JPH0435065B2 - - Google Patents
Info
- Publication number
- JPH0435065B2 JPH0435065B2 JP23624983A JP23624983A JPH0435065B2 JP H0435065 B2 JPH0435065 B2 JP H0435065B2 JP 23624983 A JP23624983 A JP 23624983A JP 23624983 A JP23624983 A JP 23624983A JP H0435065 B2 JPH0435065 B2 JP H0435065B2
- Authority
- JP
- Japan
- Prior art keywords
- charge
- amount
- resin
- phenylenediamine
- pigment
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 229920005989 resin Polymers 0.000 claims description 20
- 239000011347 resin Substances 0.000 claims description 20
- 108091008695 photoreceptors Proteins 0.000 claims description 11
- 239000000049 pigment Substances 0.000 description 14
- 230000007423 decrease Effects 0.000 description 9
- 239000000203 mixture Substances 0.000 description 6
- 230000014759 maintenance of location Effects 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 150000004986 phenylenediamines Chemical class 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 239000004925 Acrylic resin Substances 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- 150000004989 p-phenylenediamines Chemical class 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- QIUGUNHEXAZYIY-UHFFFAOYSA-N 1,2-dinitroacridine Chemical compound C1=CC=CC2=CC3=C([N+]([O-])=O)C([N+](=O)[O-])=CC=C3N=C21 QIUGUNHEXAZYIY-UHFFFAOYSA-N 0.000 description 1
- NMNSBFYYVHREEE-UHFFFAOYSA-N 1,2-dinitroanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C([N+]([O-])=O)C([N+](=O)[O-])=CC=C3C(=O)C2=C1 NMNSBFYYVHREEE-UHFFFAOYSA-N 0.000 description 1
- WQGWMEKAPOBYFV-UHFFFAOYSA-N 1,5,7-trinitrothioxanthen-9-one Chemical compound C1=CC([N+]([O-])=O)=C2C(=O)C3=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C3SC2=C1 WQGWMEKAPOBYFV-UHFFFAOYSA-N 0.000 description 1
- JOERSAVCLPYNIZ-UHFFFAOYSA-N 2,4,5,7-tetranitrofluoren-9-one Chemical compound O=C1C2=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C2C2=C1C=C([N+](=O)[O-])C=C2[N+]([O-])=O JOERSAVCLPYNIZ-UHFFFAOYSA-N 0.000 description 1
- VHQGURIJMFPBKS-UHFFFAOYSA-N 2,4,7-trinitrofluoren-9-one Chemical compound [O-][N+](=O)C1=CC([N+]([O-])=O)=C2C3=CC=C([N+](=O)[O-])C=C3C(=O)C2=C1 VHQGURIJMFPBKS-UHFFFAOYSA-N 0.000 description 1
- DCJKUXYSYJBBRD-UHFFFAOYSA-N 2,5-diphenyl-1,3,4-oxadiazole Chemical compound C1=CC=CC=C1C1=NN=C(C=2C=CC=CC=2)O1 DCJKUXYSYJBBRD-UHFFFAOYSA-N 0.000 description 1
- HDVGAFBXTXDYIB-UHFFFAOYSA-N 2,7-dinitrofluoren-9-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)C3=CC([N+](=O)[O-])=CC=C3C2=C1 HDVGAFBXTXDYIB-UHFFFAOYSA-N 0.000 description 1
- OEEJLOZQSKNWQQ-UHFFFAOYSA-N 2-nitro-1-benzothiophene Chemical compound C1=CC=C2SC([N+](=O)[O-])=CC2=C1 OEEJLOZQSKNWQQ-UHFFFAOYSA-N 0.000 description 1
- AJEAHBZZHSLIQP-UHFFFAOYSA-N 2-nitrofluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC([N+](=O)[O-])=CC=C3C2=C1 AJEAHBZZHSLIQP-UHFFFAOYSA-N 0.000 description 1
- WUPHOULIZUERAE-UHFFFAOYSA-N 3-(oxolan-2-yl)propanoic acid Chemical compound OC(=O)CCC1CCCO1 WUPHOULIZUERAE-UHFFFAOYSA-N 0.000 description 1
- BZKRKPGZABEOSM-UHFFFAOYSA-N 4-[2-[3-[4-(diethylamino)phenyl]-2-phenyl-3,4-dihydropyrazol-5-yl]ethenyl]-n,n-diethylaniline Chemical compound C1=CC(N(CC)CC)=CC=C1C=CC1=NN(C=2C=CC=CC=2)C(C=2C=CC(=CC=2)N(CC)CC)C1 BZKRKPGZABEOSM-UHFFFAOYSA-N 0.000 description 1
- YCHDSDSNBXYNHE-UHFFFAOYSA-N 4-[3-[4-(diethylamino)phenyl]-1h-1,2,4-triazol-5-yl]-n,n-diethylaniline Chemical compound C1=CC(N(CC)CC)=CC=C1C1=NN=C(C=2C=CC(=CC=2)N(CC)CC)N1 YCHDSDSNBXYNHE-UHFFFAOYSA-N 0.000 description 1
- VRKQEIXDEZVPSY-UHFFFAOYSA-N 4-n-phenyl-4-n-propan-2-ylbenzene-1,4-diamine Chemical compound C=1C=C(N)C=CC=1N(C(C)C)C1=CC=CC=C1 VRKQEIXDEZVPSY-UHFFFAOYSA-N 0.000 description 1
- YFZNTUOMAQXCQZ-UHFFFAOYSA-N 4-n-propan-2-ylbenzene-1,4-diamine Chemical compound CC(C)NC1=CC=C(N)C=C1 YFZNTUOMAQXCQZ-UHFFFAOYSA-N 0.000 description 1
- GMTFCGRJROKMAJ-UHFFFAOYSA-N 5-(1h-imidazol-2-yl)benzene-1,2,4-triamine Chemical compound C1=C(N)C(N)=CC(N)=C1C1=NC=CN1 GMTFCGRJROKMAJ-UHFFFAOYSA-N 0.000 description 1
- XYPMAZCBFKBIFK-UHFFFAOYSA-N 9,10-dinitroanthracene Chemical compound C1=CC=C2C([N+](=O)[O-])=C(C=CC=C3)C3=C([N+]([O-])=O)C2=C1 XYPMAZCBFKBIFK-UHFFFAOYSA-N 0.000 description 1
- PLAZXGNBGZYJSA-UHFFFAOYSA-N 9-ethylcarbazole Chemical compound C1=CC=C2N(CC)C3=CC=CC=C3C2=C1 PLAZXGNBGZYJSA-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- CARVRJHOKWFHAI-UHFFFAOYSA-N [3-(4-aminoanilino)-2-hydroxypropyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)CNC1=CC=C(N)C=C1 CARVRJHOKWFHAI-UHFFFAOYSA-N 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 229910052980 cadmium sulfide Inorganic materials 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- JGOAZQAXRONCCI-SDNWHVSQSA-N n-[(e)-benzylideneamino]aniline Chemical compound C=1C=CC=CC=1N\N=C\C1=CC=CC=C1 JGOAZQAXRONCCI-SDNWHVSQSA-N 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000001132 ultrasonic dispersion Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- -1 γ-methacryloxy-β-hydroxypropyl group Chemical group 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
- G03G5/0601—Acyclic or carbocyclic compounds
- G03G5/0618—Acyclic or carbocyclic compounds containing oxygen and nitrogen
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/05—Organic bonding materials; Methods for coating a substrate with a photoconductive layer; Inert supplements for use in photoconductive layers
- G03G5/0503—Inert supplements
- G03G5/051—Organic non-macromolecular compounds
- G03G5/0517—Organic non-macromolecular compounds comprising one or more cyclic groups consisting of carbon-atoms only
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Photoreceptors In Electrophotography (AREA)
Description
【発明の詳細な説明】
本発明は、電子写真感光体に関するもので、よ
り詳細には、反復複写時における帯電量の減衰傾
向に対して耐性を有する電子写真感光体に関す
る。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to an electrophotographic photoreceptor, and more particularly, to an electrophotographic photoreceptor that is resistant to the tendency of charge amount to decrease during repeated copying.
従来、電子写真感光体の１種として、光導電性
顔料を電気絶縁性の結着剤樹脂中に分散させた組
成物の層を導電性基質上に設けたものや、導電性
基質上に電荷発生顔料の層及びその上に電荷輸送
性を有する樹脂層を設けたもの、更には、上記電
荷輸送媒質中に電荷発生顔料を分散させた組成物
を導電性基質上に設けたもの等が知られている。 Conventionally, as a type of electrophotographic photoreceptor, there has been one in which a layer of a composition in which a photoconductive pigment is dispersed in an electrically insulating binder resin is provided on a conductive substrate, or one in which a layer of a composition in which a photoconductive pigment is dispersed in an electrically insulating binder resin is provided on a conductive substrate, Examples include a layer of a generating pigment and a resin layer having charge transporting properties thereon, and furthermore, a composition comprising a charge generating pigment dispersed in the charge transporting medium on a conductive substrate. It is being
これらの電子写真感光体は、感光層中に樹脂を
含有することに関連して、静電像形成、トナー像
形成、トナー像転写の各工程を反復する複写に用
いた場合、一つの欠点を有することが認められ
る。その欠点とは、感光体の使用初期において
は、比較的高い帯電量（帯電電位）が得られると
しても、反復複写回数の増加に伴ない、この帯電
量が著しく減少することが認められる。この帯電
量の減衰傾向は、樹脂がコロナ放電、特にオゾン
の攻撃により劣化するためと思われる。このよう
な帯電量の減衰傾向は、感光層の感度低下を伴な
つて生じる場合もある。 These electrophotographic photoreceptors have one drawback when used for copying in which the steps of electrostatic image formation, toner image formation, and toner image transfer are repeated due to the fact that they contain a resin in the photosensitive layer. It is permitted to have. The drawback is that even though a relatively high amount of charge (charging potential) can be obtained in the initial stage of use of the photoreceptor, this amount of charge decreases significantly as the number of repeated copies increases. This tendency for the amount of charge to decrease is thought to be due to the resin being degraded by corona discharge, particularly by attack by ozone. Such a tendency to attenuate the amount of charge may be accompanied by a decrease in sensitivity of the photosensitive layer.
本発明者等は、以下に述べる特定のフエニレン
ジアミンを感光層中に配合することにより、反復
複写時における帯電量の減衰傾向が有効に改善さ
れることを見出した。 The present inventors have discovered that by incorporating a specific phenylenediamine described below into the photosensitive layer, the tendency of the charge amount to decrease during repeated copying can be effectively improved.
本発明によれば、Ｎ−フエニル−N′−γ−メ
タクリルオキシ−β−ヒドロキシ−プロピル−ｐ
−フエニレンジアミンを含有する感光層を備えて
成ることを特徴とする電子写真感光体が提供され
る。 According to the invention, N-phenyl-N′-γ-methacryloxy-β-hydroxy-propyl-p
- There is provided an electrophotographic photoreceptor comprising a photosensitive layer containing phenylenediamine.
本発明に用いるフエニレンジアミン誘導体は、
下記式
で表わされる化学構造を有する。上記構造式から
明らかな通り、この誘導体は、フエニレンジアミ
ン骨格に結合したγ−メタクリルオキシ−β−ヒ
ドロキシプロピル基を有することが特徴であり、
類縁のフエニレンジアミン誘導体は、例えばＮ−
フエニル−N′−イソプロピル−ｐ−フエニレン
ジアミンに比して、帯電量の減衰傾向に対する耐
性において優れている。 The phenylenediamine derivative used in the present invention has the following formula: It has a chemical structure represented by As is clear from the above structural formula, this derivative is characterized by having a γ-methacryloxy-β-hydroxypropyl group bonded to a phenylenediamine skeleton,
Related phenylenediamine derivatives include, for example, N-
It is superior to phenyl-N'-isopropyl-p-phenylenediamine in terms of resistance to the tendency for charge amount to decrease.
上記ｐ−フエニレンジアミン誘導体は、感光層
中の樹脂当り0.1乃至1.0重量％、特に0.3乃至0.7
重量％の量で配合するのがよい。即ちｐ−フエニ
レンジアミン誘導体の配合量が上記範囲よりも低
い場合には、反復複写時における帯電量減衰を実
質上防止することが困難であり、一方この配合量
が上記範囲を越えると、該誘導体を配合すること
によつて帯電量そのものが初期から減少するよう
になる。 The above p-phenylenediamine derivative is contained in an amount of 0.1 to 1.0% by weight, particularly 0.3 to 0.7% by weight, based on the resin in the photosensitive layer.
It is preferable to mix it in an amount of % by weight. That is, if the amount of the p-phenylenediamine derivative is lower than the above range, it is difficult to substantially prevent the charge amount from decreasing during repeated copying, while if the amount exceeds the above range, By incorporating the derivative, the amount of charge itself can be reduced from the initial stage.
電子写真感光体の帯電量の減衰傾向は、反復複
写回数と帯電電位とをプロツトすることにより確
認し得る。添付図面第１図において、曲線Ａは、
染料増感光導電性酸化亜鉛−樹脂分散体から成る
感光層の帯電量減衰傾向、曲線Ｂは、上記感光層
中に、樹脂当り0.5重量％のＮ−フエニル−N′−
γ−メタクリルオキシ−β−ヒドロキシ−プロピ
ル−ｐ−フエニレンジアミンを配合したものの帯
電量減衰傾向を示す。この図面から、本発明の感
光体では未配合のものに比して帯電量減衰傾向が
なだらかであり、3000枚複写後における帯電量保
持率が、未配合のものでは68％であるのに対し
て、本発明のものでは84％であつて、顕著に優れ
ていることがわかる。因みに、Ｎ−フエニル−
N′−イソプロピル−ｐ−フエニレンジアミンで
はこの保持率は76％であり、本発明のものが優れ
ていることがわかる。 The tendency of the charge amount of the electrophotographic photoreceptor to decrease can be confirmed by plotting the number of repeated copies versus the charging potential. In FIG. 1 of the accompanying drawings, curve A is
Curve B shows the charge decay tendency of a photosensitive layer made of a dye-sensitized photoconductive zinc oxide-resin dispersion.
The graph shows the tendency of the charge amount to decrease when γ-methacryloxy-β-hydroxy-propyl-p-phenylenediamine is blended. From this drawing, it can be seen that in the photoreceptor of the present invention, the charge amount decay tendency is gentler than that of the one without the compound, and the charge retention rate after copying 3,000 sheets is 68% in the photoconductor without the compound. It can be seen that the value of the present invention is 84%, which is significantly superior. By the way, N-phenyl-
For N'-isopropyl-p-phenylenediamine, this retention rate was 76%, which shows that the product of the present invention is superior.
感光層の形成に用いられる樹脂としては、従来
のこの分野に使用されている任意の樹脂、例えば
エポキシ樹脂、シリコーン樹脂、ウレタン樹脂、
アクリル樹脂、飽和ポリエステル樹脂、ポリカー
ボネート樹脂、アルキド樹脂、ビニル樹脂等の電
気絶縁性樹脂や、ポリビニルカルバゾール等の光
導電性樹脂を挙げることができる。 As the resin used for forming the photosensitive layer, any resin conventionally used in this field, such as epoxy resin, silicone resin, urethane resin,
Examples include electrically insulating resins such as acrylic resins, saturated polyester resins, polycarbonate resins, alkyd resins, and vinyl resins, and photoconductive resins such as polyvinyl carbazole.
感光層の種類は、前に例示した３種のタイプの
何れであつてもよい。例えば、光導電性顔料−樹
脂分散体タイプのものでは、前述したフエニレン
ジアミン誘導体を配合した樹脂層中に、染料増感
酸化亜鉛、硫化カドミウム等を分散させて感光層
とする。光導電性顔料と樹脂との比率は、重量で
20：１乃至２：１の範囲とすることができる。 The type of photosensitive layer may be any of the three types exemplified above. For example, in the case of a photoconductive pigment-resin dispersion type, dye-sensitized zinc oxide, cadmium sulfide, etc. are dispersed in a resin layer containing the aforementioned phenylenediamine derivative to form a photosensitive layer. The ratio of photoconductive pigment to resin is
It can be in the range of 20:1 to 2:1.
機能分離型の多層感光層の場合には、導電性基
質上に、フタロシアニン顔料、ペリレン系顔料、
ジスアゾ顔料、トリスアゾ顔料、キナクリドン顔
料等の電荷発生顔料を蒸着層或いは樹脂顔料分散
体層として設け、この上に、前述したフエニレン
ジアミン誘導体を前述した量比で含み、更に電荷
輸送物質を含む樹脂層を設ける。 In the case of a functionally separated multilayer photosensitive layer, phthalocyanine pigments, perylene pigments,
A charge generating pigment such as a disazo pigment, a trisazo pigment, or a quinacridone pigment is provided as a vapor deposited layer or a resin pigment dispersion layer, and a resin containing the above-mentioned phenylenediamine derivative in the above-mentioned amount ratio and further containing a charge transporting substance is provided thereon. Provide layers.
電荷輸送物質としては、それ自体公知の正孔輸
送物質或いは電子輸送物質が何れも本発明の目的
に使用される。適当な正孔輸送物質の例は、
ポリ−Ｎ−ビニルカルバゾール、フエナントレ
ン、Ｎ−エチルカルバゾール、２，５−ジフエニ
ル−１，３，４−オキサジアゾール、２，５−ビ
ス（４−ジエチルアミノフエニル）−１，３，４
−オキサジアゾール、ビス−ジエチルアミノフエ
ニル−１，３，６−オキサジアゾール、４，4′−
ビス（ジエチルアミノ）−２，2′−ジメチルトリ
フエニルメタン、２，４，５−トリアミノフエニ
ルイミダゾール、２，５−ビス（４−ジエチルア
ミノフエニル）−１，３，４−トリアゾール、１
−フエニル−３−（４−ジエチルアミノスチリル）
−５−（４−ジエチルアミノフエニル）−２−ピラ
ゾリン、ｐ−ジエチルアミノベンツアルデヒド−
（ジフエニルヒドラゾン）などであり、適当な電
荷輸送物質の例は２−ニトロ−９−フルオレノ
ン、２，７−ジニトロ−９−フルオレノン、２，
４，７−トリニトロ−９−フルオレノン、２，
４，５，７−テトラニトロ−９−フルオレノン、
２−ニトロベンゾチオフエン、２，４，８−トリ
ニトロチオキサントン、ジニトロアントラセン、
ジニトロアクリジン、ジニトロアントラキノンな
どである。 As the charge transport substance, any hole transport substance or electron transport substance known per se can be used for the purpose of the present invention. Examples of suitable hole transport materials are poly-N-vinylcarbazole, phenanthrene, N-ethylcarbazole, 2,5-diphenyl-1,3,4-oxadiazole, 2,5-bis(4-diethylaminophyl). enyl)-1,3,4
-oxadiazole, bis-diethylaminophenyl-1,3,6-oxadiazole, 4,4'-
Bis(diethylamino)-2,2'-dimethyltriphenylmethane, 2,4,5-triaminophenyl imidazole, 2,5-bis(4-diethylaminophenyl)-1,3,4-triazole, 1
-Phenyl-3-(4-diethylaminostyryl)
-5-(4-diethylaminophenyl)-2-pyrazoline, p-diethylaminobenzaldehyde-
(diphenylhydrazone), and examples of suitable charge transport materials are 2-nitro-9-fluorenone, 2,7-dinitro-9-fluorenone, 2,
4,7-trinitro-9-fluorenone, 2,
4,5,7-tetranitro-9-fluorenone,
2-nitrobenzothiophene, 2,4,8-trinitrothioxanthone, dinitroanthracene,
These include dinitroacridine and dinitroanthraquinone.
電荷輸送物質は、高分子の場合は単独で、或い
は前に例示した樹脂補強剤との組合せで使用さ
れ、低分子物質の場合は、樹脂当り１乃至30重量
％の量で配合して用いる。 When the charge transport material is a polymer, it is used alone or in combination with the resin reinforcing agent exemplified above, and when it is a low molecular material, it is used in an amount of 1 to 30% by weight based on the resin.
また、電荷輸送媒質中電荷発生顔料分散構造の
感光体では、電荷発生顔料を、媒質当り１乃至40
重量％の量で分散させて用いる。 In addition, in a photoreceptor having a structure in which a charge-generating pigment is dispersed in a charge-transporting medium, the amount of the charge-generating pigment is 1 to 40 per medium.
It is used by dispersing it in an amount of % by weight.
本発明を次の例で説明する。 The invention is illustrated by the following example.
実施例 １
酸化亜鉛（SOX−100、正同化学工業社製）
10ｇ
アクリル樹脂（LR−108、三菱レーヨン社
製、solid40％） ５ｇ
ローズベンガル（2wt％MeOH溶液） ２ml
トルエン 10ｇ
Ｎ−フエニル−N′−γ−メタクリルオキシ
−β−ヒドロキシプロピル−ｐ−フエニレンジア
ミン 0.01ｇ
上記処方の混合物を超音波分散機により分散し
た塗布液を、アルミ箔をラミネートしたポリエス
テルフイルムのアルミ面上に、ワイヤーバーにて
塗工量25ｇ／m2で塗布、乾燥し、感光板を得た。Example 1 Zinc oxide (SOX-100, manufactured by Seido Kagaku Kogyo Co., Ltd.)
10g Acrylic resin (LR-108, manufactured by Mitsubishi Rayon Co., Ltd., solid 40%) 5g Rose Bengal (2wt% MeOH solution) 2ml Toluene 10g N-phenyl-N'-γ-methacryloxy-β-hydroxypropyl-p-phenylenediamine 0.01g A coating solution prepared by dispersing the mixture of the above formulation using an ultrasonic dispersion machine is applied onto the aluminum surface of a polyester film laminated with aluminum foil at a coating amount of 25g/m 2 using a wire bar, dried, and coated on a photosensitive plate. I got it.
この感光板に対して、印加電圧−6.0kvolt、後
照射光量白色タングステンランプ40luxを照射し、
初期における特性を測定したところ、感度26
（lux・sec）、帯電量560voltと良好な特性を得た。 This photosensitive plate was irradiated with a white tungsten lamp with an applied voltage of -6.0 kvolt and a post-irradiation light intensity of 40 lux.
When we measured the initial characteristics, the sensitivity was 26.
(lux・sec) and a charge amount of 560 volts, good characteristics were obtained.
次に、感光板をドラムに装着し、印加電圧を
7.2kvoltに設定し、帯電−露光の工程を繰り返し
た。１サイクル目の表面電位をV1とし、各サイ
クル目の表面電位をVnとし、次式により表面電
位保持率を求めた。 Next, attach the photosensitive plate to the drum and apply the voltage.
The voltage was set to 7.2 kvolt and the charging-exposure process was repeated. The surface potential at the first cycle was V1 , the surface potential at each cycle was Vn, and the surface potential retention rate was determined by the following formula.
表面電位保持率＝V1／Vn×100（％）
実験では、4000サイクルまで行なつた。その結
果を第１図の曲線Ｂで表わした。 Surface potential retention rate=V 1 /Vn×100 (%) In the experiment, up to 4000 cycles were performed. The results are represented by curve B in FIG.
比較例
実施例の処方から、Ｎ−フエニル−N′−γ−
メタクリルオキシ−β−ヒドロキシプロピル−ｐ
−フエニレンジアミンを除く以外はまつたく同様
にして感光板を作製した。Comparative Example From the formulation of the example, N-phenyl-N'-γ-
methacryloxy-β-hydroxypropyl-p
- A photosensitive plate was prepared in the same manner as Matsutaku except that phenylenediamine was omitted.
初期特性の測定結果は感度30lux・sec、帯電量
597voltと良好であつた。 Initial characteristic measurement results are sensitivity 30lux・sec, charge amount
It was good at 597 volts.
また、繰り返し特性においては、実施例と同様
な測定方法で行なつた。その結果を第１図の曲線
Ａで表わした。 In addition, the repeatability was measured using the same measurement method as in the examples. The results are represented by curve A in FIG.
第１図からも明らかなように、実施例での感光
板が比較例と比べて表面電位の保持率は、良好で
あつた。 As is clear from FIG. 1, the surface potential retention rate of the photosensitive plate in the example was better than that in the comparative example.
第１図は、実施例、比較例での感光板の帯電量
の減衰傾向を示したグラフである。
FIG. 1 is a graph showing the tendency of the charge amount of the photosensitive plate to decrease in Examples and Comparative Examples.
Claims (1)
−β−ヒドロキシ−プロピル−ｐ−フエニレンジ
アミンを含有する感光層を備えて成ることを特徴
とする電子写真感光体。 ２ Ｎ−フエニル−N′−γ−メタクリルオキシ
−β−ヒドロキシ−プロピル−ｐ−フエニレンジ
アミンは、感光層の樹脂当り0.1乃至1.0重量％の
量で存在する特許請求の範囲第１項記載の感光
体。[Scope of Claims] 1. An electrophotographic photoreceptor comprising a photosensitive layer containing 1 N-phenyl-N'-γ-methacryloxy-β-hydroxy-propyl-p-phenylenediamine. 2 N-phenyl-N'-γ-methacryloxy-β-hydroxy-propyl-p-phenylenediamine is present in an amount of 0.1 to 1.0% by weight based on the resin of the photosensitive layer. Photoreceptor.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP23624983A JPS60129754A (en) | 1983-12-16 | 1983-12-16 | Electrophotographic sensitive body |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP23624983A JPS60129754A (en) | 1983-12-16 | 1983-12-16 | Electrophotographic sensitive body |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60129754A JPS60129754A (en) | 1985-07-11 |
| JPH0435065B2 true JPH0435065B2 (en) | 1992-06-09 |
Family
ID=16997983
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP23624983A Granted JPS60129754A (en) | 1983-12-16 | 1983-12-16 | Electrophotographic sensitive body |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60129754A (en) |
-
1983
- 1983-12-16 JP JP23624983A patent/JPS60129754A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60129754A (en) | 1985-07-11 |
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