JPH012053A - Photoconductive coating and electrophotographic photoreceptor using the same - Google Patents
Photoconductive coating and electrophotographic photoreceptor using the sameInfo
- Publication number
- JPH012053A JPH012053A JP62-158441A JP15844187A JPH012053A JP H012053 A JPH012053 A JP H012053A JP 15844187 A JP15844187 A JP 15844187A JP H012053 A JPH012053 A JP H012053A
- Authority
- JP
- Japan
- Prior art keywords
- group
- carrier
- groups
- lower alkyl
- tables
- 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
- 108091008695 photoreceptors Proteins 0.000 title claims description 18
- 238000000576 coating method Methods 0.000 title claims description 12
- 239000011248 coating agent Substances 0.000 title claims description 11
- 239000000126 substance Substances 0.000 claims description 28
- 239000000049 pigment Substances 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 150000002430 hydrocarbons Chemical group 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 description 16
- 239000010408 film Substances 0.000 description 7
- 239000011230 binding agent Substances 0.000 description 6
- 239000000975 dye Substances 0.000 description 5
- 230000035945 sensitivity Effects 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- 239000004677 Nylon Substances 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229920006026 co-polymeric resin Polymers 0.000 description 2
- -1 etc.) Polymers 0.000 description 2
- 239000010419 fine particle Substances 0.000 description 2
- 238000010030 laminating Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 229920001778 nylon Polymers 0.000 description 2
- 150000004866 oxadiazoles Chemical class 0.000 description 2
- 150000007978 oxazole derivatives Chemical class 0.000 description 2
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 229910052711 selenium Inorganic materials 0.000 description 2
- 239000011669 selenium Substances 0.000 description 2
- 150000004961 triphenylmethanes Chemical class 0.000 description 2
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 1
- WUPHOULIZUERAE-UHFFFAOYSA-N 3-(oxolan-2-yl)propanoic acid Chemical compound OC(=O)CCC1CCCO1 WUPHOULIZUERAE-UHFFFAOYSA-N 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- 229920000305 Nylon 6,10 Polymers 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000001000 anthraquinone dye Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 229910052980 cadmium sulfide Inorganic materials 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 239000012461 cellulose resin Substances 0.000 description 1
- 238000007600 charging Methods 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000007786 electrostatic charging Methods 0.000 description 1
- 229920006242 ethylene acrylic acid copolymer Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 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
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Abstract
(57)【要約】本公報は電子出願前の出願データであるた
め要約のデータは記録されません。(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.
Description
【発明の詳細な説明】
「技術分野」
本発明は、新規な有機光導電性化合物を含有する光導電
性被膜およびそれを用いた電子写真感光体に関する。DETAILED DESCRIPTION OF THE INVENTION [Technical Field] The present invention relates to a photoconductive coating containing a novel organic photoconductive compound and an electrophotographic photoreceptor using the same.
[従来技術およびその問題点」
電子写真感光体としては、セレン、酸化亜鉛、硫化カド
ミウム等の無機光導電性化合物を主成分として含有、す
る感光層を有するものが広く知られでいた。しかし、こ
れらは、熱安定性、耐久性等の特性上必ずしも満足し得
るものではなく、さらに、毒性を有するために製造上、
取扱い上にも問題があった。[Prior Art and its Problems] As electrophotographic photoreceptors, those having a photosensitive layer containing as a main component an inorganic photoconductive compound such as selenium, zinc oxide, or cadmium sulfide have been widely known. However, these are not necessarily satisfactory in terms of properties such as thermal stability and durability, and furthermore, due to their toxicity, they are difficult to manufacture.
There were also problems in handling.
一方ζ有機光導電性化合物を主成分とする感光層を有す
る電子写真感光体は、製造が比較的容易であること、安
価であること、取扱いが容易であること、また、一般に
セレン感光体に比べ熱安定性が優れていること、などの
多くの利点を有するので、近年、注目を集めている。こ
のような有機光導電性化合物としては、ポリ−N−ビニ
ルカルバゾールが最もよく知られており、これと2.4
.7−t−ウニトロ−9−フルオレノン等のルイス酸と
から形成される電倚移動錯体を主成分とする感光層を有
する電子写真感光体が既に実用化されている。On the other hand, an electrophotographic photoreceptor having a photosensitive layer containing a ζ organic photoconductive compound as a main component is relatively easy to manufacture, inexpensive, and easy to handle; It has attracted attention in recent years because it has many advantages such as superior thermal stability. Poly-N-vinylcarbazole is the most well-known such organic photoconductive compound;
.. Electrophotographic photoreceptors having a photosensitive layer containing as a main component an electrostatic transfer complex formed from a Lewis acid such as 7-t-unitro-9-fluorenone have already been put to practical use.
また、光導電体のキャリヤ発生機能と、キャリヤ輸送機
能とを、それぞれ別個の物質に分担させるようにした積
層クイブあるいは分散タイプの機能分離型感光層を有す
る電子写真感光体が知られており、例えば無定形セレン
薄膜からなるキャリヤ発生層と、ポリ−N−ビニルカル
バゾールを主成分として含有するキャリヤ輸送層とから
なる感光層を有する電子写真感光体が既に実用化されで
いる。Furthermore, electrophotographic photoreceptors are known that have a laminated quib or dispersion type functionally separated photosensitive layer in which the carrier generation function and the carrier transport function of the photoconductor are assigned to separate substances, respectively. For example, an electrophotographic photoreceptor having a photosensitive layer consisting of a carrier generation layer made of an amorphous selenium thin film and a carrier transport layer containing poly-N-vinylcarbazole as a main component has already been put into practical use.
ざらに、上記機能分離型感光Rを有する電子写真感光体
においで、キャリヤ発生物質およびキャリヤ輸送物質の
両方を有機光導電性化合物にする試みもなされている。Furthermore, attempts have been made to use organic photoconductive compounds as both the carrier generating substance and the carrier transporting substance in the electrophotographic photoconductor having the above-mentioned functionally separated type photoconductor R.
この場合、キャリヤ発生物質としては、アゾ色素、フク
ロシアニン色素、アントラキノン色素、ペリレン色素、
シアニン色素、チアどリリウム色素、スクェアリウム色
素などが知られている。また、キャリヤ輸送物質として
は、アミン誘導体、オキサゾール誘導体、オキサジアゾ
ール誘導体、トリフェニルメタン誘導体などが知られて
いる。In this case, carrier-generating substances include azo dyes, fuccyanine dyes, anthraquinone dyes, perylene dyes,
Known examples include cyanine dyes, thiadolylium dyes, and squareium dyes. Further, as carrier transport substances, amine derivatives, oxazole derivatives, oxadiazole derivatives, triphenylmethane derivatives, etc. are known.
これらのキャリヤ発生物質およびキャリヤ輸送物質は、
それ自身被膜形成能を有ざない場合には、各種の結着剤
中と併用され、それによって被膜が形成されている。そ
して、導電性支持体上にキャリヤ発生物質を有する層と
、キャリヤ輸送物質を有する層とを積層してなる電子写
真感光体、あるいはキャリヤ発生物質とキャリヤ輸送物
質とを分散させた状態で含有する層を形成しでなる電子
写真感光体が知られている。These carrier-generating substances and carrier-transporting substances are
When it does not have the ability to form a film by itself, it is used in combination with various binders to form a film. Then, an electrophotographic photoreceptor is formed by laminating a layer having a carrier-generating substance and a layer having a carrier-transporting substance on a conductive support, or it contains a carrier-generating substance and a carrier-transporting substance in a dispersed state. 2. Description of the Related Art Electrophotographic photoreceptors formed of layers are known.
しかしながら、このようにキャリヤ発生物質として有機
光導電性化合物を用いた電子写真感光体は、無機光導電
性化合物を用いたものと比べると、未だ光導電゛iの感
度が低く、かつ、耐久性の点ても劣っているため、実用
化可能なものは極めで少ないのが現状である。However, electrophotographic photoreceptors using organic photoconductive compounds as carrier generating substances still have lower photoconductivity sensitivity and durability than those using inorganic photoconductive compounds. Currently, there are very few products that can be put into practical use because they are inferior in terms of both.
「発明の目的」
本発明の目的は、新規な有機光導電性化合物を採用する
ことにより、高感度な光導電性被膜およびそれを用いた
電子写真感光体を提供することにある。"Object of the Invention" An object of the present invention is to provide a highly sensitive photoconductive coating and an electrophotographic photoreceptor using the same by employing a novel organic photoconductive compound.
「発明の構成」
本発明による光導電性被膜は、下記一般式(1)で示さ
れるビスアゾ顔料を少なくとも一種類含有することを特
徴とする。"Structure of the Invention" The photoconductive film according to the present invention is characterized by containing at least one type of bisazo pigment represented by the following general formula (1).
(式中、Cpは、
を表わし、Rは水素原子、低級アルキル基、アリール基
、アルコキシカルボニル基、アリールオキシカルボニル
基、アシル基、ハロゲン原子または1価の有機残基を表
わす、Xはベンゼン環と縮合しでM換または無言換の炭
化水素系もしくは複素系芳香環を形成するために必要な
原子団を表わを表わす、Rはそれぞれ同一でも異なって
いでもよい、また、R6、R2は水素原子、低級アルキ
ル基、アリール基、アルコキシカルボニル基、アリール
オキシカルボニル基、アシル基、ハロゲン原子または1
価の有機残基を表わす、)また、本発明による電子写真
感光体は、導電性支持体の上に、前記一般式(1)で示
されるとスアゾ順料を少なくとも一種類含有する光導電
性被膜を有する感光層を設けたことを特徴とする。(In the formula, Cp represents, R represents a hydrogen atom, a lower alkyl group, an aryl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an acyl group, a halogen atom, or a monovalent organic residue, and X represents a benzene ring. Represents an atomic group necessary for condensing with M to form an M-substituted or silent hydrocarbon or heteroaromatic ring, R may be the same or different, and R6 and R2 are hydrogen. atom, lower alkyl group, aryl group, alkoxycarbonyl group, aryloxycarbonyl group, acyl group, halogen atom or 1
Furthermore, the electrophotographic photoreceptor according to the present invention includes a photoconductive material containing at least one kind of suazo additive represented by the general formula (1) above, on a conductive support. It is characterized by providing a photosensitive layer having a coating.
これまでに前記一般式(1)で示されるビスアゾ顔料を
電子写真用光導電′11価物としで用いた試みはなく、
本発明者は、この化合物を電子写真用光導電性化合物、
特にはキャリセ発生物質としで用いることにより、優れ
た感度を有する電子写真感光体が得られることを見出し
、本発明を完成するに至ったものである。Until now, there has been no attempt to use the bisazo pigment represented by the general formula (1) as a photoconductive compound for electrophotography.
The present inventor has developed this compound into a photoconductive compound for electrophotography,
In particular, the inventors have discovered that an electrophotographic photoreceptor with excellent sensitivity can be obtained by using it as a calice generating substance, and have completed the present invention.
一般式(1)で示される化合物の具体例としでは、例え
ば次のようなものが挙げられる。Specific examples of the compound represented by general formula (1) include the following.
70.
上記(2)式中、81〜R3の組合せ例を第1表に示す
。70. Examples of combinations of 81 to R3 in the above formula (2) are shown in Table 1.
上記(3)式中、Cpの組合せ例を第2表に示す。Examples of combinations of Cp in the above formula (3) are shown in Table 2.
(以下、余白)
第1
前記一般式(1)で示される化合物は、例えば第7図に
示すような反応式によって合成できる。なお、第7図に
おいで、式中の記号は、前記一般式(1)中の記号と同
し意味である。この合成法の詳細は、J、Schimi
dt、A、に:fflmpf、 Ber、、 36.3
745(1903)、J、 Schmidt、 et
al、、 Ber、、 35.311?。(Hereinafter, blank spaces) 1. The compound represented by the general formula (1) can be synthesized, for example, by a reaction formula as shown in FIG. In FIG. 7, the symbols in the formula have the same meanings as those in the general formula (1). Details of this synthesis method can be found in J. Schimi.
dt, A, to: fflmpf, Ber,, 36.3
745 (1903), J. Schmidt, et.
al,, Ber,, 35.311? .
3129、 (1920)、 A、 Ga5co、 G
、Ru’a、 E、Menziani。3129, (1920), A, Ga5co, G
, Ru'a, E., Menziani.
G、M、Nano、 G、Tappi、 J、Hete
rocycl、 Chem、、 6゜769(196,
9)に記載されている。G, M, Nano, G, Tappi, J, Hete.
rocycle, Chem,, 6°769 (196,
9).
本発明の電子写真感光体は、前記一般式(1)で示され
る何機光導電性化合物をキャリヤ発生物質としで用いる
もので、例えば次のような構成とすることができる。The electrophotographic photoreceptor of the present invention uses a photoconductive compound represented by the general formula (1) as a carrier generating substance, and can have, for example, the following structure.
第1図または第2図に示すように、導電性支持体1上に
、キャリヤ発生物質を主成分とするキャリヤ発生層2と
、キャリヤ輸送物質を主成分とするキャリヤ輸送層3と
の積層体よりなる感光層4を設ける。第1図はキャリヤ
発生層2の上にキャリヤ輸送層3を設けた例であり、第
2唄はキャリヤ輸送層3の上にキャリヤ発生層2を設け
た例である。As shown in FIG. 1 or FIG. 2, a laminate of a carrier generating layer 2 containing a carrier generating substance as a main component and a carrier transporting layer 3 containing a carrier transporting substance as a main component on a conductive support 1 is formed. A photosensitive layer 4 is provided. FIG. 1 shows an example in which the carrier transport layer 3 is provided on the carrier generation layer 2, and the second song is an example in which the carrier generation layer 2 is provided on the carrier transport layer 3.
第3図または第4図に示すように、導電性支持体1上に
、上記と同様な感光層4を中間層5を介しで設ける。As shown in FIG. 3 or 4, a photosensitive layer 4 similar to that described above is provided on a conductive support 1 with an intermediate layer 5 interposed therebetween.
第5図または第6図に示すように、キャリヤ輸送物質を
主成分とする層6中に、微粒子状のキャリヤ発生物質7
を分散しでなる感光層4を、導電性支持体1上に直接、
あるいは中間層5を介しで設置する。As shown in FIG. 5 or 6, a fine particle carrier generating substance 7 is contained in a layer 6 mainly composed of a carrier transporting substance.
A photosensitive layer 4 consisting of a dispersion of
Alternatively, it is installed via the intermediate layer 5.
導電性支持体1としては、金属板、あるいは、導電性ポ
リマー、酸化インジウム等の導電性化合物、もしくはア
ルミニウム、パラジウム、金等の金属薄膜を塗布、蒸着
またはラミネートして導電化した紙、プラスチックなど
が用いられる。The conductive support 1 may be a metal plate, or paper or plastic made conductive by coating, vapor depositing, or laminating a conductive compound such as a conductive polymer or indium oxide, or a metal thin film such as aluminum, palladium, or gold. is used.
キャリヤ発生層2は、前記一般式(1)で示されるキャ
リヤ発生物質を、ボールミル、ホモミキサー、サンドミ
ル、コロイドミル等によって分散媒中で微粒子状とし、
必要に応じて結着剤と混合分散しで得られる分散液を塗
布するか、またはキャリヤ発生物質を溶媒中で結着剤に
溶かし込まぜで得られる溶液を、浸漬法、スプレー法、
スどシナ−法などの方法で、塗布することで形成するこ
とができる。The carrier generation layer 2 is formed by turning the carrier generation substance represented by the general formula (1) into fine particles in a dispersion medium using a ball mill, a homomixer, a sand mill, a colloid mill, etc.
If necessary, a dispersion obtained by mixing and dispersing with a binder is applied, or a solution obtained by dissolving a carrier-generating substance in a binder in a solvent is applied by dipping, spraying, etc.
It can be formed by coating using a method such as a coating method.
この場合、結着剤としては、例えばフェノール樹脂、ポ
リエステル樹脂、酢酸ビニル樹脂、ポリカーボネート樹
脂、ポリペプチド樹脂、セルロース樹脂、ポリビニルピ
ロリドン、ポリエチレンオキサイド、ポリ塩化ビニル樹
脂、澱粉類、ポリビニルアルコール、アクリル系共重合
体樹脂、メタクリル系共重合体樹脂、シリコーン樹脂、
ポリアクリロニトリル系共重合体樹脂、ポリアクリルア
ミド、ポリビニルブチラール等が使用できる。In this case, examples of the binder include phenol resin, polyester resin, vinyl acetate resin, polycarbonate resin, polypeptide resin, cellulose resin, polyvinylpyrrolidone, polyethylene oxide, polyvinyl chloride resin, starch, polyvinyl alcohol, acrylic resin, etc. Polymer resin, methacrylic copolymer resin, silicone resin,
Polyacrylonitrile copolymer resin, polyacrylamide, polyvinyl butyral, etc. can be used.
なお、キャリヤ発生層2は、前記一般式(1)で示され
る化合物を真空蒸着などの方法によって薄膜化して形成
することもできる。Note that the carrier generation layer 2 can also be formed by forming a compound represented by the general formula (1) into a thin film by a method such as vacuum deposition.
キャリセ@送層3は、キャリヤ輸送物質を上記と同様な
結着剤中に分散もしくは溶解しで塗布すること(こより
形成できる。本発明においで、キャリヤ輸送物質は、特
に限定されないが、例えばアミン誘・1体、オキサゾー
ル誘導体、オキサジアゾール誘導体、トリフェニルメタ
ン誘導体などが使用できる。The carrier transport layer 3 can be formed by dispersing or dissolving a carrier transport material in a binder similar to the above and applying it. In the present invention, the carrier transport material is not particularly limited, but for example, amine. Di-1 derivatives, oxazole derivatives, oxadiazole derivatives, triphenylmethane derivatives, etc. can be used.
なお、導電性支持体1と感光層4との間に配置される中
間層5は、バリヤー機能と接着機能とを付与するもので
あり、例えばカゼイン、ポリビニルアルコール、ニトロ
セルロース、エチレン−アクリル酸コポリマー、ポリア
ミド(ナイロン6、ナイロン66、ナイロン610、共
重合ナイロン、アルコキシメチル化ナイロンなど)、ポ
リウレタン、ゼラチン、酸化アルミニウムなどで形成す
ることができる。Note that the intermediate layer 5 disposed between the conductive support 1 and the photosensitive layer 4 provides a barrier function and an adhesive function, and is made of, for example, casein, polyvinyl alcohol, nitrocellulose, ethylene-acrylic acid copolymer. , polyamide (nylon 6, nylon 66, nylon 610, copolymerized nylon, alkoxymethylated nylon, etc.), polyurethane, gelatin, aluminum oxide, etc.
ざらに、キャリヤ輸送物質を主成分とする層6中に、微
粒子状のキャリヤ発生物質7を分散しでなる感光層4は
、キャリヤ輸送物質を上記のような結着剤中に分散もし
くは溶解し、ざらにキャリヤ発生物質を分散させた液を
塗布することによって形成することかできる。Roughly speaking, the photosensitive layer 4 is made by dispersing a fine particulate carrier generating substance 7 in a layer 6 mainly composed of a carrier transporting substance, and the photosensitive layer 4 is made by dispersing or dissolving the carrier transporting substance in the above-mentioned binder. It can be formed by coating a liquid in which a carrier-generating substance is dispersed.
[発明の実施例J
実施例1〜10
ブチラール樹脂2重1部をインブロビルアルコール10
0重量部で溶かした溶液に、下記表に挙げた10151
類のビスアゾ顔料5重量部をボールミルで粉砕したもの
を加えて分子4!Iさせ、31!頚の塗工液を調製した
。そして、各塗工液を50umのAIプレート上に乾燥
後の膜厚が0.3μmとな′るようにドククーブレード
を用いて塗布し、乾燥して電荷発生層を形成した。[Example J of the invention Examples 1 to 10 1 part of 2 parts butyral resin and 10 parts of inbrovir alcohol
10151 listed in the table below is added to the solution dissolved at 0 parts by weight.
Add 5 parts by weight of similar bisazo pigments ground in a ball mill to make molecule 4! Let me, 31! A cervical coating solution was prepared. Then, each coating solution was applied onto a 50 um AI plate using a doku blade so that the film thickness after drying would be 0.3 μm, and dried to form a charge generation layer.
次に、下記構造式
で示されるヒドラゾン化合物5重量部とポリビニルカル
バゾール5重量部を、モノクロルベンゼン70重量部に
溶解し、これを前記電荷発生層の上に、乾燥後の膜厚が
20μmとなるようにドククープレードを用いて塗布し
、乾燥して電荷輸送層を形成した。Next, 5 parts by weight of a hydrazone compound represented by the following structural formula and 5 parts by weight of polyvinylcarbazole are dissolved in 70 parts by weight of monochlorobenzene, and this is placed on the charge generation layer so that the film thickness after drying is 20 μm. A charge transport layer was formed by applying the coating using a Doc Couplade and drying it.
このようにして得た10種類の電子写真感光体について
、静電気帯電試験装置!(川口電気■製、EP^−81
00型)を用いて、スタチック方式で一6KVでコロナ
帯電させ、続いて5秒間暗減衰を観測し、照度151u
xの5秒間露光で光減衰を観測して、−光電気特性を評
価した。こうして測定した初期帯電電位(Vo)、感度
(El/2)、残留電位(VR)(7)結果を第3表に
示す。Electrostatic charging test equipment for the 10 types of electrophotographic photoreceptors obtained in this way! (Made by Kawaguchi Electric ■, EP^-81
00 type), statically charged the corona at 16KV, then observed the dark decay for 5 seconds, and set the illuminance to 151u.
The photoelectric properties were evaluated by observing the optical attenuation by x exposure for 5 seconds. The results of the initial charging potential (Vo), sensitivity (El/2), and residual potential (VR) (7) thus measured are shown in Table 3.
第3表
ただし、感度は、O=良好、△=普通、×=悪い、を示
している。Table 3, however, shows the sensitivity as O=good, Δ=fair, and ×=poor.
「発明の効果」
以上説明したように、本発明によれば、一般式(1)で
示される新規なヒスアゾ顔料を用いることにより、高感
度の光導電性を有する光導電性被膜を得ることができる
。また、一般式(1)で示される新規などスアゾ顔料を
用いることにより、得られる高感度の光導電性被膜を使
用し、良好な特性を持った電子写真感光体を得ることが
できる。したがって、本発明は、電子写真複写機、レー
ザービームプリンター、LEDプリンター、CRTプリ
ンタまたは他の電子写真応用分野全般に広く適用するこ
とができる。"Effects of the Invention" As explained above, according to the present invention, a photoconductive film having high sensitivity photoconductivity can be obtained by using the novel hisazo pigment represented by the general formula (1). can. Further, by using the novel suazo pigment represented by the general formula (1), an electrophotographic photoreceptor with good characteristics can be obtained using the resulting highly sensitive photoconductive film. Therefore, the present invention can be widely applied to electrophotographic copiers, laser beam printers, LED printers, CRT printers, or other electrophotographic applications in general.
第1図、笥2図、第3図、第4図、第5図および第6図
は本発明による電子写真感光体の層構成のそれぞれ異な
る具体例を示す断面図、第7図は本発明で用いるどスア
ゾ顔料を合成するための反応式を示す図である。
第1図 第2図
第、3図 第4図
第5図 第6図FIG. 1, FIG. 2, FIG. 3, FIG. 4, FIG. 5, and FIG. 6 are cross-sectional views showing different specific examples of the layer structure of the electrophotographic photoreceptor according to the present invention, and FIG. FIG. 2 is a diagram showing a reaction formula for synthesizing a dosuazo pigment used in . Figure 1 Figure 2 Figure 3 Figure 4 Figure 5 Figure 6
Claims (2)
くとも一種類含有することを特徴とする光導電性被膜。 ▲数式、化学式、表等があります▼・・・(1) (式中、Cpは、 ▲数式、化学式、表等があります▼ ▲数式、化学式、表等があります▼または▲数式、化学
式、表等があります▼ を表わし、Rは水素原子、低級アルキル基、アリール基
、アルコキシカルボニル基、アリールオキシカルボニル
基、アシル基、ハロゲン原子または1価の有機残基を表
わす。Xはベンゼン環と縮合して置換または無置換の炭
化水素系もしくは複素系芳香環を形成するために必要な
原子団を表わす。Yは▲数式、化学式、表等があります
▼または▲数式、化学式、表等があります▼ を表わす。Rはそれぞれ同一でも異なっていてもよい。 また、R_1、R_2は水素原子、低級アルキル基、ア
リール基、アルコキシカルボニル基、アリールオキシカ
ルボニル基、アシル基、ハロゲン原子または1価の有機
残基を表わす。)(1) A photoconductive film characterized by containing at least one bisazo pigment represented by the following general formula (1). ▲There are mathematical formulas, chemical formulas, tables, etc.▼...(1) (In the formula, Cp is, ▲There are mathematical formulas, chemical formulas, tables, etc.) etc. ▼ where R represents a hydrogen atom, a lower alkyl group, an aryl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an acyl group, a halogen atom or a monovalent organic residue. represents an atomic group necessary to form a substituted or unsubstituted hydrocarbon or heteroaromatic ring. R_1 and R_2 are hydrogen atoms, lower alkyl groups, aryl groups, alkoxycarbonyl groups, aryloxycarbonyl groups, acyl groups, halogen atoms, or monovalent organic residues. )
るビスアゾ顔料を少なくとも一種類含有する光導電性被
膜を有する感光層を設けたことを特徴とする電子写真感
光体。 ▲数式、化学式、表等があります▼・・・(1) (式中、Cpは、 ▲数式、化学式、表等があります▼ ▲数式、化学式、表等があります▼または▲数式、化学
式、表等があります▼ を表わし、Rは水素原子、低級アルキル基、アリール基
、アルコキシカルボニル基、アリールオキシカルボニル
基、アシル基、ハロゲン原子または1価の有機残基を表
わす。Xはベンゼン環と縮合して置換または無置換の炭
化水素系もしくは複素系芳香環を形成するために必要な
原子団を表わす。Yは▲数式、化学式、表等があります
▼または▲数式、化学式、表等があります▼ を表わす。Rはそれぞれ同一でも異なっていてもよい。 また、R_1、R_2は水素原子、低級アルキル基、ア
リール基、アルコキシカルボニル基、アリールオキシカ
ルボニル基、アシル基、ハロゲン原子または1価の有機
残基を表わす。)(2) An electrophotographic photoreceptor comprising, on a conductive support, a photosensitive layer having a photoconductive coating containing at least one type of bisazo pigment represented by the following general formula (1). ▲There are mathematical formulas, chemical formulas, tables, etc.▼...(1) (In the formula, Cp is, ▲There are mathematical formulas, chemical formulas, tables, etc.) etc. ▼ where R represents a hydrogen atom, a lower alkyl group, an aryl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an acyl group, a halogen atom or a monovalent organic residue. represents an atomic group necessary to form a substituted or unsubstituted hydrocarbon or heteroaromatic ring. R_1 and R_2 each represent a hydrogen atom, a lower alkyl group, an aryl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an acyl group, a halogen atom, or a monovalent organic residue. )
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP15844187A JPS642053A (en) | 1987-06-25 | 1987-06-25 | Photoconductive film and electrophotographic sensitive body using same |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP15844187A JPS642053A (en) | 1987-06-25 | 1987-06-25 | Photoconductive film and electrophotographic sensitive body using same |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH012053A true JPH012053A (en) | 1989-01-06 |
JPS642053A JPS642053A (en) | 1989-01-06 |
Family
ID=15671838
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP15844187A Pending JPS642053A (en) | 1987-06-25 | 1987-06-25 | Photoconductive film and electrophotographic sensitive body using same |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS642053A (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
RU2723014C1 (en) * | 2019-12-27 | 2020-06-08 | Федеральное государственное бюджетное учреждение науки Институт органического синтеза им. И.Я. Постовского Уральского отделения Российской академии наук | Method of producing dibenzo[f,h]furazano[3,4-b]quinoxaline and substituted derivatives thereof, having charge-transport semiconductor properties |
-
1987
- 1987-06-25 JP JP15844187A patent/JPS642053A/en active Pending
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