JPS5849951A - Electrophotographic receptor - Google Patents
Electrophotographic receptorInfo
- Publication number
- JPS5849951A JPS5849951A JP11707881A JP11707881A JPS5849951A JP S5849951 A JPS5849951 A JP S5849951A JP 11707881 A JP11707881 A JP 11707881A JP 11707881 A JP11707881 A JP 11707881A JP S5849951 A JPS5849951 A JP S5849951A
- Authority
- JP
- Japan
- Prior art keywords
- group
- electrophotographic photoreceptor
- ring
- layer
- 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
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
- G03G5/0679—Disazo dyes
- G03G5/0683—Disazo dyes containing polymethine or anthraquinone groups
-
- 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
- G03G5/0679—Disazo dyes
- G03G5/0683—Disazo dyes containing polymethine or anthraquinone groups
- G03G5/0685—Disazo dyes containing polymethine or anthraquinone groups containing hetero rings in the part of the molecule between the azo-groups
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Photoreceptors In Electrophotography (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は電“子写真感光体に関し、更に詳細には特定の
ジスアゾ顔料を含む電子写真感光体に“:::、。、4
1.。+b*、it−+□8.。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to an electrophotographic photoreceptor, and more particularly to an electrophotographic photoreceptor containing a specific disazo pigment. , 4
1. . +b*, it-+□8. .
体としては、セレン、硫化カドミウム、酸化亜鉛等を用
いたものが広く知られている。As materials, those using selenium, cadmium sulfide, zinc oxide, etc. are widely known.
体としては、ポリーN−ビニルカルバソールニ代表され
る光導電性ポリマーや、2.5−ビス(P−ジエチルア
ミノフェニル)−1,3,4−オキサジケゾールの如き
低分tの有機光導電物質を用いたもの、更にはこうした
有機光導電物質と各種染料、顔料を組合せたもの等が知
ら有機光導電物質を用いた電子写真感光体は′成膜性が
良く、塗工により生産できるため、極めて生産性が高く
、安価な感光体を提供できる。Examples of photoconductive materials include photoconductive polymers typified by poly-N-vinylcarbasol and organic photoconductive substances with low fractions such as 2,5-bis(P-diethylaminophenyl)-1,3,4-oxadikesol. Electrophotographic photoreceptors using organic photoconductive substances have good film-forming properties and can be produced by coating, so they are extremely popular. A highly productive and inexpensive photoreceptor can be provided.
また使用する顔料−染料等の増感剤の選択により、感色
性を自在にコントロールでき、る等の利点を有し、これ
まで幅広い検討がなされてきた。In addition, it has the advantage that color sensitivity can be freely controlled by selecting the sensitizer such as a pigment or dye to be used, and a wide range of studies have been made to date.
しかしながら感度、耐久性等において難があり、これま
で実用に至ったものはごくわずかである。However, there are problems with sensitivity, durability, etc., and so far only a few have been put into practical use.
本発明の目的は第一に特定のジスアゾ顔料を含む電子写
真感光体を提供することIfCh9、第二に高感度電子
写真感光体を提供することにあり、第三に高耐久性の電
子写真感光体を提供することにある。The purpose of the present invention is, first, to provide an electrophotographic photoreceptor containing a specific disazo pigment, secondly, to provide a highly sensitive electrophotographic photoreceptor, and third, a highly durable electrophotographic photoreceptor. It's about offering your body.
本発明者等は一般式
で示されるジスアゾ顔料を感光層に用いた電子写真感光
体が電子写真的に極めて有用″chることに着目し、本
発明に到達したものである。The present inventors have arrived at the present invention by noting that an electrophotographic photoreceptor using a disazo pigment represented by the general formula in a photosensitive layer is extremely useful in electrophotography.
前記一般式(1)における人は単結合又は共役二重結合
を有する炭化水素基又扛共役二重結合内に窒素原子を有
する炭化水素基又は芳香族環と縮合若−しくは置換して
もよい複素環基であり、かつ隣接するアゾメチン基と共
役二重結合系を形成するものとし、
(式中鳥。The person in the general formula (1) may be fused or substituted with a hydrocarbon group having a single bond or a conjugated double bond, or a hydrocarbon group having a nitrogen atom within the conjugated double bond, or an aromatic ring. It is a good heterocyclic group and forms a conjugated double bond system with the adjacent azomethine group, (in the formula bird).
鳥は同−又は異なってもよい水素原子、)・ロゲ′ ノ
基から成る群より選ばれ
た基を表わす。)で表わされるような基が挙げられる。``Bird'' represents a group selected from the group consisting of hydrogen atoms, which may be the same or different; ).
R11はメチル、エチル、プロピル、ブチル等の直鎖状
アルキル基を表わす。Xはベンゼン環と縮合してナフタ
レン環、アンスラセン環、カルバゾール環、ペンズカル
ノ< ’/−JS/ 環、へ:/シフラン環を形成する
残基を表わし、形成された残基は水酸基、−CONHR
,以外の置換基を有し本発明の電子写真感光体に用いる
ジスアゾ顔料と同じ主骨格を有するジスアゾ顔料を用い
た一電子写真感光体について特願昭55−21670と
して本発明者等が提案しているが、本発明の電子写真感
光体は、一般式(1)のル、をメチル、エチル、プロピ
ル、ブチル等の直鎖状アルキル基に特定したことにより
、高感度、高耐久性の電子写真感光体が得られることを
見い出したものである。R11 represents a linear alkyl group such as methyl, ethyl, propyl, butyl. X represents a residue that is condensed with a benzene ring to form a naphthalene ring, an anthracene ring, a carbazole ring, a penzcarno<'/-JS/ ring, and a sifurane ring, and the formed residue is a hydroxyl group, -CONHR
The present inventors proposed in Japanese Patent Application No. 55-21670 an electrophotographic photoreceptor using a disazo pigment having a substituent other than , and having the same main skeleton as the disazo pigment used in the electrophotographic photoreceptor of the present invention. However, the electrophotographic photoreceptor of the present invention has a linear alkyl group such as methyl, ethyl, propyl, butyl, etc. in general formula (1), so that the electrophotographic photoreceptor has high sensitivity and high durability. It has been discovered that a photographic photoreceptor can be obtained.
一般式(1)で示されるジスアゾ顔料は一般には下記の
方法により合成することができる。P−アミノベンズア
ルデヒドを常法にょクジ7ノ化し、次いで一般式
式(1)と同じ意味を有する。)で示されるカプラーを
アルカリの存在下、カップリングするムたは、P−アミ
ノベンズアルデヒドのジアゾニウム塩をホウフッ化塩あ
るいは塩化亜鉛複塩等の形で、一旦単離した後、適当な
溶媒例えばN、N−ジメチルホルムアミド、ジメチルス
ルホキシド等の溶媒中でアルカリの存在下、一般式(8
)で示されるカプラーとカップリングして一般式(式中
り、Xは一般式(1)と同じ“意味を有する。)で示さ
れるモノアゾ顔料を合成する。次に前記モノアゾ顔料と
一般式H,N−A−NH,(10)(式中AFi一般式
(1)と同じ意味を有する。)で示されるジアミンとを
継合することにより容易に一般式(1)で示されるジス
アゾ顔料が得られる。The disazo pigment represented by the general formula (1) can generally be synthesized by the following method. P-aminobenzaldehyde is converted into a di-7tyl compound by a conventional method, and then has the same meaning as the general formula (1). ) in the presence of an alkali, the diazonium salt of P-aminobenzaldehyde is isolated in the form of a borofluoride salt or zinc chloride double salt, and then a suitable solvent such as N , N-dimethylformamide, dimethyl sulfoxide, etc. in the presence of an alkali, the general formula (8
) to synthesize a monoazo pigment represented by the general formula (wherein, X has the same meaning as in general formula (1)).Next, the monoazo pigment and the general formula H , N-A-NH, (10) (in the formula, AFi has the same meaning as the general formula (1)), and the disazo pigment represented by the general formula (1) can be easily obtained. can get.
導電層上に有機顔料を含む電子写真感光体としては、
■特公昭52−1667に開示される様な導電層上に顔
料をバインダーに分散した層を設けるもの。An electrophotographic photoreceptor containing an organic pigment on a conductive layer includes: (1) A layer in which a pigment is dispersed in a binder is provided on a conductive layer as disclosed in Japanese Patent Publication No. 52-1667.
■特公昭47−1’8545.%開昭47−30328
に開示される様な電荷輸送物質あるいは尚該物質と絶縁
性バインダー(バインダー自身が電荷輸送物質であり、
て、も良い)から成る電荷輸送媒体中に顔料を分散した
層を導電層上に設けたもの。■Tokuko Showa 47-1'8545. % Kaisho 47-30328
A charge transporting material such as that disclosed in , or furthermore, the material and an insulating binder (the binder itself is a charge transporting material,
A layer in which a pigment is dispersed in a charge transporting medium consisting of a conductive layer formed on a conductive layer.
■特開昭49−105537に開示される様な導電層、
有機顔料を含む電荷発生層、電荷輸送層から成るもの。■A conductive layer as disclosed in JP-A No. 49-105537,
Consisting of a charge generation layer and a charge transport layer containing organic pigments.
■特Hj@49−91648に開示される様な電荷移動
錯体中に有機顔料を添加したもの。等がある。(2) An organic pigment added to a charge transfer complex as disclosed in Special Hj@49-91648. etc.
本発明の電子写真感光体は、前記一般式(1)で示され
るジスアゾ顔料を含有することを特徴としており、かか
る特徴を有するいづれのタイプの電子写真感光体くも適
用できるが、一般式(1)で示されるジス啼ゾ顔料の光
吸収によって生ずる電荷担体の輸送効率を高めるために
は、■、■■のタイプの電子写真感光体として用いるこ
とが望ましい。The electrophotographic photoreceptor of the present invention is characterized by containing a disazo pigment represented by the general formula (1), and can be applied to any type of electrophotographic photoreceptor having such characteristics, but the general formula (1) ) In order to increase the transport efficiency of charge carriers generated by light absorption of the disulfide pigments shown in (), it is desirable to use them as electrophotographic photoreceptors of type (1) and (2).
!に電荷担体の発生機能と輸送機能を分離した■タイプ
の感光体が前記顔料の特性を生かす上で最も望ましい。! A photoreceptor of type (2), in which charge carrier generation and transport functions are separated, is most desirable in order to take advantage of the characteristics of the pigment.
そこで、この■タイプの電子写真感光体について詳しく
説明する。Therefore, this type 2 electrophotographic photoreceptor will be explained in detail.
層構成としては導電層、電荷発生層、電荷輸送層が必須
であり、電荷発生層は電荷輸送層の上部あるいは下部の
いずれであって4良いが、繰り返し使用するタイプの電
子写真感光体においては主として物理強度の面から、場
合によっては帯電性の面から導電層、電荷発生層、電荷
輸送層との接着を向上する目的で必要に応じて接着層を
設けることができる。As for the layer structure, a conductive layer, a charge generation layer, and a charge transport layer are essential, and the charge generation layer can be either above or below the charge transport layer, but in an electrophotographic photoreceptor of the type that is used repeatedly, An adhesive layer may be provided as necessary for the purpose of improving adhesion with the conductive layer, charge generation layer, and charge transport layer mainly from the viewpoint of physical strength and in some cases from the viewpoint of chargeability.
導電層としては、アルミニウム等の金属板又は金属箔、
アルミニウム等の金属を蒸着したプラスチックフィルム
あるい嬬アルミニウム箔を紙とはり合わせたもの、導電
処理を施した紙等が使用される。As the conductive layer, a metal plate or metal foil such as aluminum,
Plastic films coated with a metal such as aluminum, aluminum foil laminated with paper, paper treated with conductivity, etc. are used.
接着層の材質として杜、カゼイン、ポリビニルアルコー
ル、水溶性ポリエチレン、ニトロセルロース等の樹−が
効果的である。接着層の厚さは、α1〜5.0μ、好ま
しく扛α5〜3.0#が適当である。As a material for the adhesive layer, trees such as Japanese pine, casein, polyvinyl alcohol, water-soluble polyethylene, and nitrocellulose are effective. The appropriate thickness of the adhesive layer is α1 to 5.0μ, preferably α5 to 3.0#.
導電層あるいは導電層に施した接着層の上に一般式(]
)で示されるジスアゾ顔料を微粒子化した後、バインダ
ーなしで、あるいは必要があれば適当なバインダー溶液
〒に分散し、これを塗布乾燥して設けるジスアゾ顔料の
分散に際しては、ボールミル、アトライター等の方法を
用いることができ、顔料粒子が5.0μ以下好ましくは
zOμ以下、最適にはα5μ以下とすることが望ましい
。The general formula (] is applied to the conductive layer or the adhesive layer applied to the conductive layer.
) After the disazo pigment shown in ) is made into fine particles, it is dispersed without a binder or, if necessary, in an appropriate binder solution, and the disazo pigment is coated and dried. It is desirable that the pigment particles have a particle size of 5.0μ or less, preferably zOμ or less, optimally α5μ or less.
ジスアゾ顔料はエチレンジアミン婢のアミン系溶剤に溶
かして塗布することもできる。The disazo pigment can also be applied by dissolving it in an amine solvent such as ethylenediamine.
塗布方法はブレード、マイヤーバー、スプレー、浸漬等
の通常の方法が用いられる。Conventional methods such as blade, Mayer bar, spray, and dipping methods are used for application.
電荷発生層の膜厚は5.OA以下、好ましく紘o、oi
〜Logが望ましい。電荷発生層にバインダーを用する
場合、バインダーが多いと感度に影響するため、電荷発
生層中に占めるバインダーの割合は、801以下好まし
くは40%以下が望まし10
使用されるバインダーとしては、ポリビニルブチラール
、ポリ酢酸ビニル、ポリエステル、ポリカーボネート、
フェノキシ樹脂、アクリル系樹脂、ポリアクリルアミド
、ポリアミド、ポリビニルピリジン樹脂、セルローズ系
樹脂、ウレタン樹脂、エポキシ樹脂、カゼイン、ポリビ
ニルアルコール等の各種樹脂類が用いられる。The thickness of the charge generation layer is 5. Below OA, preferably Hiro o, oi
~Log is desirable. When using a binder in the charge generation layer, the ratio of the binder in the charge generation layer is desirably 80% or less, preferably 40% or less, since a large amount of binder affects sensitivity10. Butyral, polyvinyl acetate, polyester, polycarbonate,
Various resins such as phenoxy resin, acrylic resin, polyacrylamide, polyamide, polyvinylpyridine resin, cellulose resin, urethane resin, epoxy resin, casein, and polyvinyl alcohol are used.
仁の様にして設けた電荷発生層上に電荷輸送層を設ける
。電荷輸送物が被膜形成能をもたない場合には、バイン
ダーを適当な溶媒に溶かした液を通常の方法で塗布乾燥
し、電荷輸送層を形成する。A charge transport layer is provided on the charge generation layer provided like a layer. If the charge transport material does not have film-forming ability, a charge transport layer is formed by applying a solution prepared by dissolving a binder in a suitable solvent and drying it by a conventional method.
電荷輸送物質としては、クロルアニル、ブロモアニル、
テトラシアノエチレン、テトラシアノキノジメタン、!
4.7−ドリニトロー9−フルオレノン、1417−チ
トラニ)O−9−フルオレノ7.2.47−)リニトロ
ー9−ジシアノメチレンフルオレノン、 2.45.7
−チトラニトロキサントン、Z4B−)リニトロチオキ
サントン等の電子吸引物質や仁れら電子吸引物質を高分
子化したもの等がある。As charge transport substances, chloranil, bromoanil,
Tetracyanoethylene, tetracyanoquinodimethane,!
4.7-dolinitro9-fluorenone, 1417-titrani)O-9-fluoreno7.2.47-)linitro9-dicyanomethylenefluorenone, 2.45.7
-Titranitroxanthone, Z4B-) There are electron-withdrawing substances such as linitrothioxanthone, and polymerization of electron-withdrawing substances.
正孔輸送物質として社、ピレン、N−エチル力A/ /
(ソール、N−イソプロピルカルバゾール。As a hole transport substance, pyrene, N-ethyl force A//
(Sole, N-isopropylcarbazole.
ヘーメチルーN−フェニルヒドラジノ−3−メチリゾy
−9−エチルカルバゾール、N、N−ジフェニルヒドラ
ジノ−3−メチリテンニ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−10−
エチルフェッチアジy、 N、N−ジフェニルヒドラ
ジノ−3−メチリデン−1O−エチルフェノ牛すジン、
P−ジエチルアiノベンズアルデヒドーN、N−ジフェ
ニルヒドラゾ/、P−ジエチルアミノベンズアルf ヒ
ト−N −01−t 79ルーN −7xニルヒドラ7
’y、P−ビ四すジノペンズアルデヒドーN、N−ジフ
ェニルヒドラゾン、13.3−)リメチルインドレニン
ーW−アルデヒド−N、N −ジフェニルヒドラゾン、
P−ジエチルアミノベンズアルデヒド−3−メチルベン
ゾチアゾリノン−2−ヒドラゾン等のヒドラゾン類。Hemethyl-N-phenylhydrazino-3-methylisoy
-9-ethylcarbazole, N,N-diphenylhydrazino-3-methylethylcarbazole, N
, N-diphenylhydrazino-3-methylidene-10-
Ethyl fetch adiy, N,N-diphenylhydrazino-3-methylidene-1O-ethylphenol beef gin,
P-diethylaminobenzaldehyde N, N-diphenylhydrazo/, P-diethylaminobenzalf human-N -01-t 79-N-7x nylhydra7
'y, P-bi-tetradinopenzaldehyde N, N-diphenylhydrazone, 13.3-)limethylindolenine-W-aldehyde-N, N-diphenylhydrazone,
hydrazones such as P-diethylaminobenzaldehyde-3-methylbenzothiazolinone-2-hydrazone;
2、.5−ビス(P−ジエチルアミノフェニル)−13
,4−オキサジ肯ゾール、1−フェニル−3−(P−ジ
エチルアミノスチリル)−5−(P−ジエチルアミノフ
ェニル)ピラゾリン、1−〔キノリル(2) ) −3
−(P−ジエチルアミノスチリル)−5−(P−ジエチ
ルアミノフェニル)ピラゾリン、1−〔ビリジルー(2
) ) −3−(P−ジエチルアミノスチリル)−5−
(P−ジエチルアミノフェニル)ピラゾリン等のピラゾ
リ7−0
2−(P −−/エチルアミノスチリル)−6−ジニチ
ルアミノベンズオ喫すゾール、2−(P−ジエチルア電
ノフェニル)−4(P−ジメチル7(/フェニル’)−
5−(2−クロルフェニル)オキサゾール等のオキサゾ
ール系化合物。2. 5-bis(P-diethylaminophenyl)-13
, 4-oxadinzole, 1-phenyl-3-(P-diethylaminostyryl)-5-(P-diethylaminophenyl)pyrazoline, 1-[quinolyl(2))-3
-(P-diethylaminostyryl)-5-(P-diethylaminophenyl)pyrazoline, 1-[pyridyl(2
) ) -3-(P-diethylaminostyryl)-5-
Pyrazoli such as (P-diethylaminophenyl)pyrazoline 7-0 2-(P--/ethylaminostyryl)-6-dinithylaminobenzosol, 2-(P-diethyladenophenyl)-4(P-dimethyl 7(/phenyl')-
Oxazole compounds such as 5-(2-chlorophenyl)oxazole.
2−(P−ジメチルアミノスチリを)−6−ジニチルア
ミノペンゾチアゾール等のチアゾール系化合物、ビス(
4−ジエチルアミノ−2−メチルフェニル)−フェニル
メタン等のトリアリールメタン系化合物1.1−ビス(
4−N、N−ジエチルアミノ−2−,7’チルフエニル
)へブタン、1、1. Z 2−テトラキス(4−N、
N−ジメチルアミノ−2−メチルフェニル)エタン等の
ボリアリールフルカン類。Thiazole compounds such as 2-(P-dimethylaminostyrene)-6-dinithylaminopenzothiazole, bis(
Triarylmethane compounds such as 4-diethylamino-2-methylphenyl)-phenylmethane 1.1-bis(
4-N,N-diethylamino-2-,7'tylphenyl)hebutane, 1,1. Z 2-tetrakis (4-N,
Polyarylfurcanes such as N-dimethylamino-2-methylphenyl)ethane.
トリフェニルアミン、ポリ−N−ビニルカルバソール、
ホリビニルピレン、ポリヒニル77トラセン、ピレン−
ホルムアルデヒド樹脂、エチルカルバゾールホルムアル
デヒド樹−等がある。電荷移動物質は、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電
荷輸送物質を1.It類あるいは2種類以上混合して電
荷輸送層の膜厚は5〜304、好ましくは。triphenylamine, poly-N-vinylcarbasol,
Holivinylpyrene, polyhinyl 77thracene, pyrene-
Formaldehyde resin, ethyl carbazole formaldehyde resin, etc. The charge transport material is not limited to those described here, and when used, the charge transport material may be 1. The thickness of the charge transport layer of It or a mixture of two or more is preferably 5 to 30 mm.
8〜20Jlである。It is 8 to 20 Jl.
バインダーとしてはアクリル予樹脂、ポリスチレン、ポ
リエステル、ポリカーボネート等を用いることができる
。低分子の正孔輸送物質物のバインダーに#i先に述べ
たポリ−N−ビニルカルバゾール等の正孔輸送性ポリマ
ーをバインダーICJIいることができる。一方、低分
子の電子輸送物質のバインダーにはtysp4tzzt
taKある様な電子輸送性ギノマーの重合体を:用いる
ことができる。As the binder, acrylic pre-resin, polystyrene, polyester, polycarbonate, etc. can be used. A hole transporting polymer such as the poly-N-vinylcarbazole described above can be used as the binder for the low molecular hole transport substance. On the other hand, tysp4tzzt is used as a binder for low-molecular electron transport materials.
Electron-transporting gynomer polymers such as taK can be used.
導電層、電荷発生層、電荷輸送層の順に積層し良悪光体
を使用する場合において電荷輸送物質が電子輸送物質か
ら成るときは、電荷輸送層表面を正に帯電する必要がh
D、帯電後露光すると露光部で紘電荷発生層において生
成し良電子が電荷輸送層に注入され、そのあと表面に達
して正電荷を中和し、表面電位の減衰が生じ未露−yt
lKとの間に静電コントラストが生じる。このようKし
てできた静電潜像を負荷電性のトナーで現像すれば可視
像が得られる。これを直接定着するか、あるいはトナー
像を紙やプラスチックフィルム等に転写後、現儂後定着
することができる。When a conductive layer, a charge generation layer, and a charge transport layer are laminated in this order and a good or poor photoreceptor is used, and the charge transport material is an electron transport material, it is necessary to positively charge the surface of the charge transport layer.
D. When exposed to light after charging, good electrons are generated in the charge-generating layer in the exposed area and injected into the charge transport layer, and then reach the surface and neutralize the positive charge, resulting in attenuation of the surface potential and unexposed -yt
An electrostatic contrast occurs between the IK and the IK. A visible image can be obtained by developing the electrostatic latent image formed by K in this manner with a negatively charged toner. This can be directly fixed, or the toner image can be transferred to paper, plastic film, etc. and then fixed after printing.
また感光体上の静電潜像を転写紙の絶縁層上に転写後現
像し、定着する方法奄とれる。現僚剤の種類や現像方法
、一定着方法は公知のものや公知の方法のいずれを採用
してもよく、特定のものに限定されるものでない。There is also a method of transferring the electrostatic latent image on the photoreceptor onto an insulating layer of transfer paper, developing it, and fixing it. The type of developing agent, the developing method, and the constant deposition method may be any known ones or known methods, and are not limited to specific ones.
一方、電荷輸送物質が正孔輸送物質から成る場合、電荷
輸送層表面を負に帯電する必要があり、帯電後、露光す
ると露光部では電荷発生層において生成した正孔が電荷
輸送層に注入され、その後表面に達して負電荷を中和し
、表面電位の減衰が生じ未露光部との間に静電コントラ
ストが生じる。現侭時には電子輸送物質を用いた場合と
は逆に正電荷性トナーを用いる必要がある。On the other hand, when the charge transport material consists of a hole transport material, the surface of the charge transport layer must be negatively charged, and when exposed to light after charging, holes generated in the charge generation layer are injected into the charge transport layer in the exposed area. , which then reaches the surface and neutralizes the negative charges, resulting in attenuation of the surface potential and an electrostatic contrast between the surface potential and the unexposed area. At present, it is necessary to use a positively charged toner, contrary to the case where an electron transport material is used.
■タイプの感光体は■タイプの感光体の電荷輸送層に用
いられる様な絶縁性バインダー溶液に一般式(,1)に
示されるジスアゾ顔料を添加し、分散径導電性支持体に
塗布乾燥して得られる。The ■ type photoreceptor is made by adding a disazo pigment represented by the general formula (, 1) to an insulating binder solution such as that used for the charge transport layer of the type ■ photoreceptor, coating it on a conductive support with a dispersion diameter, and drying it. can be obtained.
■タイプの感光体は■タイプの感光体の電荷輸送材料と
電荷輸送層に使われる様な絶縁性ノ(イングーを適当な
溶剤に溶かした後、一般式(1)で示されるジスアゾ顔
料を添加した後、分散後、導電性支持体に塗布乾燥して
得られる。The ■ type photoreceptor is a charge transport material of the ■ type photoreceptor, and the insulating material used for the charge transport layer (ingu) is dissolved in a suitable solvent, and then a disazo pigment represented by the general formula (1) is added. Then, after dispersion, it is obtained by coating and drying on a conductive support.
■タイプの感光体昧■タイプの感光体で述べ良電子輸送
材料と正孔輸送材料を組合せると電荷移動錯体を形成す
るので、この電荷移動錯体の溶液中に一般式(1)で示
されるジスアゾ顔料を添加し、分散後、導電性支持体に
塗布乾燥して得られる。■Type of photoconductor As described in ■Type of photoconductor, when an electron transport material and a hole transport material are combined, a charge transfer complex is formed, so in the solution of this charge transfer complex, a compound expressed by the general formula (1) is formed. It is obtained by adding a disazo pigment, dispersing it, coating it on a conductive support and drying it.
いずれの感光体にお部ても用い
式(1)で示されるジスアゾ顔料から選ばれる少なくと
も1種類の顔料を含有し、必要に応じて元て使用した感
光体の
感度を高めたり、パンクロマチックな感覚体を一般式(
1)で示されるジスアゾ
顔料を2種類以上組合せたり、または公知の染料、顔料
から選ばれた電荷発生材料と組合せて使用することも可
能である。Each of the photoreceptors contains at least one pigment selected from the disazo pigments represented by formula (1), and can be used to increase the sensitivity of the photoreceptor originally used or to provide panchromatic The sensory body is expressed by the general formula (
It is also possible to use a combination of two or more types of disazo pigments shown in 1), or a combination with a charge generating material selected from known dyes and pigments.
本発明の電子写真感光体は電子写真複写様に利用するの
みならず、レーザープリ/ターやCRTプリンター等の
電子写真応用分野にも広く用いることが毎きる。 ゛
次に本発明に!用するジスアゾ顔料について合成例を具
体的に説明する。The electrophotographic photoreceptor of the present invention can be used not only for electrophotographic copying but also for a wide range of electrophotographic applications such as laser printers and CRT printers.゛Next, on to the present invention! A synthesis example of the disazo pigment to be used will be specifically explained.
(顔料41)
4−(P−ホルミルフェニルア/)−3−ヒドロキシ−
ナフタレン−2−カルボン酸メチルアミド5.07g(
0,0152モル)をDMF900+aJK添加し、加
熱攪拌して液温を70℃とした。(Pigment 41) 4-(P-formylphenyl-a/)-3-hydroxy-
Naphthalene-2-carboxylic acid methylamide 5.07 g (
0,0152 mol) of DMF900+aJK was added thereto, and the mixture was heated and stirred to bring the liquid temperature to 70°C.
次に硫酸ヒドラジン化s9g(o、oo7sモル)を水
14 mlに溶解させ、液温を11″atで高め、同温
度にて3時間攪拌を継続した。その後反応液を濾過し析
出した固形分をf別、次にDMF300 all 、
M E K 300 sJを用い、順次熱濾過洗浄し、
更に減圧熱乾燥し目的の顔料4.73g(収本941G
)を得た。Next, 9 g (o, oo 7 s mol) of sulfuric acid hydrazine was dissolved in 14 ml of water, the temperature of the solution was raised to 11"at, and stirring was continued at the same temperature for 3 hours. The reaction solution was then filtered to remove the precipitated solids. f separately, then DMF300 all,
Using M E K 300 sJ, sequentially hot filtration and washing,
Furthermore, it was dried under reduced pressure with heat to obtain 4.73g of the desired pigment (collection: 941G).
) was obtained.
280℃以上
赤外黴収スペクトル アミド1660fi1
元素分析 分子式 〇、H,N、04
分析値[%)
C6fL86 6&80
H4,6O
N 16.91 16.85本発明に用い
る他のジスアゾ顔料も同様にして合成することができる
。 次に本発明のジスアゾ顔料を用いた電子
写真感光体の実施例を示す。Infrared mold yield spectrum above 280°C Amide 1660fi1 Elemental analysis Molecular formula 〇, H, N, 04 Analysis value [%] C6fL86 6&80 H4,6O N 16.91 16.85 Other disazo pigments used in the present invention were synthesized in the same manner can do. Next, examples of electrophotographic photoreceptors using the disazo pigment of the present invention will be shown.
厚さ100sのアルミ板上にポリビニルアルコール水溶
液を塗布乾燥し、塗工量0.8 f/WLs o接着層
を一形成した。An aqueous polyvinyl alcohol solution was applied onto an aluminum plate having a thickness of 100 seconds and dried to form an adhesive layer with a coating weight of 0.8 f/WLs o.
次に前記IJn1顔料と表1に誉す各顔料5gとポリエ
ステルアドヒーシブ49.000(デエボン社製、固型
分20%)10g〒HF80−gt分1&後、上記接着
層上に塗布し、乾燥後の塗工量を0.20g/6L”と
した。Next, the above-mentioned IJn1 pigment, 5 g of each pigment listed in Table 1, and 10 g of Polyester Adhesive 49.000 (manufactured by Devon, solid content 20%) were applied on the adhesive layer after HF80-gt min. The coating amount after drying was 0.20 g/6L''.
次に1−〔ビリジルー(2) ) −3(P−ジエチル
アミノスチリル)−5−(P−ジエチルアミノフェニル
)ビラゾ、リン(電荷輸送材斜陽])51、ポリメチル
メタクリレート樹脂(数平均分子量10万)5fをTH
F70a/に溶解し電荷発生層上に塗工し、乾燥後の塗
工量を10 #frL”とした。Next, 1-[Viridyl(2))-3(P-diethylaminostyryl)-5-(P-diethylaminophenyl)virazo, phosphorus (charge transporting material) 51, polymethyl methacrylate resin (number average molecular weight 100,000) 5f TH
It was dissolved in F70a/ and coated on the charge generation layer, and the coating amount after drying was 10 #frL''.
このようにして作成した電子写真感光体を川口電機(株
)製、静電複写紙試験装置Mode18F−428を用
いてスタチック方式でQ 5 KVでコロナ帯電し、暗
所で10秒間保持した後、照度5/uxで露光し、帯電
特性を調べた。The electrophotographic photoreceptor thus prepared was statically charged with corona at Q 5 KV using an electrostatic copying paper tester Model 18F-428 manufactured by Kawaguchi Electric Co., Ltd., and held in a dark place for 10 seconds. It was exposed to light at an illuminance of 5/ux, and the charging characteristics were examined.
初期電位をVo(−V)、暗所での10秒間の電位保持
率をBY(*)、半減衰露光量をB V2 (lux、
5ec)とし、各感光体の帯電特性を調べ、その結果
も害 1
実施例1で作成した電荷発生層の上に2,4,7−ドリ
ニトロフルオレノ/(電荷輸送材料A2)5gとポリ−
4,4“−ジオキシジフェニル−2,270rnjに溶
解し、塗布乾燥後の塗工量を12g/llrとした0実
施例1と同様にして帯電測定を行い、その特定値は次の
通pであった0但し、?電極性はeとした。The initial potential is Vo (-V), the potential retention rate for 10 seconds in the dark is BY (*), and the half-decay exposure amount is B V2 (lux,
5ec), the charging characteristics of each photoreceptor were investigated, and the results were also positive. −
4,4"-Dioxydiphenyl-2,270rnj, and the coating amount after coating and drying was 12 g/llr. Charge measurement was carried out in the same manner as in Example 1, and the specific values are as follows. 0 However, the polarity was set to e.
Vo +500V
凡v 83%
’B’4 131ux−see
実施例32〜43
・=*施例1で用いた/I61の顔料5gとブチラール
樹脂(ブチラール化度Sモル−)2gをエタノール95
mJK11かした液とともに分散し九後、アル建蒸着マ
イラーフィルムのアルミ面に塗布し、乾燥後ojk工量
、を0.2 g/Wtとした0次に表2に示す電荷輸送
材料5g生ラフエノキシ樹脂υ00社製、ベークライト
PKHH)5 g tt T HF 10m1に溶解し
た液を上記電荷尭生層Klk布、乾燥し、塗工量が11
g#の電荷輸送層を形成した0このようにして作成した
感光体を実棒例1と同様にして、帯電測定を行い、その
特性値を表3に示す。Vo +500V approx. 83% 'B'4 131ux-see Examples 32 to 43 ・=* 5 g of /I61 pigment used in Example 1 and 2 g of butyral resin (degree of butyralization S mol-) were mixed with ethanol 95
After dispersing with mJK11 liquid, it was applied to the aluminum surface of an aluminium-deposited mylar film, and after drying, the charge transporting material shown in Table 2 was 5 g raw rough phenoxy, with an OJK working amount of 0.2 g/Wt. Resin υ00 manufactured by Bakelite PKHH) 5 g tt A solution dissolved in 10 ml of T HF was applied to the above-mentioned charge ray layer Klk cloth, and dried until the coating amount was 11
The photoreceptor thus prepared, on which a charge transport layer of g# was formed, was subjected to charge measurement in the same manner as Actual Bar Example 1, and the characteristic values are shown in Table 3.
表3 W電特性
直径120IIIIII゛のアルオ宍管に実施例1,8
.21と同様にして接着層、電荷発生層、電荷輸送層を
順次積層し、感光ドラム44〜46を作成した0次にコ
ピア(株)製電子写真豪写機80−120の改造機(ド
ラム回シに負極性コロナ帯電器、露光光学系、現像器、
転写帯電器、除電露光光学系、およびクリーナを順次配
備)を用い、初期の暗部電位をesso vに設定し、
−成分磁性現像剤によシ耐久試験を行ったところ、いず
れのドラムも2万枚後、原画に忠実な美し−コピーが得
られ九〇
出願人 コピア株式会社
手続補正書(方式)
唱和57年と117J’日
一許庁長富 島 ffl 春樹 緻
工事件の表示
昭和56都4I許願第117078号
龜am06称
電子写真感光体
事件との関係 41WIF出願人
住yrt 東京都をlジ?giv6丁m5es号名称
ツビア株式条社
代表者松井友正
本代雇人
居所 〒14東京都大田区下九子!−!4)−26、
補正の対象
明細書全文
7、 補正の゛内容
明細書の浄書(内容に変更なし)Table 3 W electric characteristics Examples 1 and 8 for Aluo Shishi tube with a diameter of 120III
.. The adhesive layer, the charge generation layer, and the charge transport layer were sequentially laminated in the same manner as in 21 to create the photosensitive drums 44 to 46. Negative corona charger, exposure optical system, developer,
Using a transfer charger, a static elimination exposure optical system, and a cleaner (sequentially deployed), set the initial dark potential to esso v,
-A durability test was conducted using component magnetic developer, and after 20,000 copies of each drum, a beautiful copy that was faithful to the original was obtained. Relationship between 117J' and 117J' Nichiichi Permit Office Nagatomi Island FFL Haruki Prefecture Case Showa 56 Metropolitan 4I Permit No. 117078 龜AM06 Electrophotographic Photoreceptor Case 41WIF Applicant Residence Yrt Tokyo? giv6chom5es No. Tsuvia Co., Ltd. Representative Tomomasa Matsui Residence Shimo-Kyuko, Ota-ku, Tokyo 14! -! 4)-26,
Full text of the specification to be amended 7, Reprint of the specification of contents to be amended (no change in content)
Claims (1)
料を用いたことを特徴とする電子写真感光体。 一般式(i) 式中1人は単結合又社共役二重結合系を有する炭化水素
基又紘共役二重結合内に窒素原子を有する炭化水素基又
は芳香族環と縮合若しくは置換してもよい複素環基であ
り、かつ隣接するアゾメチン基と共役二重結合系を形成
するものとし、馬は直鎖状アルキル基を表わす。Xはで
ン(ン職と一合してナフタレン環、アノスラセン!、カ
ルバゾール環、ベンズカルバゾール環、ベンゾ7チン環
を形成する残基を表わL%形成された残基は、水酸基、
eONH氏以外の置換基を有してもよい。 (式中82.几。 は同−又は異なってもよい水゛素原子、ハロゲン原子、
低級アルキル基、低級アルコキシ基ならびにニトロ基か
ら成る群より選ばれ、鴇は水素原子、ハロゲン原子なら
びにシアノ基から成る群より選一れ九基を表わす。)か
ら選ばれたことを特徴とする特許請求の範囲第一項記載
の電子写真感光体。 (3) 導電層と電荷発生層と電荷輸送層から成る電
子写真感光体において、電荷発生層に一般式(1)で示
さ・れるジスアゾ原料を用いえこ七を特徴とする特許請
求の範囲第一項記載の電子軍真感光(4)下記1−造の
′x7ゾ顔料を電荷発生層に用い友ことを特徴とする特
許請求の範囲第三項記載の電子写真感光体。 (5) 下記構造のジスアゾ顔料を電荷発生層に用い
たことを特徴とする特許請求の範囲第三項記載の電子写
真感光体。[Scope of Claims] (1) An electrophotographic photoreceptor characterized by using a disazo pigment represented by the following general formula (1). General formula (i) In the formula, one person may be a hydrocarbon group having a single bond or a conjugated double bond system, or a hydrocarbon group having a nitrogen atom in the conjugated double bond, or may be fused or substituted with an aromatic ring. It is a good heterocyclic group and forms a conjugated double bond system with the adjacent azomethine group, and horse represents a straight-chain alkyl group. X represents a residue that forms a naphthalene ring, anosthracene!, carbazole ring, benzcarbazole ring, or benzo7tine ring when combined with the densine group. L% The formed residue is a hydroxyl group,
It may have substituents other than eONH. (In the formula, 82.⇠ is a hydrogen atom, a halogen atom, which may be the same or different,
It is selected from the group consisting of a lower alkyl group, a lower alkoxy group, and a nitro group, and 雇 represents nine groups selected from the group consisting of a hydrogen atom, a halogen atom, and a cyano group. ) The electrophotographic photoreceptor according to claim 1, wherein the electrophotographic photoreceptor is selected from the following. (3) An electrophotographic photoreceptor comprising a conductive layer, a charge generation layer, and a charge transport layer, wherein the charge generation layer uses a disazo raw material represented by the general formula (1). (4) The electrophotographic photoreceptor according to claim 3, characterized in that a 'x7 pigment of the following 1-formation is used in the charge generation layer. (5) An electrophotographic photoreceptor according to claim 3, characterized in that a disazo pigment having the following structure is used in the charge generation layer.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP11707881A JPS5849951A (en) | 1981-07-28 | 1981-07-28 | Electrophotographic receptor |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP11707881A JPS5849951A (en) | 1981-07-28 | 1981-07-28 | Electrophotographic receptor |
Publications (1)
Publication Number | Publication Date |
---|---|
JPS5849951A true JPS5849951A (en) | 1983-03-24 |
Family
ID=14702850
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP11707881A Pending JPS5849951A (en) | 1981-07-28 | 1981-07-28 | Electrophotographic receptor |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS5849951A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7381806B2 (en) * | 2004-10-29 | 2008-06-03 | The Procter & Gamble Company | Cationic azo azine dyes and colorants that contain these compounds |
-
1981
- 1981-07-28 JP JP11707881A patent/JPS5849951A/en active Pending
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7381806B2 (en) * | 2004-10-29 | 2008-06-03 | The Procter & Gamble Company | Cationic azo azine dyes and colorants that contain these compounds |
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JPS63163363A (en) | Electrophotographic sensitive body | |
JPH0153458B2 (en) | ||
JPS5843459A (en) | Electrophotographic receptor | |
JPS6255778B2 (en) |