JPS61228451A - Electrophotographic sensitive body - Google Patents

Electrophotographic sensitive body

Info

Publication number
JPS61228451A
JPS61228451A JP60069091A JP6909185A JPS61228451A JP S61228451 A JPS61228451 A JP S61228451A JP 60069091 A JP60069091 A JP 60069091A JP 6909185 A JP6909185 A JP 6909185A JP S61228451 A JPS61228451 A JP S61228451A
Authority
JP
Japan
Prior art keywords
group
layer
charge
substituted
aralkyl
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
Application number
JP60069091A
Other languages
Japanese (ja)
Inventor
Masakazu Matsumoto
正和 松本
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Canon Inc
Original Assignee
Canon Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Canon Inc filed Critical Canon Inc
Priority to JP60069091A priority Critical patent/JPS61228451A/en
Publication of JPS61228451A publication Critical patent/JPS61228451A/en
Pending legal-status Critical Current

Links

Classifications

    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03GELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02Charge-receiving layers
    • G03G5/04Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0601Acyclic or carbocyclic compounds
    • G03G5/0612Acyclic or carbocyclic compounds containing nitrogen
    • G03G5/0614Amines
    • G03G5/06142Amines arylamine
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03GELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02Charge-receiving layers
    • G03G5/04Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0601Acyclic or carbocyclic compounds
    • G03G5/0612Acyclic or carbocyclic compounds containing nitrogen
    • G03G5/0614Amines
    • G03G5/06142Amines arylamine
    • G03G5/06147Amines arylamine alkenylarylamine

Landscapes

  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Photoreceptors In Electrophotography (AREA)

Abstract

PURPOSE:To enhance sensitivity and to reduce changes of the potential in the light and that in the dark at the time of repeated cycles of electrostatic charging and exposure by forming a layer contg. a specified compd. CONSTITUTION:The layer contains the compd. represented by formula I embodied by formula I-1, and in a preferable example, an electrophotographic sensitive body functionally is separated into a charge generating layer and a charge transfer layer and this layer can use the compd. of formula I as the charge transfer material and its preferable thickness is 8-20mum.

Description

【発明の詳細な説明】 産業上の利用分野 本発明は、電子写真感光体に関し、詳しくは改善された
電子写真特性を与える低分子の有機光導電体を有する電
子写真感光体に関するものである。
DETAILED DESCRIPTION OF THE INVENTION Field of the Invention The present invention relates to electrophotographic photoreceptors, and more particularly to electrophotographic photoreceptors having a low molecular organic photoconductor that provides improved electrophotographic properties.

従来の技術 従来、電子写真感光体で用いる光導電材料として、セレ
ン、硫化カドミウム、酸化亜鉛などの無機光導電性材料
が知られている。これらの光導電性材料は、数多くの利
点1例えは暗所で適当な電位に帯電できること、暗所で
電荷の逸散が少ないことあるいは光照射によって速かに
電荷を逸散できるなどの利点をもっている反面、各種の
欠点を有している。例えば、セレン系感光体では、温度
、湿度、ごみ、圧力などの要因で容易に結晶化が進み1
%に雰囲気温度が400i越えると結晶化が著しくなり
、帯電性の低下や画像に白い斑点が発生するといつ友欠
点がある。硫化カドミウム系感光体は、多湿の環境下で
安定し友感度が得られない点や酸化亜鉛系感光体ではロ
ーズベンガルに代表される増感色素による増感効果を必
要としているが、この様な増感色素がコロナ帯電による
帯電劣化や露光光による光退色を生じるため長期に亘っ
て安定した画像を与えることができない欠点を有してい
る。
2. Description of the Related Art Conventionally, inorganic photoconductive materials such as selenium, cadmium sulfide, and zinc oxide have been known as photoconductive materials used in electrophotographic photoreceptors. These photoconductive materials have many advantages, such as being able to be charged to an appropriate potential in the dark, having little charge dissipation in the dark, and being able to rapidly dissipate charge when irradiated with light. On the other hand, it has various drawbacks. For example, selenium-based photoreceptors easily crystallize due to factors such as temperature, humidity, dust, and pressure.
%, when the ambient temperature exceeds 400 i, crystallization becomes significant, resulting in deterioration in chargeability and the appearance of white spots on the image. Cadmium sulfide photoreceptors are stable in humid environments and do not exhibit friendly sensitivity, and zinc oxide photoreceptors require the sensitizing effect of sensitizing dyes such as rose bengal. The sensitizing dye suffers from charging deterioration due to corona charging and photobleaching due to exposure light, so it has the disadvantage that it cannot provide stable images over a long period of time.

一方、ポリビニルカルバゾールをはじめとする各攬の有
機光導電性ポリマーが提案されて来九が、これらのポリ
マーは、前述の無機系光導電材料に較べ成膜性、軽量性
などの点で優れているにもかかわらず今日までその実用
化が困難で6つ之のは、未だ十分な成膜性が得られてお
らず、tた感度、耐久性および環境変化による安定性の
点で無機系光導電材料に較べ劣っているためであつ几。
On the other hand, various organic photoconductive polymers including polyvinylcarbazole have been proposed, but these polymers are superior in terms of film formability and lightness compared to the aforementioned inorganic photoconductive materials. However, it has been difficult to put them into practical use to date, and inorganic light has not yet achieved sufficient film-forming properties. This is because it is inferior to conductive materials.

ま几、米国特許第4150987号明砒書などに開示の
ヒドラゾン化合物、米国特許第3837851号明細瞥
などに明細のトリアリールピラゾリン化合物S%開昭5
1−94828号公報、特開昭51−94829号公報
などに記載の9−スチリルアントラセン化合物などの低
分子の有機光導電体が提案されている。この様な低分子
の有機光導電体は、使用するバインダーを適当に選択す
ることによって、有機光導電性ポリマーの分野で問題と
なってい友成膜性の欠点を解消できる様になっ九が、感
度の点で十分なものとは言えない。
Hydrazone compounds disclosed in U.S. Pat. No. 4,150,987, etc., triarylpyrazoline compounds disclosed in U.S. Pat. No. 3,837,851, etc. S% Kaisho 5
Low-molecular organic photoconductors such as 9-styrylanthracene compounds described in JP-A-1-94828 and JP-A-51-94829 have been proposed. By appropriately selecting the binder used, such low-molecular-weight organic photoconductors can overcome the drawbacks of poor film formability that have been a problem in the field of organic photoconductive polymers. It cannot be said that the sensitivity is sufficient.

このようなことから、近年感光層を電荷発生層と電荷輸
送層に機能分離でせた積層構造体が提案された。この積
層構造を感光層とした電子写真感光体は、可視光に対す
る感度、電荷保持力1表面強度などの点で改善できる様
になった。
For these reasons, a laminated structure in which the photosensitive layer is functionally separated into a charge generation layer and a charge transport layer has been proposed in recent years. An electrophotographic photoreceptor having this laminated structure as a photosensitive layer can now be improved in terms of sensitivity to visible light, charge retention power, surface strength, etc.

この様な電子写真感光体は1例えば米国特許第3837
851号明細書、同第171882号明細書などに開示
されている。
Such an electrophotographic photoreceptor is disclosed in US Pat. No. 3,837, for example.
It is disclosed in the specification No. 851, the specification No. 171882, etc.

しかし、従来の低分子の有機光導電体を電荷輸送層に用
いた電子写真感光体では、感度、特性が必らずしも十分
でなく、また繰り返し帯電および露光を行なった際には
明部電位と暗部電位の変動が大きく改善すべき点がある
However, electrophotographic photoreceptors using conventional low-molecular organic photoconductors in the charge transport layer do not always have sufficient sensitivity and characteristics, and when repeatedly charged and exposed, bright areas There are some points that need to be greatly improved, such as fluctuations in potential and dark potential.

発明が解決しようとする問題点 本発明の目的は前述の欠点又は不利を解消した電子写真
感光体を提供することにある。
Problems to be Solved by the Invention It is an object of the present invention to provide an electrophotographic photoreceptor which eliminates the above-mentioned drawbacks or disadvantages.

本発明の別の目的は、新規な有機光導電体を提供するこ
とにある。
Another object of the invention is to provide a new organic photoconductor.

本発明の他の目的は、電荷発生層と電荷輸送層に機能分
離し次積層型感光層における新規な電荷輸送物質を提供
することにある。
Another object of the present invention is to provide a novel charge transport material in a photosensitive layer of a laminated type in which the charge generation layer and the charge transport layer are functionally separated.

問題点を解決するための手段、作用 本発明は、下記一般式で示される化合物を含有する膚を
有する電子写真感光体によって達成される。
Means for Solving the Problems and Effects The present invention is achieved by an electrophotographic photoreceptor having a skin containing a compound represented by the following general formula.

一般式 ただし1式中”fbR2はメチル、エチル、プロピル、
ブチル等のアルキル基、ベンジル、フェネチル等のアラ
ルキル基、フェニル、ナフチル吟のアリール基又はN原
子と共にピロリジノ基、ビ、4 リジン基等の環状アミ
ン基を形成する残基全庁し、該アルキル基、アラルキル
基、アIJ−ル基はメチル、エチル、プロピル、ブチル
等のアルキル基、メトキク、エトキシ、プロポキク吟の
アルコキ7基、PA素、臭素、ヨウ累等のハロゲン原子
で置換されていてもよい。
General formula However, in formula 1, "fbR2 is methyl, ethyl, propyl,
Alkyl groups such as butyl; aralkyl groups such as benzyl and phenethyl; aryl groups such as phenyl and naphthyl; , an aralkyl group, and an aralkyl group may be substituted with an alkyl group such as methyl, ethyl, propyl, or butyl, an alkoxy group such as methoxy, ethoxy, or propoxy, or a halogen atom such as PA, bromine, or iodine. good.

R5は上記R1%R2と同様の置換基を有してもよいア
ルキル基、アラルキル基を示し、又はナフチル基、アン
トリル基金示し、該ナフチル基、アントリル基はアルキ
ル基、アルコキシ基又はハロゲン原子で置換されるか、
アルキル−、フェニル−又はアラルキル置換アミノ基、
シアノ基あるいはニトロ基で置換されていてもよい、A
r1はフェニレン、ナフチレン等のアリーレン基を示し
、該アリーレン基はR1、R2と同様のアルキル基、ア
ラルキル基、アルコキシ基又はハロメン原子で置換され
るか、アルキル−、アリール又はアラルキル置換アミノ
基で置換されていてもよい。
R5 represents an alkyl group or aralkyl group that may have the same substituent as R1%R2 above, or represents a naphthyl group or anthryl group, and the naphthyl group or anthryl group is substituted with an alkyl group, an alkoxy group, or a halogen atom. Will it be done?
alkyl-, phenyl- or aralkyl-substituted amino groups,
A which may be substituted with a cyano group or a nitro group
r1 represents an arylene group such as phenylene or naphthylene, and the arylene group is substituted with the same alkyl group, aralkyl group, alkoxy group, or halomene atom as R1 and R2, or substituted with an alkyl-, aryl-, or aralkyl-substituted amino group. may have been done.

ムr2はフェニル、す7チル等のアリール基又はピリジ
ル、キノリル等のへテロ芳香環基を示し%該アリール基
、ヘテロ芳香壊基はアルキル基、アラルキル基、アルキ
ル−、アリール−又はアラルキル置換アミノ基、ピロリ
ジノ、ピはリシノ等5〜6員の環状アミノ基、フェニル
オキシ等のアリールオキシ基、フェニルチオ等のアリー
ルチオ基又はハロゲン原子で置換されていてもよい。
Mr2 represents an aryl group such as phenyl, 7-tyl, or a heteroaromatic group such as pyridyl or quinolyl. The groups pyrrolidino and pi may be substituted with a 5- to 6-membered cyclic amino group such as ricino, an aryloxy group such as phenyloxy, an arylthio group such as phenylthio, or a halogen atom.

以下に前記の一般式で示す化合物についての代表例を挙
げる。
Representative examples of the compounds represented by the above general formula are listed below.

化合物例 S−17 日−28 次に前記化合物の合成例を示す。Compound example S-17 Sun-28 Next, a synthesis example of the above compound will be shown.

合成例 s−1の合成 攪拌系と塩化カルシウム管を付した冷却管と、温度計、
ガス導入口をセットしたフラスコにDMF120m、!
=ベンゼン290−を秤取し、窒素ガスを流しながら水
素化ナトリウム(50チ鉱油)6.62を加えた。
Synthesis Example s-1 Synthesis stirring system, cooling tube with calcium chloride tube, thermometer,
DMF120m in a flask with a gas inlet set!
= 290 - of benzene was weighed out, and 6.62 of sodium hydride (50% mineral oil) was added while flowing nitrogen gas.

次に4−アセチル−N、N−ジエチルアニリン35.2
t、ジエチル−(2,4−ジメチルベンジル)フオスフ
オネート47.2tの順に加え、室温で攪拌金続は九。
Next, 4-acetyl-N,N-diethylaniline 35.2
t and 47.2 t of diethyl-(2,4-dimethylbenzyl)phosphonate were added in this order, and the mixture was stirred at room temperature for 9 hours.

気泡が発生し、液温か徐々に上昇し九ため、水冷して4
0℃にコントロールした。
Bubbles are generated and the temperature of the liquid gradually rises, so it is cooled with water.
The temperature was controlled at 0°C.

気泡の発生が終了した後30分間攪拌放置し。After the generation of bubbles ended, the mixture was left stirring for 30 minutes.

後、徐々に温度を上げ還流温度に達してから更に3時間
還流を続けた。還流時には多量の淡黄色沈澱が生成して
いた。室温まで冷却し友後。
Thereafter, the temperature was gradually raised and after reaching the reflux temperature, reflux was continued for an additional 3 hours. A large amount of pale yellow precipitate was formed during reflux. Cool to room temperature and serve.

水1Lt−加え油層を分離し、水層はベンゼン300m
/で計3回抽出処理した。先に分離し定油層とベンゼン
抽出液を合わせて水洗し、乾燥した。乾燥後、液を濃縮
し、エタノールを加えて再結晶し友。更にMKK−エタ
ノール糸で再結、精製し、目的のEl−1化合物を得た
。収*sq、at(収率73慢) 元素分析値 CHN 理論値  85.95  927 4.77測定値  
85.88  9.32  4.80他の化合物につい
ても同様に所定のケトンとジエチルアリールメチルフォ
スフォネートの誘導体とを水素化ナトリウムの存在下で
縮合することによって容易に合成される。なお、上記条
件下ではシス体の混入は極めて少ない。
Add 1Lt of water, separate the oil layer, and remove the water layer with 300ml of benzene.
/ was extracted three times in total. First, the fixed oil layer and benzene extract were separated, washed with water, and dried. After drying, concentrate the liquid and add ethanol to recrystallize it. Furthermore, it was religated using MKK-ethanol thread and purified to obtain the target El-1 compound. Yield*sq, at (yield 73%) Elemental analysis value CHN Theoretical value 85.95 927 4.77 Measured value
85.88 9.32 4.80 Other compounds are similarly easily synthesized by condensing a given ketone with a diethylarylmethylphosphonate derivative in the presence of sodium hydride. Note that under the above conditions, the contamination of the cis isomer is extremely small.

本発明の好ましい具体例では、感光層を電荷発生層と電
荷輸送層に機能分離した電子写真感光体の電荷輸送物質
に前記一般式で示される化合物を用いることができる。
In a preferred embodiment of the present invention, a compound represented by the above general formula can be used as a charge transport material in an electrophotographic photoreceptor in which the photosensitive layer is functionally separated into a charge generation layer and a charge transport layer.

本発明による電荷輸送層は、前記の一般式で示される化
合物と結着剤とを適邑な溶剤に溶解せしめた溶液を塗布
し、乾燥せしめることにより形成させることが好ましい
。ここに用いる結着剤としては1例えばポリ了りレート
、ホリスルホン、ポリアミド、アクリル樹脂、アクリロ
ニトリル樹脂、メタクリル樹脂、塩化ビニル樹脂、酢酸
ビール樹脂、フェノール樹脂、エポキシ樹脂、ポリエス
テル、アルキド樹脂%ポリカーボネート、ポリウレタン
あるいはこれらの樹脂の繰り返し単位のうち2つ以上を
含む共重合体樹脂例えばスチレン−ブタジェンコポリマ
ー。
The charge transport layer according to the present invention is preferably formed by applying a solution prepared by dissolving the compound represented by the above general formula and a binder in an appropriate solvent and drying the solution. Binders used here include 1, such as polyester, folysulfone, polyamide, acrylic resin, acrylonitrile resin, methacrylic resin, vinyl chloride resin, acetic acid beer resin, phenol resin, epoxy resin, polyester, alkyd resin% polycarbonate, polyurethane. Alternatively, a copolymer resin containing two or more of the repeating units of these resins, such as a styrene-butadiene copolymer.

スチレン−アクリロニトリルコポリマー、スチレン−マ
レイン酸コポリマーなどを挙げることができる。ILこ
の様な絶縁性ポリマーの他に、ポリビニルカルバゾール
、ポリビニルアントラセンやポリビールピレンなどの有
機光導電性ホリマーも使用できる。
Examples include styrene-acrylonitrile copolymer and styrene-maleic acid copolymer. IL In addition to such insulating polymers, organic photoconductive polymers such as polyvinylcarbazole, polyvinylanthracene and polyvirpyrene can also be used.

この結着剤と該一般式の化合物との配合割合  □は、
結着剤100重量部当シ該一般式の化合物t−10〜5
00重量とすることが好ましい。
The blending ratio □ of this binder and the compound of the general formula is:
100 parts by weight of a binder Compounds of the general formula t-10 to 5
00 weight is preferable.

電荷輸送層は、下達の電荷発生層と電気的に接続されて
おり、電界の存在下で電荷発生層から注入された電荷キ
ャリアを受は取るとともに、これらの電荷キャリアを表
面まで輸送できる機能を有している。この際、この電荷
輸送層は。
The charge transport layer is electrically connected to the underlying charge generation layer, and has the function of receiving and taking charge carriers injected from the charge generation layer in the presence of an electric field and transporting these charge carriers to the surface. have. At this time, this charge transport layer.

電荷発生層の上に積層されていても工〈、ま几その下に
積層されていてもよい。しかし、電荷輸送層は、電荷発
生層の上に積層されていることが望ましい。この電荷輸
送層は、電荷キャリアを輸送できる限界があるので、必
要以上に膜厚を厚くすることができない。一般的には、
5〜30μであるが、好ましい範囲は8〜20μである
It may be laminated on top of the charge generation layer or under it. However, it is desirable that the charge transport layer is laminated on the charge generation layer. Since this charge transport layer has a limit in its ability to transport charge carriers, it cannot be made thicker than necessary. In general,
It is 5 to 30μ, with a preferred range of 8 to 20μ.

この様な電荷輸送層を形成する際に用いる有機溶剤は、
使用する結着剤の種類によって異なり、又は電荷発生層
や下達の下引層を溶解しないものから選択することが好
ましい。具体的な有機溶剤としては、メタノール、エタ
ノール。
The organic solvent used when forming such a charge transport layer is
The binder varies depending on the type of binder used, and it is preferable to select one that does not dissolve the charge generation layer or underlying subbing layer. Specific organic solvents include methanol and ethanol.

インプロパツールなどのアルコール類、アセトン、メチ
ルエチルケトン、シクロヘキサノンなどのケトン類、 
N、N−ジメチルホルムアミド。
Alcohols such as Impropatool, ketones such as acetone, methyl ethyl ketone, cyclohexanone,
N,N-dimethylformamide.

N、N−ジメチルアセトアミドなどのアミド類。Amides such as N,N-dimethylacetamide.

ジメチルスルホキシドなどのスルホキシド類、テトラヒ
ドロフラン、ジオキサン、エチレングリコール七ツメチ
ルエーテルなどのエーテル類。
Sulfoxides such as dimethyl sulfoxide, ethers such as tetrahydrofuran, dioxane, and ethylene glycol 7-methyl ether.

酢酸メチル、酢酸エチルなどのエステル類、クロロホル
ム、塩化メチレン、ジクロルエチレン。
Esters such as methyl acetate and ethyl acetate, chloroform, methylene chloride, dichloroethylene.

四塩化炭素、トリクロルエチレンなどの脂肪族ハロゲン
化炭化水素類あるいはベンゼン、トルエン、キシレン、
リグロイン、モノクロルヘンゼン、ジクロルベンゼシな
どの芳香族類などを用いることができる。
Aliphatic halogenated hydrocarbons such as carbon tetrachloride and trichloroethylene, or benzene, toluene, xylene,
Aromatics such as ligroin, monochlorobenzene, dichlorobenzene, etc. can be used.

塗工は、浸漬コーティング法、スプレーコーティング法
、スピンナーコーティング法、ビードコーティング法、
マイヤーパーコーティング法、ブレードコーティング法
、ローラーコーティング法、カーテンコーティング法な
どのコーティング法全用いて行なうことができる。乾燥
は、室温における指触乾燥後、加熱乾燥する方法が好ま
しい。加熱乾燥は、50〜200℃の温度で5分〜2時
間の範囲の時間で、静止または送風下で行なうことがで
きる。
Coating methods include dip coating, spray coating, spinner coating, bead coating,
All coating methods such as Mayer-Per coating method, blade coating method, roller coating method, and curtain coating method can be used. For drying, it is preferable to dry to the touch at room temperature and then heat dry. Heat drying can be carried out at a temperature of 50 to 200°C for a period of time ranging from 5 minutes to 2 hours, either stationary or under ventilation.

本発明の電荷輸送層には、種々の添加剤を含有させるこ
とができる。かかる添加剤としては。
The charge transport layer of the present invention can contain various additives. As such additives.

ジフェニル、塩化ジフェニル、0−ターフェニル、p−
ターフェニル、シフチルフタレート。
diphenyl, diphenyl chloride, 0-terphenyl, p-
Terphenyl, cyphthylphthalate.

ジメチルグリコールフタレート、ジオクチルフタレート
、トリフェニル燐酸、メチルナフタリン、ベンゾフェノ
ン、塩素化パラフィン、ジラウリルチオプロピオネ−)
、3.5−ジ二トロサ’)fktR,各種フルオロカー
ボン類などを°挙げることができる。
dimethyl glycol phthalate, dioctyl phthalate, triphenyl phosphoric acid, methylnaphthalene, benzophenone, chlorinated paraffin, dilaurylthiopropione)
, 3,5-dinitrosa')fktR, and various fluorocarbons.

本発明で用いる電荷発生層は、セレン、セレン−テルル
、ピリリウム、チオピリリウム、アズレニウム系染料、
フタロシアニン71%顔料、アントアントロン顔料、ジ
ベンズピレンキノン顔料、ピラントロン顔料、トリスア
ゾ顔料、ジスアゾ顔料、アゾ顔料、インジゴ顔料、キナ
クリドン糸顔料、チアシアニン、非対称キノシアニン、
キノシアニンあるいは特開昭54−145645号公報
に記載のアモルファスシリコンなどの電荷発生物質から
選ばれ穴別個の蒸着層あるいは樹脂分散層を用いること
ができる。
The charge generation layer used in the present invention includes selenium, selenium-tellurium, pyrylium, thiopyrylium, azulenium dyes,
Phthalocyanine 71% pigment, anthanthrone pigment, dibenzpyrenequinone pigment, pyranthrone pigment, trisazo pigment, disazo pigment, azo pigment, indigo pigment, quinacridone thread pigment, thiacyanine, asymmetric quinocyanine,
A vapor-deposited layer or a resin-dispersed layer with separate holes selected from charge-generating substances such as quinocyanine or amorphous silicon described in JP-A-54-145645 can be used.

本発明の電子写真感光体に用いる電荷発生物質は1例え
ば下記に示す無機化合物あるいは有機化合物を挙げるこ
とができる。
Examples of the charge generating substance used in the electrophotographic photoreceptor of the present invention include the following inorganic compounds and organic compounds.

電荷発生物質 ;1(アモルファスシリコン 121  セレン−テルル (3)  セレンーヒ素 (4)  硫化カドミウム 02H5C2H5 諺 スクエアリック酸メチン染相 [株] インジゴ染料(C,工、扁7 a 000)1
)チオインジゴ染料(C,工、A78800)旬 β−
型鋼フタロシアニン @4 電荷発生層は、前述の電荷発生物質を適当な結着剤に分
散させ、これを基体の上に塗エテることによって形成で
き、ま九真空蒸着装置によシ蒸着膜を形成することによ
って得ることができる。電荷発生層を塗工によって形成
する際に用りうる結着剤としては広範な絶縁性樹脂から
選択でき、またポリ−N−ビニルカルJ〈ゾール。
Charge generating substance; 1 (amorphous silicon 121 selenium-tellurium (3) selenium-arsenic (4) cadmium sulfide 02H5C2H5 proverb methine squaric acid dyeing [Co., Ltd.] indigo dye (C, engineering, flat 7 a 000) 1
) Thioindigo dye (C, engineering, A78800) Shun β-
Type steel phthalocyanine @ 4 The charge generation layer can be formed by dispersing the above-mentioned charge generation substance in a suitable binder, coating it on the substrate, and forming a vapor deposited film using a vacuum evaporation apparatus. You can get it by doing The binder that can be used when forming the charge generation layer by coating can be selected from a wide variety of insulating resins, including poly-N-vinylcal J<sol.

ポリビニルアントラセンやポリビニルピレンなどの有機
光導電体ポリマーから選択できる。好ましくは%ポリビ
ニルブチラール、ボリアリレート(ビスフェノールAと
フタル酸の縮重合体など)、ポリカーボネート、ポリエ
ステル、フェノキシ樹脂、ポリ酢酸ビニル、アクリル樹
脂、ポリアクリルアミド樹脂、ポリアミド、ポリビニル
ピリジン、セルロース系樹脂、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、ポリビニルピ
ロリドンなどの絶縁性樹脂を挙げることができる。電荷
発生層中に含有する樹脂は、80重量饅以下、好・まし
くけ40重量−以下が適している。塗工の際に用いる有
機溶剤としては、メタノール、エタノール、インプロパ
ツールなどのアルコール類、アセトン、メチルエチルケ
トン、シクロヘキサノンなどのケトン類、N、N−ジメ
チルホルムアミl’、N、N−ジメチルアセトアミドな
どのアミド類、ジメチルスルホキシドなどのスルホキシ
ド類、テトラヒドロフラン、ジオキサン、エチレングリ
フール七ツメチルエーテルなどのエーテル類、酢酸メチ
ル、酢酸エチルなどのエステル類、クロロホルム、塩化
メチレン、ジクロルエチレン。
One can choose from organic photoconductor polymers such as polyvinylanthracene and polyvinylpyrene. Preferably % polyvinyl butyral, polyarylate (condensation polymer of bisphenol A and phthalic acid, etc.), polycarbonate, polyester, phenoxy resin, polyvinyl acetate, acrylic resin, polyacrylamide resin, polyamide, polyvinylpyridine, cellulose resin, urethane resin , epoxy resin, casein, polyvinyl alcohol, polyvinylpyrrolidone, and other insulating resins. The resin contained in the charge generation layer is suitably 80% by weight or less, preferably 40% by weight or less. Examples of organic solvents used during coating include alcohols such as methanol, ethanol, and impropatul, ketones such as acetone, methyl ethyl ketone, and cyclohexanone, N,N-dimethylformamyl', N,N-dimethylacetamide, etc. amides, sulfoxides such as dimethyl sulfoxide, ethers such as tetrahydrofuran, dioxane, ethylene glycol methyl ether, esters such as methyl acetate, ethyl acetate, chloroform, methylene chloride, dichloroethylene.

四塩化炭素、トリクロルエチレンなどの脂肪族ハロゲン
化炭化水素類あるいはベンゼン、トルエン、キシレン、
リクロイン、モノクロルベンゼン、ジクロルベンゼンな
どの芳香族類などt用いることができる。
Aliphatic halogenated hydrocarbons such as carbon tetrachloride and trichloroethylene, or benzene, toluene, xylene,
Aromatic compounds such as licroin, monochlorobenzene, dichlorobenzene, etc. can be used.

塗工は、浸漬コーティング法、スプレーコーティング法
、スピンナーコーティング法、ビードコーティング法、
マイヤーパーコーティング法、ブレードコーティング法
、ローラーコーティング法、カーテンコーティング法な
どのコーティング法を用いて行なうことができる。
Coating methods include dip coating, spray coating, spinner coating, bead coating,
This can be carried out using a coating method such as a Mayer coating method, a blade coating method, a roller coating method, or a curtain coating method.

電荷発生層は、十分な吸光度を得る丸めに。Round the charge generating layer to obtain sufficient absorbance.

できる限夛多くの前記有機光導電体を含有し。Contain as much of the organic photoconductor as possible.

且つ発生し次電荷キャリアの飛程を短かくする几めに、
薄膜層1例えば5輛−瞳以下、好ましくはQ、01+=
p=$=w〜1←―中−の膜厚をもつ薄膜層とすること
が好ましい。このことは、入射光量の大部分が電荷発生
層で吸収されて、多くの電荷キャリアを生成すること、
さらに発生し九電荷キャリアを再結合や捕獲(トラップ
)により失活することなく電荷輸送層に注入する必要が
あることに起因している。
In order to shorten the range of the generated charge carriers,
Thin film layer 1, for example, 5 or less pupils, preferably Q, 01+=
It is preferable to form a thin film layer having a thickness of p=$=w~1←-medium-. This means that most of the incident light is absorbed by the charge generation layer, producing many charge carriers.
This is due to the fact that it is necessary to inject the generated charge carriers into the charge transport layer without being deactivated by recombination or trapping.

この様な電荷発生層と電荷輸送層の積層構造からなる感
光層は%導電層を有する基体の上に設けられる。導電庵
ヲ有する基体としては、基体自体が導電性をもつもの1
例えばアルミニウム、アルミニウム合金、銅、亜鉛、ス
テンレス。
A photosensitive layer having such a laminated structure of a charge generation layer and a charge transport layer is provided on a substrate having a conductive layer. Substrates with conductivity include those in which the substrate itself is electrically conductive.
For example, aluminum, aluminum alloy, copper, zinc, stainless steel.

バナジウム、モリブデン、クロム、チタン、ニッケル、
インジウム、金や白金などを用いることができ、その他
にアルミニウム、アルミニウム合金、酸化インジウム、
酸化錫、酸化インジウム−酸化錫合金などを真空蒸着法
によって被膜形成されytNを有するプラスチック(例
えば。
vanadium, molybdenum, chromium, titanium, nickel,
Indium, gold, platinum, etc. can be used, and in addition, aluminum, aluminum alloy, indium oxide,
Plastics having ytN formed by coating tin oxide, indium oxide-tin oxide alloy, etc. by vacuum evaporation method (for example).

ポリエチレン、ポリプロピレン、ポリ331.ビニル、
ポリエチレンテレフタレート、アクリル樹脂、ポリフッ
化エチレンなど)、鴫!注粒子(例えば、カーボンブラ
ック、4s粒子など)を適当なバインダーとともにプラ
スチックの上に被覆した基体、導電性粒子をプラスチッ
クや紙に含浸した基体や導電性、d IJママ−有する
プラスチックなどを用いることができる。
Polyethylene, polypropylene, poly331. vinyl,
Polyethylene terephthalate, acrylic resin, polyfluoroethylene, etc.), Shizuku! Use a substrate made of plastic coated with particles (e.g., carbon black, 4S particles, etc.) together with a suitable binder, a substrate made of plastic or paper impregnated with conductive particles, or a plastic with conductivity or d IJ mother. I can do it.

導電層と感光層の中間に、バリヤー機能と接着機能をも
つ下引層を設けることもできる。下引層は、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によって形成できる。
A subbing layer having barrier and adhesive functions can also be provided between the conductive layer and the photosensitive layer. The subbing layer is casein,
Polyvinyl alcohol, nitrocellulose, ethylene-
Acrylic acid copolymer, polyamide (nylon 6, nylon 66°, nylon 610, copolymerized nylon, alkoxymethylated nylon, etc.), polyurethane, gelatin,
It can be formed from aluminum oxide, etc.

下引層の膜厚は、0.1〜5μ好ましくは0.5〜3μ
が適当である。
The thickness of the subbing layer is 0.1 to 5μ, preferably 0.5 to 3μ.
is appropriate.

導電層、電荷発生層、電荷輸送層の順に積層し友感光体
を使用する場合において、化合物は正孔輸送性であるの
で、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1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。現偉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。
When a conductive layer, a charge generation layer, and a charge transport layer are laminated in this order and a photosensitive member is used, the compound has hole transport properties, so the surface of the charge transport layer must be negatively charged, and when exposed to light after charging, In the exposed area, holes generated in the charge generation layer are injected into the charge transport layer, and then reach the surface to neutralize the negative charges, causing attenuation of the surface potential and creating electrostatic contrast with the unexposed area. When printing, it is necessary to use a positively charged toner, contrary to the case where an electron transport material is used.

本発明の別の具体例では、前述のジスアゾ顕示のピリリ
ウム染料、チアピリリウム染料、セレナピリリウム染料
、ベンゾピリリウム染料。
In another embodiment of the invention, the aforementioned disazo-displaying pyrylium dyes, thiapyrylium dyes, selenapyrylium dyes, benzopyrylium dyes.

ベンゾチアピリリウム染料、ナフトピリリウム染料、ナ
フトチアピリリウム染料などの光導電性を有する顔料や
染料を増感剤としても用いることができる。
Photoconductive pigments and dyes such as benzothiapyryllium dyes, naphthopyryllium dyes, and naphthothiapyrylium dyes can also be used as sensitizers.

ま穴、別の具体例では、米国特許第3684502号明
細書などに開示のピリリウム染料とアルキリデンジアリ
ーレン部分を有する電気絶縁重合体との共晶錯体金増感
剤として用いることもできる。この共晶錯体は1例えば
4−〔4−ビス−(2−/ロロエチル)アミノフェニル
] −2,6−シフエニルチアピリリウムパークロレー
トとポリ(4,4’−インプロピリデンジフェニレンカ
ーボネート)t−ハロゲン化炭化水素系溶剤(例エバ、
ジクロルメタン、クロロホルム、四塩化炭3,1.1−
ジクロルエタン、1,2−ジクロルエタン、  1.1
.2− )ジクロルエタン、クロルベンゼン、フロモベ
ンゼン、1.2−ジクロルベンゼン)に溶解した後、こ
れに非他性溶剤(例えば、ヘキサン、オクタン、デカン
、 2,2,4−トリメチルベンゼン、リグロインを加
えることによって粒子状共晶錯体として得られる。この
具体例における電子写真感光体には、スチレンーブタジ
エンフボリマー、シリコン樹脂、ビニル樹脂、塩化ビニ
リデン−7クリロ二トリルコポリマー、スチレンーアク
リロニトリルコポリマー、ヒニルアセテートー塙化ビニ
ルフボリマー、ポリビニルブチラール、ポリメチルメタ
クリレート、ポリ−N−ブチルメタクリレート、ポリエ
ステル類、セルロースエステル類ナトt−結着剤として
含有することができる。
In another embodiment, a eutectic complex of a pyrylium dye and an electrically insulating polymer having an alkylidene diarylene moiety, such as disclosed in US Pat. No. 3,684,502, can be used as a gold sensitizer. This eutectic complex is composed of 1 e.g. - halogenated hydrocarbon solvents (e.g. Eva,
Dichloromethane, chloroform, carbon tetrachloride 3,1.1-
Dichloroethane, 1,2-dichloroethane, 1.1
.. 2-) dichloroethane, chlorobenzene, fromobenzene, 1,2-dichlorobenzene) and then add a non-external solvent (e.g. hexane, octane, decane, 2,2,4-trimethylbenzene, ligroin) to this. The electrophotographic photoreceptor in this example includes styrene-butadiene fubolymer, silicone resin, vinyl resin, vinylidene chloride-7-acrylonitrile copolymer, styrene-acrylonitrile copolymer, Acetate-containing vinyl fluoride polymer, polyvinyl butyral, polymethyl methacrylate, poly-N-butyl methacrylate, polyesters, and cellulose esters can be contained as a binder.

本発明の電子写真感光体は、電子写真複写機に利用する
のみならず、レーザープリンター。
The electrophotographic photoreceptor of the present invention can be used not only in electrophotographic copying machines but also in laser printers.

C’RTプリンター、電子写真式製版システムなどの電
子写真応用分野にも広く用いることができる。
It can also be widely used in electrophotographic applications such as C'RT printers and electrophotographic plate making systems.

本発明によれば、高感度の電子写真感光体を与えること
ができ、また繰り返し帯電および露光を行なつ九時の明
部電位と暗部電位の変動が小さい利点を有している。
According to the present invention, it is possible to provide a highly sensitive electrophotographic photoreceptor, and it has the advantage that the variation in bright area potential and dark area potential at 9 o'clock when charging and exposure are repeated is small.

以下、本発明を実施例に従って説明する。Hereinafter, the present invention will be explained according to examples.

実施例 1 東洋インキ製造■製のβ型銅フタロシアニン(商品名L
1on(11Bie NCB TOner ) k水、
エタノールおよびベンゼン中で順次環流後、濾過して精
製し九顔料7t+デュポン社製の「商品名二ポリエステ
ルアドヒーシプ49,000(固形分20優)J 14
f+ )ルエン35t;ジオキサン65fQ混合し、ボ
ールミルで6時間分散することによって迩工液を調製し
た。この塗工液をアルミニウムシート上に乾燥膜厚が0
.5μとなる様にマイヤーバーで塗布して電荷発生J’
dk作成し友。
Example 1 β-type copper phthalocyanine (trade name L) manufactured by Toyo Ink Manufacturing ■
1on (11Bie NCB TONer) k water,
After sequentially refluxing in ethanol and benzene, it was purified by filtration to obtain 9 pigments 7t + DuPont's "Product Name: Polyester Adhesive 49,000 (solid content 20%) J 14".
f+) 35 t of toluene and 65 fQ of dioxane were mixed and dispersed in a ball mill for 6 hours to prepare a working solution. This coating solution was applied onto an aluminum sheet until the dry film thickness was 0.
.. Apply it with a Mayer bar so that it becomes 5μ to generate a charge J'
dk created friend.

次に、i!荷輸送化合物として前記例示化合物s−6y
 7 tとポリカーボネート樹脂(今人化成■製の商品
名「パンライトに−1300J ) 7 fとをテトラ
ヒドロフラン551とクロロベンゼン35tの混合溶媒
中に攪拌溶解させて得文溶液金先の電荷発生層の上に、
マイヤーパーで乾燥膜厚が11μとなる様に塗工して、
2層構造からなる感光層重もつ電子写真感光体を作成し
几。
Next, i! The above-mentioned exemplified compound s-6y as a cargo transporting compound
7T and polycarbonate resin (trade name "Panlite-1300J" manufactured by Konjin Kasei) and 7F were stirred and dissolved in a mixed solvent of 551 tetrahydrofuran and 35t of chlorobenzene, and a solution was prepared on the charge generation layer of the gold tip. To,
Apply with Meyer Par to a dry film thickness of 11μ,
An electrophotographic photoreceptor with two photosensitive layers was created.

この様にして作成し九電子写真感光体を川口電機■製静
電複写紙試験装置Model−8P−428を用いてス
タチック方式で一5KVでコロナ帯電し。
The nine electrophotographic photoreceptors thus prepared were statically corona charged at 15 KV using an electrostatic copying paper tester Model-8P-428 manufactured by Kawaguchi Electric.

暗所で1秒間保持した後、照度5 Lugで露光し帯電
特性を調べた。
After being held in a dark place for 1 second, it was exposed to light at an illuminance of 5 Lug to examine the charging characteristics.

帯電特性としては1表面電位(Vo)と1秒間暗減衰さ
せた時の電位(V、)を捧に減衰するに必要な露光量(
E捧)tl−測定した。
The charging characteristics are as follows: 1 surface potential (Vo) and the amount of light exposure required to attenuate the potential (V,) when dark decayed for 1 second (
E) tl-measured.

さらに、繰り返し使用した時の明部電位と暗部電位の変
動を測定する九めに、本実施例で作成した感光体管キャ
ノン■製ppc複写機NP−15ozの感光ドラム用シ
リンダーに貼シ付けて同機で5oooo枚複写を行ない
、初期と5ooo。
Furthermore, in order to measure the fluctuations in bright area potential and dark area potential during repeated use, the photosensitive drum cylinder prepared in this example was pasted on the photosensitive drum cylinder of the Canon NP-15oz PPC copier. I made 5ooo copies with the same machine, and the initial and 5ooo copies.

枚複写後の明部電位(VL)及び暗部電位(V’n)の
変動を測定した。
Fluctuations in bright area potential (VL) and dark area potential (V'n) after copying were measured.

また前記例示化合物の代シに下記構造式のスチルベン化
合物を用いて全く同様の操作により比較試料1を作成、
同様に測定し皮。この結果を次に示す。
Comparative sample 1 was also prepared in exactly the same manner using a stilbene compound having the following structural formula in place of the exemplified compound.
Measure the skin in the same way. The results are shown below.

表   1 実施例2〜1に の各実施例においては、前記実施例1で用いた電荷輸送
化合物として例示化合物S−6の代シに例示化合物S”
−1、B−2* S−4s S−7% S−8−8−1
0、5−12、5−13、8−14%B−16、5−1
7、5−21。
Table 1 In each of Examples 2 to 1, Exemplified Compound S'' was substituted for Exemplified Compound S-6 as the charge transport compound used in Example 1.
-1, B-2* S-4s S-7% S-8-8-1
0, 5-12, 5-13, 8-14%B-16, 5-1
7, 5-21.

5−24 、8−26.8−!10  t−用いかつ電
荷発生物質として例示(5)の顔料を用い文ほかは、実
施例1と同様の方法によって電子写真感光体を作成し九
5-24, 8-26.8-! An electrophotographic photoreceptor was prepared in the same manner as in Example 1, except that the pigment of Example (5) was used as the charge generating material.

各感光体の電子写真特性を実施例1と同様の方法によっ
て測定した。その結果を次に示す。
The electrophotographic properties of each photoreceptor were measured in the same manner as in Example 1. The results are shown below.

実施例 17 4−(4−ジメチルアミノフェニル) −2,6−シフ
エニルチアピリリウムハークロレート3tと前記例示化
合物(S−20) ? 5 f t−J IJエステル
(ポリエステルアドヒーシプ49000:デュポン社製
)のトルエン(50)−ジオキサン(50)溶液100
mに混合し、ボールミルで6時間分散した。この分散液
を乾燥後の膜厚が15μとなる様にマイヤーパーでアル
ミニウムシート上に塗布し几。
Example 17 4-(4-dimethylaminophenyl)-2,6-cyphenylthiapyrylium hachlorate 3t and the above exemplary compound (S-20)? 5 f t-J IJ ester (Polyester Adhesive 49000: manufactured by DuPont) toluene (50)-dioxane (50) solution 100
and dispersed in a ball mill for 6 hours. This dispersion was coated onto an aluminum sheet using a Mayer parr so that the film thickness after drying was 15 μm.

この様にして作成し交感光体の電子写真特性を実施例1
と同様の方法で測定した。この結果を次に示す。
Example 1 The electrophotographic properties of the sympathizer produced in this way
It was measured in the same manner as. The results are shown below.

VO:  −600V vl :  −585v 11:17:   2.5ムx、sec初期 VD: −700V VL: −70V soooo枚耐久後 vn:  −6551 VLニー105V 実施例 18 アルミ板上にカゼインのアンモニア水溶液(カゼイン1
129.28%アンモニア水1f、水222m)をマイ
ヤーバーで塗布乾燥し、膜厚が1μの接着層を形成した
VO: -600V vl: -585v 11:17: 2.5 mm x, sec Initial VD: -700V VL: -70V VN after soooo sheet durability: -6551 VL knee 105V Example 18 Ammonia aqueous solution of casein on an aluminum plate (Casein 1
1f of 129.28% ammonia water, 222ml of water) was applied using a Mayer bar and dried to form an adhesive layer with a thickness of 1 μm.

次に下記構造を有するジスアゾ顔料5fと。Next, a disazo pigment 5f having the following structure.

ブチラール樹脂(ブチラール化度63モルチ)2tk工
タノール95IIIgVC@かし次液と共に分散した後
、接着層上に塗工し乾燥後の膜厚が04μとなる電荷発
生層を形成した。
Butyral resin (degree of butyralization: 63 mol) 2tk polytanol 95IIIgVC @ After being dispersed with a liquid solution, it was coated on the adhesive layer to form a charge generation layer having a dry film thickness of 0.4μ.

次に、前記例示のs−5化合物t−5fとポリ−4,4
′−ジオキシジフェニル−2,2−プロパンカーボネー
ト(粘度平均分子量30000)5 fをジクロルメタ
ン150mgに溶かし比液金電荷発生層上に塗布、乾燥
し、膜厚が11μの電荷輸送Me影形成ることによって
電子写真感光体を作成し九。
Next, the above-mentioned s-5 compound t-5f and poly-4,4
'-Dioxydiphenyl-2,2-propane carbonate (viscosity average molecular weight 30,000) 5f was dissolved in 150 mg of dichloromethane and applied onto the liquid-specific gold charge generation layer, dried, and a charge transport Me shadow having a film thickness of 11 μm was formed. Create an electrophotographic photoreceptor by

この様にして作成し良電子写真感光体の電子写真特性を
実施例1と同様の方法で測定した。
The electrophotographic properties of the good electrophotographic photoreceptor prepared in this manner were measured in the same manner as in Example 1.

この結果を次に示す。The results are shown below.

VO: −620V Vl : −610V g14 :   3.1 tux、sec初期 VD ニー730V v1ニーaov soooo枚耐久後 VD : −6657 vL : −115V 実施例 19 表面が清浄にされた0、2M厚のモリブデン板(基板)
をグロー放電蒸着槽内の所定位置に固定した。次に槽内
全排気し、約5X10−6 torrの真空度にした。
VO: -620V Vl: -610V g14: 3.1 tux, sec Initial VD knee 730V v1 knee aov soooo sheet durability VD: -6657 vL: -115V Example 19 0.2M thick molybdenum with cleaned surface Board (board)
was fixed at a predetermined position in a glow discharge deposition tank. Next, the tank was completely evacuated to a vacuum level of approximately 5×10 −6 torr.

その後ヒーターの入力電圧を上昇させモリブデン基板温
度を150℃に安定させ九〇その後水素ガスとシランガ
ス(水素ガスに対し15容盆%)t一槽内へ導入しガス
流量と蒸眉榴メインパルプt!#整して0.5 tor
rに安定させた。次に誘導コイルだ5 MHzの高周波
電力を投入し槽内のコイル内部にグロー放電全発生させ
30Wの入力電力とした。上記粂件で基板上にアモルフ
ァスシリコン膜を生長させ膜厚が2μとなるまで同条件
を保った後グロー放電を中止し穴、、その後加熱ヒータ
ー、高周波電源をオフ状態とし、基板温度が100℃に
なるのを待ってから水素°ガス、シランガスの流出パル
プ、ヲ閉じ、一旦檀内t−1Q−5torr以下にし文
後大気圧にもどし基板を取シ出した。次いでこのアモル
ファスシリコン層の上に電荷輸送化合物として例示化合
物5−27 k用いる以外は実施例1と全く同様にして
電荷輸送層を形成したわ こうして得られ交感光体を帯電露光実験装置に設置し一
6KVでコロナ帯電し直ちに光像を照射した。光像はタ
ングステンランプ光源を用い透過溢のテストチャートラ
通して照射され友。
After that, the input voltage of the heater is increased to stabilize the molybdenum substrate temperature at 150℃.90 After that, hydrogen gas and silane gas (15% of the hydrogen gas) are introduced into the tank, and the gas flow rate and the steamed main pulp are changed. ! # Adjust to 0.5 tor
stabilized at r. Next, 5 MHz high-frequency power was applied to the induction coil to generate a glow discharge inside the coil in the tank, resulting in an input power of 30 W. In the above case, an amorphous silicon film was grown on the substrate and the same conditions were maintained until the film thickness reached 2μ, then the glow discharge was stopped and the hole was turned off.Then, the heating heater and high frequency power were turned off, and the substrate temperature was raised to 100℃. After waiting for the hydrogen gas and silane gas to flow out of the pulp, the chamber was closed, and the temperature inside the chamber was once lowered to below t-1Q-5 torr, after which the pressure was returned to atmospheric pressure and the substrate was taken out. Next, a charge transport layer was formed on this amorphous silicon layer in exactly the same manner as in Example 1 except that Exemplary Compound 5-27k was used as a charge transport compound.The thus obtained sympathizer was placed in a charging exposure experimental apparatus. It was corona charged at -6 KV and immediately irradiated with a light image. The light image is illuminated through a transparent test chart using a tungsten lamp light source.

その後直ちに十荷電性の現像剤(トナーとキャリヤーを
含む)を感光体表面にカスケードすることによって感光
体表面に良好なトナー画像を得た。
Immediately thereafter, a highly charged developer (containing toner and carrier) was cascaded onto the surface of the photoreceptor to obtain a good toner image on the surface of the photoreceptor.

実施例 20 4−(4−ジメチルアミノフェニル) −2,6−シフ
エニルチアピリリウムパークロレート3tとポリ(4,
4’−イソプロピリデンジフェニレンカーボネート)s
r@ジクロルメタン200Mtに十分に溶解し次後、ト
ルエン1oOd!加え。
Example 20 4-(4-dimethylaminophenyl)-2,6-cyphenylthiapyrylium perchlorate 3t and poly(4,
4'-isopropylidene diphenylene carbonate)s
After sufficiently dissolving in 200Mt of r@dichloromethane, 10Od of toluene! Addition.

共晶錯体を沈殿させた。この沈殿物t−F別した後、ジ
クロルメタンを加えて再溶解し、次いでこの溶液にn−
ヘキサンIQGdk加えて共晶錯体の沈殿物を得几。
A eutectic complex was precipitated. After separating this precipitate by t-F, dichloromethane was added to redissolve it, and then this solution was added with n-
Add hexane to IQGdk to obtain a precipitate of eutectic complex.

この共晶錯体5tt−ポリビニルブチラール2ft−含
有するメタノール溶液95−に加え、6時間ボールミル
で分散し九。この分散液をカゼイン層を有するアルミ板
の上に乾燥後の膜厚が(L4声となる様にマイヤーバー
で塗布して電荷発生層を形成し几。
This eutectic complex was added to a methanol solution containing 5tt and 2ft of polyvinyl butyral and dispersed in a ball mill for 6 hours. This dispersion was applied onto an aluminum plate having a casein layer using a Mayer bar so that the film thickness after drying was L4 to form a charge generation layer.

次いで、この電荷発生層の上に例示化合物8−3 t−
用いる以外は実施例1と全く同様にして電荷輸送層の被
覆層を形成した。
Next, Exemplified Compound 8-3 t-
A cover layer of a charge transport layer was formed in the same manner as in Example 1 except that the coating layer was used.

こうして作成し交感光体の電子写真特性全実施例1と同
様の方法によって測定し几。この結果を次に示す。
The electrophotographic properties of the photoreceptor thus prepared were measured in the same manner as in Example 1. The results are shown below.

vQ ” −615V Vl: −6oov ” ”   AD tu;c、aec 初期 Vnニー7oov VLニーB□v 5000回耐久後 WD:  −6a□v VX=”  −115V 実施例 21 実施例20で用いた共晶錯体と同様のもの52と前記例
示の5−28化合@5tkポリエステル(ポリエステル
アドヒージプ49000 :デュポン社製)のテトラヒ
ドロフラン液150−に加えて、十分に混合攪拌した。
vQ ” -615V Vl: -6oov ” ” AD tu;c, aec Initial Vn knee 7oov VL knee B□v WD after 5000 times endurance: -6a□v VX=” -115V Example 21 Common used in Example 20 A product similar to the crystal complex 52 and a tetrahydrofuran solution 150 of the exemplified 5-28 compound@5tk polyester (Polyester Adhesip 49000, manufactured by DuPont) were added to the mixture and thoroughly mixed and stirred.

この液をアルミニラ・ムシート上にマイヤーパーにより
乾燥後の膜厚が15μとなる様に塗布し次。
This solution was applied onto an aluminum sheet using a Mayer par so that the film thickness after drying would be 15 μm.

この感光体の電子写真特性全実施例1と同様の方法で測
定した。この結果を次に示す、vQ : −600V vl + −590V x% :   2.B &x、sea 初期 VD : −7107 VLニー757 soooo枚耐久後 VD : −6207 VL : −115V 特許田麩 キャノン株式会社
The electrophotographic properties of this photoreceptor were measured in the same manner as in Example 1. The results are shown below: vQ: -600V vl + -590V x%: 2. B & x, sea Initial VD: -7107 VL knee 757 VD after soooo sheet durability: -6207 VL: -115V Patented Field Canon Co., Ltd.

Claims (1)

【特許請求の範囲】[Claims] (1)下記の一般式で示される化合物を含有する層を有
することを特徴とする電子写真感光体。 一般式 ▲数式、化学式、表等があります▼ ただし、式中R_1、R_2はアルキル基、アラルキル
基、アリール基又はN原子と共に環状アミノ基を形成す
る残基を示し、該アルキル基、アラルキル基及びアリー
ル基はアルキル基、アルコキシ基あるいはハロゲン原子
で置換されていてもよい。 R_3は上記R_1、R_2と同様の置換基を有しても
よいアルキル基又はアラルキル基を示し、又はナフチル
基あるいはアントリル基を示し、該ナフチル基及びアン
トリル基はアルキル基、アルコキシ基、ハロゲン原子、
置換アミノ基、シアノ基あるいはニトロ基で置換されて
いてもよい。 Ar_1はアリーレン基を示し、該アリーレン基はR_
1、R_2と同様のアルキル基、アラルキル基、アルコ
キシ基、ハロゲン原子あるいは置換アミノ基で置換され
ていてもよい。 Ar_2はアリール基又はヘテロ芳香環基を示し、該ア
リール基、ヘテロ芳香環基はアルキル基、アラルキル基
、置換アミノ基、5〜6員の環状アミノ基、アリールオ
キシ基、アリールチオ基あるいはハロゲン原子で置換さ
れていてもよい。
(1) An electrophotographic photoreceptor characterized by having a layer containing a compound represented by the following general formula. General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ However, in the formula, R_1 and R_2 represent an alkyl group, an aralkyl group, an aryl group, or a residue that forms a cyclic amino group together with the N atom, and the alkyl group, aralkyl group, and The aryl group may be substituted with an alkyl group, an alkoxy group, or a halogen atom. R_3 represents an alkyl group or aralkyl group that may have the same substituents as R_1 and R_2 above, or represents a naphthyl group or anthryl group, and the naphthyl group and anthryl group are an alkyl group, an alkoxy group, a halogen atom,
It may be substituted with a substituted amino group, cyano group or nitro group. Ar_1 represents an arylene group, and the arylene group is R_
1. May be substituted with the same alkyl group, aralkyl group, alkoxy group, halogen atom, or substituted amino group as in R_2. Ar_2 represents an aryl group or a heteroaromatic group, and the aryl group or heteroaromatic group is an alkyl group, an aralkyl group, a substituted amino group, a 5- to 6-membered cyclic amino group, an aryloxy group, an arylthio group, or a halogen atom. May be replaced.
JP60069091A 1985-04-03 1985-04-03 Electrophotographic sensitive body Pending JPS61228451A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP60069091A JPS61228451A (en) 1985-04-03 1985-04-03 Electrophotographic sensitive body

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP60069091A JPS61228451A (en) 1985-04-03 1985-04-03 Electrophotographic sensitive body

Publications (1)

Publication Number Publication Date
JPS61228451A true JPS61228451A (en) 1986-10-11

Family

ID=13392577

Family Applications (1)

Application Number Title Priority Date Filing Date
JP60069091A Pending JPS61228451A (en) 1985-04-03 1985-04-03 Electrophotographic sensitive body

Country Status (1)

Country Link
JP (1) JPS61228451A (en)

Cited By (66)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS63149652A (en) * 1986-12-15 1988-06-22 Konica Corp Photosensitive body
JPH0253065A (en) * 1988-08-17 1990-02-22 Konica Corp Photosensitive body
EP0616020A1 (en) 1989-03-20 1994-09-21 Idemitsu Kosan Company Limited Aromatic dimethylidyne compounds and process for preparation thereof
WO2000041443A1 (en) 1998-12-28 2000-07-13 Idemitsu Kosan Co., Ltd. Organic electroluminescence device
WO2007007553A1 (en) 2005-07-14 2007-01-18 Idemitsu Kosan Co., Ltd. Biphenyl derivatives, organic electroluminescent materials, and organic electroluminescent devices made by using the same
WO2007017995A1 (en) 2005-08-08 2007-02-15 Idemitsu Kosan Co., Ltd. Aromatic amine derivative and organic electroluminescence device making use of the same
WO2007029410A1 (en) 2005-09-08 2007-03-15 Idemitsu Kosan Co., Ltd. Organic electroluminescent element using polyarylamine
WO2007032162A1 (en) 2005-09-16 2007-03-22 Idemitsu Kosan Co., Ltd. Pyrene derivative and organic electroluminescence device making use of the same
WO2007032161A1 (en) 2005-09-15 2007-03-22 Idemitsu Kosan Co., Ltd. Asymmetric fluorene derivative and organic electroluminescent element containing the same
WO2007052759A1 (en) 2005-11-07 2007-05-10 Idemitsu Kosan Co., Ltd. Organic electroluminescent element
WO2007058044A1 (en) 2005-11-15 2007-05-24 Idemitsu Kosan Co., Ltd. Aromatic amine derivative and organic electroluminescent element employing the same
WO2007058172A1 (en) 2005-11-17 2007-05-24 Idemitsu Kosan Co., Ltd. Organic electroluminescent device
WO2007058127A1 (en) 2005-11-16 2007-05-24 Idemitsu Kosan Co., Ltd. Aromatic amine derivative and organic electroluminescent element using the same
WO2007060795A1 (en) 2005-11-28 2007-05-31 Idemitsu Kosan Co., Ltd. Amine compound and organic electroluminescent element employing the same
WO2007061063A1 (en) 2005-11-28 2007-05-31 Idemitsu Kosan Co., Ltd. Organic electroluminescent device
WO2007063993A1 (en) 2005-12-02 2007-06-07 Idemitsu Kosan Co., Ltd. Nitrogenous heterocyclic derivative and organic electroluminescence device making use of the same
WO2007077766A1 (en) 2005-12-27 2007-07-12 Idemitsu Kosan Co., Ltd. Material for organic electroluminescent device and organic electroluminescent device
WO2007097178A1 (en) 2006-02-23 2007-08-30 Idemitsu Kosan Co., Ltd. Material for organic electroluminescent device, method for producing same and organic electroluminescent device
WO2007100010A1 (en) 2006-02-28 2007-09-07 Idemitsu Kosan Co., Ltd. Organic electroluminescent device
WO2007099983A1 (en) 2006-02-28 2007-09-07 Idemitsu Kosan Co., Ltd. Organic electroluminescent device using fluoranthene derivative and indenoperylene derivative
WO2007102361A1 (en) 2006-03-07 2007-09-13 Idemitsu Kosan Co., Ltd. Aromatic amine derivative and organic electroluminescent device using same
WO2007105448A1 (en) 2006-02-28 2007-09-20 Idemitsu Kosan Co., Ltd. Naphthacene derivative and organic electroluminescent device using same
WO2007111263A1 (en) 2006-03-27 2007-10-04 Idemitsu Kosan Co., Ltd. Nitrogen-containing heterocyclic derivative and organic electroluminescent device using same
WO2007111262A1 (en) 2006-03-27 2007-10-04 Idemitsu Kosan Co., Ltd. Nitrogen-containing heterocyclic derivative and organic electroluminescent device using same
WO2007116750A1 (en) 2006-03-30 2007-10-18 Idemitsu Kosan Co., Ltd. Material for organic electroluminescent device and organic electroluminescent device using the same
WO2007125714A1 (en) 2006-04-26 2007-11-08 Idemitsu Kosan Co., Ltd. Aromatic amine derivative, and organic electroluminescence element using the same
WO2007132678A1 (en) 2006-05-11 2007-11-22 Idemitsu Kosan Co., Ltd. Organic electroluminescent device
WO2007132704A1 (en) 2006-05-11 2007-11-22 Idemitsu Kosan Co., Ltd. Organic electroluminescence element
WO2007138906A1 (en) 2006-05-25 2007-12-06 Idemitsu Kosan Co., Ltd. Organic electroluminescent device and full color light-emitting device
WO2007148660A1 (en) 2006-06-22 2007-12-27 Idemitsu Kosan Co., Ltd. Organic electroluminescent device employing heterocycle-containing arylamine derivative
WO2008001551A1 (en) 2006-06-27 2008-01-03 Idemitsu Kosan Co., Ltd. Aromatic amine derivative, and organic electroluminescence device using the same
WO2008015949A1 (en) 2006-08-04 2008-02-07 Idemitsu Kosan Co., Ltd. Organic electroluminescence device
WO2008023623A1 (en) 2006-08-22 2008-02-28 Idemitsu Kosan Co., Ltd. Organic electroluminescent device
WO2008023549A1 (en) 2006-08-23 2008-02-28 Idemitsu Kosan Co., Ltd. Aromatic amine derivatives and organic electroluminescent devices made by using the same
WO2008056722A1 (en) 2006-11-09 2008-05-15 Idemitsu Kosan Co., Ltd. Organic el material-containing solution, method for forming thin film of organic el material, thin film of organic el material, and organic el device
WO2008056652A1 (en) 2006-11-09 2008-05-15 Idemitsu Kosan Co., Ltd. Organic el material-containing solution, method for synthesizing organic el material, compound synthesized by the synthesizing method, method for forming thin film of organic el material, thin film of organic el material, and organic el device
WO2008056723A1 (en) 2006-11-09 2008-05-15 Idemitsu Kosan Co., Ltd. Organic el material-containing solution, method for forming thin film of organic el material, thin film of organic el material, and organic el device
WO2008059713A1 (en) 2006-11-15 2008-05-22 Idemitsu Kosan Co., Ltd. Fluoranthene compound, organic electroluminescent device using the fluoranthene compound, and organic electroluminescent material-containing solution
WO2008062636A1 (en) 2006-11-24 2008-05-29 Idemitsu Kosan Co., Ltd. Aromatic amine derivative and organic electroluminescent element using the same
WO2008081823A1 (en) 2006-12-29 2008-07-10 Idemitsu Kosan Co., Ltd. Solution containing organic el material, method for synthesis of organic el material, compound synthesized by the synthesis method, method for formation of thin film of organic el material, thin film of organic el material, organic el element
WO2008102740A1 (en) 2007-02-19 2008-08-28 Idemitsu Kosan Co., Ltd. Organic electroluminescent device
WO2008111554A1 (en) 2007-03-09 2008-09-18 Idemitsu Kosan Co., Ltd. Organic el device and display
WO2008123178A1 (en) 2007-03-23 2008-10-16 Idemitsu Kosan Co., Ltd. Organic el device
WO2008126802A1 (en) 2007-04-06 2008-10-23 Idemitsu Kosan Co., Ltd. Organic electroluminescent element
WO2009011327A1 (en) 2007-07-18 2009-01-22 Idemitsu Kosan Co., Ltd. Organic electroluminescent device material and organic electroluminescent device
WO2009020095A1 (en) 2007-08-06 2009-02-12 Idemitsu Kosan Co., Ltd. Aromatic amine derivative and organic electroluminescent device using the same
WO2009066778A1 (en) 2007-11-22 2009-05-28 Idemitsu Kosan Co., Ltd. Organic el element and solution containing organic el material
WO2009069717A1 (en) 2007-11-30 2009-06-04 Idemitsu Kosan Co., Ltd. Azaindenofluorenedione derivative, organic electroluminescent device material, and organic electroluminescent device
WO2009081857A1 (en) 2007-12-21 2009-07-02 Idemitsu Kosan Co., Ltd. Organic electroluminescent device
WO2009145016A1 (en) 2008-05-29 2009-12-03 出光興産株式会社 Aromatic amine derivative and organic electroluminescent device using the same
WO2010074181A1 (en) 2008-12-26 2010-07-01 出光興産株式会社 Organic electroluminescence element and compound
WO2010074087A1 (en) 2008-12-26 2010-07-01 出光興産株式会社 Material for organic electroluminescent element, and organic electroluminescent element
WO2010076878A1 (en) 2009-01-05 2010-07-08 出光興産株式会社 Organic electroluminescent element material and organic electroluminescent element comprising same
EP2229039A1 (en) 2003-07-02 2010-09-15 Idemitsu Kosan Co., Ltd. Organic electroluminescent device and display using same
WO2010116970A1 (en) 2009-04-06 2010-10-14 出光興産株式会社 Organic electroluminescent element and material for organic electroluminescent element
EP2262032A2 (en) 1999-04-05 2010-12-15 Idemitsu Kosan Co., Ltd. Organic electroluminescence device and its manufacturing method
WO2011046182A1 (en) 2009-10-16 2011-04-21 出光興産株式会社 Fluorene-containing aromatic compound, material for organic electroluminescent element, and organic electroluminescent element using same
EP2371810A1 (en) 2005-01-05 2011-10-05 Idemitsu Kosan Co., Ltd. Aromatic amine derivative and organic electroluminescent device using same
WO2012014841A1 (en) 2010-07-26 2012-02-02 出光興産株式会社 Organic electroluminescence element
EP2448374A2 (en) 2003-12-01 2012-05-02 Idemitsu Kosan Co., Ltd. Asymmetric monoanthracene derivative, material for organic electroluminescent device and organic electroluminescent device utilizing the same
US8268457B2 (en) 2006-06-05 2012-09-18 Idemitsu Kosan Co., Ltd. Organic electroluminescent device and material for organic electroluminescent device
WO2012157211A1 (en) 2011-05-13 2012-11-22 ソニー株式会社 Organic el multi-color light-emitting device
WO2013035275A1 (en) 2011-09-09 2013-03-14 出光興産株式会社 Nitrogen-containing heteroaromatic ring compound
WO2013046635A1 (en) 2011-09-28 2013-04-04 出光興産株式会社 Material for organic electroluminescent element, and organic electroluminescent element produced using same
WO2013069242A1 (en) 2011-11-07 2013-05-16 出光興産株式会社 Material for organic electroluminescent elements, and organic electroluminescent element using same
EP2910619A1 (en) 2003-12-19 2015-08-26 Idemitsu Kosan Co., Ltd Light-emitting material for organic electroluminescent device, organic electroluminescent device using same, and material for organic electroluminescent device

Cited By (71)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS63149652A (en) * 1986-12-15 1988-06-22 Konica Corp Photosensitive body
JPH0518424B2 (en) * 1986-12-15 1993-03-11 Konishiroku Photo Ind
JPH0253065A (en) * 1988-08-17 1990-02-22 Konica Corp Photosensitive body
EP0616020A1 (en) 1989-03-20 1994-09-21 Idemitsu Kosan Company Limited Aromatic dimethylidyne compounds and process for preparation thereof
WO2000041443A1 (en) 1998-12-28 2000-07-13 Idemitsu Kosan Co., Ltd. Organic electroluminescence device
EP2270117A2 (en) 1998-12-28 2011-01-05 Idemitsu Kosan Co., Ltd. Organic electroluminescence device
EP2262032A2 (en) 1999-04-05 2010-12-15 Idemitsu Kosan Co., Ltd. Organic electroluminescence device and its manufacturing method
EP2229039A1 (en) 2003-07-02 2010-09-15 Idemitsu Kosan Co., Ltd. Organic electroluminescent device and display using same
EP2448374A2 (en) 2003-12-01 2012-05-02 Idemitsu Kosan Co., Ltd. Asymmetric monoanthracene derivative, material for organic electroluminescent device and organic electroluminescent device utilizing the same
EP2910619A1 (en) 2003-12-19 2015-08-26 Idemitsu Kosan Co., Ltd Light-emitting material for organic electroluminescent device, organic electroluminescent device using same, and material for organic electroluminescent device
EP2371810A1 (en) 2005-01-05 2011-10-05 Idemitsu Kosan Co., Ltd. Aromatic amine derivative and organic electroluminescent device using same
WO2007007553A1 (en) 2005-07-14 2007-01-18 Idemitsu Kosan Co., Ltd. Biphenyl derivatives, organic electroluminescent materials, and organic electroluminescent devices made by using the same
WO2007017995A1 (en) 2005-08-08 2007-02-15 Idemitsu Kosan Co., Ltd. Aromatic amine derivative and organic electroluminescence device making use of the same
WO2007029410A1 (en) 2005-09-08 2007-03-15 Idemitsu Kosan Co., Ltd. Organic electroluminescent element using polyarylamine
WO2007032161A1 (en) 2005-09-15 2007-03-22 Idemitsu Kosan Co., Ltd. Asymmetric fluorene derivative and organic electroluminescent element containing the same
WO2007032162A1 (en) 2005-09-16 2007-03-22 Idemitsu Kosan Co., Ltd. Pyrene derivative and organic electroluminescence device making use of the same
WO2007052759A1 (en) 2005-11-07 2007-05-10 Idemitsu Kosan Co., Ltd. Organic electroluminescent element
WO2007058044A1 (en) 2005-11-15 2007-05-24 Idemitsu Kosan Co., Ltd. Aromatic amine derivative and organic electroluminescent element employing the same
WO2007058127A1 (en) 2005-11-16 2007-05-24 Idemitsu Kosan Co., Ltd. Aromatic amine derivative and organic electroluminescent element using the same
WO2007058172A1 (en) 2005-11-17 2007-05-24 Idemitsu Kosan Co., Ltd. Organic electroluminescent device
WO2007061063A1 (en) 2005-11-28 2007-05-31 Idemitsu Kosan Co., Ltd. Organic electroluminescent device
WO2007060795A1 (en) 2005-11-28 2007-05-31 Idemitsu Kosan Co., Ltd. Amine compound and organic electroluminescent element employing the same
WO2007063993A1 (en) 2005-12-02 2007-06-07 Idemitsu Kosan Co., Ltd. Nitrogenous heterocyclic derivative and organic electroluminescence device making use of the same
WO2007077766A1 (en) 2005-12-27 2007-07-12 Idemitsu Kosan Co., Ltd. Material for organic electroluminescent device and organic electroluminescent device
WO2007097178A1 (en) 2006-02-23 2007-08-30 Idemitsu Kosan Co., Ltd. Material for organic electroluminescent device, method for producing same and organic electroluminescent device
WO2007100010A1 (en) 2006-02-28 2007-09-07 Idemitsu Kosan Co., Ltd. Organic electroluminescent device
WO2007099983A1 (en) 2006-02-28 2007-09-07 Idemitsu Kosan Co., Ltd. Organic electroluminescent device using fluoranthene derivative and indenoperylene derivative
WO2007105448A1 (en) 2006-02-28 2007-09-20 Idemitsu Kosan Co., Ltd. Naphthacene derivative and organic electroluminescent device using same
WO2007102361A1 (en) 2006-03-07 2007-09-13 Idemitsu Kosan Co., Ltd. Aromatic amine derivative and organic electroluminescent device using same
WO2007111262A1 (en) 2006-03-27 2007-10-04 Idemitsu Kosan Co., Ltd. Nitrogen-containing heterocyclic derivative and organic electroluminescent device using same
WO2007111263A1 (en) 2006-03-27 2007-10-04 Idemitsu Kosan Co., Ltd. Nitrogen-containing heterocyclic derivative and organic electroluminescent device using same
WO2007116750A1 (en) 2006-03-30 2007-10-18 Idemitsu Kosan Co., Ltd. Material for organic electroluminescent device and organic electroluminescent device using the same
WO2007125714A1 (en) 2006-04-26 2007-11-08 Idemitsu Kosan Co., Ltd. Aromatic amine derivative, and organic electroluminescence element using the same
WO2007132704A1 (en) 2006-05-11 2007-11-22 Idemitsu Kosan Co., Ltd. Organic electroluminescence element
WO2007132678A1 (en) 2006-05-11 2007-11-22 Idemitsu Kosan Co., Ltd. Organic electroluminescent device
WO2007138906A1 (en) 2006-05-25 2007-12-06 Idemitsu Kosan Co., Ltd. Organic electroluminescent device and full color light-emitting device
US8268457B2 (en) 2006-06-05 2012-09-18 Idemitsu Kosan Co., Ltd. Organic electroluminescent device and material for organic electroluminescent device
WO2007148660A1 (en) 2006-06-22 2007-12-27 Idemitsu Kosan Co., Ltd. Organic electroluminescent device employing heterocycle-containing arylamine derivative
WO2008001551A1 (en) 2006-06-27 2008-01-03 Idemitsu Kosan Co., Ltd. Aromatic amine derivative, and organic electroluminescence device using the same
WO2008015949A1 (en) 2006-08-04 2008-02-07 Idemitsu Kosan Co., Ltd. Organic electroluminescence device
WO2008023623A1 (en) 2006-08-22 2008-02-28 Idemitsu Kosan Co., Ltd. Organic electroluminescent device
WO2008023759A1 (en) 2006-08-23 2008-02-28 Idemitsu Kosan Co., Ltd. Aromatic amine derivatives and organic electroluminescence devices using the same
WO2008023549A1 (en) 2006-08-23 2008-02-28 Idemitsu Kosan Co., Ltd. Aromatic amine derivatives and organic electroluminescent devices made by using the same
WO2008056723A1 (en) 2006-11-09 2008-05-15 Idemitsu Kosan Co., Ltd. Organic el material-containing solution, method for forming thin film of organic el material, thin film of organic el material, and organic el device
WO2008056652A1 (en) 2006-11-09 2008-05-15 Idemitsu Kosan Co., Ltd. Organic el material-containing solution, method for synthesizing organic el material, compound synthesized by the synthesizing method, method for forming thin film of organic el material, thin film of organic el material, and organic el device
WO2008056722A1 (en) 2006-11-09 2008-05-15 Idemitsu Kosan Co., Ltd. Organic el material-containing solution, method for forming thin film of organic el material, thin film of organic el material, and organic el device
WO2008059713A1 (en) 2006-11-15 2008-05-22 Idemitsu Kosan Co., Ltd. Fluoranthene compound, organic electroluminescent device using the fluoranthene compound, and organic electroluminescent material-containing solution
WO2008062636A1 (en) 2006-11-24 2008-05-29 Idemitsu Kosan Co., Ltd. Aromatic amine derivative and organic electroluminescent element using the same
EP2518045A1 (en) 2006-11-24 2012-10-31 Idemitsu Kosan Co., Ltd. Aromatic amine derivative and organic electroluminescent element using the same
WO2008081823A1 (en) 2006-12-29 2008-07-10 Idemitsu Kosan Co., Ltd. Solution containing organic el material, method for synthesis of organic el material, compound synthesized by the synthesis method, method for formation of thin film of organic el material, thin film of organic el material, organic el element
WO2008102740A1 (en) 2007-02-19 2008-08-28 Idemitsu Kosan Co., Ltd. Organic electroluminescent device
WO2008111554A1 (en) 2007-03-09 2008-09-18 Idemitsu Kosan Co., Ltd. Organic el device and display
WO2008123178A1 (en) 2007-03-23 2008-10-16 Idemitsu Kosan Co., Ltd. Organic el device
WO2008126802A1 (en) 2007-04-06 2008-10-23 Idemitsu Kosan Co., Ltd. Organic electroluminescent element
WO2009011327A1 (en) 2007-07-18 2009-01-22 Idemitsu Kosan Co., Ltd. Organic electroluminescent device material and organic electroluminescent device
WO2009020095A1 (en) 2007-08-06 2009-02-12 Idemitsu Kosan Co., Ltd. Aromatic amine derivative and organic electroluminescent device using the same
WO2009066778A1 (en) 2007-11-22 2009-05-28 Idemitsu Kosan Co., Ltd. Organic el element and solution containing organic el material
WO2009069717A1 (en) 2007-11-30 2009-06-04 Idemitsu Kosan Co., Ltd. Azaindenofluorenedione derivative, organic electroluminescent device material, and organic electroluminescent device
WO2009081857A1 (en) 2007-12-21 2009-07-02 Idemitsu Kosan Co., Ltd. Organic electroluminescent device
WO2009145016A1 (en) 2008-05-29 2009-12-03 出光興産株式会社 Aromatic amine derivative and organic electroluminescent device using the same
EP2713415A1 (en) 2008-12-26 2014-04-02 Idemitsu Kosan Co., Ltd Material for organic electroluminescent element, and organic electroluminescent element
WO2010074087A1 (en) 2008-12-26 2010-07-01 出光興産株式会社 Material for organic electroluminescent element, and organic electroluminescent element
WO2010074181A1 (en) 2008-12-26 2010-07-01 出光興産株式会社 Organic electroluminescence element and compound
WO2010076878A1 (en) 2009-01-05 2010-07-08 出光興産株式会社 Organic electroluminescent element material and organic electroluminescent element comprising same
WO2010116970A1 (en) 2009-04-06 2010-10-14 出光興産株式会社 Organic electroluminescent element and material for organic electroluminescent element
WO2011046182A1 (en) 2009-10-16 2011-04-21 出光興産株式会社 Fluorene-containing aromatic compound, material for organic electroluminescent element, and organic electroluminescent element using same
WO2012014841A1 (en) 2010-07-26 2012-02-02 出光興産株式会社 Organic electroluminescence element
WO2012157211A1 (en) 2011-05-13 2012-11-22 ソニー株式会社 Organic el multi-color light-emitting device
WO2013035275A1 (en) 2011-09-09 2013-03-14 出光興産株式会社 Nitrogen-containing heteroaromatic ring compound
WO2013046635A1 (en) 2011-09-28 2013-04-04 出光興産株式会社 Material for organic electroluminescent element, and organic electroluminescent element produced using same
WO2013069242A1 (en) 2011-11-07 2013-05-16 出光興産株式会社 Material for organic electroluminescent elements, and organic electroluminescent element using same

Similar Documents

Publication Publication Date Title
JPS61228451A (en) Electrophotographic sensitive body
JPS61210363A (en) Electrophotographic sensitive body
JPS62280850A (en) Electrophotographic sensitive body
JPH026048B2 (en)
JPS62208054A (en) Electrophotographic sensitive body
JPS62264055A (en) Electrophotographic sensitive body
JPS63163361A (en) Electrophotographic sensitive body
JPS6313047A (en) Electrophotographic sensitive body
JPS6327848A (en) Electrophotographic sensitive body
JPH01161245A (en) Electrophotographic sensitive body
JPS59168456A (en) Electrophotographic sensitive body
JPS62200359A (en) Electrophotographic sensitive body
JPS62283341A (en) Electrophotographic sensitive body
JPS6313048A (en) Electrophotographic sensitive body
JPH0513499B2 (en)
JPS63292141A (en) Electrophotographic sensitive body
JPS62200358A (en) Electrophotographic sensitive body
JPS62244058A (en) Electrophotographic sensitive body
JPH026049B2 (en)
JPH0244362A (en) Electrophotographic sensitive body
JPS63141067A (en) Electrophotographic sensitive body
JPS63292143A (en) Electrophotographic sensitive body
JPS63293550A (en) Electrophotographic sensitive body
JPS63244042A (en) Electrophotographic sensitive body
JPS59168452A (en) Electrophotographic sensitive body