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Electrophotographic photosensitive member with pyrazoline charge transport material

Assignee: Canon Inc
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Filing: 1982-06-01
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Granted: 1984-06-12
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Expires: 2002-06-01
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Abstract

Abstract An electrophotographic photosensitive member is characterized by comprising a layer which contains at least one pyrazoline compound represented by the following formula (I) or (II): ##STR1## wherein m and n represent 0 or 1; when both m and n are 0, X 1 represents a substituted or unsubstituted heterocyclic residue; R 1 represents a substituted or unsubstituted aryl or heterocyclic residue; R 2 and R 3 each represent hydrogen or a substituted or unsubstituted aryl or heterocyclic residue; or they form spiropyrazoline cojointly with the carbon atom to which they are linked; and R 5 represents hydrogen, a halogen, or a substituted or unsubstituted alkyl or aryl; when m is 1 and n is 0, X 1 represents a substituted or unsubstituted heterocyclic residue; R 1 and R 2 each represent a substituted or unsubstituted aryl or heterocyclic residue; R 3 represents hydrogen; and R 4 and R 5 each represent hydrogen, a halogen, or a substituted or unsubstituted alkyl or aryl; when m is 0 and n is 1, X 1 , R 1 , R 2 , and R 3 each represent a substituted or unsubstituted aryl or heterocyclic residue, R 2 and R 3 may also form spiropyrazoline cojointly with the carbon atom to which they are linked, and one of R 2 and R 3 can also be hydrogen but X 1 is not a substituted or unsubstituted aryl unless R 2 and R 3 form spiropyrazoline as mentioned above; and R 4 and R 5 each represent hydrogen, a halogen, or a substituted or unsubstituted alkyl or aryl; if R 3 , R 4 , and R 5 each are hydrogen, neither R 1 nor R 2 is a di-substituted aminophenyl; when both m and n are 1, X 1 represents a substituted or unsubstituted heterocyclic residue; R 1 and R 2 each represent a substituted or unsubstituted aryl or heterocyclic residue; and R 4 and R 5 each represent hydrogen, a halogen, or a substituted or unsubstituted alkyl or aryl. ##STR2## wherein X 2 and X 3 each represent a substituted or unsubstituted heterocyclic residue; R 6 represents a substituted or unsubstituted divalent hydrocarbon residue; R 7 and R 8 each represent a substituted or unsubstituted aryl or heterocyclic residue; and R 9 and R 10 each represent hydrogen, a halogen, or a substituted or unsubstituted alkyl or aryl.

Inventors

  • 👤 Yoshio Takasu
  • 👤 Shozo Ishikawa

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-07 14:06
CPC Classifications
G; G03; G03G; G03G5/00; G03G5/02; G03G5/04; G03G5/06; G03G5/0664; G03G5/0666; G03G5/0668; G03G5/067; G03G5/0622; G03G5/0644; G03G5/0661; G03G5/0672; G03G5/0674

Claims Analysis

Total Claims: 11
Claim 1
Independent Claim 130 words
An electrophotographic photosensitive member comprising a charge generation layer and a charge transport layer which includes at least one pyrazoline compound represented by the following formula: ##STR23## wherein X 1 is a substituted or unsubstituted heterocyclic residue selected from the group consisting of substituted or unsubstituted pyridyl, quinolyl, carbazolyl, furyl, imidazolyl, oxazolyl, and isoxazolyl; R 1 is a substituted or unsubstituted aryl or heterocyclic residue; R 4 is hydrogen, a halogen, or a substituted or unsubstituted alkyl or aryl; R 11 is a substituted or unsubstituted alkyl; R 12 is hydrogen, a halogen, or an organic monovalent residue; Z is ##STR24## or --CH═CH--, wherein R 13 and R 14 are each a substituted or unsubstituted alkyl; n is 0 or 1; and l is an integer of 1 to 4.
Claim 2
Dependent Claim 130 words
An electrophotographic photosensitive member comprising a charge generation layer and a charge transport layer which includes at least one pyrazoline compound represented by the following formula: ##STR23## wherein X 1 is a substituted or unsubstituted heterocyclic residue selected from the group consisting of substituted or unsubstituted pyridyl, quinolyl, carbazolyl, furyl, imidazolyl, oxazolyl, and isoxazolyl; R 1 is a substituted or unsubstituted aryl or heterocyclic residue; R 4 is hydrogen, a halogen, or a substituted or unsubstituted alkyl or aryl; R 11 is a substituted or unsubstituted alkyl; R 12 is hydrogen, a halogen, or an organic monovalent residue; Z is ##STR24## or --CH═CH--, wherein R 13 and R 14 are each a substituted or unsubstituted alkyl; n is 0 or 1; and l is an integer of 1 to 4.
Claim 3
Dependent Claim 15 words
An electrophotographic photosensitive member of claim 1, wherein said R 1 is a di-substituted aminophenyl.
Claim 4
Dependent Claim 14 words
An electrophotographic photosensitive member of claim 2, wherein said di-substituted aminophenyl is a dialkylaminophenyl.
Claim 5
Dependent Claim 23 words
An electrophotographic photosensitive member of claim 3, wherein said dialkylaminophenyl is selected from the group consisting of dimethylaminophenyl, diethylaminophenyl, dipropylaminophenyl, dibutylaminophenyl, and dibenzylaminophenyl.
Claim 6
Dependent Claim 12 words
An electrophotographic photosensitive member of claim 4, wherein said dialkylamino is diethylaminophenyl.
Claim 7
Dependent Claim 26 words
An electrophotographic photosensitive member of claim 1, wherein said R 1 is a heterocyclic residue selected from the group consisting of pyridyl, quinolyl, carbazolyl, and imidazolyl.
Claim 8
Dependent Claim 13 words
An electrophotographic photosensitive member of claim 6, wherein said R 1 is carbazolyl.
Claim 9
Dependent Claim 31 words
An electrophotographic photosensitive member of claim 1, wherein said X 1 is a heterocyclic residue selected from the group consisting of 2-pyridyl, 3-pyridyl, 4-pyridyl, 6-methoxy-2-pyridyl, 2-quinolyl, 4-quinolyl, 2-lepidyl, 3-carbazolyl, and 9-ethyl-3-carbazolyl.
Claim 10
Dependent Claim 127 words
An electrophotographic photosensitive member comprising a layer which includes a charge generating material, a binder and at least one pyrazoline compound of the formula: ##STR25## wherein X 1 is a substituted or unsubstituted heterocyclic residue selected from the group consisting of substituted or unsubstituted pyridyl, quinolyl, carbazolyl, furyl, imidazolyl, oxazolyl and isoxazolyl; R 1 is a substituted or unsubstituted aryl or heterocyclic residue; R 4 is hydrogen, a halogen, or a substituted or unsubstituted alkyl or aryl; R 11 is a substituted or unsubstituted alkyl; R 12 is hydrogen, a halogen or an organic monovalent residue; Z is ##STR26## or --CH═CH--, wherein R 13 and R 14 are each substituted or unsubstituted alkyl; n is 0 or 1; and l is an integer of 1 to 4.
Claim 11
Dependent Claim 127 words
An electrophotographic photosensitive member comprising a layer which includes a charge generating material, a binder and at least one pyrazoline compound of the formula: ##STR25## wherein X 1 is a substituted or unsubstituted heterocyclic residue selected from the group consisting of substituted or unsubstituted pyridyl, quinolyl, carbazolyl, furyl, imidazolyl, oxazolyl and isoxazolyl; R 1 is a substituted or unsubstituted aryl or heterocyclic residue; R 4 is hydrogen, a halogen, or a substituted or unsubstituted alkyl or aryl; R 11 is a substituted or unsubstituted alkyl; R 12 is hydrogen, a halogen or an organic monovalent residue; Z is ##STR26## or --CH═CH--, wherein R 13 and R 14 are each substituted or unsubstituted alkyl; n is 0 or 1; and l is an integer of 1 to 4.

References Cited (Backward Citations)

US3180729A Cited
GB1030024A Cited
US3859303A Cited
US3837851A Cited
JPS552285A Cited
US4278746A Cited
JPS5588065A Cited
US4315982A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1987-06-12 1987-12-12 1988-06-12 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1991-06-12 1991-12-12 1992-06-12 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1995-06-12 1995-12-12 1996-06-12 $7700.00 Window Closed / Lapsed

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