JPH01107264A - Electrophotographic sensitive body - Google Patents
Electrophotographic sensitive bodyInfo
- Publication number
- JPH01107264A JPH01107264A JP26575187A JP26575187A JPH01107264A JP H01107264 A JPH01107264 A JP H01107264A JP 26575187 A JP26575187 A JP 26575187A JP 26575187 A JP26575187 A JP 26575187A JP H01107264 A JPH01107264 A JP H01107264A
- Authority
- JP
- Japan
- Prior art keywords
- charge
- photoreceptor
- group
- layer
- weight
- 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.)
- Pending
Links
- -1 (substituted)amino group Chemical group 0.000 claims abstract description 20
- 125000003118 aryl group Chemical group 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 2
- 108091008695 photoreceptors Proteins 0.000 claims description 46
- 239000000126 substance Substances 0.000 claims description 27
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 230000035945 sensitivity Effects 0.000 abstract description 7
- 150000007857 hydrazones Chemical class 0.000 abstract description 4
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 46
- 239000000463 material Substances 0.000 description 19
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- 239000011347 resin Substances 0.000 description 14
- 229920005989 resin Polymers 0.000 description 14
- 239000000758 substrate Substances 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000011230 binding agent Substances 0.000 description 12
- 239000011248 coating agent Substances 0.000 description 12
- 238000000576 coating method Methods 0.000 description 12
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class 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 11
- 239000000243 solution Substances 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 10
- 239000011247 coating layer Substances 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- 238000001035 drying Methods 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 7
- 239000002904 solvent Substances 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 5
- 239000011368 organic material Substances 0.000 description 5
- 239000004926 polymethyl methacrylate Substances 0.000 description 5
- 229920001225 polyester resin Polymers 0.000 description 4
- 239000004645 polyester resin Substances 0.000 description 4
- 239000004952 Polyamide Substances 0.000 description 3
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 3
- 229910010272 inorganic material Inorganic materials 0.000 description 3
- 239000011147 inorganic material Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 229920002647 polyamide Polymers 0.000 description 3
- 229910052711 selenium Inorganic materials 0.000 description 3
- 239000011669 selenium Substances 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 238000004898 kneading Methods 0.000 description 2
- 230000031700 light absorption Effects 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920006267 polyester film Polymers 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 229920002050 silicone resin Polymers 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- WUPHOULIZUERAE-UHFFFAOYSA-N 3-(oxolan-2-yl)propanoic acid Chemical compound OC(=O)CCC1CCCO1 WUPHOULIZUERAE-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 235000000177 Indigofera tinctoria Nutrition 0.000 description 1
- 239000004419 Panlite Substances 0.000 description 1
- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- 229910001370 Se alloy Inorganic materials 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 235000010724 Wisteria floribunda Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229910052980 cadmium sulfide Inorganic materials 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000005496 eutectics Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 229940097275 indigo Drugs 0.000 description 1
- COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000007885 magnetic separation Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 229920003145 methacrylic acid copolymer Polymers 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- SJHHDDDGXWOYOE-UHFFFAOYSA-N oxytitamium phthalocyanine Chemical compound [Ti+2]=O.C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 SJHHDDDGXWOYOE-UHFFFAOYSA-N 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- 229920003217 poly(methylsilsesquioxane) Polymers 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical class C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 description 1
- 229940065287 selenium compound Drugs 0.000 description 1
- 150000003343 selenium compounds Chemical class 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 229920005573 silicon-containing polymer Polymers 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 1
- 238000001132 ultrasonic dispersion Methods 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/28—Halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/42—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms with nitro or nitroso radicals directly attached to ring carbon atoms
- C07D333/44—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms with nitro or nitroso radicals directly attached to ring carbon atoms attached in position 5
-
- 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
- G03G5/0622—Heterocyclic compounds
- G03G5/0624—Heterocyclic compounds containing one hetero ring
- G03G5/0627—Heterocyclic compounds containing one hetero ring being five-membered
- G03G5/0629—Heterocyclic compounds containing one hetero ring being five-membered containing one hetero atom
-
- 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
- G03G5/0622—Heterocyclic compounds
- G03G5/0644—Heterocyclic compounds containing two or more hetero rings
- G03G5/0661—Heterocyclic compounds containing two or more hetero rings in different ring systems, each system containing at least one hetero ring
-
- 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
- G03G5/0664—Dyes
- G03G5/0666—Dyes containing a methine or polymethine group
- G03G5/0668—Dyes containing a methine or polymethine group containing only one methine or polymethine group
- G03G5/067—Dyes containing a methine or polymethine group containing only one methine or polymethine group containing hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Photoreceptors In Electrophotography (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は電子写真用感光体に関し、詳しくは導電性基体
上に形成せしめた感光層の中に、新規なヒドラゾン化合
物を含有することを特徴とする電子写真用感光体に関す
る。[Detailed Description of the Invention] [Industrial Application Field] The present invention relates to an electrophotographic photoreceptor, and more specifically, it is characterized in that a novel hydrazone compound is contained in a photosensitive layer formed on a conductive substrate. The present invention relates to an electrophotographic photoreceptor.
従来より電子写真用感光体(以下感光体とも称する)の
感光材料としてはセレンまたはセレン合金などの無機光
導電性物質、酸化亜鉛あるいは硫化カドミウムなどの無
機光導電性物質を樹脂結着剤中に分散させたもの、ポリ
−N−ビニルカルバゾールまたはポリビニルアントラセ
ンなどの有機光導電性物質、フタロシアニン化合物ある
いはビスアゾ化合物などの有機光導電性物質、またはこ
れら有機光導電性物質を樹脂結着剤中に分散させたもの
などが利用されている。Conventionally, photosensitive materials for electrophotographic photoreceptors (hereinafter also referred to as photoreceptors) include inorganic photoconductive substances such as selenium or selenium alloys, or inorganic photoconductive substances such as zinc oxide or cadmium sulfide in a resin binder. dispersion, organic photoconductive materials such as poly-N-vinylcarbazole or polyvinylanthracene, organic photoconductive materials such as phthalocyanine compounds or bisazo compounds, or dispersion of these organic photoconductive materials in a resin binder. Those that have been made are used.
また感光体には暗所で表面電荷を保持する機能。The photoreceptor also has the ability to retain surface charge in the dark.
光を受容して電荷を発生する機能、同じく光を受容して
電荷を輸送する機能とが必要であるが、一つの層でこれ
らの機能をあわせもったいわゆる単層型感光体と、主と
して電荷発生に寄与する層と暗所での表面電荷の保持と
光受容時の電荷輸送に寄与する層とに機能分離した層を
積層したいわゆる積層型感光体がある。これらの感光体
を用いた電子写真法による画像形成には、例えばカール
ソン方式が適用される。この方式での画像形成は暗所で
の感光体へのコロナ放電による帯電、帯電された感光体
表面上への露光による原稿の文字や絵などの静電潜像の
形成、形成された静電潜像のトナーによる現像、現像さ
れたトナー像の紙などの支持体への転写、定着により行
われ、トナー像転写後の感光体は除電、残留トナーの除
去、光除電などを行った後、再使用に供される。It is necessary to have the function of receiving light and generating a charge, as well as the function of receiving light and transporting a charge. There is a so-called laminated photoreceptor in which functionally separated layers are laminated, including a layer that contributes to charge generation, a layer that contributes to surface charge retention in the dark, and a layer that contributes to charge transport during light reception. For example, the Carlson method is applied to image formation by electrophotography using these photoreceptors. Image formation in this method involves charging the photoconductor in a dark place by corona discharge, forming electrostatic latent images such as letters and pictures on the document by exposing the surface of the charged photoconductor, and This is done by developing a latent image with toner, transferring the developed toner image to a support such as paper, and fixing it. After the toner image has been transferred, the photoreceptor is subjected to static neutralization, removal of residual toner, photostatic static elimination, etc. Subject to reuse.
近年、可とう性、熱安定性、膜形成性などの利点により
、有機材料を用いた電子写真用感光体が実用化されてき
ている。例えば、ポリ−N−ビニルカルバゾールと2.
4.7−ドリニトロフルオレンー9−オンとからなる感
光体(米国特許第3484237号明細書に記載)、有
機顔料を主成分とする感光体(特開昭47−37543
号公報に記載)、染料と樹脂とからなる共晶錯体を主成
分とする感光体(特開昭47−10735号公報に記載
)などである。さらに、新規ヒドラゾン化合物も数多く
実用化されている。In recent years, electrophotographic photoreceptors using organic materials have been put into practical use due to their advantages such as flexibility, thermal stability, and film-forming properties. For example, poly-N-vinylcarbazole and 2.
4,7-dolinitrofluoren-9-one (described in U.S. Pat. No. 3,484,237), a photoreceptor containing organic pigment as a main component (JP-A-47-37543)
(described in Japanese Unexamined Patent Publication No. 10735/1983), and a photoreceptor whose main component is a eutectic complex consisting of a dye and a resin (described in Japanese Patent Application Laid-open No. 10735/1983). Furthermore, many new hydrazone compounds have also been put into practical use.
上述のように、有機材料は無機材料にない多くの長所を
持つが、しかしながら、電子写真用感光体に要求される
すべての特性を充分満足するものがまだ得られていない
のが現状であり、特に光感度および繰り返し連続使用時
の特性に問題があった。As mentioned above, organic materials have many advantages that inorganic materials do not have, but at present, no material has yet been obtained that fully satisfies all the characteristics required of electrophotographic photoreceptors. In particular, there were problems with photosensitivity and characteristics during repeated and continuous use.
本発明は、上述の点に鑑みてなされたものであって、感
光層に電荷輸送性物質として今まで用いられたことのな
い新しい有機材料を用いることにより、高感度で繰り返
し特性の優れた複写機用およびプリンタ用の電子写真用
感光体を提供することを目的とする。The present invention has been made in view of the above points, and by using a new organic material that has never been used as a charge transporting substance in the photosensitive layer, copying with high sensitivity and excellent repeatability can be achieved. The purpose of the present invention is to provide electrophotographic photoreceptors for machines and printers.
上記目的を達成するために、本発明によれば、下記一般
式(1)で示されるヒドラゾン化合物のうちの少なくと
も一種類を含む感光層を有する電子写真用感光体とする
。In order to achieve the above object, the present invention provides an electrophotographic photoreceptor having a photosensitive layer containing at least one type of hydrazone compound represented by the following general formula (1).
〔式(I)中、R1は置換基を有してもよいアリール基
を表し、R2,R3,R4,R5,R,、RvおよびR
8はそれぞれ水素原子、ハロゲン原子、アル;キシ基、
アルキル基、ニトロ基、ヒドロキシ基。[In formula (I), R1 represents an aryl group which may have a substituent, R2, R3, R4, R5, R,, Rv and R
8 is a hydrogen atom, a halogen atom, an alkyl group,
Alkyl group, nitro group, hydroxy group.
アリール基、置換されてもよいアミノ基を表し、nは整
数1,2.3.4のいずれかを表す。〕〔作用〕
前記一般式(I)で示されるヒドラゾン化合物を感光層
に用いた例は知られていない。本発明者らは、前記目的
を達成するために各種有機材料について鋭意検討を進め
るなかで、これらヒドラゾン化合物について数多くの実
験を行った結果、その技術的解明はまだ充分なされては
いないが、このような前記一般式(1)で示される特定
のヒドラゾン化合物を電荷輸送性物質として使用するこ
とが、電子写真特性の向上に極めて有効であることを見
出し、高感度で繰り返し特性の優れた感光体を得るに至
ったのである。It represents an aryl group or an optionally substituted amino group, and n represents any of the integers 1, 2.3.4. [Function] There is no known example in which a hydrazone compound represented by the general formula (I) is used in a photosensitive layer. In order to achieve the above objective, the present inventors conducted a number of experiments on these hydrazone compounds while conducting intensive studies on various organic materials. It has been discovered that the use of a specific hydrazone compound represented by the above general formula (1) as a charge transporting substance is extremely effective in improving electrophotographic properties, and a photoreceptor with high sensitivity and excellent repeatability has been developed. I was able to obtain this.
本発明に用いられる前記一般式(I)のヒドラゾン化合
物は、通常の方法により合成することができる。すなわ
ち、必要に応じて縮合剤として少量の酸を用い、アルコ
ールなどの適当な有機溶媒中でアルデヒド類またはカル
ボニル化合物とヒドラジン類を縮合させることにより得
られる。The hydrazone compound of general formula (I) used in the present invention can be synthesized by a conventional method. That is, it can be obtained by condensing aldehydes or carbonyl compounds with hydrazines in a suitable organic solvent such as alcohol, using a small amount of acid as a condensing agent if necessary.
こうして得られる一般式(I)で表されるヒドラゾン化
合物の具体例を例示すると次の通りである。Specific examples of the hydrazone compound represented by the general formula (I) thus obtained are as follows.
化合物NαI
Nα2
Nα3
化合物Nα4
N(15
Nα6
Nα7
Nα8
魚9
Nα12
Nα13
Nα14
Nα15
Nα17
Nα18
Nα19
Nα21
N(127
化合物Nα34
Nα35
No、36
Nα38
Nα42
Nα43
Nα44
Nα45
Nα51
Nα56
化合物Nα58
Nα59
Nα6O
Nα61
化合物N164
Nα69
Nα72
本発明の感光体は前述のようなヒドラゾン化合物を感光
層中に含有させたものであるが、これらヒドラゾン化合
物の応用の仕方によって、第1図。Compound NαI Nα2 Nα3 Compound Nα4 N(15 Nα6 Nα7 Nα8 Fish 9 Nα12 Nα13 Nα14 Nα15 Nα17 Nα18 Nα19 Nα21 N(127 Compound Nα34 Nα35 No, 36 Nα38 Nα42 Nα43 Nα 44 Nα45 Nα51 Nα56 Compound Nα58 Nα59 Nα6O Nα61 Compound N164 Nα69 Nα72 of the present invention The photoreceptor has the above-mentioned hydrazone compound contained in the photosensitive layer, and the method shown in FIG.
東2図あるいは第3図に示したごとくに用いることがで
きる。It can be used as shown in Figure 2 or Figure 3.
第1図、第2図および第3図は本発明の感光体のそれぞ
れ異なる実施例の概念的断面図で、1は導電性基体、2
0.21.22は感光層、3は電荷発生物質、4は電荷
発生層、5は電荷輸送性物質、6は電荷輸送層、7は被
覆層である。1, 2, and 3 are conceptual cross-sectional views of different embodiments of the photoreceptor of the present invention, in which 1 is a conductive substrate, 2 is a conductive substrate, and 2 is a conductive substrate.
0.21.22 is a photosensitive layer, 3 is a charge generating material, 4 is a charge generating layer, 5 is a charge transporting material, 6 is a charge transporting layer, and 7 is a coating layer.
第1図は、導電性基体1上に電荷発生物質3と電荷輸送
性物質5であるヒドラゾン化合物を樹脂バインダー(結
着剤)中に分散した感光層20(通常単層型感光体と称
せられる構成)が設けられたものである。FIG. 1 shows a photosensitive layer 20 (usually referred to as a single-layer photoreceptor) in which a charge-generating substance 3 and a hydrazone compound as a charge-transporting substance 5 are dispersed in a resin binder on a conductive substrate 1. configuration) is provided.
第2図は、導電性基体1上に電荷発生物質3を主体とす
る電荷発生層4と、電荷輸送性物質5であるヒドラゾン
化合物を含有する電荷輸送層6との積層からなる感光層
21(通常積層型感光体と称せられる構成)が設けられ
たものである。この構成の感光体は通常負帯電方式で用
いられる。FIG. 2 shows a photosensitive layer 21( The structure is usually referred to as a laminated photoreceptor). A photoreceptor having this configuration is normally used in a negative charging system.
第3図は、第2図の逆の層構成のものであり、通常正帯
電方式で用いられる。この場合には、電荷発生層4を保
護するためにさらに被覆層7を設−けるのが一般的であ
る。FIG. 3 shows a layer structure opposite to that in FIG. 2, and is normally used in a positive charging system. In this case, it is common to further provide a coating layer 7 to protect the charge generation layer 4.
このように、積層型感光体として二種類の層構成をとる
理由としては、第2図の層構成の感光体を正帯電方式で
用いようとしても、これに適合する電荷輸送性物質は現
在まだ見つかっていないためである。現段階では、積層
型感光体で正帯電方式を適用する場合には、第3図に示
した層構成の感光体とすることが必要なのである。The reason why the laminated photoreceptor has two types of layer configurations is that even if a photoreceptor with the layer configuration shown in Figure 2 is used in a positive charging system, there is currently no charge transporting material that is compatible with this. This is because it has not been found. At present, when applying a positive charging method to a laminated type photoreceptor, it is necessary to use a photoreceptor having the layer structure shown in FIG.
第1図の感光体は、電荷発生物質を電荷輸送性物質およ
び樹脂バインダーを溶解した溶液中に分散せしめ、この
分散液を導電性基体上に塗布することによって作製でき
る。The photoreceptor shown in FIG. 1 can be produced by dispersing a charge generating substance in a solution containing a charge transporting substance and a resin binder, and applying this dispersion onto a conductive substrate.
第2図の感光体は、導電性基体上に電荷発生物質を真空
蒸着するか、あるいは電荷発生物質の粒子を溶剤または
樹脂バインダー中に分散して得た分散液を塗布、乾燥し
、その上に電荷輸送性物質および樹脂バインダーを溶解
した溶液を塗布、乾燥することにより作製できる。The photoreceptor shown in Figure 2 is produced by vacuum-depositing a charge-generating substance on a conductive substrate, or by coating and drying a dispersion obtained by dispersing particles of a charge-generating substance in a solvent or resin binder, and then It can be produced by applying a solution containing a charge transporting substance and a resin binder to a substrate and drying the solution.
第3図の感光体は、電荷輸送性物質および樹脂バインダ
ーを溶解した溶液を導電性基体上に塗布、乾燥し、その
上に電荷発生物質を真空蒸着するか、あるいは電荷発生
物質の粒子を溶剤または樹脂バインダー中に分散して得
た分散液を塗布、乾燥することにより作製できる。The photoreceptor shown in Figure 3 is produced by coating a conductive substrate with a solution containing a charge-transporting substance and a resin binder and drying it, and then vacuum-depositing a charge-generating substance thereon, or by depositing particles of the charge-generating substance in a solvent. Alternatively, it can be produced by coating and drying a dispersion obtained by dispersing in a resin binder.
導電性基体1は感光体の電極としての役目と同時に他の
各層の支持体となっており、円筒状、板状、フィルム状
のいずれでも良く、材質的にはアルミニウム、ステンレ
ス鋼、ニッケルナトの金属、あるいはガラス、樹脂など
の上に導電処理をほどこしたものでも良い。The conductive substrate 1 serves as an electrode for the photoreceptor and at the same time serves as a support for other layers, and may be cylindrical, plate-shaped, or film-shaped, and may be made of metal such as aluminum, stainless steel, or nickel. Alternatively, it may be made of glass, resin, or the like and subjected to conductive treatment.
電荷発生層4は、前記したように電荷発生物質3の粒子
を樹脂バインダー中に分散させた材料を塗布するか、あ
るいは、真空蒸着などの方法により形成され、光を受容
して電荷を発生する。また、その電荷発生効率が高いこ
とと同時に発生した電荷の電荷輸送層6および被覆層7
への注入性が重要で、電場依存性が少なく低電場でも注
入の良いことが望ましい。電荷発生物質としては、無金
属フタロシアニン、チタニルフタロシアニンなどのフタ
ロシアニン化合物、各種アゾ、キノン、インジゴ顔料あ
るいは、シアニン、スクアリリウム。The charge generation layer 4 is formed by applying a material in which particles of the charge generation substance 3 are dispersed in a resin binder as described above, or by a method such as vacuum deposition, and generates charges by receiving light. . In addition, the charge transport layer 6 and the coating layer 7 for the generated charges at the same time have a high charge generation efficiency.
It is important to have good injection properties even in low electric fields with little dependence on electric fields. Examples of the charge generating substance include phthalocyanine compounds such as metal-free phthalocyanine and titanyl phthalocyanine, various azo, quinone, and indigo pigments, or cyanine and squarylium.
アズレニウム、ピリリウム化合物などの染料や、セレン
またはセレン化合物などが用いられ、画像形成に使用さ
れる露光光源の光波長領域に応じて好適な物質を選ぶこ
とができる。電荷発生層は電荷発生機能を有すればよい
ので、その膜厚は電荷発生物質の光吸収係数より決まり
一般的には5μm以下であり、好適には1μm以下であ
る。電荷発生層は電荷発生物質を主体としてこれに電荷
輸送性物質などを添加して使用することも可能である。Dyes such as azulenium and pyrylium compounds, selenium or selenium compounds, and the like are used, and suitable substances can be selected depending on the light wavelength range of the exposure light source used for image formation. Since the charge generation layer only needs to have a charge generation function, its thickness is determined by the light absorption coefficient of the charge generation substance and is generally 5 μm or less, preferably 1 μm or less. The charge generation layer is mainly composed of a charge generation substance, and a charge transporting substance can also be added thereto.
樹脂バインダーとしては、ポリカーボネート、ポリエス
テル、ポリアミド、ポリウレタン、エポキシ、シリコン
樹脂、メタクリル酸エステルの重合体および共重合体な
どを適宜組み合わせて使用することが可能である。As the resin binder, polycarbonate, polyester, polyamide, polyurethane, epoxy, silicone resin, polymers and copolymers of methacrylic acid ester, etc. can be used in appropriate combinations.
電荷輸送層6は樹脂バインダー中に有機電荷輸送性物質
として前記一般式(1)で示されるヒドラゾン化合物を
分散させた塗膜であり、暗所では絶縁体層として感光体
の電荷を保持し、光受容時には電荷発生層から注入され
る電荷を輸送する機能を発揮する。樹脂バインダーとし
ては、ポリカーボネート、ポリエステル、ポリアミド、
ポリウレタン、エポキシ、シリコン樹脂、メタクリル酸
エステルの重合体および共重合体などを用いることがで
きる。The charge transport layer 6 is a coating film in which a hydrazone compound represented by the general formula (1) as an organic charge transport substance is dispersed in a resin binder, and serves as an insulating layer in the dark to retain the charge on the photoreceptor. During light reception, it functions to transport charges injected from the charge generation layer. As a resin binder, polycarbonate, polyester, polyamide,
Polyurethane, epoxy, silicone resin, methacrylic acid ester polymers and copolymers, etc. can be used.
被覆層7は暗所ではコロナ放電の電荷を受容して保持す
る機能を有しており、かつ電荷発生層が感応する光を透
過する性能を有し、露光時に光を透過し、電荷発生層に
到達させ、発生した電荷の注入を受けて表面電荷を中和
消滅させることが必要である。被覆材料としては、ポリ
エステル、ポリアミドなどの有機絶縁性皮膜形成材料が
適用できる。また、これら有機材料とガラス樹脂、 S
in。The coating layer 7 has the function of receiving and retaining the charge of corona discharge in a dark place, and has the ability to transmit the light to which the charge generation layer is sensitive, and transmits the light upon exposure, and the charge generation layer It is necessary to neutralize and eliminate the surface charges by injecting the generated charges. As the coating material, organic insulating film-forming materials such as polyester and polyamide can be used. In addition, these organic materials and glass resin, S
in.
などの無機材料さらには金属、金属酸化物などの電気抵
抗を低減せしめる材料とを混合して用いることもできる
。被覆材料としては有機絶縁性皮膜形成材料に限定され
ることはな(Sin、などの無機材料さらには金属、金
属酸化物などを蒸着、スパッタリングなどの方法により
形成することも可能である。被覆材料は前述の通り電荷
発生物質の光の吸収極大の波長領域においてできるだけ
透明であることが望ましい。It is also possible to use a mixture of inorganic materials such as metals, metal oxides, and other materials that reduce electrical resistance. The coating material is not limited to organic insulating film forming materials (inorganic materials such as Sin, metals, metal oxides, etc. can also be formed by methods such as vapor deposition and sputtering.Coating materials As mentioned above, it is desirable that the material be as transparent as possible in the wavelength region where the light absorption of the charge generating material is maximum.
被覆層自体の膜厚は被覆層の配合組成にも依存するが、
繰り返し連続使用したとき残留電位が増大するなどの悪
影響が出ない範囲で任意に設定できる。The thickness of the coating layer itself depends on the composition of the coating layer, but
It can be set arbitrarily within a range that does not cause adverse effects such as an increase in residual potential when used repeatedly and continuously.
以下、本発明の具体的な実施例について説明する。Hereinafter, specific examples of the present invention will be described.
実施例1
ボールミルで150時間粉砕した無金属フタロシアニン
(東京化成製)50重量部と前記化合物Nα1で示され
るヒドラゾン化合物100重量部をポリエステル樹脂(
商品名バイロン200:東洋動部)100重量部とテト
ラヒドロフラン(THF)溶剤とともに3時間混合機に
より混練して塗布液を調整し、導電性基体であるアルミ
蒸着ポリエステルフィルム(A f −P E T )
上に、ワイヤーバー法にて塗布して、乾燥後の膜厚が1
5μmになるように感光層を形成し、第1図に示した構
成の感光体を作製した。Example 1 A polyester resin (
A coating solution was prepared by kneading 100 parts by weight of Byron 200 (trade name: Toyo Doube) and a tetrahydrofuran (THF) solvent in a mixer for 3 hours, and the aluminum-deposited polyester film (A f -P ET ), which is a conductive substrate, was prepared.
The film thickness after drying is 1.
A photosensitive layer was formed to have a thickness of 5 μm, and a photosensitive member having the structure shown in FIG. 1 was produced.
実施例2
まず、α型無金属フタロシアニンを出発原料とし、二つ
のリニアモーターを対向して配置した間にα型無金属フ
タロシアニンと作用小片としてテフロンピースを内蔵し
た非磁性離体をおいて粉砕するL I MMA C(L
inear Induction Motor Mix
−ing and (:rashing :富士電機製
)処理を20分間行い微粉末化した。この微粉末化され
た試料1重量部とDMF (N、N−ジメチルホルムア
ミド)溶剤50重量部とを超音波分散処理を行った。そ
の後、試料とDMFとを分離濾過し、乾燥して無金属フ
タロシアニンの処理を行った。Example 2 First, α-type metal-free phthalocyanine is used as a starting material, and while two linear motors are placed facing each other, α-type metal-free phthalocyanine and a non-magnetic separation body containing a Teflon piece as a working piece are placed and pulverized. L I MMA C(L
inear Induction Motor Mix
-ing and (:rashing: manufactured by Fuji Electric) treatment was performed for 20 minutes to form a fine powder. 1 part by weight of this finely powdered sample and 50 parts by weight of DMF (N,N-dimethylformamide) solvent were subjected to ultrasonic dispersion treatment. Thereafter, the sample and DMF were separated and filtered, dried, and treated for metal-free phthalocyanine.
次に、前記化合物Nα2で示されるヒドラゾン化合物1
00重量部をテトラヒドロフラン(THF)700重量
部に溶かした液とポリメタクリル酸メチルポリマー(P
MMA :東京化成製)100重量部をトルエン700
重量部に溶かした液とを混合してできた塗液をアルミ蒸
着ポリエステルフィルム基体上にワイヤーバー法にて塗
布し、乾燥後の膜厚が15μmになるように電荷輸送層
を形成した。このようにして得られた電荷輸送層上に上
記の処理をされた無金属フタロシアニン50重量部、ポ
リエステル樹脂(商品名バイロン200:東洋動部)5
0重量部、PMMA50重量部をTHF溶剤とともに3
時間混合機により混練して塗布液を調整し、ワイヤーバ
ー法にて塗布し、乾燥後の膜厚が1μmになるように電
荷発生層を形成し、第3図に示した構成に対応する感光
体を作製した。ただし、本発明に直接関与しない被覆層
は設けなかった。Next, a hydrazone compound 1 represented by the above compound Nα2
00 parts by weight dissolved in 700 parts by weight of tetrahydrofuran (THF) and polymethyl methacrylate polymer (P
MMA: manufactured by Tokyo Kasei Co., Ltd.) 100 parts by weight to 700 parts by weight of toluene
A coating solution prepared by mixing parts by weight of the solution was coated onto an aluminum-deposited polyester film substrate by a wire bar method to form a charge transport layer so that the film thickness after drying was 15 μm. 50 parts by weight of the above-treated metal-free phthalocyanine and 5 parts by weight of a polyester resin (trade name: Vylon 200: Toyo Doube) are placed on the charge transport layer thus obtained.
0 parts by weight, 50 parts by weight of PMMA with THF solvent
A coating solution was prepared by kneading with a time mixer, and applied using a wire bar method to form a charge generation layer with a film thickness of 1 μm after drying. The body was created. However, a coating layer not directly related to the present invention was not provided.
実施例3
実施例1の感光層の組成を、無金属フタロシアニン50
重量部、化合物Nα3で示されるヒドラゾン化合物10
0重量部、ポリエステル樹脂(商品名バイロン200:
東洋動部)50重量部、PMMA50重量部とに変更し
、その他は実施例1と同様にして感光層を形成し感光体
を作製した。Example 3 The composition of the photosensitive layer of Example 1 was changed to 50% metal-free phthalocyanine.
Part by weight, hydrazone compound 10 represented by compound Nα3
0 parts by weight, polyester resin (trade name Byron 200:
A photosensitive layer was formed in the same manner as in Example 1 except that 50 parts by weight of PMMA and 50 parts by weight of PMMA were used to form a photosensitive layer to produce a photoreceptor.
実施例4
実施例3において、無金属フタロシアニンに変えて例え
ば特開昭47−37543に示されるようなビスアゾ顔
料であるクロログイアンプル−を用い、その他は実施例
1と同様にして感光層を形成し感光体を作製した。Example 4 In Example 3, a photosensitive layer was formed in the same manner as in Example 1, except that a chlorodiapolymer, which is a bisazo pigment as disclosed in JP-A No. 47-37543, was used instead of the metal-free phthalocyanine. A photoreceptor was prepared.
このようにして得られた感光体の電子写真特性を川口電
機製静電記録紙試験装置r S P−428Jを用いて
測定した。The electrophotographic properties of the photoreceptor thus obtained were measured using an electrostatic recording paper tester RSP-428J manufactured by Kawaguchi Electric.
感光体の表面電位V、(ボルト)は暗所で+6.0kV
のコロナ放電を10秒間行って感光体表面を正帯電せし
めたときの初期の表面電位であり、続いてコロナ放電を
中止した状態で2秒間暗所保持したときの表面電位vd
(ボルト)を測定し、さらに続いて感光体表面に照度2
ルツクスの白色光を照射してvdが半分にするまでの時
間(秒)を求め半減衰露光量E−/−(ルックス・秒)
とした。また、照度2ルツクスの白色光を10秒間照射
したときの表面電位を残留電位vr(ボルト)とした。The surface potential V, (volt) of the photoreceptor is +6.0kV in the dark.
This is the initial surface potential when corona discharge is performed for 10 seconds to positively charge the surface of the photoreceptor, and the surface potential when the photoconductor surface is then held in the dark for 2 seconds with corona discharge stopped is vd.
(volts), and then the illuminance 2 on the photoreceptor surface.
Calculate the time (seconds) it takes for VD to be halved by irradiating lux white light and half-attenuation exposure amount E-/- (lux seconds)
And so. Further, the surface potential when white light with an illuminance of 2 lux was irradiated for 10 seconds was defined as the residual potential vr (volt).
また、フタロシアニン化合物を電荷発生物質とした場合
、長波長光での高感度が期待できるので、波長780n
mの単色光を用いたときの電子写真特性も同時に測定し
た。すなわち、Vd までは同様に測定し、次に白色光
の替わりに1μWの単色光(7gOron )を照射し
て半減衰露光量(μJ/cIll)を求め、また、この
光を10秒間感光体表面に照射したときの残留電位Vバ
ボルト〉を測定した。測定結果を第1表に示す。In addition, when a phthalocyanine compound is used as a charge generating substance, high sensitivity can be expected with long wavelength light, so the wavelength is 780 nm.
At the same time, electrophotographic characteristics were measured using m monochromatic light. That is, measurements are made in the same manner up to Vd, then 1 μW monochromatic light (7 gOron) is irradiated instead of white light to determine the half-attenuation exposure amount (μJ/cIll), and this light is applied to the photoreceptor surface for 10 seconds. The residual potential Vvavolt> was measured when irradiation was performed. The measurement results are shown in Table 1.
第 1 表
第1表に見られるように、実施例1,2,3゜4の感光
体は半減衰露光量、残留電位ともに差異はなく、表面電
位でも良好な特性を示している。Table 1 As seen in Table 1, the photoreceptors of Examples 1, 2, and 3°4 had no difference in half-attenuation exposure and residual potential, and exhibited good characteristics in terms of surface potential.
また、780nmの長波゛長先に対しても、フタロシア
ニン化合物を電荷発生物質とした実施例1.2゜3の感
光体は優れた電子写真特性を示している。In addition, the photoreceptor of Example 1.2.3 in which a phthalocyanine compound was used as a charge generating material exhibited excellent electrophotographic properties even at the long wavelength range of 780 nm.
実施例5
厚さ500μmのアルミニウム板上に、セレンを厚さ1
.5μmに真空蒸着し電荷発生層を形成し、次に、化合
物Nα4で示されるヒドラゾン化合物100重量部をテ
トラヒドロフラン(THF)700重予部に溶かした液
とポリメタクリル酸メチルポリマー(PMMA :東京
化成製)100重量部をトルエン700重量部に溶かし
た液とを混合してできた塗液をワイヤーバー法にて塗布
し、乾燥後の膜厚が20μmになるように電荷輸送層を
形成し、第2図に示した構成の感光体を作製した。この
感光体に−6,0kVのコロナ帯電を0.2秒間行い電
子写真特性を測定しタトコロ、V、 =−700V、
V、 =−100V、 E l/2 =4.0 ルック
ス・秒と良好な結果が得られた。Example 5 Selenium was deposited to a thickness of 1 on a 500 μm thick aluminum plate.
.. A charge generation layer was formed by vacuum evaporation to a thickness of 5 μm, and then a solution prepared by dissolving 100 parts by weight of a hydrazone compound represented by compound Nα4 in 700 parts by weight of tetrahydrofuran (THF) and polymethyl methacrylate polymer (PMMA: manufactured by Tokyo Kasei) were added. ) was mixed with a solution prepared by dissolving 100 parts by weight of toluene in 700 parts by weight of toluene, and the resulting coating liquid was applied using a wire bar method to form a charge transport layer so that the film thickness after drying was 20 μm. A photoreceptor having the configuration shown in FIG. 2 was manufactured. This photoreceptor was corona charged at -6.0 kV for 0.2 seconds and its electrophotographic characteristics were measured.
Good results were obtained with V = -100V and E l/2 = 4.0 lux seconds.
実施例6
実施例1で処理された無金属フタロシアニン50重量部
、ポリエステル樹脂(商品名バイロン200:東洋動部
)50重量部、PMMA50重量部をTHF溶剤ととも
に3時間混合機により混練して塗布液を調整し、アルミ
ニウム支持体上に約1μmになるように塗布し、電荷発
生層を形成した。次に、化合゛物魔5で示されるヒドラ
ゾン化合物100重量部、ポリカーボネート樹脂(パン
ライトL−1250)100重量部、シリコンオイル0
.1重量部をTHF700重量部とトルエン700重量
部で混合し、電荷発生層の上に約15μmとなるように
塗布し、電荷輸送層を形成した。Example 6 50 parts by weight of the metal-free phthalocyanine treated in Example 1, 50 parts by weight of polyester resin (trade name Byron 200: Toyo Dobu), and 50 parts by weight of PMMA were kneaded with a THF solvent in a mixer for 3 hours to prepare a coating solution. was prepared and coated on an aluminum support to a thickness of about 1 μm to form a charge generation layer. Next, 100 parts by weight of a hydrazone compound represented by the compound "Foma 5", 100 parts by weight of polycarbonate resin (Panlite L-1250), and 0 parts by weight of silicone oil were added.
.. 1 part by weight was mixed with 700 parts by weight of THF and 700 parts by weight of toluene and coated on the charge generation layer to a thickness of about 15 μm to form a charge transport layer.
このようにして得られた感光体を実施例5と同様にして
、−6,9kVのコロナ帯電を0.2秒間行い電子写真
特性を測定したところ、V−=−750V、 E I/
□=5.2ルツクス・秒と良好な結果が得られた。The thus obtained photoreceptor was subjected to corona charging at -6.9 kV for 0.2 seconds in the same manner as in Example 5, and its electrophotographic characteristics were measured.
A good result of □=5.2 Lux·sec was obtained.
実施例7
化合物Nα6〜No、72それぞれについて実施例4と
同様、感光層を作製して感光体とし、rSP−428」
を用いて半減衰露光量を測定した結果を第2表に示す。Example 7 A photosensitive layer was prepared in the same manner as in Example 4 for each of the compounds Nα6 to No. 72, and a photoreceptor was prepared, rSP-428.
Table 2 shows the results of measuring the half-attenuation exposure using .
暗所で+6. OkVのコロナ放電を10秒間行い正帯
電せしめ、照度2ルツクスの白色光を照射した場合の半
減衰露光量E l/2 (ルックス・秒)を示した。+6 in the dark. The half-attenuation exposure amount E 1/2 (lux seconds) is shown when corona discharge of OKV is performed for 10 seconds to positively charge the sample and white light with an illuminance of 2 lux is irradiated.
第 2 表 (その1)
第 2 表 (その2)
第 2 表 (その3)
第 2 表 (その4)
第 2 表 (その5)
第2表に見られるように、前記ヒドラゾン化合物Nα6
〜Nα72を用いた感光体についても、半減衰露光量E
+72.すなわち感度は良好であった。Table 2 (Part 1) Table 2 (Part 2) Table 2 (Part 3) Table 2 (Part 4) Table 2 (Part 5) As seen in Table 2, the hydrazone compound Nα6
~ Also for the photoreceptor using Nα72, the half-attenuation exposure amount E
+72. In other words, the sensitivity was good.
本発明によれば、導電性基体上に電荷輸送性物質として
前記一般式(1)で示されるヒドラゾン化合物を用いる
こととしたため、正帯電および負帯電においても高感度
でしかも繰り返し特性の優れた感光体を得ることができ
る。また、電荷発生物質は露光光源の種類に対応して好
適な物質を選ぶことができ、−例をあげるとフタロシア
ニン化合物およびある種のビスアゾ化合物を用いれば半
導体レーザプリンタに使用可能な感光体を得ることがで
きる。さらに、必要に応じて表面に被覆層を設置して耐
久性を向上することが可能である。According to the present invention, since a hydrazone compound represented by the general formula (1) is used as a charge transporting substance on a conductive substrate, a photosensitive material with high sensitivity and excellent repeatability even in positive and negative charging can be obtained. You can get a body. In addition, a suitable charge-generating substance can be selected depending on the type of exposure light source; for example, by using phthalocyanine compounds and certain bisazo compounds, a photoreceptor that can be used in semiconductor laser printers can be obtained. be able to. Furthermore, if necessary, it is possible to provide a coating layer on the surface to improve durability.
第1図、第2図$よび第3図は本発明の感光体のそれぞ
れ異なる実施例を示す概念的断面図である。
1 導電性基体、3 電荷発生物質、4 電荷発生層、
5 電荷輸送性物質、6 電荷輸送層、7 被覆層、2
0.21.22 感光層。
4ぐ二人
第1図
第 2 図
第3図FIGS. 1, 2 and 3 are conceptual sectional views showing different embodiments of the photoreceptor of the present invention. 1 conductive substrate, 3 charge generation substance, 4 charge generation layer,
5 charge transport substance, 6 charge transport layer, 7 coating layer, 2
0.21.22 Photosensitive layer. 4 people Figure 1 Figure 2 Figure 3
Claims (1)
うちの少なくとも一種類を含む感光層を有することを特
徴とする電子写真用感光体。 ▲数式、化学式、表等があります▼・・・( I ) 〔式( I )中、R_1は置換基を有してもよいアリー
ル基を表し、R_2、R_3、R_4、R_5、R_6
、R_7およびR_8はそれぞれ水素原子、ハロゲン原
子、アルコキシ基、アルキル基、ニトロ基、ヒドロキシ
基、アリール基、置換されてもよいアミノ基を表し、n
は整数1、2、3、4のいずれかを表す。〕[Scope of Claims] 1) An electrophotographic photoreceptor comprising a photosensitive layer containing at least one hydrazone compound represented by the following general formula (I). ▲There are mathematical formulas, chemical formulas, tables, etc.▼...(I) [In formula (I), R_1 represents an aryl group that may have a substituent, R_2, R_3, R_4, R_5, R_6
, R_7 and R_8 each represent a hydrogen atom, a halogen atom, an alkoxy group, an alkyl group, a nitro group, a hydroxy group, an aryl group, or an optionally substituted amino group, and n
represents an integer 1, 2, 3, or 4. ]
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP26575187A JPH01107264A (en) | 1987-10-21 | 1987-10-21 | Electrophotographic sensitive body |
US07/257,260 US4957837A (en) | 1987-10-15 | 1988-10-13 | Photosensitive member for electrophotography containing hydrazone in charge transport layer |
DE3835108A DE3835108C2 (en) | 1987-10-15 | 1988-10-14 | Electrophotographic recording material |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP26575187A JPH01107264A (en) | 1987-10-21 | 1987-10-21 | Electrophotographic sensitive body |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH01107264A true JPH01107264A (en) | 1989-04-25 |
Family
ID=17421500
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP26575187A Pending JPH01107264A (en) | 1987-10-15 | 1987-10-21 | Electrophotographic sensitive body |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH01107264A (en) |
-
1987
- 1987-10-21 JP JP26575187A patent/JPH01107264A/en active Pending
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