IP Library Patent Application 10562859
Patent Application
App. No. 10/562,859

Novel compound, and electrophotographic photoreceptor and electrophotographic apparatus made by using the same

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Quick Facts
Patent No.
US None
App. No.
10/562,859
Abstract

A compound useful for a positive charge type electrophotographic photoreceptor with high sensitivity for copiers and printers by using such a novel organic material as a charge transport substance in a photosensitive layer and an electrophotographic apparatus using the same. The compound has a structure represented by the following general formula (I). (In the general formula (I), R 1 , R 2 , R 3 , and R 4 each is an alkyl group or the like; R 5 and R 6 each-is an aryl group or the like; and Z represents a structure having the following general formula (F-A), (F-B) or (F-C). (In the formulae, R 7 and R 8 each is an optionally substituted alkyl group; m and n each represents an integer of from 0 to 2; and X is a sulfur atom or an oxygen atom.).

Claims (28)

1 . A compound having a structure represented by the following general formula (I):

wherein in the general formula (I), R 1 , R 2 , R 3 , and R 4 can be the same or different and each is a hydrogen atom, an optionally substituted alkyl group having from 1 to 12 carbon atoms, or an optionally substituted aryl group; R 5 and R 6 can be the same or different and each is an optionally substituted aryl group or an optionally substituted heterocyclic group; and Z represents a structure having the following general formula (F-A), (F-B) or (F-C):

wherein in the formulae, R 7 and R 8 can be the same or different and each is an optionally substituted alkyl group having from 1 to 12 carbon atoms; m and n each represents an integer of from 0 to 2; X is a sulfur atom or an oxygen atom; and any substituent of any of R 1 to R 8 is a halogen atom, a nitro group, an alkyl group, an aryl group, a heterocyclic group, a halogenated alkyl group, or an alkoxy group, and any two adjacent substituents of any of R 1 to R 8 can be taken together to form a ring.

2 . The novel compound according to claim 1 , having a structure represented by the following general formula (I-A):

wherein in the formula (I-A), R 1-A , R 2-A , R 3-A , and R 4-A can be the same or different and each is a hydrogen atom, an optionally substituted alkyl group having from 1 to 12 carbon atoms, or an optionally substituted aryl group; R 5-A and R 6-A can be-the same or different and each is an optionally substituted aryl group or an optionally substituted heterocyclic group; R 7-A is an optionally substituted alkyl group having from 1 to 12 carbon atoms; X is a sulfur atom or an oxygen atom; m represents an integer of from 0 to 2; and any substituent of any of R 1-A to R 7-A is a halogen atom, a nitro group, an alkyl group having from 1 to 6 carbon atoms, an aryl group, a halogenated alkyl group having from 1 to 6 carbon atoms, or an alkoxy group having from 1 to 6 carbon atoms.

3 . The compound according to claim 1 , having a structure represented by the following general formula (I-B):

wherein in the formula (I-B), R 1-B , R 2-B , R 3-B , and R 4-B can be the same or different and each is a hydrogen atom or an optionally substituted alkyl group having from 1 to 12 carbon atoms; R 5-B and R 6-B can be the same or different and each is an optionally substituted aryl group or an optionally substituted heterocyclic group; and any substituent of any of R 1-B to R 6-B is a halogen atom, an alkyl group, an alkoxy group, an aryl group, a heterocyclic group, a fluorinated alkyl group, or a nitro group, and any two adjacent substituents of any of R 1-B to R 6-B can be-taken together to form a ring.

4 . The compound according to claim 1 , having a structure represented by the following general formula (I-C):

wherein in the formula (I-C), R 1-C , R 2-C , R 3-C , and R 4-C can be the same or different and each is a hydrogen atom, an optionally substituted alkyl group having from 1 to 6 carbon atoms, or an optionally substituted aryl group; R 5-C and R 6-C can be the same or different and each is an optionally substituted aryl group or a heterocyclic group; R 7-C and R 8-C each is a hydrogen atom or an optionally substituted alkyl group having from 1 to 10 carbon atoms; X is a sulfur atom or an oxygen atom; m and n each represents an integer of from 1 to 2; and any substituent of any of R 1-C to R 8-C is a halogen atom, a nitro group, an alkyl group, an aryl group, a heterocyclic group, a halogenated alkyl group, or an alkoxy group, and any two adjacent substituents of any of R 1-C to R 8-C can be taken together to form a ring.

5 . An electrophotographic photoreceptor including an electrically conductive substrate having thereon a photosensitive layer containing a charge generation substance and a charge transport substance that includes at least one compound having electron transport properties as represented by the following general formula (I):

wherein in the general formula (I), R 1 , R 2 , R 3 , and R 4 can be the same or different and each is a hydrogen atom, an optionally substituted alkyl group having from 1 to 12 carbon atoms, or an optionally substituted aryl group; R 5 and R 6 can be the same or different and each is an optionally substituted aryl group or an optionally substituted heterocyclic group; and Z represents a structure having the following general formula (F-A), (F-B) or (F-C):

wherein in the formulae, R 7 and R 8 can be the same or different and each is an optionally substituted alkyl group having from 1 to 12 carbon atoms; m and n each represents an integer of from 0 to 2; X is a sulfur atom or an oxygen atom; and any substituents of any of R 1 to R 8 is a halogen atom, a nitro group, an alkyl group, an aryl group, a heterocyclic group, a halogenated alkyl group, or an alkoxy group, and any two adjacent substituents of any of R 1 to R 8 can be taken together to form a ring.

6 . The electrophotographic photoreceptor including an electrically conductive substrate having thereon a photosensitive layer containing a charge generation substance and a charge transport substance according to claim 5 , containing, as said charge transport substance, at least one compound having electron transport properties as represented by the following general formula (I-A):

wherein in the formula (I-A), R 1-A , R 2-A , R 3-A , and R 4-A can be the same or different and each is a hydrogen atom, an optionally substituted alkyl group having from 1 to 12 carbon atoms, or an optionally substituted aryl group; R 5-A and R 6-A can be the same or different and each is an optionally substituted aryl group or an optionally substituted heterocyclic group; R 7-A is an optionally substituted alkyl group having from 1 to 12 carbon atoms; X is a sulfur atom or an oxygen atom; m represents an integer of from 0 to 2; and any substituents of any of R 1-A to R 7-A is a halogen atom, a nitro group, an alkyl group having from 1 to 6 carbon atoms, an aryl group, a halogenated alkyl group having from 1 to 6 carbon atoms, or an alkoxy group having from 1 to 6 carbon atoms.

7 . The electrophotographic photoreceptor including an electrically conductive substrate having thereon a photosensitive layer containing a charge generation substance and a charge transport substance according to claim 5 , containing, as said charge transport substance, at least one compound having electron transport properties as represented by the following general formula (I-B):

wherein in the formula (I-B), R 1-B , R 2-B , R 3-B , and R 4-B can be the same or different and each is a hydrogen atom or an optionally substituted alkyl group having from 1 to 12 carbon atoms; R 5-B and R 6-B can be the same or different and each is an optionally substituted aryl group or an optionally substituted heterocyclic group; and any substituents of any of R 1-B to R 6-B is a halogen atom, an alkyl group, an alkoxy group, an aryl group, a heterocyclic group, a fluorinated alkyl group, or a nitro group, and any substituent of any of R 1-B to R 6-B can be taken together to form a ring.

8 . The electrophotographic photoreceptor including an electrically conductive substrate having thereon a photosensitive layer containing a charge generation substance and a charge transport substance according to claim 5 , containing, as said charge transport substance, at least one compound having electron transport properties as represented by the following general formula (I-C):

wherein in the formula (I-C), R 1-C , R 2-C , R 3-C , and R 4-C can be the same or different and each is a hydrogen atom, an optionally substituted alkyl group having from 1 to 6 carbon atoms, or an optionally substituted aryl group; R 5-C and R 6-C can be the same or different and each is an optionally substituted aryl group or a heterocyclic group; R 7-C and R 8-C each is a hydrogen atom or an optionally substituted alkyl group having from 1 to 10 carbon atoms; X is a sulfur atom or an oxygen atom; m and n each represents an integer of from 1 to 2; and any substituent of any of R 1-C to R 8-C is a halogen atom, a nitro group, an alkyl group, an aryl group, a heterocyclic group, a halogenated alkyl group, or an alkoxy group, and any substituents of any of R 1-C to R 8-C can be taken together to form a ring.

9 . An electrophotographic photoreceptor including an electrically conductive substrate having thereon directly or via the undercoat layer a single layer type photosensitive layer containing a charge generation substance, a charge transport substance, and a resin binder, containing, as said charge transport substance, a hole transport substance and at least one compound having electron transport properties as represented by the following general formula (I):

wherein in the general formula (I), R 1 , R 2 , R 3 , and R 4 can be the same or different and each is a hydrogen atom, an optionally substituted alkyl group having from 1 to 12 carbon atoms, or an optionally substituted aryl group; R 5 and R 6 can be the same or different and each is an optionally substituted aryl group or an optionally substituted heterocyclic group; and Z represents a structure having the following general formula (F-A), (F-B) or (F-C):

wherein in the formulae, R 7 and R 8 can be the same or different and each is an optionally substituted alkyl group having from 1 to 12 carbon atoms; m and n each represents an integer of from 0 to 2; X is a sulfur atom or an oxygen atom; and any substituent of any of R 1 to R 8 is a halogen atom, a nitro group, an alkyl group, an aryl group, a heterocyclic group, a halogenated alkyl group, or an alkoxy group, and any two adjacent substituents of any of R 1 to R 8 can be taken together to form a ring.

10 . The electrophotographic photoreceptor including an electrically conductive substrate having thereon directly or via the undercoat layer a single layer type photosensitive layer containing a charge generation substance, a charge transport substance, and a resin binder according to claim 9 , containing, as said charge transport substance, a hole transport substance and at least one kind of a compound having electron transport properties as represented by the following general formula (I-A):

wherein in the formula (I-A), R 1-A , R 2-A , R 3-A , and R 4-A can be the same or different and each is a hydrogen atom, an optionally substituted alkyl group having from 1 to 12 carbon atoms, or an optionally substituted aryl group; R 5-A and R 6-A can be the same or different and each is an optionally substituted aryl group or an optionally substituted heterocyclic group; R 7-A is an optionally substituted alkyl group having from 1 to 12 carbon atoms; X is a sulfur atom or an oxygen atom; m represents an integer of from 0 to 2; and any substituent of any of R 1-A to R 7-A is a halogen atom, a nitro group, an alkyl group having from 1 to 6 carbon atoms, an aryl group, a halogenated alkyl group having from 1 to 6 carbon atoms, or an alkoxy group having from 1 to 6 carbon atoms.

11 . The electrophotographic photoreceptor including an electrically conductive substrate having thereon directly or via the undercoat layer a single layer type photosensitive layer containing a charge generation substance, a charge transport substance, and a resin binder according to claim 9 , containing, as said charge transport substance, a hole transport substance and at least one kind of a compound having electron transport properties as represented by the following general formula (I-B):

wherein in the formula (I-B), R 1-B , R 2-B , R 3-B , and R 4-B can be the same or different and each is a hydrogen atom or an optionally substituted alkyl group having from 1 to 12 carbon atoms; R 5-B and R 6-B can be the same or different and each is an optionally substituted aryl group or an optionally substituted heterocyclic group; and any substituent of any of R 1-B to R 6-B is a halogen atom, an alkyl group, an alkoxy group, an aryl group, a heterocyclic group, a fluorinated alkyl group, or a nitro group, and any two adjacent substituents of any of R 1-A to R 6-B can be taken together to form a ring.

12 . The electrophotographic photoreceptor including an electrically conductive substrate having thereon directly or via the undercoat layer a single layer type photosensitive layer containing a charge generation substance, a charge transport substance, and a resin binder according to claim 9 , containing, as said charge transport substance, a hole transport substance and at least one kind of a compound having electron transport properties as represented by the following general formula (I-C):

wherein in the is a hydrogen atom, an optionally substituted alkyl group having from 1 to 6 carbon atoms, or an optionally substituted aryl group; R 5-C and R 6-C can be the same or different and each is an optionally substituted aryl group or a heterocyclic group; R 7-C and R 8-C each is a hydrogen atom or an optionally substituted alkyl group having from 1 to 10 carbon atoms; X is a sulfur atom or an oxygen atom; m and n each represents an integer of from 1 to 2; and any substituent of any of R 1-C to R 8-C is a halogen atom, a nitro group, an alkyl group, an aryl group, a heterocyclic group, a halogenated alkyl group, or an alkoxy group, and any two adjacent substituents of any of R 1 to R 8 can be taken together to form a ring.

13 . An electrophotographic apparatus which is characterized by being provided with the electrophotographic photoreceptor according to claim 5 and performing a charge process by a positive charge process.

Assignments (2)
MERGER Recorded Oct 16, 2006
From: FUJI ELECTRIC IMAGING DEVICE CO., LTD
To: FUJI ELECTRIC DEVICE TECHNOLOGY CO., LTD
Reel/Frame 018392/0071 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 5, 2006
From: SEKINE, NOBUYUKI; KURODA, MASAMI; OHKURA, KENICHI; UENO, YOSHIHIRO; TAKESHIMA, MOTOHIRO
To: FUJI ELECTRIC IMAGING DEVICE CO., LTD.
Reel/Frame 017989/0700 →