JPH0391762A - Electrophotoraphic sensitive body - Google Patents
Electrophotoraphic sensitive bodyInfo
- Publication number
- JPH0391762A JPH0391762A JP22970489A JP22970489A JPH0391762A JP H0391762 A JPH0391762 A JP H0391762A JP 22970489 A JP22970489 A JP 22970489A JP 22970489 A JP22970489 A JP 22970489A JP H0391762 A JPH0391762 A JP H0391762A
- Authority
- JP
- Japan
- Prior art keywords
- group
- photoreceptor
- compound
- bismesoionic
- charge
- 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
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- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 2
- 108091008695 photoreceptors Proteins 0.000 claims description 57
- 239000000126 substance Substances 0.000 claims description 12
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- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- DZVCFNFOPIZQKX-LTHRDKTGSA-M merocyanine Chemical compound [Na+].O=C1N(CCCC)C(=O)N(CCCC)C(=O)C1=C\C=C\C=C/1N(CCCS([O-])(=O)=O)C2=CC=CC=C2O\1 DZVCFNFOPIZQKX-LTHRDKTGSA-M 0.000 description 1
- 239000000113 methacrylic resin Substances 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 125000006533 methyl amino methyl group Chemical group [H]N(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- DCZNSJVFOQPSRV-UHFFFAOYSA-N n,n-diphenyl-4-[4-(n-phenylanilino)phenyl]aniline Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 DCZNSJVFOQPSRV-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000004971 nitroalkyl group Chemical group 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- 229930184652 p-Terphenyl Natural products 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 239000013034 phenoxy resin Substances 0.000 description 1
- 229920006287 phenoxy resin Polymers 0.000 description 1
- 229920002382 photo conductive polymer Polymers 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 238000007761 roller coating Methods 0.000 description 1
- 229930187593 rose bengal Natural products 0.000 description 1
- 229940081623 rose bengal Drugs 0.000 description 1
- STRXNPAVPKGJQR-UHFFFAOYSA-N rose bengal A Natural products O1C(=O)C(C(=CC=C2Cl)Cl)=C2C21C1=CC(I)=C(O)C(I)=C1OC1=C(I)C(O)=C(I)C=C21 STRXNPAVPKGJQR-UHFFFAOYSA-N 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- AUHHYELHRWCWEZ-UHFFFAOYSA-N tetrachlorophthalic anhydride Chemical compound ClC1=C(Cl)C(Cl)=C2C(=O)OC(=O)C2=C1Cl AUHHYELHRWCWEZ-UHFFFAOYSA-N 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 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
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
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、更に詳しくは、ビ
スメソイオン化合物を含有する感光層を有する電子写真
用感光体に関するものである。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to an electrophotographic photoreceptor, and more particularly to an electrophotographic photoreceptor having a photosensitive layer containing a bismesoion compound.
光導電性物質と静電現象を結び付けて画像記録を行なう
、いわゆる電子写真法は、カールソンが米国特許第22
1776号に於いて明らかにした「エレクトロン フォ
トグラフィ」に端を発している。電子写真法では、光の
照射量に応じてその電気抵抗が変化する光導電物質を、
絶縁性のバインダー樹脂に分散し、これを支持体上に塗
布した光導電性材料が感光体として用いられる。この光
導電材料は、暗所でコロナ帯電により一様な表面電荷を
与えられたのち、画像露光の明るさの値に応じた表面電
荷を失い静電潜像が形戊される。この様な静電潜像は、
次にその表面が適当な検電表示物質、すなわちトナーで
処理されて可視像となる。トナーは乾燥担体と共に、或
いは有機溶剤中にコロイド状に懸濁して用いられ、静電
潜像の電荷に応じてクーロン力によって付着させること
ができる。付着した表示物質は、熱、圧力などにより定
着させることができる。So-called electrophotography, which combines photoconductive substances and electrostatic phenomena to record images, was developed by Carlson in U.S. Pat.
It originated from the ``electron photography'' that was revealed in issue 1776. In electrophotography, a photoconductive material whose electrical resistance changes depending on the amount of light irradiation is used.
A photoconductive material that is dispersed in an insulating binder resin and coated on a support is used as a photoreceptor. After this photoconductive material is given a uniform surface charge by corona charging in a dark place, it loses its surface charge depending on the brightness value of image exposure, and an electrostatic latent image is formed. This kind of electrostatic latent image is
The surface is then treated with a suitable electrolytic indicator material, ie, toner, to form a visible image. The toner can be used with a dry carrier or colloidally suspended in an organic solvent and can be deposited by Coulomb force depending on the charge of the electrostatic latent image. The attached display substance can be fixed by heat, pressure, or the like.
また、静電潜像は第2の支持体(例えば、紙、フィルム
等)に転写し、現像、定着させることもできる。The electrostatic latent image can also be transferred to a second support (eg, paper, film, etc.), developed, and fixed.
この様な電子写真法に於いて、電子写真用感光体に要求
される基本的な特性としては、(I)暗所で適当な電位
に帯電できること、(2)暗所における電荷の保持能力
が大きいこと、(3)光照射によって速やかに電荷を散
逸できること、などが挙げられる。In such electrophotography, the basic characteristics required of an electrophotographic photoreceptor are (I) ability to be charged to an appropriate potential in the dark, and (2) ability to retain charge in the dark. and (3) the ability to quickly dissipate charge by light irradiation.
また、実用面からは、(4)適当な面積を持つ感光体が
容易に造れること、(5)繰り返し安定性が良いこと、
(6)耐久性があること、(7)安価なこと、などが要
求されている。In addition, from a practical standpoint, (4) a photoreceptor with an appropriate area can be easily manufactured, (5) it has good repeat stability,
(6) It must be durable, and (7) It must be inexpensive.
従来、電子写真用感光体の光導電性材料としては、セレ
ン、硫化カドミウム、酸化亜鉛などが広く用いられてき
た。しかしながら、これらの無機化合物は、多くの長所
を持つ反面、様々な欠点を有していることも事実である
。例えば、セレンは製造する条件が難しく、製造コスト
が高い、温度、湿度、指紋などにより容易に結晶化が進
み、感光体としての特性が劣化してしまう為に取り扱い
に注意を要するなどの欠点を持っていた。また、硫化カ
ドミウムは、特に耐湿性が悪く、感光体の吸湿を防止す
る為にヒーターを設置するなどの補助手段が必要であっ
た。また、酸化亜鉛は、硬度、耐摩耗性など機械的な強
度に問題がある他、ローズベンガルに代表される染料で
増感しているため、コロナ帯電による染料の光退色が感
光体の寿命を縮めていた。これらの無機化合物は、重金
属を含有し、取扱いを誤まると公害問題に発展する危険
性もあった。Conventionally, selenium, cadmium sulfide, zinc oxide, and the like have been widely used as photoconductive materials for electrophotographic photoreceptors. However, while these inorganic compounds have many advantages, they also have various disadvantages. For example, selenium has drawbacks such as difficult manufacturing conditions, high manufacturing costs, and the need for careful handling as it easily crystallizes due to temperature, humidity, fingerprints, etc., and deteriorates its properties as a photoreceptor. had. Further, cadmium sulfide has particularly poor moisture resistance, and auxiliary means such as installing a heater are required to prevent the photoreceptor from absorbing moisture. In addition, zinc oxide has problems with mechanical strength such as hardness and abrasion resistance, and since it is sensitized with dyes such as rose bengal, photobleaching of the dye due to corona charging can shorten the life of the photoreceptor. It was shrinking. These inorganic compounds contain heavy metals, and if handled incorrectly, there is a risk of developing a pollution problem.
近年、これらの無機化合物の光導電性材料の欠点を克服
する為に、種々の有機光導電性化合物を用いた電子写真
用感光体の研究開発が盛んに行なわれている。例えば、
ポリーN−ビニルカルハゾールと2.4.7−トリニト
ロフルオレノンとからなる電子写真用感光体(米国特許
第3, 484, 237号)、ポリーN−ビニル力ル
バゾールをピリリウム塩系色素で増感したもの(特公昭
48−25658号)、染料と樹脂とからなる共晶体を
光導電性材料とするもの(特開昭47−10785号)
などがある。この様な有機化合物系電子写真用感光体は
、無機化合物系電子写真感光体に比べて、成膜が容易で
あり、極めて生産性が高く、安価な感光体を提供できる
と言う利点を持っている。しかしながら、例えば、ポリ
ーN−ビニルカルバゾールの様な光導電性ボリマーに関
しては、ボリマー単独では被膜性、可撓性、接着性など
が不良であり、これらの欠点を改良する為に可塑材、バ
インダーなどが添加されるが、この為に感度の低下や、
残留電位の上昇を招くなどの問題点があった。In recent years, in order to overcome the drawbacks of these inorganic compound photoconductive materials, research and development of electrophotographic photoreceptors using various organic photoconductive compounds has been actively conducted. for example,
An electrophotographic photoreceptor made of poly-N-vinylcarhazole and 2,4,7-trinitrofluorenone (U.S. Pat. No. 3,484,237), poly-N-vinylcarhazole enhanced with a pyrylium salt dye. (Japanese Patent Publication No. 48-25658), and one using a eutectic consisting of dye and resin as a photoconductive material (Japanese Patent Publication No. 47-10785)
and so on. Compared to inorganic compound-based electrophotographic photoreceptors, such organic compound-based electrophotographic photoreceptors have the advantage of being easier to form a film, have extremely high productivity, and can provide inexpensive photoreceptors. There is. However, for photoconductive polymers such as poly-N-vinylcarbazole, the polymer alone has poor filmability, flexibility, adhesion, etc., and in order to improve these defects, plasticizers, binders, etc. is added, but this may cause a decrease in sensitivity or
There were problems such as an increase in residual potential.
また、有機化合物系の低分子光導電性化合物は、バイン
ダーの選択範囲も広く、適当なポリマーを選択すれば、
被膜性、接着性など機械的特性の優れたものを造ること
ができるが、反面、光感度、繰り返し特性など電子写真
用感光体としての要求を十分に満たすものではなかった
。In addition, organic compound-based low-molecular photoconductive compounds have a wide range of binders to choose from, and if an appropriate polymer is selected,
Although it is possible to produce products with excellent mechanical properties such as filmability and adhesiveness, on the other hand, they do not fully satisfy the requirements for electrophotographic photoreceptors such as photosensitivity and repeatability.
本発明が解決しようとする課題は、従来の無機化合物系
電子写真用感光体の欠点を克服し、且つこれまで提案さ
れてきた有機化合物系電子写真用感光体の欠点を改良し
、十分に実用に供しうる程度の高感度、高耐久性を有す
る電子写真用感光体を提供することにある。The problem to be solved by the present invention is to overcome the drawbacks of conventional inorganic compound-based electrophotographic photoreceptors, and improve the drawbacks of the organic compound-based electrophotographic photoreceptors that have been proposed so far, so as to be fully practical. The object of the present invention is to provide an electrophotographic photoreceptor having high sensitivity and high durability that can be used for various purposes.
[課題を解決するための手段]
本発明は上記課題を解決するために、感光層に一般式(
I)
(式中、Aはフエニレン基又はナフチレン基を表わし、
Rは置換基を有しても良い炭化水素基又は置換基を有し
ても良い複素環基を表わす。)で表わされるビスメソイ
オン化合物を含有することを特徴とする電子写真用感光
体を提供する。[Means for Solving the Problems] In order to solve the above problems, the present invention provides a photosensitive layer containing the general formula (
I) (wherein A represents a phenylene group or a naphthylene group,
R represents a hydrocarbon group which may have a substituent or a heterocyclic group which may have a substituent. ) Provided is an electrophotographic photoreceptor characterized by containing a bismesoionic compound represented by:
一般式(I)におけるRとしては、例えば、好ましくは
炭素数1〜20のアルキル基、フェニル基、ナフチル基
などの芳香族炭化水素基、ビリジル基、カルバゾリル基
、ペンゾトリアゾリル基などの芳香族複素環基などが挙
げられる。具体例としては、Rがアルキル基の場合は、
メチル基、エチル基、プロビル基、ブチル基、ベンチル
基、ヘキシル基、イソブロビル基、イソブチル基、イソ
アミル基、イソへキシル基、ネオペンチル基、ter
t−ブチル基などを挙げることができる。Rが置換アル
キル基の場合は、置換基としては、ハロゲン原子、ニト
ロ基、シアノ基、ヒドロキシ基、置換ヒドロキシ基、チ
オール基、置換チオール基、アミノ基、置換アξノ基、
アリール基などが挙げられる。R in general formula (I) is preferably an alkyl group having 1 to 20 carbon atoms, an aromatic hydrocarbon group such as a phenyl group or a naphthyl group, a biridyl group, a carbazolyl group, a penzotriazolyl group, etc. Examples include aromatic heterocyclic groups. As a specific example, when R is an alkyl group,
Methyl group, ethyl group, probyl group, butyl group, bentyl group, hexyl group, isobrobyl group, isobutyl group, isoamyl group, isohexyl group, neopentyl group, ter
Examples include t-butyl group. When R is a substituted alkyl group, examples of the substituent include a halogen atom, a nitro group, a cyano group, a hydroxy group, a substituted hydroxy group, a thiol group, a substituted thiol group, an amino group, a substituted ξ group,
Examples include aryl groups.
Rの具体例としては、ハロゲノアルキル基(例えば、ク
ロロメチル基、トリフルオロメチル基、2−プロモエチ
ル基等)、ニトロアルキル基(例えば、ニトロメチル基
、3〜ニトロプロビル基等)シアノアルキル基(例えば
、シアノメチル基、2一シアノエチル基等)、ヒドロキ
シアルキル基(例えば、ヒドロキシメチル基、2−ヒド
ロキシエチル基、3−ヒドロキシプ口ピル基、2−ヒド
ロキシプロビル基等)、置換ヒドロキシアルキル基(例
えば、メトキシメチル基、2−メトキシエチル基、エト
キシメチル基、フエノキシメチル基等)、チオヒドロキ
シアルキル基(例えば、チオヒドロキシメチル基、2−
チオヒドロキシエチル基等)、置換チオヒドロキシアル
キル基(例えば、メチルチオメチル基、2−メチルチオ
エチル基)、アミノアルキル基(例えば、アミノメチル
基、2一アミノエチル基等)、置換アミノアルキル基(
例えば、メチルアミノメチル基、エチルアミノメチル基
、ジメチルア4ノメチル基、2−(ジメチルアミノ)エ
チル基、フ五ニルアごノメチル基、ジフェニルアミノメ
チル基等)を挙げることができる。Specific examples of R include halogenoalkyl groups (e.g., chloromethyl group, trifluoromethyl group, 2-promoethyl group, etc.), nitroalkyl groups (e.g., nitromethyl group, 3-nitroprobyl group, etc.), cyanoalkyl groups ( For example, cyanomethyl group, 2-cyanoethyl group, etc.), hydroxyalkyl group (e.g., hydroxymethyl group, 2-hydroxyethyl group, 3-hydroxybutypyl group, 2-hydroxyprobyl group, etc.), substituted hydroxyalkyl group ( For example, methoxymethyl group, 2-methoxyethyl group, ethoxymethyl group, phenoxymethyl group, etc.), thiohydroxyalkyl group (for example, thiohydroxymethyl group, 2-
thiohydroxyethyl group, etc.), substituted thiohydroxyalkyl group (e.g., methylthiomethyl group, 2-methylthioethyl group), aminoalkyl group (e.g., aminomethyl group, 2-aminoethyl group, etc.), substituted aminoalkyl group (
For example, methylaminomethyl group, ethylaminomethyl group, dimethyla4nomethyl group, 2-(dimethylamino)ethyl group, phenylagonomethyl group, diphenylaminomethyl group, etc.) can be mentioned.
Rが芳香族炭化水素基或いは芳香族複素環基である場合
の置換基としては、アルキル基、ハロゲン原子、二トロ
基、シアノ基、ヒドロキシ基、置換ヒドロキシ基、チオ
ール基、置換チオール基、アξノ基、置換アξノ基など
がある。具体例としてRが置換フェニル基の場合を挙げ
ると、アルキルフェニル基(例えば、トリル基、エチル
フェニル基等)、クロロフェニル基、ニトロフェニル基
、シアノフエニル基、ヒドロキシフェニル基、Kt’A
ヒドロキシフェニル基(例えば、メトキシフェニル基、
エトキシフェニル基等)、チオヒド口キシフエニル基、
置換チオール基(例えば、メチルチオフエニル基、エチ
ルチオフエニル基等)、アミノフエニル基、置換アミノ
基(例えば、メチルアξノフェニル基、ジメチルアミノ
フェニル基、フエニルアミノフヱニル基、ジフェニルア
ミノフェニル基等)がある。Rが縮合芳香族炭化水素基
の例として、置換ナフチル基の場合を挙げると、アルキ
ルナフチル基(例えば、メチルナフチル基、エチルナフ
チル基等)、クロロナフチル基、ニトロナフチル基、シ
アノナフチル基、ヒドロキシナフチル基、置換ヒドロキ
シナフチル基(例えば、メトキシナフチル基、エトキシ
ナフチル基等)、チオヒド口キシナフチル基、置換チオ
ール基(例えば、メチルチオナフチル基、エチルチオナ
フチル基等)、アミノナフチル基、置換アミノ基(例え
ば、メチルアξノナフチル基、ジメチルアミノナフチル
基、フヱニルアミノナフチル基、ジフエニルアミノナフ
チル基等)がある。芳香族複素環基の例として、置換ヘ
ンゾチアゾリル基の場合を上げると、アルキルベンゾチ
アゾリル基(例えば、メチルベンゾチアゾリル基、エチ
ルベンゾベンゾチアゾリル基等)、クロロペンゾチアゾ
リル基、ニトロベンゾチアゾリル基、シアノベンゾチア
ゾリル基、ヒドロキシベンゾチアゾリル基、置換ヒドロ
キシベンゾチアゾリル基(例えば、メトキシベンゾチア
ゾリル基、エトキシベンドチアゾリル基等)、チオヒド
ロキシベンゾチアヅリル基、置換チオール基(例えば、
メチルチオベンゾチアゾリル基、エチルチオヘンゾチア
ゾリル基等)、アミノベンゾチアゾリル基、置換アミノ
ベンゾチアゾリル基(例えば、メチルア旦ノベンゾチア
ゾリル基、ジメチルアξノベンゾチアゾリル基、フェニ
ルアミノベンヅチアヅリル基、ジフェニルア5ノナベン
ゾチアヅリル基等)がある。尚、これらの例中置換基の
位置の指定のないものは、可能な異性体のいずれでも良
い。また、これらの置換基(互いに同しでも異なってい
ても良い。)を2個以上を有する置換芳香族炭化水素基
又は置換芳香族複素環基であってもよい。When R is an aromatic hydrocarbon group or an aromatic heterocyclic group, examples of the substituent include an alkyl group, a halogen atom, a ditro group, a cyano group, a hydroxy group, a substituted hydroxy group, a thiol group, a substituted thiol group, and an alkyl group. There are ξ-no groups, substituted ξ-no groups, etc. Specific examples of R being a substituted phenyl group include alkylphenyl group (e.g. tolyl group, ethylphenyl group, etc.), chlorophenyl group, nitrophenyl group, cyanophenyl group, hydroxyphenyl group, Kt'A
Hydroxyphenyl group (e.g. methoxyphenyl group,
ethoxyphenyl group, etc.), thiohydroxyphenyl group,
Substituted thiol groups (e.g., methylthiophenyl group, ethylthiophenyl group, etc.), aminophenyl groups, substituted amino groups (e.g., methylanξnophenyl group, dimethylaminophenyl group, phenylaminophenyl group, diphenylaminophenyl group) etc.). Examples of fused aromatic hydrocarbon groups in which R is a substituted naphthyl group include alkylnaphthyl groups (e.g., methylnaphthyl group, ethylnaphthyl group, etc.), chloronaphthyl group, nitronaphthyl group, cyanonaphthyl group, hydroxy Naphthyl group, substituted hydroxynaphthyl group (e.g., methoxynaphthyl group, ethoxynaphthyl group, etc.), thiohydride xynaphthyl group, substituted thiol group (e.g., methylthionaphthyl group, ethylthionaphthyl group, etc.), aminonaphthyl group, substituted amino group ( For example, there are methylaminonaphthyl group, dimethylaminonaphthyl group, phenylaminonaphthyl group, diphenylaminonaphthyl group, etc.). Examples of aromatic heterocyclic groups include substituted henzothiazolyl groups, such as alkylbenzothiazolyl groups (e.g., methylbenzothiazolyl group, ethylbenzobenzothiazolyl group, etc.), chloropenzothiazolyl group, etc. group, nitrobenzothiazolyl group, cyanobenzothiazolyl group, hydroxybenzothiazolyl group, substituted hydroxybenzothiazolyl group (e.g., methoxybenzothiazolyl group, ethoxybenzothiazolyl group, etc.), thio Hydroxybenzothiazuryl group, substituted thiol group (e.g.
(methylthiobenzothiazolyl group, ethylthiohenzothiazolyl group, etc.), aminobenzothiazolyl group, substituted aminobenzothiazolyl group (e.g., methylanobenzothiazolyl group, dimethylanobenzothiazolyl group) group, phenylaminobenzthiazuryl group, diphenyl-5nonabenzothiazuryl group, etc.). In these examples, if the position of the substituent is not specified, any of the possible isomers may be used. Further, it may be a substituted aromatic hydrocarbon group or a substituted aromatic heterocyclic group having two or more of these substituents (which may be the same or different).
本発明に係わる一般式(I)で表わされるビスメソイオ
ン化合物は、従来公知の方法で製造することができる。The bismesoionic compound represented by the general formula (I) according to the present invention can be produced by a conventionally known method.
例えば、「ヘミソシュ ベリンヒテ」第120巻、61
頁(I987年)に記載の如く、次のような経路で合成
することができる。For example, "Hemisos Berinhte", vol. 120, 61
(1987), it can be synthesized by the following route.
S S S COOH (r) 本発明で使用される前記一般式(I) のビスメ ソイオン化合物の具体例を第1表に構造弐で示す。S S S COOH (r) The above general formula (I) used in the present invention The bisme of Specific examples of soyionic compounds are shown in Table 1 with structure 2.
第
■
表
ノ
?−
ン
?
本発明の電子写真用感光体は種々の構造をとることがで
きる。その例を第1〜4図に示した。第l図の感光体は
、導電性支持体(I〉上にビスメソイオン化合物(3〉
をバインダー(4)中に分散させてなる感光層(2a)
を設けたものである。Part ■ Table No? - N? The electrophotographic photoreceptor of the present invention can have various structures. Examples are shown in Figures 1-4. The photoreceptor in FIG.
A photosensitive layer (2a) formed by dispersing in a binder (4)
It has been established.
第2図の感光体は、導電性支持体上にビスメソイオン化
合物(3)を電荷輸送物質(5)及びバインダーから成
る電荷輸送媒体に分散させて或る感光層(2b)を設け
たものである。第3図及び第4図の感光体はビスメソイ
オン化合物(3)を主体とする電荷担体発生層(6)と
、電荷輸送物質とバインダーから成る電荷輸送J?i!
(7)とから或る感光層(2C)又は〈2d〉をそれ
ぞれ設けたものである。第l図の場合には、ビスメソイ
オン化合物(3)は、光減衰に必要な電荷担体の発生及
び電荷輸送の両作用を行なっている。第2図の感光体の
場合には、電荷輸送物質はバインダーと共に電荷輸送媒
体(5)を形威し、一方ビスメソイオン化合物(3)は
電荷担体発生物質として作用する。この電荷輸送媒体(
5)はビスメソイオン化合物(3)の如き電荷担体の生
威能力は持たないが、ビスメソイオン化合物から発生し
た電荷担体を受け入れ、これを輸送する能力を持ってい
る。即ち、第2図の感光体では光減衰に必要な電荷担体
の生威はビスメソイオン化合物(3)によって行なわれ
、一方、電荷担体の輸送は主として電荷輸送媒体(5〉
により行なわれる。第3図及び第4図の感光体の場合に
は、電荷担体発生層(6)に含まれるビスメソイオン化
合物(3)は電荷担体を発生し、一方、電荷輸送層(7
)は電荷担体の注入を受けその輸送を行なう。即ち、光
減衰に必要な電荷担体の生成がビスメソイオン化合物で
行なわれ、又、電荷担体の輸送が電荷輸送媒体で行なわ
れると言う作用機構は第2図の感光体の場合と同様であ
る。The photoreceptor shown in FIG. 2 has a photosensitive layer (2b) provided on a conductive support by dispersing a bismeso ion compound (3) in a charge transport medium consisting of a charge transport substance (5) and a binder. . The photoreceptor shown in FIGS. 3 and 4 includes a charge carrier generating layer (6) mainly composed of a bismesoionic compound (3), a charge transport material and a binder. i!
A certain photosensitive layer (2C) or <2d> is provided from (7) and (7), respectively. In the case of FIG. 1, the bismesoionic compound (3) performs both the functions of generating charge carriers necessary for light attenuation and transporting charges. In the case of the photoreceptor of FIG. 2, the charge transport material together with the binder forms the charge transport medium (5), while the bismesoionic compound (3) acts as a charge carrier generating material. This charge transport medium (
Although 5) does not have the ability to generate charge carriers like the bismesoionic compound (3), it has the ability to accept and transport charge carriers generated from the bismesoionic compound. That is, in the photoreceptor of FIG. 2, the generation of charge carriers necessary for photoattenuation is carried out by the bismeso ion compound (3), while the transport of charge carriers is mainly carried out by the charge transport medium (5).
This is done by In the case of the photoreceptors shown in FIGS. 3 and 4, the bismesoionic compound (3) contained in the charge carrier generation layer (6) generates charge carriers, while the charge transport layer (7) generates charge carriers.
) receives injection of charge carriers and transports them. That is, the mechanism of action is the same as that of the photoreceptor shown in FIG. 2, in which the generation of charge carriers necessary for light attenuation is carried out by a bismeso ion compound, and the transport of charge carriers is carried out by a charge transport medium.
第1図の感光体はビスメソイオン化合物をバインダー溶
液中に分散させ、この分散液を導電性支持体上に塗布、
乾燥することによって製造することができる。第2図の
感光体はビスメソイオン化合物を電荷輸送物質及びバイ
ンダーを溶解した溶液中に分散せしめ、この分散液を導
電性支持体上に塗布、乾燥することによって製造するこ
とができる。また、第3図の感光体は、導電性支持体上
にビスメソイオン化合物を真空蒸着するか、或いは、ビ
スメソイオン化合物の微粒子を溶剤又はバインダー溶液
中に分敗して得た分散液を塗布、乾燥し、その上に電荷
輸送物質及びバインダーを溶解した溶液を塗布、乾燥す
ることにより製造することができる。第4図の感光体は
電荷輸送物質及びバインダーを溶解した溶液を導電性支
持体上に塗布、乾燥し、その上にビスメソイオン化合物
を真空蒸着するか、或いはビスメソイオン化合物の微粒
子を溶剤又はバインダー溶液中に分散して得た分散液を
塗布、乾燥することにより製造することができる。The photoreceptor shown in FIG. 1 is made by dispersing a bismeso ion compound in a binder solution, coating this dispersion on a conductive support,
It can be manufactured by drying. The photoreceptor shown in FIG. 2 can be manufactured by dispersing a bismeso ion compound in a solution containing a charge transporting substance and a binder, coating this dispersion on a conductive support, and drying it. The photoreceptor shown in FIG. 3 can be produced by vacuum-depositing a bismesoion compound on a conductive support, or by applying a dispersion obtained by dissolving fine particles of a bismesoion compound in a solvent or binder solution and drying it. It can be manufactured by applying a solution containing a charge transporting substance and a binder thereon and drying it. The photoreceptor shown in Fig. 4 is produced by coating a conductive support with a solution containing a charge transport substance and a binder and drying it, and then vacuum-depositing a bismesoion compound thereon, or by depositing fine particles of a bismesoion compound in a solvent or binder solution. It can be manufactured by applying and drying a dispersion obtained by dispersing the liquid into a liquid.
これらの感光体の感光層の厚さは、第1図及び第2図の
感光体の場合、3〜50μm、好ましくは5〜20μm
である。又第3図及び第4図の感光体の場合には、電荷
担体発生層の厚さは5μm以下、好ましくは0.01〜
2μmであり、電荷輪送層の厚さは3〜50μm、好ま
しくは5〜20μmである。又、第1図の感光体に於い
て、感光層中のビスメソイオン化合物の割合は、感光層
に対して10〜70重量%、好ましくは30〜50重量
%である。第2図の感光体に於いては、感光層中のビス
メソイオン化合物の割合は1〜50重量%、好ましくは
3〜30重量%であり、又、電荷輸送物質の割合は10
〜90重量%、好ましくは10〜60重量%である。第
3図及び第4図の感光体における電荷輸送媒体中の電荷
輸送物質の割合はlO〜95重景%、好ましくは10〜
60重量%である。The thickness of the photosensitive layer of these photoreceptors is 3 to 50 μm, preferably 5 to 20 μm in the case of the photoreceptors shown in FIGS.
It is. In the case of the photoreceptor shown in FIGS. 3 and 4, the thickness of the charge carrier generation layer is 5 μm or less, preferably 0.01 to 5 μm.
2 μm, and the thickness of the charge transport layer is 3 to 50 μm, preferably 5 to 20 μm. In the photoreceptor shown in FIG. 1, the proportion of the bismeso ion compound in the photosensitive layer is 10 to 70% by weight, preferably 30 to 50% by weight, based on the photosensitive layer. In the photoreceptor shown in FIG. 2, the proportion of the bismeso ion compound in the photosensitive layer is 1 to 50% by weight, preferably 3 to 30% by weight, and the proportion of the charge transport substance is 10% by weight.
-90% by weight, preferably 10-60% by weight. The proportion of the charge transport substance in the charge transport medium in the photoreceptor of FIGS. 3 and 4 is 10 to 95%, preferably 10 to 95%.
It is 60% by weight.
本発明の感光体に用いられる導電性支持体としては、例
えば、アルミニウム、鋼、亜鉛、ステンレス、クロム、
チタン、ニッケル、モリブデン、バナジウム、インジウ
ム、金、白金等の金属または合金を用いた金属板、金属
ドラム、或いは、導電性ボリマー、酸化インジウム等の
導電性化合物やアルミニウム、パラジウム、金等の金属
又は合金を塗布、蒸着、或いはラミネートした紙、ブラ
スチソクフィルム等が挙げられる。Examples of the conductive support used in the photoreceptor of the present invention include aluminum, steel, zinc, stainless steel, chromium,
Metal plates or metal drums using metals or alloys such as titanium, nickel, molybdenum, vanadium, indium, gold, platinum, or conductive polymers, conductive compounds such as indium oxide, metals such as aluminum, palladium, gold, etc. Examples include paper coated with, vapor-deposited, or laminated with an alloy, and a plastic film.
バインダーとしては、疎水性で、電気絶縁性のフィルム
形戒可能な高分子重合体を用いるのが好ましい。この様
な高分子重合体としては、例えば、ポリカーボネート、
ポリエステル、メタクリル樹脂、アクリル樹脂、ポリ塩
化ビニル、ポリ塩化ビニリデン、ボリスチレン、ポリビ
ニルアセテート、スチレンーブタジエン共重合体、塩化
ビニリデンーアクリロニトリル共重合体、塩化ビニルー
酢酸ビニル共重合体、塩化ビニルー酢酸ビニルー無水マ
レインMl合体、シリコン樹脂、シリコンーアルキッド
樹脂、フェノールーホルムアルデヒト樹脂、スチレンー
アルキソド樹脂、ポリーN−ビニル力ルバゾール、ポリ
ビニルブチラール、ポリビニルフォルマール、ポリスル
ホン等が挙げられるが、これらに限定されるものではな
い。As the binder, it is preferable to use a hydrophobic, electrically insulating, film-formable polymer. Examples of such high molecular weight polymers include polycarbonate,
Polyester, methacrylic resin, acrylic resin, polyvinyl chloride, polyvinylidene chloride, polystyrene, polyvinyl acetate, styrene-butadiene copolymer, vinylidene chloride-acrylonitrile copolymer, vinyl chloride-vinyl acetate copolymer, vinyl chloride-vinyl acetate-maleic anhydride Examples include, but are not limited to, Ml combination, silicone resin, silicone-alkyd resin, phenol-formaldehyde resin, styrene-alkyd resin, poly-N-vinyl-rubazole, polyvinyl butyral, polyvinyl formal, polysulfone, etc. do not have.
これらの結着剤は、単独で、或いは2種類以上の混合物
として用いることもできる。These binders can be used alone or as a mixture of two or more.
又、これらのハインダーと共に、可塑剤、増感剤、表面
改質剤等の添加剤を使用することもできる。Additionally, additives such as plasticizers, sensitizers, and surface modifiers can also be used together with these hinderers.
可塑剤としては、例えば、ビフェニル、塩化ビフエニル
、0−ターフェル、p一ターフエニル、ジブチルフタレ
ート、ジエチレングリコールフタレート、ジオクチルフ
タレート、トリフエニル燐酸、メチルナフタレン、ペン
ゾフェノン塩素化バラフィン、ポリプロピレン、ボリス
チレン、各種フルオロ炭化水素等が挙げられる。Examples of plasticizers include biphenyl, biphenyl chloride, 0-terphenyl, p-terphenyl, dibutyl phthalate, diethylene glycol phthalate, dioctyl phthalate, triphenyl phosphoric acid, methylnaphthalene, penzophenone, chlorinated paraffin, polypropylene, polystyrene, various fluorohydrocarbons, and the like. Can be mentioned.
増感剤としては、例えばクロラニル、テトラシアノエチ
レン、メチルバイオレット、ローダミンB1シアニン染
料、メロシアニン染料、ピリリウム染料、チアビリリウ
ム染料等が挙げられる。Examples of the sensitizer include chloranil, tetracyanoethylene, methyl violet, rhodamine B1 cyanine dye, merocyanine dye, pyrylium dye, and thiavirylium dye.
表面改質剤としては、例えばシリコンオイル、フ,ソ樹
脂等が挙げられる。Examples of the surface modifier include silicone oil, fluorine resin, and the like.
更に本発明に於いては、導電性支持体と感光層との接着
性を向上させたり、導電性支持体から感光層への自由電
荷の注入を阻止する為、導電性支持体と感光層の間に、
必要に応して接着層或いはバリャー層を設けることもで
きる。これらの層に用いられる材料としては、前記バイ
ンダーに用いられる高分子化合物のほか、カゼイン、ゼ
ラチン、ポリビニルアルコール、エチルセルロース、ニ
トロセルロース、ポリビニルブチラール、フェノール樹
脂、ボリアミド、カルポキシーメチルセルロース塩化ビ
ニリデン系ポリマーラテソクス、スチレンーブタジエン
系ボリマーラテックス、ポリウレタン、ゼラチン、酸化
アルごニウム、酸化スズ、酸化チタン等が挙げられる。Furthermore, in the present invention, in order to improve the adhesion between the conductive support and the photosensitive layer and to prevent the injection of free charges from the conductive support to the photosensitive layer, Between,
An adhesive layer or barrier layer can also be provided if necessary. In addition to the polymer compounds used in the binder, materials used for these layers include casein, gelatin, polyvinyl alcohol, ethyl cellulose, nitrocellulose, polyvinyl butyral, phenolic resin, polyamide, carpoxymethyl cellulose, vinylidene chloride-based polymer latex. , styrene-butadiene polymer latex, polyurethane, gelatin, argonium oxide, tin oxide, titanium oxide, and the like.
又、電荷輸送物質としては、一般に電子を輸送する化合
物と正孔を輸送する化合物との二種類に分類されるが、
本発明の電子写真用感光体には両者とも使用することが
できる。In addition, charge transport materials are generally classified into two types: compounds that transport electrons and compounds that transport holes.
Both can be used in the electrophotographic photoreceptor of the present invention.
電子輸送物質としては、例えば、クロラニル、プロモア
ニル、テトラシアノエチレン、テl・ラシアノキノジメ
タン、2.4.7 − 1−リニトロ−9−フルオレノ
ン、2.4,5.7 −テトラニト口−9−フルオレノ
ン、9−ジシアノメチレン−2.4.7 − トリニト
ロフルオレノン、9−ジシアノメチレン−2,4.5.
7 −テトラニトロフルオレノン、2,4,5.7テト
ラニトロキサントン、2.4.8 − }リニトロチオ
キサントン、テトラニトロカルバゾールクロラニル、2
.3−ジクロロ−5,6−ジシアノベンゾキノン、2.
4.7 − トリニトロー9.10−フエナントレンキ
ノン、テトラクロ口無水フタール酸等を挙げることがで
きる。Examples of the electron transport substance include chloranil, promoanil, tetracyanoethylene, teracyanoquinodimethane, 2.4.7-1-linitro-9-fluorenone, and 2.4,5.7-tetranitro-9. - Fluorenone, 9-dicyanomethylene-2.4.7 - Trinitrofluorenone, 9-dicyanomethylene-2,4.5.
7-tetranitrofluorenone, 2,4,5.7tetranitroxanthone, 2.4.8-}linitrothioxanthone, tetranitrocarbazole chloranil, 2
.. 3-dichloro-5,6-dicyanobenzoquinone, 2.
Examples include 4.7-trinitro9.10-phenanthrenequinone and tetrachlorophthalic anhydride.
正札輸送物質としては、低分子化合物では、例えばビレ
ン、N一エチルカルバゾール、N−イソプロビル力ルバ
ゾール、N−フエニルカルバソール、或いは、N−メチ
ル−2−フエニルヒドラジノー3−メチリデン−9−エ
チルカルバゾール、N,N −ジフェニルヒドラジノ−
3−メチリデン−9−エチルカルバゾール、p−N.N
−ジメチルアミノベンズアルデヒドジフェニルヒドラゾ
ン、p−N,N −ジエチルアミノベンズアルデヒドジ
フエニルヒドラゾン、p−N,N−ジフエニルアξノベ
ンズアルデヒドジフヱニルヒドラゾン等のヒドラゾン[
、2.5−ビス(p−ジエチルアミノフエニル)−1.
3.4−オキサジアゾール、■−フエニル−3−(p−
ジエチルアミノスチリル)−5=(p−ジエチルアミノ
フエニル)ピラゾリン等のビラゾリン類、トリフエニル
アミン、N,N,N ’ ,N ’一テトラフェニル−
1.1′−ビフェニル−4.4′ジアミン、N,N’−
ジフェニルーN,N’−ビス(3−メチルフェニル’)
− 1.1’−ビフエニル−4,4′−ジアξン等が
挙げられる。又、高分子化合物としては、例えばポリー
N−ビニルカルバゾール、ハロゲン化ポリーN−ビニル
カルバゾール、ポリビニルビレン、ポリビニルアンスラ
セン、ポリビニルアクリジン、ビレンーホルムアルデヒ
ド樹脂、エチル力ルバゾールーホルムアルデヒド樹脂、
トリフエニルメタンボリマー等が挙げられる。Examples of low-molecular-weight compounds as transport substances include birene, N-ethylcarbazole, N-isopropyrubazole, N-phenylcarbazole, or N-methyl-2-phenylhydrazino-3-methylidene-9. -Ethylcarbazole, N,N-diphenylhydrazino-
3-methylidene-9-ethylcarbazole, p-N. N
Hydrazones such as -dimethylaminobenzaldehyde diphenylhydrazone, p-N,N-diethylaminobenzaldehyde diphenylhydrazone, p-N,N-diphenylaminobenzaldehyde diphenylhydrazone [
, 2.5-bis(p-diethylaminophenyl)-1.
3.4-oxadiazole, ■-phenyl-3-(p-
Birazolines such as diethylaminostyryl)-5=(p-diethylaminophenyl)pyrazoline, triphenylamine, N,N,N',N'-tetraphenyl-
1.1'-biphenyl-4.4'diamine, N,N'-
Diphenyl-N,N'-bis(3-methylphenyl')
- 1,1'-biphenyl-4,4'-diaξene and the like. Further, examples of the polymer compound include poly-N-vinylcarbazole, halogenated poly-N-vinylcarbazole, polyvinylpyrene, polyvinylanthracene, polyvinylacridine, birene-formaldehyde resin, ethyl rubazole-formaldehyde resin,
Examples include triphenylmethane polymer.
電荷輸送物質は、ここに記載したものに限定されるもの
ではなく、その使用に際しては単独、或いは2種類以上
混合して用いることができる。The charge transport materials are not limited to those described here, and can be used alone or in combination of two or more kinds.
積層型感光体を塗工によって形成する場合、バインダー
を溶解する溶剤は、バインダーの種類によって異なるが
、下層を溶解しないものの中から選択することが好まし
い。具体的な有機溶剤の例としては、例えば、メタノー
ル、再タノール、n一プロバノール等のアルコール類;
アセトン、メチルエチルケトン、シクロヘキサノン等の
ケトン11.N,N−ジメチルホルムアミド、N,N−
ジメチルアセトアごド等のアミド類;テトラヒド口フラ
ン、ジオキサン、メチルセロソルブ等のエーテル類;酢
酸メチル、酢酸エチル等のエステル類;ジメチルスルホ
キシド、スルホラン等のスルホキシド及びスルホン類;
塩化メチレン、クロロホルム、四塩化炭素、トリクロロ
エタン等の脂肪族ハロゲン化炭化水素;ベンゼン、トル
エン、キシレン、モノクロルベンゼン、ジクロルベンゼ
ン等の芳香族類などが挙げられる。When forming a laminated photoreceptor by coating, the solvent that dissolves the binder varies depending on the type of binder, but is preferably selected from those that do not dissolve the lower layer. Specific examples of organic solvents include alcohols such as methanol, retanol, and n-probanol;
Ketones such as acetone, methyl ethyl ketone, cyclohexanone, etc.11. N,N-dimethylformamide, N,N-
Amides such as dimethylacetate; ethers such as tetrahydrofuran, dioxane, and methyl cellosolve; esters such as methyl acetate and ethyl acetate; sulfoxides and sulfones such as dimethyl sulfoxide and sulfolane;
Examples include aliphatic halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, and trichloroethane; and aromatics such as benzene, toluene, xylene, monochlorobenzene, and dichlorobenzene.
塗工法としては、例えば浸漬コーティング法、スプレー
コーティング法、スビンナーコーティング法、ビードコ
ーティング法、ワイヤーバーコーティング法、ブレード
コーティング法、ローラーコーティング法、カーテンコ
ーティング法等のコーティング法を用いることができる
。As the coating method, for example, a dip coating method, a spray coating method, a sinter coating method, a bead coating method, a wire bar coating method, a blade coating method, a roller coating method, a curtain coating method and the like can be used.
以下、実施例により本発明を具体的に説明するが、これ
により本発明が実施例に限定されるもの?はない。尚、
実施例中「部」とあるのは「重量部」を示す。又、ビス
メソイオン化合物の魚は第1表中の磁を意味する。Hereinafter, the present invention will be specifically explained with reference to Examples, but does this mean that the present invention is limited to the Examples? There isn't. still,
In the examples, "parts" indicate "parts by weight." In addition, the bismesoionic compound fish means the magnetic substance in Table 1.
実施例1
ポリエステル樹脂(商品名「バイロン200」東洋紡社
製)10部、磁1のビスメソイオン化合物10部及びテ
トラヒド口フラン80部を振動ミル中で粉砕混合し、得
られた分散液をアルミニウム蒸着したポリエステルフィ
ルム上にワイヤーハーで塗布、乾燥し厚さ約10μの感
光層を持った第1図の構造の感光体を得た。次にこの感
光体の感光層面に静電複写紙試験装置Model SP
−428(川口電機製作所社製)を用いて、まず感光
体を暗所で印加電圧−6kVのコロナ放電により帯電さ
せ、10秒間暗所に放置し、ついでタングステンランプ
から、その表面が照度5ルックスになるように感光層に
光照射を行ない、その表面電位が暗所に10秒間放置後
の表面電位の%に減少する迄の時間を測定し、感光度E
I/t (ルソクス・秒)を求めたところ、El/■=
1 6. 0ルックス・秒であった。Example 1 10 parts of a polyester resin (trade name "Vylon 200" manufactured by Toyobo Co., Ltd.), 10 parts of a bismethionic compound of Magnetic 1, and 80 parts of tetrahydrofuran were pulverized and mixed in a vibrating mill, and the resulting dispersion was deposited with aluminum. It was coated on a polyester film with a wire shear and dried to obtain a photoreceptor having the structure shown in FIG. 1 having a photosensitive layer with a thickness of about 10 μm. Next, an electrostatic copying paper testing device Model SP was applied to the photosensitive layer surface of this photoreceptor.
-428 (manufactured by Kawaguchi Denki Seisakusho Co., Ltd.), the photoreceptor was first charged in the dark by corona discharge with an applied voltage of -6 kV, left in the dark for 10 seconds, and then a tungsten lamp was used to charge the surface with an illumination intensity of 5 lux. The photosensitive layer is irradiated with light so that the photosensitive layer becomes
When I/t (Rusox seconds) was calculated, El/■=
1 6. It was 0 lux seconds.
実施例2
ポリエステル樹脂(実施例1と同製品)3部、2,4.
7−トリニト口−9−フルオレノン3部、患1のビスメ
ソイオン化合物0. 6部及びテトラヒド口フラン30
部をボール亀ル中で粉砕混合し、得られた分散液をアル
ミニウムを蒸着したポリエステルフィルム上にワイヤー
バーを用いて塗布乾燥し厚さ約9μの感光層をもった第
2図の構造の感光体を作製した。次にこの感光体の感度
を実施例lに準じて測定したところE I/! = 3
. 5ルックス・秒であった。Example 2 3 parts of polyester resin (same product as Example 1), 2, 4.
3 parts of 7-trinitol-9-fluorenone, 0.0 parts of bismesoionic compound of patient 1. 6 parts and 30 parts of tetrahydrofuran
The resulting dispersion was applied onto a polyester film coated with aluminum using a wire bar and dried to form a photosensitive layer with a thickness of approximately 9 μm as shown in Figure 2. The body was created. Next, the sensitivity of this photoreceptor was measured according to Example 1, and it was found to be E I/! = 3
.. It was 5 lux seconds.
実施例3
PkLlのビスメソイオン化合物3部をフェノキシ樹脂
(商品名rPKHI{Jユニオンカーバイド社製)1部
をジオキサン75部に溶解させた液中で振動ミルを用い
て粉砕混合し、得られた分散液をアルミニウム蒸着ポリ
エステルフィルム上にワイヤーバーを用いて塗布乾燥し
、厚さlμの電荷発生層を形威させた。この電荷発生層
の上にp−ジエチルアミノベンズアルデヒドージフエニ
ルヒドラゾン5部、ポリカーボネート樹脂(商品名「バ
ンライ} L−1250WJ帝人化戒社製)5部を塩化
メチレン65部に溶かした溶液をワイヤーバーを用いて
塗布乾燥(7厚さ10μの電荷輸送層を形成せしめ第3
図の構造の感光体を得た。こうして作製した感光体の感
度を実施例1に準じて測定したところE+zz=2.8
ルックス・秒であった。Example 3 3 parts of a bismethionic compound of PkLl was ground and mixed in a solution in which 1 part of phenoxy resin (trade name rPKHI {manufactured by J Union Carbide) was dissolved in 75 parts of dioxane using a vibrating mill, and the resulting dispersion was prepared. was coated on an aluminum vapor-deposited polyester film using a wire bar and dried to form a charge generating layer with a thickness of lμ. A solution of 5 parts of p-diethylaminobenzaldehyde diphenylhydrazone and 5 parts of polycarbonate resin (trade name "Banrai" L-1250WJ manufactured by Teijin Kakaisha) dissolved in 65 parts of methylene chloride was placed on top of this charge generation layer using a wire bar. Coating and drying (7 to form a charge transport layer with a thickness of 10μ)
A photoreceptor having the structure shown in the figure was obtained. The sensitivity of the photoreceptor thus prepared was measured according to Example 1 and found to be E+zz=2.8.
It was a look second.
実施例4〜17
11hlのビスメソイオン化合物の代りに下記第2表の
ビスメソイオン化合物を夫々用いた以外は実施例3と同
じ方法で第3図の構造の感光体を作威し、実施例1に準
じて感度の測定を行ない第2表に掲げる結果を得た。Examples 4 to 17 A photoreceptor having the structure shown in FIG. 3 was prepared in the same manner as in Example 3, except that the bismeso ion compounds shown in Table 2 below were used in place of the 11hl bismeso ion compound, and the photoreceptor was prepared in the same manner as in Example 1. The sensitivity was measured and the results listed in Table 2 were obtained.
第
2
表
?施例l8
電荷輸送物質としてp−ジェチルアミノベンズアルデヒ
ドージフエニルヒドラゾンの代りにNエチル力ルバゾー
ル−3−メチリデンーN−アミノインドリンを用いた以
外は実施例3と同じ方法で第3図の構造の感光体を作威
し、実施例工に準じてその感度を測定したところEl/
■=2.5ルックス・秒であった。Second table? Example 18 The structure shown in FIG. 3 was prepared in the same manner as in Example 3, except that N-ethyl rubazole-3-methylidene-N-aminoindoline was used instead of p-jethylaminobenzaldehyde diphenylhydrazone as the charge transport material. When a photoreceptor was prepared and its sensitivity was measured according to the example, El/
■ = 2.5 lux seconds.
実施例19〜32
Na Iのビスメソイオン化合物の代りに下記第3表の
ビスメソイオン化合物を夫々用い、且つ電荷輸送物質と
してp−ジェチルアミノベンズアルデヒドージフェニル
ヒドラゾンの代りにN一エチルカルバゾールー3−メチ
リデンーN−アξノインドリンを用いた以外は実施例3
と同し方法で第3図の構造の感光体を作威し、実施例1
に準じて感度の測定を行ない第゜3表に掲げる結果を得
た。Examples 19 to 32 The bismesoionic compounds shown in Table 3 below were used instead of the bismesoionic compound of NaI, and N-ethylcarbazole-3-methylidene-N was used instead of p-jethylaminobenzaldehyde diphenylhydrazone as the charge transport material. -Example 3 except that ξanoindoline was used
A photoreceptor having the structure shown in FIG. 3 was prepared in the same manner as in Example 1.
The sensitivity was measured according to the method and the results listed in Table 3 were obtained.
/
◇レ′
/
/
第
3
表
実施例33
電荷輸送物質としてp−ジエチルアミノベンズアルデヒ
ドージフエニルヒドラヅンの代りにNエチルカルバゾー
ルー3−メチリデンーN−アミノテトラヒドロキノリン
を用いた以外は実施例3と同じ方法で第3図の構造の感
光体を作威し、実施例1に準じて感度を測定したところ
El/Z=2.6ルックス・秒であった。/ ◇Re' / / Table 3 Example 33 Same as Example 3 except that N-ethylcarbazole-3-methylidene-N-aminotetrahydroquinoline was used instead of p-diethylaminobenzaldehyde diphenylhydradun as the charge transport material. A photoreceptor having the structure shown in FIG. 3 was produced using the same method, and the sensitivity was measured according to Example 1, and the sensitivity was found to be El/Z=2.6 lux·sec.
実施例34〜47
btのビスメソイオン化合物の代りに下記第4表のビス
メソイオン化合物を夫々用い、且つ電荷輸送物賞として
P−ジエチルアξノヘンズアルデヒドージフェニルヒド
ラゾンの代りにN一エチル力ルバゾール−3−メチリデ
ンーN−アミノテトラヒドロキノリンを用いた以外は実
施例3と同じ方法で第3図の構造の感光体を作或し、実
施例1に準じて感度の測定を行ない、第4表に掲げる結
果を得た。Examples 34 to 47 Each of the bismesoionic compounds shown in Table 4 below was used in place of the bt bismesoionic compound, and N-ethyl Rubazole-3- was substituted for P-diethylanohenzaldehyde diphenylhydrazone as the charge transport material. A photoreceptor having the structure shown in Figure 3 was prepared in the same manner as in Example 3, except that methylidene-N-aminotetrahydroquinoline was used, and the sensitivity was measured in accordance with Example 1. The results are shown in Table 4. Obtained.
第
4
表
?施例48
ポリカーボネート樹脂(実施例3と同製品)3部、p−
ジエチルアごノベンズアルデヒドージフエニルヒドラゾ
ン3部をテトラヒド口フラン35部に溶かした溶液をア
ルミニウムを蒸着したポリエステルフィルム上にワイヤ
ーバーを用いて塗布乾燥し厚さ約10μの電荷輸送層を
形威せしめた。Table 4? Example 48 3 parts of polycarbonate resin (same product as Example 3), p-
A solution of 3 parts of diethylanobenzaldehyde diphenylhydrazone dissolved in 35 parts of tetrahydrofuran was applied onto an aluminum-deposited polyester film using a wire bar and dried to form a charge transport layer with a thickness of about 10 μm. .
次に実施例3において電荷発生層の形成に用いた塗料を
上記電荷輸送層の上にワイヤーバーを用いて塗布乾燥し
厚さ約0.8μの電荷発生層を形成せしめ第4図の構造
の感光体を得た。こうして作製した感光体の感度を印加
電圧+6kVのコロナ放電を行ない実施例1に準じて測
定したところEl/■=3.0ルックス・秒であった。Next, the paint used to form the charge generation layer in Example 3 was applied onto the charge transport layer using a wire bar and dried to form a charge generation layer with a thickness of about 0.8 μm. A photoreceptor was obtained. The sensitivity of the thus produced photoreceptor was measured according to Example 1 by performing corona discharge at an applied voltage of +6 kV, and found that El/■=3.0 lux·sec.
本発明の電子写真用感光体は、耐久性に優れ、高感度で
あるので、’PPC複写機等に広く利用することができ
る。Since the electrophotographic photoreceptor of the present invention has excellent durability and high sensitivity, it can be widely used in 'PPC copying machines and the like.
第1〜4図は、本発明に係わる電子写真用感光体の拡大
部分断面図である。
1・・・導電性支持体、2a,2b,2c,2d−・・
感光層、3・・・ビスメソイオン化合物、4・・・バイ
ンダー、5・・・電荷輸送物質、6・・・電荷担体発生
層、7・・・電荷輸送層。
代
理
人1 to 4 are enlarged partial cross-sectional views of the electrophotographic photoreceptor according to the present invention. 1... Conductive support, 2a, 2b, 2c, 2d-...
Photosensitive layer, 3... bismesoionic compound, 4... binder, 5... charge transport material, 6... charge carrier generation layer, 7... charge transport layer. agent
Claims (1)
Rは置換基を有しても良い炭化水素基又は置換基を有し
ても良い複素環基を表わす。)で表わされる化合物を含
有することを特徴とする電子写真用感光体。[Claims] 1. The photosensitive layer has the general formula (I) ▲mathematical formula, chemical formula, table, etc.▼ (wherein A represents a phenylene group or a naphthylene group,
R represents a hydrocarbon group which may have a substituent or a heterocyclic group which may have a substituent. ) A photoreceptor for electrophotography, characterized in that it contains a compound represented by:
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP22970489A JPH0391762A (en) | 1989-09-05 | 1989-09-05 | Electrophotoraphic sensitive body |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP22970489A JPH0391762A (en) | 1989-09-05 | 1989-09-05 | Electrophotoraphic sensitive body |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH0391762A true JPH0391762A (en) | 1991-04-17 |
Family
ID=16896391
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP22970489A Pending JPH0391762A (en) | 1989-09-05 | 1989-09-05 | Electrophotoraphic sensitive body |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH0391762A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2007101433A (en) * | 2005-10-06 | 2007-04-19 | Horiba Ltd | Gas analyzer |
-
1989
- 1989-09-05 JP JP22970489A patent/JPH0391762A/en active Pending
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2007101433A (en) * | 2005-10-06 | 2007-04-19 | Horiba Ltd | Gas analyzer |
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