# US 9,751,880 B2 · Electrophotographic photosensitive member, process cartridge, electrophotographic apparatus, and imide compound

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- Number: US 9,751,880 B2
- Document ID: US9751880B2
- Status: Granted
- Kind: B2
- Application number: 14/919,112
- Filed: 2015-10-21
- Published: 2016-04-28
- Granted: 2017-09-05
- Earliest claimed: 2014-10-24
- Assignees: Canon Kabushiki Kaisha
- Applicants: Canon Kabushiki Kaisha
- Inventors: Masashi Nishi; Kunihiko Sekido; Michiyo Sekiya; Kei Tagami
- Web page: https://patentgrep.com/patent/US9751880B2

## CPC

- C07D 471/06: Peri-condensed systems
- G03G 5/142: {Inert intermediate layers}
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- G03G: ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY

## Abstract

An electrophotographic photosensitive member includes, in the following order, a support member, an undercoat layer adjacent to the support member, and a photosensitive layer adjacent to the undercoat layer. The undercoat layer contains a polymer produced by polymerizing a composition containing a crosslinking agent and a compound expressed by general formula (1): wherein R1 to R11 are defined in the specification.

## Claims

### Claim 1

An electrophotographic photosensitive member comprising in the following order:
a support member;
an undercoat layer adjacent to the support member; and
a photosensitive layer adjacent to the undercoat layer,
wherein the undercoat layer contains a polymer produced by polymerizing a composition containing a crosslinking agent and the compound expressed by general formula (1):
wherein R1 represents one selected from the group consisting of formula (2) and formula (3):
wherein R101 represents one selected from the group consisting of O, S, SO2, NR104 where R104 is selected from the group consisting of hydrogen atom, alkyl group and aryl group, carbonyl group, alkylene group, and arylene group, and the alkylene group and the arylene group each may have a substituent selected from the group consisting of alkyl group having a carbon number in the range of 1 to 5, phenyl group, and halogen atoms, and wherein R102 and R103 each represent one selected from the group consisting of alkyl group having a carbon number in the range of 1 to 3, alkoxy group, alkoxycarbonyl group, cyano group, nitro group, and halogen atoms, and m being the number of R102 and n being the number of R103 each represent an integer of 0 to 4 and may be the same as or different from each other;
wherein R201 represent one selected from the group consisting of O, S, SO2, NR204 where R204 is selected from hydrogen atom, alkyl group and aryl group, carbonyl group, alkylene group, and arylene group, and the alkylene group and the arylene group each may have a substituent selected from the group consisting of alkyl group having a carbon number in the range of 1 to 5, phenyl group, and halogen atoms, and wherein R202 and R203 each represent one selected from the group consisting of alkyl group having a carbon number of 1 or 2, alkoxy group, alkoxycarbonyl group, and halogen atoms, and s being the number of R202 and p being the number of R203 each represent an integer of 1 to 4 and may be the same as or different from each other,
wherein R2 and R3 each independently represent one selected from the group consisting of alkyl group, aryl group, and alkyl-derived groups having a main chain in which one of the carbon atoms is replaced with a species selected from the group consisting of O, S, and NR13 where R13 is selected from hydrogen atom and alkyl group, and
R2 and R3 has a polymerizable functional group selected from the group consisting of hydroxy group, thiol group, amino group and carboxy group, and
wherein R4 to R11 each independently represent one selected from the group consisting of hydrogen atom, halogen atoms, cyano group, nitro group, alkyl group, and aryl group, and
the alkyl group and the aryl group each may have a substituent selected from the group consisting of alky group, acyl group, alkoxy group, alkoxycarbonyl group, cyano group, nitro group, and halogen atoms.

### Claim 2 (depends on 1)

The electrophotographic photosensitive member according to claim 1, wherein R2 and R3 in general formula (1) are each expressed by formula (5):
wherein R401 represents hydrogen atom, R402 and R403 each represent one of alkyl group and aryl group, and each of the alkyl group and the aryl group has hydroxy group and may have at least one substituent selected from the group consisting of alkyl group having a carbon number of 1 to 6, alkoxy group, alkoxycarbonyl group, phenyl group, and halogen atoms.

### Claim 3 (depends on 1)

The electrophotographic photosensitive member according to claim 1, wherein the crosslinking agent is a compound selected from the group consisting of isocyanate compounds having an isocyanate group or a blocked isocyanate group, and amine compounds having an N-methylol group or an alkyletherified N-methylol group.

### Claim 4 (depends on 1)

The electrophotographic photosensitive member according to claim 1, wherein the composition further contains a resin having a polymerizable functional group.

### Claim 5 (depends on 4)

The electrophotographic photosensitive member according to claim 4, wherein the ratio of the total mass of the crosslinking agent and the resin having the polymerizable functional group in the composition is in the range of 0.5 to 2.5 relative to the mass of the compound expressed by general formula (1) in the composition.