present in an amount of from about 0.005 to about 10 percent by weight of said composition and said organic photoconductive compound is present in an amount of from about 15 to about 90 percent by weight of said composition.

Claim 9

A photoconductive composition as defined in claim 3 wherein said composition is a homogeneous composition having said organic photoconductive compound in solid solution with said polymeric binder.

Claim 10

An organic, homogeneous, photoconductive insulating composition comprising an electrically insulating polymeric binder, an organic photoconductive compound in an amount equal to at least about 15 percent by weight of said composition, and a sensitizer for said composition in an amount within the range of from about 0.005 to about 10 percent by weight of said composition, said organic photoconductive compound in solid solution with said binder and having the formula ##STR36## wherein R 1 and R 2 , which may be the same or different, represent, when taken separately, (i) hydrogen, (ii) an unsubstituted alkyl group or substituted alkyl group having 1 to about 18 carbon atoms, said substituted alkyl having a substituent selected from the group consisting of alkoxy, aryloxy, amino, hydroxy, aryl, alkylamino, arylamino, nitro, cyano, halogen, and acyl or (iii) when taken together, R 1 and R 2 represent the saturated carbon atoms necessary to complete a cycloalkyl group having 5 to 7 carbon atoms in the cycloalkyl ring, R 3 , r 4 , r 5 , and R 6 , which may be the same or different, each represent an unsubstituted or substituted aryl group having a substituent selected from the group consisting of alkyloxy, aryloxy, amino, hydroxy, alkylamino, arylamino, nitro, cyano, halogen, alkyl, and acyl; and A 1 and A 2 , which may be the same or different, represent an unsubstituted phenyl group or a substituted phenyl group having the substituents defined for R 3 , R 4 , R 5 and R 6 above.

Claim 11

An organic, homogeneous, photoconductive insulating composition comprising an electrically insulating polymeric binder, an organic photoconductive compound in an amount equal to at least about 15 percent by weight of said composition, and a sensitizer for said composition in an amount within the range of from about 0.005 to about 10 percent by weight of said composition, said organic photoconductive compound in solid solution with said binder and having the formula ##STR36## wherein R 1 and R 2 , which may be the same or different, represent, when taken separately, (i) hydrogen, (ii) an unsubstituted alkyl group or substituted alkyl group having 1 to about 18 carbon atoms, said substituted alkyl having a substituent selected from the group consisting of alkoxy, aryloxy, amino, hydroxy, aryl, alkylamino, arylamino, nitro, cyano, halogen, and acyl or (iii) when taken together, R 1 and R 2 represent the saturated carbon atoms necessary to complete a cycloalkyl group having 5 to 7 carbon atoms in the cycloalkyl ring, R 3 , r 4 , r 5 , and R 6 , which may be the same or different, each represent an unsubstituted or substituted aryl group having a substituent selected from the group consisting of alkyloxy, aryloxy, amino, hydroxy, alkylamino, arylamino, nitro, cyano, halogen, alkyl, and acyl; and A 1 and A 2 , which may be the same or different, represent an unsubstituted phenyl group or a substituted phenyl group having the substituents defined for R 3 , R 4 , R 5 and R 6 above.

Claim 12

A homogeneous photoconductive composition as defined in claim 8 wherein said organic photoconductive compound is selected from the group consisting of 1,1-Bis(4-di-p-tolylaminophenyl)cyclohexane; 2,2-Bis(di-p-tolylaminophenyl)propane; 4,4'-Bis(di-p-tolylamino)-1,1,1-triphenylethane; 4,4'-bis(di-p-tolylamino)tetraphenylmethane; bis(4-di-p-tolylaminophenyl)methane; bis(4-di-p-tolylaminophenyl)phenylmethane; 1,1-bis(4-di-p-tolylaminophenyl)-4-t-butylcyclohexane; 1,1-bis(4-di-p-tolylaminophenyl)-2-methylpropane; 1,1-bis(4-di-p-tolylaminophenyl)ethane; and 1,1-bis(4-di-p-tolylaminophenyl)-3-methylbutane.

Claim 13

An organic, aggregate, photoconductive insulating composition comprising a continuous, electrically insulating binder phase containing (a) dissolved therein one or more photoconductive compounds and (b) dispersed therein a particulate co-crystalline complex of (1) a dye salt selected from the group consisting of pyrylium, thiapyrylium, and selenapyrylium dye salts and (2) a polymer having an alkylidene diarylene moiety in a recurring unit thereof, at least one of said photoconductors having the formula ##STR37## wherein R 1 and R 2 , which may be the same or different, represent, when taken separately, (i) hydrogen, (ii) an unsubstituted alkyl group or substituted alkyl group having 1 to about 18 carbon atoms, said substituted alkyl having a substituent selected from the group consisting of alkoxy, aryloxy, amino, hydroxy, aryl, alkylamino, arylamino, nitro, cyano, halogen, and acyl or (iii) when taken together, R 1 and R 2 represent the saturated carbon atoms necessary to complete a cycloalkyl ring having 3 to 10 carbon atoms in the cycloalkyl ring, R 3 , r 4 , r 5 , and R 6 , which may be the same or different, each represent an unsubstituted or substituted aryl group as defined above for R 1 and R 2 , and A 1 and A 2 , which may be the same or different, represent an unsubstituted phenyl group or a substituted phenyl group having the substituents defined for R 3 , R 4 , R 5 and R 6 above.

Claim 14

An organic, aggregate, photoconductive insulating composition comprising a continuous, electrically insulating binder phase containing (a) dissolved therein one or more photoconductive compounds and (b) dispersed therein a particulate co-crystalline complex of (1) a dye salt selected from the group consisting of pyrylium, thiapyrylium, and selenapyrylium dye salts and (2) a polymer having an alkylidene diarylene moiety in a recurring unit thereof, at least one of said photoconductors having the formula ##STR37## wherein R 1 and R 2 , which may be the same or different, represent, when taken separately, (i) hydrogen, (ii) an unsubstituted alkyl group or substituted alkyl group having 1 to about 18 carbon atoms, said substituted alkyl having a substituent selected from the group consisting of alkoxy, aryloxy, amino, hydroxy, aryl, alkylamino, arylamino, nitro, cyano, halogen, and acyl or (iii) when taken together, R 1 and R 2 represent the saturated carbon atoms necessary to complete a cycloalkyl ring having 3 to 10 carbon atoms in the cycloalkyl ring, R 3 , r 4 , r 5 , and R 6 , which may be the same or different, each represent an unsubstituted or substituted aryl group as defined above for R 1 and R 2 , and A 1 and A 2 , which may be the same or different, represent an unsubstituted phenyl group or a substituted phenyl group having the substituents defined for R 3 , R 4 , R 5 and R 6 above.

Claim 15

An aggregate photoconductive composition as defined in claim 10 wherein said dye salt is a 2,4,6-substituted thiapyrylium dye salt, A 1 and A 2 represent unsubstituted phenyl groups, and R 3 , R 4 , R 5 and R 6 each represent an unsubstituted phenyl or an alkyl substituted phenyl group.

Claim 16

An organic, aggregate, photoconductive insulating composition comprising a continuous, electrically insulating binder phase containing (a) dissolved therein one or more photoconductive compounds and (b) dispersed therein a particulate co-crystalline complex of (1) a thispyrylium dye salt and (2) a carbonate polymer having a alkylidene diarylene moiety in a recurring unit thereof, at least one of said photoconductors having the formula ##STR38## wherein R 1 and R 2 , which may be the same or different, represent, when taken separately, (i) hydrogen, (ii) an unsubstituted alkyl group or substituted alkyl group having 1 to about 18 carbon atoms, said substituted alkyl having a substituent selected from the group consisting of alkoxy, aryloxy, amino, hydroxy, aryl, alkylamino, arylamino, nitro, cyano, halogen, and acyl or (iii) when taken together, R 1 and R 2 represent the saturated carbon atoms necessary to complete a cycloalkyl ring having 5 to 7 carbon atoms in the cycloalkyl ring, R 3 , r 4 , r 5 , and R 6 , which may be the same or different, each represent an unsubstituted or substituted aryl group having a substituent selected from the group consisting of alkyloxy, aryloxy, amino, hydroxy, alkylamino, arylamino, nitro, cyano, halogen, alkyl, and acyl; and

Claim 17

An organic, aggregate, photoconductive insulating composition comprising a continuous, electrically insulating binder phase containing (a) dissolved therein one or more photoconductive compounds and (b) dispersed therein a particulate co-crystalline complex of (1) a thispyrylium dye salt and (2) a carbonate polymer having a alkylidene diarylene moiety in a recurring unit thereof, at least one of said photoconductors having the formula ##STR38## wherein R 1 and R 2 , which may be the same or different, represent, when taken separately, (i) hydrogen, (ii) an unsubstituted alkyl group or substituted alkyl group having 1 to about 18 carbon atoms, said substituted alkyl having a substituent selected from the group consisting of alkoxy, aryloxy, amino, hydroxy, aryl, alkylamino, arylamino, nitro, cyano, halogen, and acyl or (iii) when taken together, R 1 and R 2 represent the saturated carbon atoms necessary to complete a cycloalkyl ring having 5 to 7 carbon atoms in the cycloalkyl ring, R 3 , r 4 , r 5 , and R 6 , which may be the same or different, each represent an unsubstituted or substituted aryl group having a substituent selected from the group consisting of alkyloxy, aryloxy, amino, hydroxy, alkylamino, arylamino, nitro, cyano, halogen, alkyl, and acyl; and

Claim 18

A 1 and A 2 , which may be the same or different, represent an unsubstituted phenyl group or a substituted phenyl group having the substituents defined for R 3 , R 4 , R 5 and R 6 above.

Claim 19

A 1 and A 2 , which may be the same or different, represent an unsubstituted phenyl group or a substituted phenyl group having the substituents defined for R 3 , R 4 , R 5 and R 6 above.

Claim 20

An aggregate photoconductive composition as defined in claim 12 wherein R 1 and R 2 , taken together, represent the saturated carbon atoms necessary to complete a 6-member cycloalkyl ring and A 1 and A 2 represent unsubstituted phenyl groups.

Claim 21

An aggregate photoconductive composition as defined in claim 12 wherein R 3 , R 4 , R 5 , and R 6 each represent an unsubstituted phenyl group or an alkyl-substituted phenyl group, and A 1 and A 2 represent unsubstituted phenyl groups.

Claim 22

An aggregate photoconductive composition as defined in claim 12 wherein at least one of said photoconductors is selected from the group consisting of 1,1-bis(4-di-p-tolylaminophenyl)cyclohexane; 2,2-bis(di-p-tolylaminophenyl)propane; 4,4'-bis(di-p-tolylamino)-1,1,1-triphenylethane; 4,4'-bis(di-p-tolylamino)tetraphenylmethane; bis(4-di-p-tolylaminophenyl)-phenylmethane; 1,1-bis(4-di-p-tolylaminophenyl)-4-t-butyl-cyclohexane; 1,1-bis(4-di-p-tolylaminophenyl)-2-methylpropane; 1,1-bis(4-di-p-tolylaminophenyl)ethane; and 1,1-bis(4-di-p-tolylaminophenyl)-3-methylbutane.

Claim 23

An aggregate photoconductive composition as defined in claim 12 wherein at least one of said photoconductors is 1,1-bis(4-di-p-tolylaminophenyl)cyclohexane.

Claim 24

In an electrophotographic element comprising a conductive support bearing an organic, photoconductive insulating layer, the improvement wherein said organic photoconductive insulating layer comprises the photoconductive composition of claim 1.

Claim 25

In an electrophotographic element comprising a conductive support bearing an organic, photoconductive insulating layer, the improvement wherein said organic, photoconductive insulating layer comprises the photoconductive composition of claim 10.

Claim 26

In an electrophotographic process wherein an electrostatic charge pattern is formed on a photoconductive element comprised of an electrically conducting support bearing a layer of an organic, photoconductive insulating composition, the improvement wherein said organic, photoconductive insulating composition comprises an electrically insulating polymeric binder and an organic photoconductive compound having the formula ##STR39## wherein R 1 and R 2 , which may be the same or different, represent, when taken separately, (i) hydrogen, (ii) an unsubstituted alkyl group or substituted alkyl group having 1 to about 18 carbon atoms, said substituted alkyl having a substituent selected from the group consisting of alkoxy, aryloxy, amino, hydroxy, aryl, alkylamino, arylamino, nitro, cyano, halogen, and acyl or (iii) when taken together, R 1 and R 2 represent the saturated carbon atoms necessary to complete a cycloalkyl ring having 3 to 10 carbon atoms in the cycloalkyl ring, R 3 , r 4 , r 5 , and R 6 , which may be the same or different, each represent an unsubstituted or substituted aryl group having a substituent selected from the group consisting of alkyloxy, aryloxy, amino, hydroxy, alkylamino, arylamino, nitro, cyano, halogen, alkyl, and acyl; and A 1 an A 2 , which may be the same or different, represent an unsubstituted phenyl group or a substituted phenyl group having the substituents defined for R 3 , R 4 , R 5 and R 6 above.

Claim 27

In an electrophotographic process wherein an electrostatic charge pattern is formed on a photoconductive element comprised of an electrically conducting support bearing a layer of an organic, photoconductive insulating composition, the improvement wherein said organic, photoconductive insulating composition comprises an electrically insulating polymeric binder and an organic photoconductive compound having the formula ##STR39## wherein R 1 and R 2 , which may be the same or different, represent, when taken separately, (i) hydrogen, (ii) an unsubstituted alkyl group or substituted alkyl group having 1 to about 18 carbon atoms, said substituted alkyl having a substituent selected from the group consisting of alkoxy, aryloxy, amino, hydroxy, aryl, alkylamino, arylamino, nitro, cyano, halogen, and acyl or (iii) when taken together, R 1 and R 2 represent the saturated carbon atoms necessary to complete a cycloalkyl ring having 3 to 10 carbon atoms in the cycloalkyl ring, R 3 , r 4 , r 5 , and R 6 , which may be the same or different, each represent an unsubstituted or substituted aryl group having a substituent selected from the group consisting of alkyloxy, aryloxy, amino, hydroxy, alkylamino, arylamino, nitro, cyano, halogen, alkyl, and acyl; and A 1 an A 2 , which may be the same or different, represent an unsubstituted phenyl group or a substituted phenyl group having the substituents defined for R 3 , R 4 , R 5 and R 6 above.