JPH0469949B2 - - Google Patents
Info
- Publication number
- JPH0469949B2 JPH0469949B2 JP61032758A JP3275886A JPH0469949B2 JP H0469949 B2 JPH0469949 B2 JP H0469949B2 JP 61032758 A JP61032758 A JP 61032758A JP 3275886 A JP3275886 A JP 3275886A JP H0469949 B2 JPH0469949 B2 JP H0469949B2
- Authority
- JP
- Japan
- Prior art keywords
- carrier
- formula
- layer
- electrophotographic photoreceptor
- general formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 108091008695 photoreceptors Proteins 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 23
- 239000000126 substance Substances 0.000 claims description 20
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 239000010410 layer Substances 0.000 description 51
- 239000011230 binding agent Substances 0.000 description 12
- 239000000463 material Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 229920001225 polyester resin Polymers 0.000 description 3
- 239000004645 polyester resin Substances 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- 150000001989 diazonium salts Chemical class 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000010419 fine particle Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 239000004431 polycarbonate resin Substances 0.000 description 2
- 229920005668 polycarbonate resin Polymers 0.000 description 2
- 229920006267 polyester film Polymers 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical group C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- WUPHOULIZUERAE-UHFFFAOYSA-N 3-(oxolan-2-yl)propanoic acid Chemical compound OC(=O)CCC1CCCO1 WUPHOULIZUERAE-UHFFFAOYSA-N 0.000 description 1
- JFGQHAHJWJBOPD-UHFFFAOYSA-N 3-hydroxy-n-phenylnaphthalene-2-carboxamide Chemical compound OC1=CC2=CC=CC=C2C=C1C(=O)NC1=CC=CC=C1 JFGQHAHJWJBOPD-UHFFFAOYSA-N 0.000 description 1
- 235000000177 Indigofera tinctoria Nutrition 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 239000004419 Panlite Substances 0.000 description 1
- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 229910052980 cadmium sulfide Inorganic materials 0.000 description 1
- 238000009125 cardiac resynchronization therapy Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- PPSZHCXTGRHULJ-UHFFFAOYSA-N dioxazine Chemical compound O1ON=CC=C1 PPSZHCXTGRHULJ-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 230000001771 impaired effect Effects 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
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- CEAPHJPESODIQL-UHFFFAOYSA-N n-[(9-ethylcarbazol-3-yl)methylideneamino]-n-phenylaniline Chemical compound C=1C=C2N(CC)C3=CC=CC=C3C2=CC=1C=NN(C=1C=CC=CC=1)C1=CC=CC=C1 CEAPHJPESODIQL-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- -1 triamino-benzyldiphenylamine Chemical compound 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
- 238000005406 washing Methods 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
- G03G5/0664—Dyes
- G03G5/0675—Azo dyes
- G03G5/0687—Trisazo dyes
- G03G5/0688—Trisazo dyes containing hetero rings
-
- 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
- G03G5/0675—Azo dyes
- G03G5/0687—Trisazo dyes
Description
（産業上の利用分野）
本発明は電子写真感光体に関し、４，4′，4″−
トリアミノ−ベンジルジフエニルアミンをジアゾ
成分に用いたトリスアゾ化合物を含有する感光層
を設けた新規な電子写真感光体を提供する。
（従来の技術およびその問題点）
近年、電子写真方式の利用は、複写機の分野に
限らず、印刷版材、スライド、フイルム、マイク
ロフイルム等の従来は写真技術が使われていた分
野へも広がり、またレーザやCRTを光源とする
高速プリンターへの応用も検討されている。従つ
て電子写真感光体に対する要求も、高度で幅広い
ものになりつつある。
これまで電子写真方式に用いる感光体として
は、非晶質セレン、硫化カドミウム、酸化亜鉛等
の無機光導電性物質を主成分とする感光層を有す
るものが主体であつた。これらの無機物質からな
る感光体は有用なものではあるが、一方でさまざ
まな欠点もある。
近年これを補うため、種々の有機物質を光導電
性物質として用いた電子写真感光体が提案され、
実用に供され始めた。電子写真感光体はいうまで
もなく、キヤリア発生機能とキヤリア輸出機能と
を有しなければならない。キヤリア発生物質とし
て使用できる有機化合物としては、フタロシアニ
ン系、多環キノン系、インジゴ系、ジオキサジン
系、キナクリドン系、アゾ系等数多くの顔料が提
案されているが、実用化に至つたものはごく限ら
れている。またキヤリア移動物質の選択の範囲も
限定されているので、電子写真プロセスの幅広い
要求に充分こたえられるものはまだ得られていな
いのが現状である。
（問題を解決するための手段）
本発明者らは有機電子写真感光体を改良すべく
鋭意研究の結果、４，4′，4″−トリアミノ−ベン
ジルジフエニルアミンをジアゾ成分に用いたトリ
スアゾ化合物を含有する感光層を設けたものが優
れた電子写真特性を有することを見出して本発明
に至つた。
すなわち、本発明は、導電性支持体に上に下記
の一般式（）で示されるトリスアゾ化合物を含
有する感光層を設けたことを特徴とする電子写真
感光体である。
（但し、上記式中Ａは、一般式
(Industrial Application Field) The present invention relates to an electrophotographic photoreceptor, and relates to an electrophotographic photoreceptor.
Provided is a novel electrophotographic photoreceptor provided with a photosensitive layer containing a trisazo compound using triamino-benzyldiphenylamine as a diazo component. (Prior art and its problems) In recent years, electrophotography has been used not only in the field of copying machines, but also in fields where photographic technology has traditionally been used, such as printing plates, slides, films, and microfilms. Applications to high-speed printers using lasers or CRTs as light sources are also being considered. Accordingly, the requirements for electrophotographic photoreceptors are becoming more sophisticated and wide-ranging. Until now, photoreceptors used in electrophotography have mainly had photosensitive layers containing inorganic photoconductive substances such as amorphous selenium, cadmium sulfide, and zinc oxide. Although photoreceptors made of these inorganic materials are useful, they also have various drawbacks. In recent years, to compensate for this, electrophotographic photoreceptors using various organic substances as photoconductive substances have been proposed.
It has begun to be put into practical use. Needless to say, the electrophotographic photoreceptor must have a carrier generation function and a carrier export function. Many pigments have been proposed as organic compounds that can be used as carrier generating substances, such as phthalocyanine, polycyclic quinone, indigo, dioxazine, quinacridone, and azo pigments, but only a limited number of them have been put into practical use. It is being In addition, the range of carrier transfer materials that can be selected is limited, so that at present no material that satisfactorily meets the wide range of requirements of electrophotographic processes has yet been obtained. (Means for Solving the Problem) As a result of intensive research to improve organic electrophotographic photoreceptors, the present inventors have developed a trisazo compound using 4,4',4''-triamino-benzyldiphenylamine as a diazo component. The inventors of the present invention discovered that a photosensitive layer containing a trisazo compound having the following general formula ( This is an electrophotographic photoreceptor characterized by being provided with a photosensitive layer containing a compound. (However, A in the above formula is a general formula
【式】【formula】
【式】または[expression] or
【式】
で表わされ、上記式においてＸは置換または非置
換の芳香族炭化水素環、または置換または非置換
の芳香族複素環を形成するのに必要な原子群であ
りＹは−NR1R2、−NHNR3R4または−NHN＝
CR5R6であり、R1〜６はＨ、置換または非置換
のアルキル基、アリール基、アラルキル基または
複素環であり、R1とR2、R3とR4、R5とR6は、
ＮまたはＣと共に環を形成してもよい。
一般式(a)で表わされる化合物の具体例として
は、例えば、次の如き様な基がある。[Formula] In the above formula, X is an atomic group necessary to form a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted aromatic heterocycle, and Y is -NR1R2, −NHNR3R4 or −NHN=
CR5R6, R1 to R6 are H, substituted or unsubstituted alkyl group, aryl group, aralkyl group, or heterocycle, and R1 and R2, R3 and R4, R5 and R6 are
It may form a ring together with N or C. Specific examples of the compound represented by general formula (a) include the following groups.
【表】【table】
【表】【table】
【表】
一般式(b)で表される化合物の具体例として、例
えば次の様な基がある。[Table] Specific examples of the compound represented by general formula (b) include the following groups.
【表】
一般式(c)で表される化合物の具体例として、次
の如き基がある。[Table] Specific examples of the compound represented by the general formula (c) include the following groups.
【表】【table】
【表】
本発明の電子写真感光体は、上記一般式（）
で示されるトリスアゾ化合物の持つ優れたキヤリ
ア発生機能を、いわゆる積層型または分散型の電
子写真感光体のキヤリア発生物質として利用する
ことにより、帯電特性、電荷保持力、感度、残留
電位等の電子写真特性に優れるばかりでなく、被
膜物性が良好で、繰り返し使用による劣化が少な
く、熱、湿度、光に対しても諸特性が変化せず安
定した性能を発揮できる感光体である。
以下に一般式（）で表わされる構造を持つト
リスアゾ化合物の具体例を挙げる。[Table] The electrophotographic photoreceptor of the present invention has the above general formula ()
By utilizing the excellent carrier generation function of the trisazo compound shown in the formula as a carrier generation material for so-called laminated or dispersion type electrophotographic photoreceptors, electrophotography with improved charging characteristics, charge retention, sensitivity, residual potential, etc. It is a photoreceptor that not only has excellent properties, but also has good coating physical properties, shows little deterioration due to repeated use, and exhibits stable performance without changing its properties even when exposed to heat, humidity, or light. Specific examples of trisazo compounds having the structure represented by the general formula () are listed below.
【表】
上記の化合物は公知の方法で合成できる。ま
ず、４，4′，4″−トリアミノ−ベンジルジフエニ
ルアミンを常法によりジアゾ化し、生じたトリス
ジアゾニウム塩をカツプリング成分とカツプリン
グさせ、一般式（）で示される構造を持つトリ
スアゾ化合物を得る。以下に合成例の１例を挙げ
るが、他の一般式（）で示される構造を持つト
リスアゾ化合物も下記の合成例に準じて合成でき
る。尚、以下の合成例において「部」または
「％」は各々重量部または重量％を示す。
合成例
（例示化合物１の場合）
４，4′，4″−トリアミノ−ベンジルジフエニル
アミン13.2部を水300部と35％濃塩酸63部に分散
し、この液を０〜５℃に保ち、よく攪拌しながら
10％亜硝酸ナトリウム水溶液115部を10分間を要
して滴下し、滴下終了後更に15分間攪拌してジア
ゾニウム塩溶液を得る。
ナフトールAS43.5部を水酸化ナトリウム水溶
液1000部に溶解した後、冷却し、０〜５℃に保ち
ながら上記ジアゾニウム塩溶液を15分間を要して
滴下した。滴下終了後、更に２時間攪拌し、生じ
たトリスアゾ化合物を瀘別し、充分に洗浄して例
示化合物１の粗成物45.1部を得た。これをDMF、
メタノール、次いで水で順次洗浄、乾燥して精製
物を得た。
本発明の電子写真感光体の物理的構造は、既知
の形態のいずれによつてもよい。導電性支持体上
に、キヤリア発生物質である上記のトリスアゾ化
合物を主成分とするキヤリア発生層と、キヤリヤ
ー輸送物質を主成分とするキヤリア輸送層を積層
してもよいし、キヤリア発生物質をキヤリヤー輸
送物質中に分散させた感光層を設けてもよい。こ
れらは中間層を介して設けてもよいので次の様な
パターンが可能である。
() 導電性支持体／キヤリア発生層／キヤリア
輸送層
() 導電性支持体／キヤリア輸送層／キヤリア
発生層
() 導電性支持体／キヤリア発生物質を含むキ
ヤリア輸送層
() 導電性支持体／中間層／キヤリア発生層／
キヤリア輸送層
() 導電性支持体／中間層／キヤリア輸送層／
キヤリア発生層
() 導電性支持体／中間層／キヤリア発生物質
を含むキヤリア輸送層
ここで中間層とは、バリア層あるいは接着層の
事である。上記構成の電子写真感光体上に表面保
護等の目的で薄い層を設ける事も可能である。
キヤリヤー輸送物質は、電子の輸送をするもの
と正孔の輸送をするものとがあるが、本発明の電
子写真感光体の形成にはどちらも使用できる。
本発明の電子写真感光体は、有機層の光導電性
物質を使用する電子写真感光体の製造において知
られている技術に従つて、通常の方法で製造でき
る。例えば、２層構成の感光層を形成するキヤリ
ア発生層は、前記のトリスアゾ化合物を適当な媒
体中で微細粒子とし、必要に応じてバインダーを
加え、導電性支持体の上に直接、または中間層を
介して塗布するか、または既に形成したキヤリア
輸送層の上に塗布し、乾燥する。
媒体中の微細粒子は、径5μｍ以下、好ましく
は3μｍ、最適には1μｍにして分散させる必要が
ある。
バインダーを用いる場合、特に限定はないが疎
水性で、誘導率が高く、電子絶縁性のフイルム形
成高分子化合物が好ましい。各種の熱可塑性また
は熱硬化性の合成樹脂が好適に使用できる。容易
に理解されるとおり、前記の媒体はバインダーを
溶解する能力をもつと好都合である。バインダー
の使用量は、前記キヤリア発生物質に対し、重量
で0.1〜５倍の範囲からえらぶ。
キヤリア発生層の膜厚は、0.01〜20μｍの範囲
とする。好ましくは0.05〜5μｍである。キヤリア
輸送層は、キヤリヤー輸送物質を適当な媒体に分
散あるいは溶解して塗布し乾燥することにより形
成できる。キヤリヤー輸送物質が、ポリーＮ−ビ
ニルカルバゾールやポリグリシジルカルバゾール
の様な、それ自身でバインダーの役割をも果すも
のを使用する場合を除き、バインダーを使用する
ことが好ましい。バインダーとしては、キヤリア
発生層の形成に使用するバインダーと同種のもの
が使用できる。バインダーの使用量は、キヤリヤ
ー輸送物質の0.2〜５重量倍が適当である。キヤ
リア輸送層の膜厚は、１〜100μｍの範囲とする
が、好ましくは５〜50μｍである。
一方、分散型のキヤリア発生層−キヤリア輸送
層を形成するには、上述のキヤリア発生層形成用
の分散液に、キヤリヤー輪送物質を溶解させて、
導電性支持体上に塗布すればよい。キヤリヤー輪
送物質は任意にえらべるが、前記したような、そ
れ自身バインダーとして役立つものを使用する場
合は別として、一般にバインダーを添加すること
が好ましい。導電性支持体と上記の積層型または
分散型の感光層の間に中間層を設ける場合、中間
層にはキヤリア発生物質、キヤリヤー輪送物質、
バインダー、添加剤等の１種あるいは２種以上の
混合物でしかも中間層としての機能を損わない範
囲で常用の材料を用いることができる。膜厚は
10μｍ以下で好ましくは1μｍ以下が良い。
本発明の電子写真感光体は、このほかにも既知
の技術を適用することもできる。例えば感光層は
増感剤を含んでいてもよい。好適な増感剤は、有
機光導電性物質と電荷移動錯体を形成するルイス
酸や染料色素等が挙げられる。また感光層の成膜
性、化撓性、機械的強度等を向上させるために必
要に応じて可塑剤、紫外線吸収剤、酸化防止剤、
滑剤、接着促進剤、分散剤等の添加剤を加えても
よく、本発明の目的とする電子写真感光体特性を
損なわない範囲でキヤリア発生物質、キヤリヤー
輪送物質を加えてもよい。
本発明においては、キヤリア発生層、キヤリア
輸送層、更に中間層あるいは表面層の形成方法と
して、通常の塗布方法を用いることができる。
本発明の電子写真感光体は、次に掲げる実施例
からも明らかなように、帯電特性、感度特性、画
形成性において優れており、感光性も良好であ
り、また繰り返し使用しても感度や帯電特性の変
動が小さく、光疲労も少ない。耐候性も高い。
次に実施例を挙げて本発明を更に具体的に説明
する。文中「部」とあるのは重量部をあらわす。
実施例 １
前記例示化合物(1)１部とポリエステル樹脂（東
洋紡「バイロン200」）１部をテトラヒドロフラン
50部中に入れてボールミルで充分に分散させ、分
散液をワイヤーコーターでアルミニウム板上に塗
布し、120℃の熱風で30分間乾燥して、膜厚が
0.3μｍのキヤリア発生層を設けた。
その上に、Ｐ−ジエチルアミノベンズアルデヒ
ド−Ｎ−フエニル−Ｎ−ベンジルヒドラゾン５部
とポリカーボネート樹脂（帝人化成「パンライト
Ｌ−1250」）５部とを１，２−ジクロエタン70部
に溶解した溶液を塗布し、60℃の温風で３時間乾
燥して、膜厚14μｍのキヤリア輸送層を形成し
た。
このようにして製造した感光板を、25℃、RH
（相対湿度）55％の雰囲気中に放置して、調湿し
た後、静電紙試験装置（川口電機製作所「SP−
428」）を用いて、スタテイツク方式で−6KVの
電圧でコロナ帯電し、暗所に10秒間保持した後、
タングステンランプを光源として試料面照度が
5.0ルクスになるように露光し、電子写真特性の
評価を行い次の結果を得られた。
Vo（帯電の初期電圧）＝−770（Ｖ）
Vd10（暗所での10秒間の電位保持率）＝90.5
（％）
Ｅ1/2（半減衰露光量）＝2.1（ルクス・秒）
実施例 ２
例示化合物(2)を用いたほかは、実施例１と同様
にして特性を測定したところ、結果はつぎのとお
りであつた。
Vo＝−680（Ｖ）
Vd10＝87.2（％）
Ｅ1/2＝3.3（ルクス・秒）
実施例 ３
例示化合物(3)1.5部とポリエステル樹脂（東洋
紡「バイロン200」）１部とを、１，２−ジクロル
エタン250部中に入れてボールミルで分散させ、
分散液をアルミニウム蒸着させたポリエステルフ
イルム上に塗布し、120℃の熱風で30分間乾燥し
て、膜厚0.5μｍのキヤリア発生層を設けた。
その上に、９−エチルカルバゾール−３−カル
ボアルデヒド−１，１−ジフエニルヒドラゾン10
部とポリエステル樹脂（前記「バイロン200」）10
部とを１，２−ジクロルエタン100部に溶解した
溶液を塗布し、60℃の温風で３時間乾燥して膜厚
15μｍのキヤリア輸送層を形成した。
この電子写真感光体の特性を測定して次の結果
を得た。
Vo＝−930（Ｖ）
Vd10＝92.5（％）
Ｅ1/2＝1.9（ルクス・秒）
実施例 ４〜14
実施例３における例示化合物３に代えて下記の
例示化合物を使用し、そのほかは実施例３と同様
にして感光体を製造した。
それぞれの特性な下記の通りである。[Table] The above compounds can be synthesized by known methods. First, 4,4',4''-triamino-benzyldiphenylamine is diazotized by a conventional method, and the resulting trisdiazonium salt is coupled with a coupling component to obtain a trisazo compound having a structure represented by the general formula (). One example of synthesis is given below, but other trisazo compounds having the structure represented by the general formula () can also be synthesized according to the synthesis example below. In the following synthesis examples, "part" or "%" indicates weight parts or weight %, respectively. Synthesis example (for exemplified compound 1) 13.2 parts of 4,4',4''-triamino-benzyldiphenylamine was dispersed in 300 parts of water and 63 parts of 35% concentrated hydrochloric acid, and this liquid was maintained at 0 to 5°C. While stirring well
115 parts of a 10% aqueous sodium nitrite solution was added dropwise over a period of 10 minutes, and after the addition was complete, the mixture was stirred for an additional 15 minutes to obtain a diazonium salt solution. After 43.5 parts of naphthol AS was dissolved in 1000 parts of an aqueous sodium hydroxide solution, the solution was cooled and the above diazonium salt solution was added dropwise over a period of 15 minutes while maintaining the temperature at 0 to 5°C. After the addition was completed, the mixture was further stirred for 2 hours, and the resulting trisazo compound was filtered off and thoroughly washed to obtain 45.1 parts of a crude product of Exemplary Compound 1. This is DMF,
A purified product was obtained by sequentially washing with methanol and then water and drying. The physical structure of the electrophotographic photoreceptor of the present invention may be in any known form. A carrier generating layer containing the above trisazo compound as a carrier generating substance as a main component and a carrier transporting layer containing a carrier transporting substance as a main component may be laminated on a conductive support, or a carrier generating substance may be used as a carrier. A photosensitive layer dispersed in the transport material may also be provided. Since these may be provided through an intermediate layer, the following patterns are possible. () Conductive support / carrier generation layer / carrier transport layer () conductive support / carrier transport layer / carrier transport layer () conductive support / carrier transport layer containing carrier generation substance () conductive support / Intermediate layer/carrier generation layer/
Carrier transport layer () Conductive support / Intermediate layer / Carrier transport layer /
Carrier generation layer () Conductive support/intermediate layer/carrier transport layer containing carrier generation substance The intermediate layer here refers to a barrier layer or an adhesive layer. It is also possible to provide a thin layer on the electrophotographic photoreceptor having the above structure for the purpose of surface protection or the like. Carrier transport materials include those that transport electrons and those that transport holes, and either can be used to form the electrophotographic photoreceptor of the present invention. The electrophotographic photoreceptor of the present invention can be manufactured in a conventional manner according to techniques known in the manufacture of electrophotographic photoreceptors using photoconductive materials in organic layers. For example, the carrier generation layer forming the two-layer photosensitive layer is prepared by forming the above-mentioned trisazo compound into fine particles in a suitable medium, adding a binder if necessary, and applying the trisazo compound directly on the conductive support or as an intermediate layer. or over a previously formed carrier transport layer and dry. The fine particles in the medium need to be dispersed with a diameter of 5 μm or less, preferably 3 μm, optimally 1 μm. When using a binder, there is no particular limitation, but a hydrophobic, high dielectric, and electronically insulating film-forming polymer compound is preferred. Various thermoplastic or thermosetting synthetic resins can be suitably used. As will be readily understood, it is advantageous for the medium to have the ability to dissolve the binder. The amount of binder used is selected from a range of 0.1 to 5 times the weight of the carrier generating substance. The thickness of the carrier generation layer is in the range of 0.01 to 20 μm. Preferably it is 0.05 to 5 μm. The carrier transport layer can be formed by dispersing or dissolving a carrier transport material in a suitable medium, coating the mixture, and drying the mixture. It is preferred to use a binder, unless the carrier transport material is one that also acts as a binder itself, such as poly N-vinyl carbazole or polyglycidyl carbazole. As the binder, the same type of binder as used for forming the carrier generation layer can be used. The amount of binder used is suitably 0.2 to 5 times the weight of the carrier transport material. The thickness of the carrier transport layer is in the range of 1 to 100 μm, preferably 5 to 50 μm. On the other hand, in order to form a dispersed carrier generation layer-carrier transport layer, a carrier transporting substance is dissolved in the above-mentioned dispersion liquid for forming the carrier generation layer.
It may be applied onto a conductive support. Although the carrier transport material is optional, it is generally preferred to add a binder, except when using one that itself serves as a binder, as described above. When an intermediate layer is provided between the conductive support and the above laminated or dispersed photosensitive layer, the intermediate layer contains a carrier generating substance, a carrier transporting substance,
One type or a mixture of two or more types of binders, additives, etc., and commonly used materials can be used as long as the function as an intermediate layer is not impaired. The film thickness is
The thickness is preferably 10 μm or less, preferably 1 μm or less. Other known techniques can also be applied to the electrophotographic photoreceptor of the present invention. For example, the photosensitive layer may contain a sensitizer. Suitable sensitizers include Lewis acids and dyes that form charge transfer complexes with organic photoconductive substances. In addition, in order to improve film formability, flexibility, mechanical strength, etc. of the photosensitive layer, plasticizers, ultraviolet absorbers, antioxidants, etc.
Additives such as lubricants, adhesion promoters, and dispersants may be added, and carrier generating substances and carrier transport substances may be added to the extent that they do not impair the characteristics of the electrophotographic photoreceptor aimed at in the present invention. In the present invention, ordinary coating methods can be used to form the carrier generation layer, carrier transport layer, intermediate layer or surface layer. As is clear from the following examples, the electrophotographic photoreceptor of the present invention has excellent charging characteristics, sensitivity characteristics, and image forming properties, and has good photosensitivity, and even after repeated use, the sensitivity and There is little variation in charging characteristics and little optical fatigue. It also has high weather resistance. Next, the present invention will be explained in more detail with reference to Examples. The word "part" in the text indicates parts by weight. Example 1 1 part of the above exemplary compound (1) and 1 part of polyester resin (Toyobo "Vylon 200") were mixed with tetrahydrofuran.
50 parts and sufficiently dispersed with a ball mill.The dispersion was applied onto an aluminum plate using a wire coater, and dried with hot air at 120℃ for 30 minutes to determine the film thickness.
A carrier generation layer of 0.3 μm was provided. On top of that, apply a solution of 5 parts of P-diethylaminobenzaldehyde-N-phenyl-N-benzylhydrazone and 5 parts of polycarbonate resin (Teijin Kasei "Panlite L-1250") dissolved in 70 parts of 1,2-dichloroethane. Then, it was dried with hot air at 60°C for 3 hours to form a carrier transport layer with a thickness of 14 μm. The photosensitive plate manufactured in this way was heated at 25℃ and RH.
(Relative humidity) After leaving it in an atmosphere of 55% and adjusting the humidity, use an electrostatic paper tester (Kawaguchi Electric Manufacturing Co., Ltd. "SP-
428'') using a static method to corona charge at a voltage of -6KV, and after keeping it in a dark place for 10 seconds,
The illuminance on the sample surface is adjusted using a tungsten lamp as a light source.
The film was exposed to light at 5.0 lux and its electrophotographic properties were evaluated, and the following results were obtained. Vo (initial charging voltage) = -770 (V) Vd10 (potential retention rate for 10 seconds in the dark) = 90.5
(%) E1/2 (half-attenuation exposure amount) = 2.1 (lux/second) Example 2 The characteristics were measured in the same manner as in Example 1, except that exemplified compound (2) was used, and the results were as follows. It was hot. Vo = -680 (V) Vd 10 = 87.2 (%) E1/2 = 3.3 (lux seconds) Example 3 1.5 parts of exemplified compound (3) and 1 part of polyester resin (Toyobo "Vylon 200") were mixed into 1 , and dispersed in 250 parts of 2-dichloroethane using a ball mill.
The dispersion was applied onto a polyester film deposited with aluminum and dried with hot air at 120° C. for 30 minutes to form a carrier generation layer with a thickness of 0.5 μm. On top of that, 9-ethylcarbazole-3-carbaldehyde-1,1-diphenylhydrazone 10
Part and polyester resin (above "Byron 200") 10
100 parts of 1,2-dichloroethane was applied and dried with warm air at 60°C for 3 hours until the film thickness
A carrier transport layer of 15 μm was formed. The characteristics of this electrophotographic photoreceptor were measured and the following results were obtained. Vo = -930 (V) Vd10 = 92.5 (%) E1/2 = 1.9 (lux seconds) Examples 4 to 14 The following exemplified compound was used in place of exemplified compound 3 in Example 3, and the other examples A photoreceptor was manufactured in the same manner as in Example 3. The characteristics of each are as follows.
【表】
実施例 15
実施例１で製造した電子写真感光体の帯電−放
電を1000回繰り返し、特性の変化をしらべた。結
果は次の通りであり、繰り返し安定性が優れてい
ることがわかつた。[Table] Example 15 The electrophotographic photoreceptor produced in Example 1 was charged and discharged 1000 times to examine changes in characteristics. The results are as follows, and it was found that the repeated stability was excellent.
【表】
実施例 16
アルミ貼り合わせポリエステルフイルム（アル
ミ箔の膜厚10μｍ）上に、塩化ビニル−酢酸ビニ
ル−無水マレイン酸共重合体（積水化学「エスレ
ツクMF−10」）からなる厚さ0.02μｍの中間層を
設け、その上に例示化合物２）１部を１，４−ジ
オキサン50部中にアトライターで分散させた分散
液を塗布し、100℃の熱風で30分間乾燥して膜厚
0.2μｍのキヤリア発生層を設けた。
その上に２，５−ビス（４−Ｎ，Ｎ−ジエチル
アミノフエニル）−１，３，４−オキサジアゾー
ル６部とポリカーボネート樹脂（三菱ガス化学
「コーピロンＳ＝1000」）10部とを１，２−ジクロ
ルエタン100部中に溶解した溶液を塗布し、60℃
の温風で３時間乾燥して、膜厚10μｍのキヤリア
発生層を形成した。
こうして得た電子写真感光体のＥ1/2を測定し
たところ、2.7ルクス・秒であつた。この電子写
真感光体を暗所で−7KVのコロナ放電により帯
電させ、最大光量30ルクス・秒で像露光した後、
磁気ブラシ法により現像し、ついて転写を行つた
ところ、コントラストが充分で階調性のよい鮮明
な画像が選られた。[Table] Example 16 A 0.02 μm thick film made of vinyl chloride-vinyl acetate-maleic anhydride copolymer (Sekisui Chemical “Eslec MF-10”) was placed on an aluminum laminated polyester film (aluminum foil thickness 10 μm). A dispersion of 1 part of Exemplified Compound 2) dispersed in 50 parts of 1,4-dioxane using an attritor was applied on top of the intermediate layer, and the film was dried with hot air at 100°C for 30 minutes to determine the film thickness.
A carrier generation layer of 0.2 μm was provided. On top of that, 6 parts of 2,5-bis(4-N,N-diethylaminophenyl)-1,3,4-oxadiazole and 10 parts of polycarbonate resin (Mitsubishi Gas Chemical "Corpilon S=1000") were added in 1 part. , a solution dissolved in 100 parts of 2-dichloroethane was applied and heated at 60℃
It was dried with hot air for 3 hours to form a carrier generation layer with a thickness of 10 μm. When the E1/2 of the electrophotographic photoreceptor thus obtained was measured, it was 2.7 lux·sec. This electrophotographic photoreceptor was charged by -7KV corona discharge in a dark place, and imagewise exposed at a maximum light intensity of 30 lux seconds.
When developed using a magnetic brush method and transferred, a clear image with sufficient contrast and good gradation was obtained.
Claims (1)
されるトリスアゾ化合物を含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。 （但し、上記式中Ａは、一般式 【式】【式】ま たは【式】 で表わされ、上記式においてＸは置換または非置
換の芳香族炭化水素環、または置換または非置換
の芳香族複素環を形成するのに必要な原子群であ
りＹは−NR1R2、−NHNR3R4または−NHN＝
CR5R6であり、R1〜６はＨ、置換または非置換
のアルキル基、アリール基、アラルキル基または
複素環であり、R1とR2、R3とR4、R5とR6は、
ＮまたはＣと共に環を形成してもよい。） ２ 感光層がキヤリア発生物質とキヤリヤー輸送
物質を含有し、この感光層が上記一般式（）で
示されるトリスアゾ化合物である特許請求の範囲
第１項に記載の電子写真感光体。[Scope of Claims] 1. An electrophotographic photoreceptor characterized in that a photosensitive layer containing a trisazo compound represented by the following general formula () is provided on a conductive support. (However, in the above formula, A is represented by the general formula [Formula] [Formula] or [Formula], and in the above formula, X is a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted aromatic hydrocarbon ring. Y is a group of atoms necessary to form a heterocycle, and Y is -NR1R2, -NHNR3R4 or -NHN=
CR5R6, R1 to R6 are H, substituted or unsubstituted alkyl group, aryl group, aralkyl group, or heterocycle, and R1 and R2, R3 and R4, R5 and R6 are
It may form a ring together with N or C. 2. The electrophotographic photoreceptor according to claim 1, wherein the photosensitive layer contains a carrier generating substance and a carrier transporting substance, and the photosensitive layer is a trisazo compound represented by the above general formula ().
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3275886A JPS62192747A (en) | 1986-02-19 | 1986-02-19 | Electrophotographic sensitive body |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3275886A JPS62192747A (en) | 1986-02-19 | 1986-02-19 | Electrophotographic sensitive body |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62192747A JPS62192747A (en) | 1987-08-24 |
| JPH0469949B2 true JPH0469949B2 (en) | 1992-11-09 |
Family
ID=12367739
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3275886A Granted JPS62192747A (en) | 1986-02-19 | 1986-02-19 | Electrophotographic sensitive body |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62192747A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01261650A (en) * | 1988-04-13 | 1989-10-18 | Canon Inc | Electrophotographic sensitive body |
| EP0940726B1 (en) * | 1998-03-06 | 2004-05-26 | Canon Kabushiki Kaisha | Electrophotographic photosensitive member, process cartridge and electrophotographic apparatus |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS53132347A (en) * | 1977-04-25 | 1978-11-18 | Ricoh Co Ltd | Photoreceptor for electrophotography |
| JPS54109438A (en) * | 1978-02-15 | 1979-08-28 | Ricoh Co Ltd | Photosensitive material for zerography |
| JPS57203062A (en) * | 1981-06-10 | 1982-12-13 | Ricoh Co Ltd | Novel triazo compound and its preparation |
| JPS57206658A (en) * | 1981-06-12 | 1982-12-18 | Ricoh Co Ltd | Novel trisazo compound and its preparation |
| JPS5831341A (en) * | 1981-08-19 | 1983-02-24 | Canon Inc | Electrophotographic receptor |
| JPS59196366A (en) * | 1983-04-21 | 1984-11-07 | Ricoh Co Ltd | Novel trisazo compound and production thereof |
| JPS6111754A (en) * | 1984-06-27 | 1986-01-20 | Mitsubishi Paper Mills Ltd | Electrophotographic sensitive body |
| JPS6122346A (en) * | 1984-07-10 | 1986-01-30 | Mitsubishi Paper Mills Ltd | Electrophotographic sensitive body |
-
1986
- 1986-02-19 JP JP3275886A patent/JPS62192747A/en active Granted
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS53132347A (en) * | 1977-04-25 | 1978-11-18 | Ricoh Co Ltd | Photoreceptor for electrophotography |
| JPS54109438A (en) * | 1978-02-15 | 1979-08-28 | Ricoh Co Ltd | Photosensitive material for zerography |
| JPS57203062A (en) * | 1981-06-10 | 1982-12-13 | Ricoh Co Ltd | Novel triazo compound and its preparation |
| JPS57206658A (en) * | 1981-06-12 | 1982-12-18 | Ricoh Co Ltd | Novel trisazo compound and its preparation |
| JPS5831341A (en) * | 1981-08-19 | 1983-02-24 | Canon Inc | Electrophotographic receptor |
| JPS59196366A (en) * | 1983-04-21 | 1984-11-07 | Ricoh Co Ltd | Novel trisazo compound and production thereof |
| JPS6111754A (en) * | 1984-06-27 | 1986-01-20 | Mitsubishi Paper Mills Ltd | Electrophotographic sensitive body |
| JPS6122346A (en) * | 1984-07-10 | 1986-01-30 | Mitsubishi Paper Mills Ltd | Electrophotographic sensitive body |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62192747A (en) | 1987-08-24 |
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