Electrophotographic photosensitive member, process-cartridge and apparatus
원문보기
IPC분류정보
국가/구분
United States(US) Patent
등록
국제특허분류(IPC7판)
G03G-005/06
G03G-015/00
출원번호
US-0652246
(2003-09-02)
우선권정보
JP-0114345 (2001-04-12)
발명자
/ 주소
Tanaka, Masato
출원인 / 주소
Canon Kabushiki Kaisha
대리인 / 주소
Fitzpatrick, Cella, Harper & Scinto
인용정보
피인용 횟수 :
12인용 특허 :
9
초록▼
An electrophotographic photosensitive member having a sensitivity to a short semiconductor laser light in a wavelength range of 380-500 nm is provided by incorporating a specific porphyrin compound in a photosensitive layer. The porphyrin compound is characterized by having a heterocyclic substituen
An electrophotographic photosensitive member having a sensitivity to a short semiconductor laser light in a wavelength range of 380-500 nm is provided by incorporating a specific porphyrin compound in a photosensitive layer. The porphyrin compound is characterized by having a heterocyclic substituent, preferably 4 heterocyclic substituents each of a pyridyl group. The porphyrin compound includes a 5,10,15,20-tetrapyridyl-21H,23H-porphyrinato-zinc compound having a novel crystal form characterized by certain peaks in a CuK α -characteristic X-ray diffraction pattern.
대표청구항▼
1. An electrophotographic photosensitive member, comprising a support and a photosensitive layer disposed on the support, wherein the photosensitive layer contains a binder resin and a porphyrin compound as a charge generating material having a structure represented by formula (1) shown below:wherei
1. An electrophotographic photosensitive member, comprising a support and a photosensitive layer disposed on the support, wherein the photosensitive layer contains a binder resin and a porphyrin compound as a charge generating material having a structure represented by formula (1) shown below:wherein M denotes hydrogen atoms or a metal capable of having an axial ligand; R 11 to R 18 independently denote a hydrogen atom, an alkyl group capable of having a substituent, an aromatic ring capable of having a substituent, an amino group capable of having a substituent, a sulfur atom capable of having a substituent, an alkoxy group, a halogen atom, a nitro group or a cyano group; and A 11 to A 14 independently denote a hydrogen atom, an alkyl group capable of having a substituent, an aromatic ring capable of having a substituent or a heterocyclic ring capable of having a substituent with the proviso that at least one of A 11 to A 14 is a pyridyl group capable of having a substituent. 2. A photosensitive member according to claim 1, wherein the porphyrin compound is a 5,10,15,20-tetrapyridyl-21H,23H-porphyrin compound represented by the formula (1) wherein each of A 11 to A 14 is a pyridyl group. 3. A photosensitive member according to claim 2, wherein the 5,10,15,20-tetrapyridyl)-21H,23H-porphyrin compound has a crystal form characterized by a Bragg angle (2θ) in a range of 20.0±1.0 deg. in a CuKα-characteristic X-ray diffraction pattern. 4. A photosensitive member according to claim 3, wherein the 5,10,15,20-tetrapyridyl)-21H,23H-porphyrin compound has a crystal form characterized by peaks at Bragg angles (2θ±0.2 deg.) of 8.2 deg., 19.7 deg., 20.8 deg. and 25.9 deg. 5. A photosensitive member according to claim 2, wherein the porphyrin compound is a 5,10,15,20-tetrapyridyl-21H,23H-porphyrinato-zinc compound. 6. A photosensitive member according to claim 5, wherein the porphyrin compound is a 5,10,15,20-tetrapyridyl-21H,23H-porphyrinato-zinc compound having a crystal form selected from the group consisting of (a), (b), (c) and (d) shown below:(a) a crystal form characterized by peaks at Bragg angles (2θ±0.2 deg.) of 9.4 deg., 14.2 deg. and 22.2 deg.,(b) a crystal form characterized by peaks at Bragg angles (2θ±0.2 deg.) of 7.0 deg., 10.5 deg. and 22.4 deg.,(c) a crystal form characterized by peaks at Bragg angles (2θ±0.2 deg.) of 7.4 deg., 10.2 deg. and 18.3 deg., and(d) a crystal form characterized by peaks at Bragg angles (2θ±0.2 deg.) of 9.1 deg., 10.6 deg., 11.2 deg. and 14.5 deg., respectively in CuKα-characteristic X-ray diffraction patterns. 7. A photosensitive member according to claim 6, wherein the porphyrin compound is a 5,10,15,20-tetrapyridyl-21H,23H-porphyrinato-zinc compound having the crystal form (a). 8. A photosensitive member according to claim 6, wherein the porphyrin compound is a 5,10,15,20-tetrapyridyl-21H,23H-porphyrinato-zinc compound having the crystal form (b). 9. A photosensitive member according to claim 6, wherein the porphyrin compound is a 5,10,15,20-tetrapyridyl-21H,23H-porphyrinato-zinc compound having the crystal form (c). 10. A photosensitive member according to claim 6, wherein the porphyrin compound is a 5,10,15,20-tetrapyridyl-21H,23H-porphrinato-zinc compound having the crystal form (d). 11. A process-cartridge, comprising an electrophotographic photosensitive member comprising a photosensitive layer, disposed on a support, and at least one means selected from the group consisting of a charging means, a developing means and a cleaning means and integrally supported together with the electrophotographic photosensitive member to form a unit, which is detachably mountable to an electrophotographic apparatus,wherein the photosensitive layer contains a binder resin and a porphyrin compound as a charge generating material having a structure represented by formula (1) shown below:wherein M denotes hydrogen atoms or a metal capable of having an axial ligand; R 11 to R 18 independently denote a hydrogen atom, an alkyl group capable of having a substituent, an aromatic ring capable of having a substituent, an amino group capable of having a substituent, a sulfur atom capable of having a substituent, an alkoxy group, a halogen atom, a nitro group or a cyano group; and A 11 to A 14 independently denote a hydrogen atom, an alkyl group capable of having a substituent, an aromatic ring capable of having a substituent or a heterocyclic ring capable a having a substituent with the proviso that at least one of A 11 to A 14 is a pyridyl group capable of having a substituent. 12. An electrophotographic apparatus, comprising: an electrophotographic photosensitive member comprising a photosensitive layer disposed on a support, a charging means, an exposure means, a developing means and a transfer means,wherein the photosensitive layer contains a binder resin and a porphyrin compound having a structure represented by formula (1) shown below:wherein M denotes hydrogen atoms or a metal capable of having an axial ligand; R 11 to R 18 independently denote a hydrogen atom, an alkyl group capable of having a substituent, an aromatic ring capable of having a substituent, an amino group capable of having a substituent, a sulfur atom capable of having a substituent, an alkoxy group, a halogen atom, a nitro group or a cyano group; and A 11 to A 14 independently denote a hydrogen atom, an alkyl group capable of having a substituent, an aromatic ring capable of having a substituent or a heterocyclic ring capable of having a substituent with the proviso that at least one of A 11 to A 14 is a pyridyl group capable of having a substituent. 13. An electrophotographic apparatus according to claim 12, wherein the exposure means comprises a semiconductor laser having an oscillation wavelength in a range of 380-500 nm. 14. An electrophotographic apparatus according to claim 13, wherein the semiconductor laser has an oscillation wavelength in a range of 400-450 nm. 15. A process-cartridge, comprising an electrophotographic photosensitive member comprising a photosensitive layer disposed on a support, and at least one means selected from the group consisting of a charging means, a developing means and a cleaning means and integrally supported together with the electrophotographic photosensitive member to form a unit, which is detachably mountable to an electrophotographic apparatus,wherein the photosensitive layer contains a binder resin and a porphyrin compound as a charge generating material having a structure represented by formula (1) shown below:wherein M denotes hydrogen atoms or a metal capable of having an axial ligand; R 11 to R 18 independently denote a hydrogen atom, an alkyl group capable of having a substituent, an aromatic ring capable of having a substituent, an amino group capable of having a substituent, a sulfur atom capable of having a substituent, an alkoxy group, a halogen atom, a nitro group or a cyano group; and A 11 to A 14 independently denote a pyridyl group, said porphyrin compound being a 5,10,15,20-tetrapyridyl-21H, 23H-porphyrin compound which has a crystal form characterizcd by peaks at Bragg angle (2θ±0.2 deg) of 8.2 deg; 19.7 deg., 20.8 deg., and 25.9 deg. 16. A process-cartridge, comprising an electrophotographic photosensitive member comprising a photosensitive layer disposed on a support, and at least one means selected from the group consisting of a charging means, a developing means and a cleaning means and integrally supported together with the electrophotographic photosensitive member to form a unit, which is detachably mountable to an electrophotographic apparatus,wherein the photosensitive layer contains a binder resin and, as charge generating material, a porphyrin compound being a 5,10,15,20-tetrapyridyl-21H, 23H-porphyrinato-zinc compound having a structure represented by formula (I) shown below:wherein M denotes zinc; R 11 to R 18 independently denote a hydrogen atom, an alkyl group capable of having a substituent, an aromatic ring capable of having a substituent, an amino group capable of having a substituent, a sulfur atom capable of having a substituent, an alkoxy group, a halogen atom, a nitro group or a cyano group; and A 11 to A 14 independently denote a pyridyl group, having a crystal form selected from the group consisting of (a), (b), (c) and (d) shown below:(a) a crystal form characteriaed by peaks at Bragg angles (2θ±0.2 deg.) of 9.4 deg., 14.2 deg. and 22.2 deg.,(b) a crystal form characterized by peaks at Bragg angles (2θ±0.2 deg.) of 7.0 deg., 10.5 deg. and 22.4 deg.,(c) a crystal form characterized by peaks at Bragg angles (2θ±0.2 deg.) of 7.4 deg., 10.2 deg.and 18.3 deg., and(d) a crystal form characterized by peaks at Bragg angles (2θ±0.2 deg.) of 9.1 deg., 10.6 deg., 11.2 deg. and 14.5 deg., respectively in CuKα-characteristic X-ray diffraction pattern. 17. An electrophotographic apparatus, comprising an electrophotographic photographic photosensitive member comprising a photosensitive layer disposed on a support, a charging means, an exposure means, a developing means and a transfer means,wherein the photosensitive layer contains a binder resin and a porphyrin compound as a charge generating material having a structure represented by formula (1) shown below:wherein M denotes a hydrogen atoms or a metal capable of having an axial ligand; R 11 to R 18 independently denote a hydrogen atom, an alkyl group capable of having a substituent, an aromatic ring capable of having a substituent, an amino group capable of having a substituent, a sulfur atom capable of having a substituent, an alkoxy group, a halogen atom, a nitro group or a cyano group; and A 11 to A 14 independently denote a pyridyl group, said porphyrin compound being a 5,10,15,20-tetrapyridyl-21H, 23H-porphyrin compound which has a crystal form characterized by peaks at Bragg angle (2θ±0.2 deg) of 8.2 deg; 19.7 deg.; 20.8 deg., and 25.9 deg. 18. An electrophotographic apparatus, comprising:an electrophotographic photosensitive member comprising a photosensitive layer disposed on a support, a charging means, an exposure means, a developing means and a transfer means,wherein the photosensitive layer contains a binder resin and, as a charge generating material, a porphyrin compound being a 5,10,15,20-tetrapyridyl-21H, 23H-porphyrinato-zinc having a structure represented by formula (I) shown below;wherein M denotes zinc; R 11 to R 18 independently denote a hydrogen atom, an alkyl group capable of having a substituent, an aromatic ring capable of having a substituent, an amino group capable of having a substituent, a sulfur atom capable of having a substituent, an alkoxy group, a halogen atom, a nitro group or a cyano group; and A 11 to A 14 independently denote a pyridyl group, having a crystal form selected from the group consisting of (a), (b), (c) and (d) shown below:(a) a crystal form characterized by peaks at Bragg angles (2θ±0.2 deg.) of 9.4 deg., 14.2 deg. and 22.2 deg.,(b) a crystal form characterized by peaks at Bragg angles (2θ±0.2 deg.) of 7.0 deg., 10.5 deg. and 22.4 deg.,(c) a crystal form characterized by peaks at Bragg angles (2θ±0.2 deg.) of 7.4 deg., 10.2 deg. and 18.3 deg., and(d) a crystal form characterized by peaks at Bragg angles (2θ±0.2 deg.) of 9.1 deg., 10.6 deg., 11.2 deg. and 14.5 deg., respectively in CuKα-characteristic X-ray diffraction pattern.
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