JP2739375B2 - Electrophotographic photoreceptor, electrophotographic apparatus provided with the electrophotographic photoreceptor, and facsimile - Google Patents
Electrophotographic photoreceptor, electrophotographic apparatus provided with the electrophotographic photoreceptor, and facsimileInfo
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- JP2739375B2 JP2739375B2 JP2152873A JP15287390A JP2739375B2 JP 2739375 B2 JP2739375 B2 JP 2739375B2 JP 2152873 A JP2152873 A JP 2152873A JP 15287390 A JP15287390 A JP 15287390A JP 2739375 B2 JP2739375 B2 JP 2739375B2
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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、詳しくは特定の構造
を有するジスアゾ顔料を含有する感光層を有する電子写
真感光体、該電子写真感光体を備えた電子写真装置並び
にファクシミリに関する。Description: TECHNICAL FIELD The present invention relates to an electrophotographic photoreceptor, and more particularly, to an electrophotographic photoreceptor having a photosensitive layer containing a disazo pigment having a specific structure, and an electrophotographic photoreceptor. The present invention relates to an electrophotographic apparatus and a facsimile provided.
[従来の技術] 従来、電子写真感光体としては、セレン、硫化カドミ
ウム、酸化亜鉛などの無機光導電性物質が広く用いられ
ていた。[Prior Art] Conventionally, inorganic photoconductive materials such as selenium, cadmium sulfide, and zinc oxide have been widely used as electrophotographic photoreceptors.
一方、有機光導電性物質からなる電子写真感光体とし
てはポリ−N−ビニルカルバゾールに代表される光導電
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−オキサジアゾールのような低分子の有機
光導電性物質を用いたもの、さらにはこのような有機光
導電性物質と各種の染料や顔料を組み合わせたものなど
が知られている。On the other hand, as an electrophotographic photoreceptor made of an organic photoconductive substance, a photoconductive polymer represented by poly-N-vinylcarbazole or 2,5-bis (p-diethylaminophenyl) -1,3,4-oxadiene Known are those using a low-molecular organic photoconductive substance such as azole, and those combining such an organic photoconductive substance with various dyes and pigments.
有機光導電性物質を用いた電子写真感光体は成膜性が
よく、塗工によって生産できるため、極めて生産性が高
く安価な感光体を提供できる利点を有している。また、
使用する染料や顔料の選択により、感色性を自在にコン
トロールできるなどの利点を有し、これまで、幅広い検
討が成されてきた。特に最近では、有機光導電性染料や
顔料を含有した電荷発生層と前述の光導電性ポリマーや
低分子の有機光導電性物質を含有した電荷輸送層を積層
した機能分離型感光体の開発により、従来の有機電子写
真感光体の欠点とされていた感度や耐久性に著しい改善
が成されてきた。An electrophotographic photoreceptor using an organic photoconductive substance has a good film-forming property and can be produced by coating, and thus has an advantage that an inexpensive photoreceptor with extremely high productivity can be provided. Also,
It has the advantage that the color sensitivity can be freely controlled by selecting the dye or pigment to be used, and a wide range of studies have been made so far. Particularly recently, with the development of a function-separated type photoreceptor in which a charge generation layer containing an organic photoconductive dye or pigment and a charge transport layer containing the aforementioned photoconductive polymer or low molecular organic photoconductive substance are laminated. Significant improvements have been made in sensitivity and durability, which have been disadvantages of conventional organic electrophotographic photosensitive members.
アゾ顔料は優れた光導電性を示し、しかも、アミン成
分とカプラー成分の組み合わせ方で様々な特性を持った
化合物が用意に得られることから、これまでに数多くの
化合物が提案されており、例えば特開昭54−22834号公
報、特開昭56−116040号公報、特開昭58−70232号公
報、特開昭60−131539号公報、特開昭61−215556号公
報、特開昭61−241763号公報及び特開昭63−158561号公
報などですでに公知である。Azo pigments exhibit excellent photoconductivity, and since compounds having various properties can be easily obtained by combining an amine component and a coupler component, a large number of compounds have been proposed so far. JP-A-54-22834, JP-A-56-116040, JP-A-58-70232, JP-A-60-11539, JP-A-61-215556, and JP-A-61-215556 It is already known in, for example, JP-A-241763 and JP-A-63-158561.
しかしながら、従来のジスアゾ顔料を用いた電子写真
感光体は、感度や繰り返し使用時の電位安定性の面で必
ずしも十分なものとは言えず、実用化されているのは極
く僅かな材料のみである。However, conventional electrophotographic photoreceptors using disazo pigments are not necessarily sufficient in terms of sensitivity and potential stability when repeatedly used, and only a few materials have been put to practical use. is there.
[発明が解決しようとする課題] 本発明の目的は新規な光導電性材料を提供すること、
実用的な高感度特性と繰り返し使用における安定な電位
特性を有する電子写真感光体を提供すること、該電子写
真感光体を備えた電子写真装置並びにファクシミリを提
供することにある。[Problems to be Solved by the Invention] An object of the present invention is to provide a novel photoconductive material,
An object of the present invention is to provide an electrophotographic photosensitive member having practical high sensitivity characteristics and stable potential characteristics in repeated use, and to provide an electrophotographic apparatus and a facsimile provided with the electrophotographic photosensitive member.
[課題を解決する手段、作用] 本発明は導電性支持体上に下記一般式(1)で示すジ
スアゾ顔料を含有する感光層を有することを特徴とする
電子写真感光体から構成される。[Means for Solving the Problems and Action] The present invention comprises an electrophotographic photosensitive member having a photosensitive layer containing a disazo pigment represented by the following general formula (1) on a conductive support.
一般式 式中、Ar1およびAr2は同一または異なって置換基を有
してもよい炭素環式芳香族基または複素環式芳香族基を
表わし、R1およびR2は水素原子、アルキル基またはシア
ノ基を表わし、A1およびA2は同一または異なってフェノ
ール性水酸基を有するカプラー残基を表わす。General formula In the formula, Ar 1 and Ar 2 are the same or different, and each represents a carbocyclic aromatic group or a heterocyclic aromatic group which may have a substituent, and R 1 and R 2 represent a hydrogen atom, an alkyl group or a cyano aromatic group. A 1 and A 2 are the same or different and represent a coupler residue having a phenolic hydroxyl group.
Ar1およびAr2は具体的にはベンゼン、ナフタレン、ア
ントラセンなどの炭素環式芳香族環から水素原子2個を
除いた基またはフラン、ピロールカルボン酸、チオフェ
ン、ピリジン、ピラジンなどの複素環式芳香族環から水
素原子2個を除いた基が挙げられ、置換基としてはフッ
素、塩素、ヨウ素、臭素などのハロゲン原子、メチル、
エチル、プロピル、イソプロピル、ブチルなどのアルキ
ル基、メトキシ、エトキシ、プロポキシなどのアルコキ
シ基、フェノキシなどのアリールオキシ基、ニトロ基、
シアノ基、ジメチルアミノ、ジベンジルアミノ、ジフェ
ニルアミノ、モルホリノ、ピペリジノ、ピロリジノなど
の置換基を有してもよいアミノ基などが挙げられる。Ar 1 and Ar 2 are specifically a group obtained by removing two hydrogen atoms from a carbocyclic aromatic ring such as benzene, naphthalene, and anthracene; or a heterocyclic aromatic ring such as furan, pyrrolecarboxylic acid, thiophene, pyridine, and pyrazine. A group in which two hydrogen atoms have been removed from the aromatic ring; examples of the substituent include halogen atoms such as fluorine, chlorine, iodine and bromine, methyl,
Ethyl, propyl, isopropyl, alkyl groups such as butyl, methoxy, ethoxy, alkoxy groups such as propoxy, aryloxy groups such as phenoxy, nitro group,
Examples include an amino group which may have a substituent such as a cyano group, dimethylamino, dibenzylamino, diphenylamino, morpholino, piperidino, pyrrolidino and the like.
R1、R2においてアルキル基としてはメチル、エチル、
プロピルなどの基が挙げられる。R 1 , R 2 as an alkyl group as methyl, ethyl,
And groups such as propyl.
A1およびA2の表わすフェノール性水酸基を有するカプ
ラー残基としては、好ましい例としては、下記一般式
(2)〜(6)で示す残基が挙げられる。Preferable examples of the coupler residue having a phenolic hydroxyl group represented by A 1 and A 2 include residues represented by the following general formulas (2) to (6).
一般式(2)、(3)および(4)中のXはベンゼン
環と縮合して置換基を有してもよいナフタレン環、アン
トラセン環、カルバゾール環、ベンズカルバゾール環、
ジベンゾフラン環などの多環芳香環または複素環を形成
するのに必要な残基を表す。 X in the general formulas (2), (3) and (4) is a naphthalene ring, an anthracene ring, a carbazole ring, a benzocarbazole ring which may be substituted with a benzene ring,
It represents a residue necessary for forming a polycyclic aromatic ring such as a dibenzofuran ring or a heterocyclic ring.
一般式(6)中のYは置換基を有してもよい2価の芳
香族炭化水素基ないしは窒素原子を環内に含む2価の複
素環基を表し、具体的にはo−フェニレン、o−ナフチ
レン、ペリナフチレン、1,2−アンスリレン、3,4−ピラ
ゾールジイル、2,3−ピリジンジイル、4,5−ピリジンジ
イル、6,7−インダゾールジイル、6,7−キノリンジイル
などの2価の基が挙げられる。Y in the general formula (6) represents a divalent aromatic hydrocarbon group which may have a substituent or a divalent heterocyclic group containing a nitrogen atom in a ring, and specifically, o-phenylene, divalent such as o-naphthylene, perinaphthylene, 1,2-anthrylene, 3,4-pyrazoldiyl, 2,3-pyridinediyl, 4,5-pyridinediyl, 6,7-indazolediyl, 6,7-quinolindiyl Groups.
一般式(2)および(3)中のR3およびR4は水素原
子、置換基を有してもよいアルキル基、アリール基、ア
ラルキル基または複素環基を表し、また、R3、R4はとも
に窒素原子と結合して窒素原子を環内に含む環状アミノ
基を形成してもよい。R 3 and R 4 in the general formulas (2) and (3) represent a hydrogen atom, an alkyl group which may have a substituent, an aryl group, an aralkyl group or a heterocyclic group, and R 3 and R 4 And may be combined with a nitrogen atom to form a cyclic amino group containing a nitrogen atom in the ring.
一般式(4)中のR5は水素原子、置換基を有してもよ
いアルキル基、アリール基、アラルキル基または複素環
基を表わす。R 5 in the general formula (4) represents a hydrogen atom, an alkyl group which may have a substituent, an aryl group, an aralkyl group or a heterocyclic group.
一般式(5)中のR6は水素原子、置換基を有してもよ
いアルキル基、アリール基、アラルキル基または複素環
基を表わす。R 6 in the general formula (5) represents a hydrogen atom, an alkyl group which may have a substituent, an aryl group, an aralkyl group or a heterocyclic group.
上記表現のアルキル基としてはメチル、エチル、プロ
ピルなどの基、アリール基の具体例としてはフェニル、
ナフチル、アンスリルなどの基、アラルキル基としては
ベンジル、フェネチルなどの基、複素環基としてはピリ
ジル、チエニル、カルバゾリル、ベンゾイミダゾリル、
ベンゾチアゾリルなどの基、窒素原子を環内に含む環状
アミノ基としてはピロール、ピロリン、ピロリジン、ピ
ロリドン、インドール、インドリン、カルバゾール、イ
ミダゾール、ピラゾール、ピラゾリン、オキサジン、フ
ェノキサジンなどが挙げられる。Examples of the alkyl group in the above expression include groups such as methyl, ethyl and propyl, and specific examples of the aryl group include phenyl and
Groups such as naphthyl and anthryl, aralkyl groups such as benzyl and phenethyl, and heterocyclic groups such as pyridyl, thienyl, carbazolyl, benzimidazolyl,
Examples of groups such as benzothiazolyl and cyclic amino groups containing a nitrogen atom in the ring include pyrrole, pyrroline, pyrrolidine, pyrrolidone, indole, indoline, carbazole, imidazole, pyrazole, pyrazoline, oxazine, phenoxazine and the like.
また置換基としては、フッ素、塩素、ヨウ素、臭素な
どのハロゲン原子、メチル、エチル、プロピルなどのア
ルキル基、メトキシ、エトキシなどのアルコキシ基、ジ
メチルアミノ、ジエチルアミノなどのアルキルアミノ
基、フェニルカルバモイル基、ニトロ基、シアノ基、ト
リフルオロメチルなどのハロメチル基などが挙げられ
る。Further, as a substituent, fluorine, chlorine, iodine, halogen atoms such as bromine, methyl, ethyl, alkyl groups such as propyl, methoxy, alkoxy groups such as ethoxy, dimethylamino, alkylamino groups such as diethylamino, phenylcarbamoyl group, Examples include a nitro group, a cyano group, and a halomethyl group such as trifluoromethyl.
一般式(2)中のZは酸素原子または硫黄原子を表わ
し、nは0または1を表わす。Z in the general formula (2) represents an oxygen atom or a sulfur atom, and n represents 0 or 1.
なお、一般式(1)で示すジスアゾ顔料において式
中、A1、A2が一般式(2)、(3)または(4)であ
り、Xがベンゼン環と縮合してベンズカルバゾール環を
形成しているカプラーを用いた顔料は、その吸収域が近
赤外領域付近まで広がるため、半導体レーザー用の電荷
発生材料としても好適である。In the disazo pigment represented by the general formula (1), in the formula, A 1 and A 2 are each a general formula (2), (3) or (4), and X is condensed with a benzene ring to form a benzocarbazole ring. Pigments using the couplers described above are also suitable as charge generation materials for semiconductor lasers because their absorption range extends to near the infrared region.
以下に本発明の一般式(1)で示すジスアゾ顔料の代
表的な具体例を列挙するが、本発明において用いる上記
ジスアゾ顔料はこれらに限定されるものではない。Hereinafter, typical specific examples of the disazo pigment represented by the general formula (1) of the present invention are listed, but the disazo pigment used in the present invention is not limited thereto.
例示顔料は、基本型において、変化部分のみを記載す
ることで具体的構造を表わすこととする。In the basic pigment, the specific structure is represented by describing only the changed portion in the basic type.
基本型 例示顔料(1) R1、R2:水素原子 例示顔料(2) Ar1、Ar2:例示顔料(1)と同じ R1、R2:例示顔料(1)と同じ 例示顔料(3) R1、R2:−CN 例示顔料(4) Ar1、Ar2:例示顔料(1)と同じ R1、R2:例示顔料(1)と同じ 例示顔料(5) Ar1、Ar2:例示顔料(1)と同じ R1、R2:−CH3 例示顔料(6) Ar1、Ar2:例示顔料(1)と同じ R1、R2:例示顔料(5)と同じ 例示顔料(7) R1、R2:例示顔料(1)と同じ 例示顔料(8) R1、R2:例示顔料(1)と同じ 例示顔料(9) Ar1、Ar2:例示顔料(1)と同じ R1、R2:例示顔料(1)と同じ 例示顔料(10) R1、R2:例示顔料(1)と同じ 例示顔料(11) R1、R2:例示顔料(1)と同じ 例示顔料(12) R1、R2:−C2H5 例示顔料(13) Ar1、Ar2:例示顔料(1)と同じ R1、R2:例示顔料(1)と同じ 例示顔料(14) Ar1、Ar2:例示顔料(1)と同じ R1、R2:例示顔料(1)と同じ 例示顔料(15) Ar1、Ar2:例示顔料(1)と同じ R1、R2:例示顔料(1)と同じ 例示顔料(16) Ar1、Ar2: R1、R2:例示顔料(1)と同じ 例示顔料(17) Ar1、Ar2:例示顔料(1)と同じ R1、R2:例示顔料(1)と同じ 例示顔料(18) Ar1、Ar2:例示顔料(1)と同じ R1、R2:例示顔料(3)と同じ 例示顔料(19) R1、R2:例示顔料(1)と同じ 例示顔料(20) Ar1、Ar2:例示顔料(19)と同じ R1、R2:例示顔料(3)と同じ 例示顔料(21) R1、R2:例示顔料(1)と同じ 例示顔料(22) Ar1、Ar2:例示顔料(1)と同じ R1、R2:例示顔料(1)と同じ 例示顔料(23) Ar1、Ar2:例示顔料(1)と同じ R1、R2:例示顔料(3)と同じ 例示顔料(24) Ar1、Ar2:例示顔料(1)と同じ R1、R2:例示顔料(1)と同じ 例示顔料(25) Ar1、Ar2:例示顔料(1)と同じ R1、R2:例示顔料(1)と同じ 例示顔料(26) Ar1、Ar2:例示顔料(1)と同じ R1、R2:例示顔料(1)と同じ 例示顔料(27) Ar1、Ar2:例示顔料(1)と同じ R1、R2:例示顔料(1)と同じ 例示顔料(28) Ar1、Ar2:例示顔料(1)と同じ R1、R2:例示顔料(1)と同じ 例示顔料(29) Ar1、Ar2:例示顔料(1)と同じ R1、R2:例示顔料(3)と同じ 例示顔料(30) Ar1、Ar2:例示顔料(1)と同じ R1、R2:例示顔料(1)と同じ 例示顔料(31) Ar1、Ar2:例示顔料(1)と同じ R1、R2:例示顔料(1)と同じ 例示顔料(32) Ar1、Ar2:例示顔料(1)と同じ R1、R2:例示顔料(1)と同じ 例示顔料(33) Ar1、Ar2:例示顔料(1)と同じ R1、R2:例示顔料(1)と同じ 例示顔料(34) Ar1、Ar2:例示顔料(1)と同じ R1、R2:例示顔料(5)と同じ 例示顔料(35) Ar1、Ar2:例示顔料(1)と同じ R1、R2:例示顔料(5)と同じ 例示顔料(36) Ar1、Ar2:例示顔料(1)と同じ R1、R2:例示顔料(1)と同じ 例示顔料(37) Ar1、Ar2:例示顔料(1)と同じ R1、R2:例示顔料(1)と同じ 例示顔料(38) Ar1、Ar2:例示顔料(1)と同じ R1、R2:例示顔料(1)と同じ 例示顔料(39) R1、R2:例示顔料(3)と同じ 例示顔料(40) Ar1、Ar2:例示顔料(1)と同じ R1、R2:例示顔料(1)と同じ 一般式(1)で示すジスアゾ顔料は、相当するジアミ
ンを常法によりテトラゾ化し、アルカリの存在下カプラ
ーと水系でカンプリングするか、テトラゾニウム塩をホ
ウフッ化塩や塩化亜鉛複塩などに変換した後、N,N−ジ
メチルホルムアミド、ジメチルスルホキシドなどの有機
溶剤中で酢酸ソーダ、トリエチルアミン、N−メチルモ
ルホリンなどの塩基の存在下、カプラーとカップリング
することによって容易に合成できる。Basic type Illustrative pigment (1) R 1 , R 2 : hydrogen atom Exemplified pigment (2) Ar 1 , Ar 2 : same as exemplified pigment (1) R 1 , R 2 : same as exemplified pigment (1) exemplified pigment (3) R 1 , R 2 : —CN Exemplified pigment (4) Ar 1 , Ar 2 : same as exemplified pigment (1) R 1 , R 2 : same as exemplified pigment (1) exemplified pigment (5) Ar 1 , Ar 2 : the same as the exemplified pigment (1) R 1 , R 2 : —CH 3 exemplified pigment (6) Ar 1 , Ar 2 : same as example pigment (1) R 1 , R 2 : same as example pigment (5) example pigment (7) R 1 and R 2 : the same as the exemplary pigment (1), the exemplary pigment (8) R 1 , R 2 : same as the exemplary pigment (1), the exemplary pigment (9) Ar 1 , Ar 2 : same as the exemplary pigment (1) R 1 , R 2 : same as the exemplary pigment (1) exemplary pigment (10) R 1 , R 2 : same as the exemplary pigment (1), the exemplary pigment (11) R 1 , R 2 : same as the exemplary pigment (1), the exemplary pigment (12) R 1 , R 2 : —C 2 H 5 Exemplified pigment (13) Ar 1 , Ar 2 : same as example pigment (1) R 1 , R 2 : same as example pigment (1) example pigment (14) Ar 1 , Ar 2 : same as exemplified pigment (1) R 1 , R 2 : same as exemplified pigment (1) exemplified pigment (15) Ar 1 , Ar 2 : same as example pigment (1) R 1 , R 2 : same as example pigment (1) example pigment (16) Ar 1 , Ar 2 : R 1 , R 2 : Same as the exemplary pigment (1) Exemplary pigment (17) Ar 1 , Ar 2 : same as the exemplary pigment (1) R 1 , R 2 : same as the exemplary pigment (1) exemplary pigment (18) Ar 1 , Ar 2 : same as exemplified pigment (1) R 1 , R 2 : same as exemplified pigment (3) exemplified pigment (19) R 1 , R 2 : same as the exemplary pigment (1), the exemplary pigment (20) Ar 1 , Ar 2 : same as exemplified pigment (19) R 1 , R 2 : same as exemplified pigment (3) exemplified pigment (21) R 1 , R 2 : the same as the exemplified pigment (1), the exemplified pigment (22) Ar 1 , Ar 2 : same as exemplified pigment (1) R 1 , R 2 : same as exemplified pigment (1) exemplified pigment (23) Ar 1 , Ar 2 : same as exemplified pigment (1) R 1 , R 2 : same as exemplified pigment (3) exemplified pigment (24) Ar 1 , Ar 2 : same as example pigment (1) R 1 , R 2 : same as example pigment (1) example pigment (25) Ar 1 , Ar 2 : same as example pigment (1) R 1 , R 2 : same as example pigment (1) example pigment (26) Ar 1 , Ar 2 : same as exemplified pigment (1) R 1 , R 2 : same as exemplified pigment (1) exemplified pigment (27) Ar 1 , Ar 2 : same as exemplified pigment (1) R 1 , R 2 : same as exemplified pigment (1) exemplified pigment (28) Ar 1 , Ar 2 : same as exemplified pigment (1) R 1 , R 2 : same as exemplified pigment (1) exemplified pigment (29) Ar 1 , Ar 2 : same as exemplified pigment (1) R 1 , R 2 : same as exemplified pigment (3) exemplified pigment (30) Ar 1 , Ar 2 : same as example pigment (1) R 1 , R 2 : same as example pigment (1) example pigment (31) Ar 1 , Ar 2 : same as example pigment (1) R 1 , R 2 : same as example pigment (1) example pigment (32) Ar 1 , Ar 2 : same as exemplified pigment (1) R 1 , R 2 : same as exemplified pigment (1) exemplified pigment (33) Ar 1 , Ar 2 : same as exemplified pigment (1) R 1 , R 2 : same as exemplified pigment (1) exemplified pigment (34) Ar 1 , Ar 2 : same as exemplified pigment (1) R 1 , R 2 : same as exemplified pigment (5) exemplified pigment (35) Ar 1 , Ar 2 : same as exemplified pigment (1) R 1 , R 2 : same as exemplified pigment (5) exemplified pigment (36) Ar 1 , Ar 2 : same as exemplified pigment (1) R 1 , R 2 : same as exemplified pigment (1) exemplified pigment (37) Ar 1 , Ar 2 : same as exemplified pigment (1) R 1 , R 2 : same as exemplified pigment (1) exemplified pigment (38) Ar 1 , Ar 2 : same as exemplified pigment (1) R 1 , R 2 : same as exemplified pigment (1) exemplified pigment (39) R 1 , R 2 : same as the exemplary pigment (3), the exemplary pigment (40) Ar 1 , Ar 2 : the same as the exemplary pigment (1) R 1 , R 2 : the same as the exemplary pigment (1) The disazo pigment represented by the general formula (1) is obtained by subjecting the corresponding diamine to tetrazotization by a conventional method and the presence of an alkali. After coupling with a lower coupler and an aqueous system, or after converting a tetrazonium salt to a borofluoride salt or a zinc chloride double salt, sodium acetate, triethylamine, N-methyl in an organic solvent such as N, N-dimethylformamide, dimethyl sulfoxide. It can be easily synthesized by coupling with a coupler in the presence of a base such as morpholine.
一般式(1)中のA1、A2が相異なるカプラー殘基であ
るジスアゾ顔料を合成する場合は、前述のテトラゾニウ
ム塩1モルに対し初めに一方のカプラー1モルをカップ
リングさせ、次いでもう一方のカプラー1モルをカップ
リングさせて合成するか、あるいはジアミンの一方のア
ミノ基をアセチル基などで保護しておき、これをジアゾ
化し一方のカプラーをカップリングさせた後、保護基を
塩酸などで加水分解し、これを再びジアゾ化しもう一方
にカプラーをカップリングさせて合成することができ
る。When synthesizing a disazo pigment in which A 1 and A 2 in the general formula (1) are different coupler residual groups, one mole of one coupler is firstly coupled to 1 mol of the above-mentioned tetrazonium salt, and then the other. One mole of one coupler is coupled for synthesis, or one amino group of the diamine is protected with an acetyl group and the like is diazotized, and the other coupler is coupled. To diazotize it again and couple it with a coupler to synthesize it.
合成例(例示顔料(2)の合成) 300mlビーカーに水150ml、濃塩酸20ml(0.23モル)と 13.45g(0.032モル)を入れ0℃まで冷却し、亜硝酸ソ
ーダ4.6g(0.067モル)を水10mlに溶かした液を液温を
5℃以下に保ちながら10分間で液中へ滴下した。15分間
撹拌した後カーボン濾過し、この中へホウフッ化ソーダ
10.5g(0.096モル)を水90mlに溶かした液を撹拌下滴下
し、析出したホウフッ化塩を濾取し、冷水で洗浄した後
アセトニトリルで洗浄し、減圧乾燥した。Synthesis Example (Synthesis of Illustrative Pigment (2)) In a 300 ml beaker, add 150 ml of water and 20 ml of concentrated hydrochloric acid (0.23 mol) 13.45 g (0.032 mol) was added, the mixture was cooled to 0 ° C., and a solution prepared by dissolving 4.6 g (0.067 mol) of sodium nitrite in 10 ml of water was dropped into the liquid over 10 minutes while keeping the liquid temperature at 5 ° C. or lower. After stirring for 15 minutes, the mixture was filtered with carbon, and sodium borofluoride was poured into the mixture.
A solution obtained by dissolving 10.5 g (0.096 mol) in 90 ml of water was added dropwise with stirring, and the precipitated borofluoride was collected by filtration, washed with cold water, washed with acetonitrile, and dried under reduced pressure.
収量13.11g、収率66.3% 次に1ビーカーにN,N−ジメチルホルムアミド(DM
F)500mlを入れ、 11.06g(0.042モル)を溶解し液温を5℃に冷却した
後、先に得たホウフッ化塩12.36g(0.020モル)を溶解
し、次いでトリエチルアミン5.1g(0.050モル)を5分
間で滴下した。2時間撹拌した後析出した顔料を濾取
し、DMFで4回、水で3回洗浄した後凍結乾燥した。13.11 g, 66.3% yield N, N-dimethylformamide (DM
F) 500ml After dissolving 11.06 g (0.042 mol) and cooling the liquid temperature to 5 ° C., dissolve 12.36 g (0.020 mol) of the previously obtained borofluoride, and then drop 5.1 g (0.050 mol) of triethylamine in 5 minutes. . After stirring for 2 hours, the precipitated pigment was collected by filtration, washed four times with DMF and three times with water, and then freeze-dried.
収量16.47g、収率85.0% 元素分析 計算値(%) 実測値(%) C 74.37 74.40 H 3.74 3.80 N 8.67 8.64 本発明の電子写真感光体は、導電性支持体上に一般式
(1)で示すジスアゾ顔料を含有する感光層を有する。
感光層の形態は公知のいかなる形態を取っていてもかま
わないが、一般式(1)で示すジスアゾ顔料を含有する
感光層を電荷発生層とし、これに電荷輸送物質を含有す
る電荷輸送層を積層した機能分離型の感光層が特に好ま
しい。Yield: 16.47 g, 85.0% Yield Elemental analysis Calculated value (%) Actual value (%) C 74.37 74.40 H 3.74 3.80 N 8.67 8.64 The electrophotographic photoreceptor of the present invention is prepared by applying the general formula (1) on a conductive support. Having a photosensitive layer containing the disazo pigment shown.
The form of the photosensitive layer may be any known form, but the photosensitive layer containing the disazo pigment represented by the general formula (1) is used as a charge generation layer, and the charge generation layer containing a charge transport material is used as the charge generation layer. A laminated function-separated type photosensitive layer is particularly preferred.
電荷発生層は、前記のジスアゾ顔料を適当な溶剤中で
バインダー樹脂と共に分散した塗布液を、導電性支持体
上に公知の方法によって塗布することによって形成する
ことができ、その膜厚は例えば5μm以下、好ましくは
0.1〜1μmの薄膜層とすることが望ましい。The charge generation layer can be formed by applying a coating solution obtained by dispersing the above disazo pigment together with a binder resin in an appropriate solvent onto a conductive support by a known method, and having a thickness of, for example, 5 μm. Below, preferably
It is desirable to form a thin film layer having a thickness of 0.1 to 1 μm.
この際用いられるバインダー樹脂は、広範な絶縁性樹
脂あるいは有機光導電性ポリマーから選択されるが、ポ
リビニルブチラール、ポリビニルベンザール、ポリアリ
レート、ポリカーボネート、ポリエステル、フェノキシ
樹脂、セルロース系樹脂、アクリル樹脂、ポリウレタン
などが好ましく、その使用量は電荷発生層中の含有率で
80重量%以下、好ましくは40重量%以下である。The binder resin used at this time is selected from a wide range of insulating resins or organic photoconductive polymers. And the like, and the amount used is determined by the content in the charge generation layer.
It is at most 80% by weight, preferably at most 40% by weight.
また使用する溶剤は前記の樹脂を溶解し、後述の電荷
輸送層や下引層を溶解しないものから選択することが好
ましい。The solvent used is preferably selected from those which dissolve the resin and do not dissolve the charge transport layer and the undercoat layer described below.
具体的には、テトラヒドロフラン、1,4−ジオキサン
などのエーテル類、シクロヘキサノン、メチルエチルケ
トンなどのケトン類、N,N−ジメチルホルムアミドなど
のアミド類、酢酸メチル、酢酸エチルなどのエステル
類、トルエン、キシレン、クロロベンゼンなどの芳香族
類、メタノール、エタノール、2−プロパノールなどの
アルコール類、クロロホルム、塩化メチレン、ジクロル
エチレン、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など挙げられる。Specifically, tetrahydrofuran, ethers such as 1,4-dioxane, cyclohexanone, ketones such as methyl ethyl ketone, amides such as N, N-dimethylformamide, methyl acetate, esters such as ethyl acetate, toluene, xylene, Examples include aromatics such as chlorobenzene, alcohols such as methanol, ethanol, and 2-propanol; and aliphatic halogenated hydrocarbons such as chloroform, methylene chloride, dichloroethylene, carbon tetrachloride, and trichloroethylene.
電荷輸送層は電荷発生層の上または下に積層され、電
界の存在下電荷発生層から電荷キャリアを受取り、これ
を輸送する機能を有している。The charge transport layer is stacked on or below the charge generation layer, and has a function of receiving charge carriers from the charge generation layer in the presence of an electric field and transporting the carriers.
電荷輸送層は電荷輸送物質を必要に応じて適当なバイ
ンダー樹脂と共に溶剤中に溶解し塗布することによって
形成され、その膜厚は一般的には5〜40μmであるが15
〜30μmが好ましい。The charge transporting layer is formed by dissolving a charge transporting material in a solvent together with a suitable binder resin if necessary, and applying the solution. The thickness of the charge transporting layer is generally 5 to 40 μm.
-30 μm is preferred.
電荷輸送物質は電子輸送性物質と正孔輸送性物質があ
り、電子輸送性物質としては、例えば2,4,7−トリニト
ロフルオレノン、2,4,5,7−テトラニトロフルオレノ
ン、クロラニル、テトラシアノキノジメタンなどの電子
吸引性物質やこれら電子吸引性物質を高分子化したもの
などが挙げられる。The charge transporting substance includes an electron transporting substance and a hole transporting substance. Examples of the electron transporting substance include 2,4,7-trinitrofluorenone, 2,4,5,7-tetranitrofluorenone, chloranil, and tetralane. Examples thereof include electron-withdrawing substances such as cyanoquinodimethane, and those obtained by polymerizing these electron-withdrawing substances.
正孔輸送性物質としてはピレン、アントラセンなどの
多環芳香族化合物、カルバゾール系、インドール系、イ
ミダゾール系、オキサゾール系、チアゾール系、オキサ
ジアゾール系、ピラゾール系、ピラゾリン系、チアジア
ゾール系、トリアゾール系化合物などの複素環化合物、
p−ジエチルアミノベンズアルデヒド−N,N−ジフェニ
ルヒドラゾン、N,N−ジフェニルヒドラジノ−3−メチ
リデン−9−エチルカルバゾールなどのヒドラゾン系化
合物、α−フェニル−4′−N,N−ジフェニルアミノス
チルベン、5−(4−(ジ−p−トリルアミノ)ベンジ
リデン]−5H−ジベンゾ[a,d]シクロヘプテンなどの
スチリル系化合物、ベンジジン系化合物、トリアリール
メタン系化合物、トリフェニルアミンあるいは、これら
の化合物から成る基を主鎖または側鎖に有するポリマー
(例えばポリ−N−ビニルカルバゾール、ポリビニルア
ントラセンなど)が挙げられる。Examples of the hole transporting substance include polycyclic aromatic compounds such as pyrene and anthracene, carbazole-based, indole-based, imidazole-based, oxazole-based, thiazole-based, oxadiazole-based, pyrazole-based, pyrazoline-based, thiadiazole-based, and triazole-based compounds. Heterocyclic compounds such as
hydrazone compounds such as p-diethylaminobenzaldehyde-N, N-diphenylhydrazone, N, N-diphenylhydrazino-3-methylidene-9-ethylcarbazole, α-phenyl-4′-N, N-diphenylaminostilbene, 5 Styryl compounds such as-(4- (di-p-tolylamino) benzylidene] -5H-dibenzo [a, d] cycloheptene; benzidine compounds; triarylmethane compounds; triphenylamine; (E.g., poly-N-vinylcarbazole, polyvinylanthracene, etc.) having a polymer in the main chain or side chain.
これらの有機電荷輸送物質の他にセレン、セレン−テ
ルル、アモルファスシリコン、硫化カドミウムなどの無
機材料も用いることができる。In addition to these organic charge transport materials, inorganic materials such as selenium, selenium-tellurium, amorphous silicon, and cadmium sulfide can be used.
また、これらの電荷輸送物質は1種または2種以上組
合せて用いることができる。These charge transport materials can be used alone or in combination of two or more.
電荷輸送物質が成膜性を有していないときには適当な
バインダーを用いることができる。具体的には、アクリ
ル樹脂、ポリアリレート、ポリエステル、ポリカーボネ
ート、ポリスチレン、アクリロニトリル−スチレンコポ
リマー、ポリアクリルアミド、ポリアミド、塩素化ゴム
などの絶縁性樹脂あるいはポリ−N−ビニルカルバゾー
ル、ポリビニルアントラセンなどの有機光導電性ポリマ
ーなどが挙げられる。When the charge transport material does not have a film-forming property, an appropriate binder can be used. Specifically, insulating resins such as acrylic resin, polyarylate, polyester, polycarbonate, polystyrene, acrylonitrile-styrene copolymer, polyacrylamide, polyamide, and chlorinated rubber; or organic photoconductive materials such as poly-N-vinylcarbazole and polyvinylanthracene And the like.
感光層が形成される導電性支持体としては、例えばア
ルミニウム、アルミニウム合金、銅、導亜鉛、ステンレ
ス、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、金や白金などが用いられる。またこう
した金属あるいは合金を、真空蒸着法によって被膜形成
したプラスチック(例えばポリエチレン、ポリプロピレ
ン、ポリ塩化ビニル、ポリエチレンテレフタレート、ア
クリル樹脂など)や、導電性粒子(例えばカーボンブラ
ック、銀粒子など)を適当なバインダー樹脂と共にプラ
スチックまたは金属基板上に被覆した支持体あるいは導
電性粒子をプラスチックや紙に含浸した支持体などを用
いることができる。As the conductive support on which the photosensitive layer is formed, for example, aluminum, aluminum alloy, copper, zinc conductor, stainless steel, vanadium, molybdenum, chromium, titanium, nickel, indium, gold, platinum and the like are used. In addition, a plastic (eg, polyethylene, polypropylene, polyvinyl chloride, polyethylene terephthalate, acrylic resin, etc.) obtained by forming a film of such a metal or alloy by a vacuum evaporation method, or conductive particles (eg, carbon black, silver particles, etc.) with an appropriate binder A support coated on a plastic or metal substrate together with a resin, a support in which conductive particles are impregnated in plastic or paper, or the like can be used.
導電性支持体と感光層の中間にバリヤー機能と接着機
能をもつ下引き層を設けることもできる。An undercoat layer having a barrier function and an adhesive function may be provided between the conductive support and the photosensitive layer.
下引き層はカゼイン、ポリビニルアルコール、ニトロ
セルロース、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、酸化アルミニウムなどによ
って形成できる。The undercoat layer can be formed of casein, polyvinyl alcohol, nitrocellulose, polyamide (nylon 6, nylon 66, nylon 610, copolymer nylon, alkoxymethylated nylon, etc.), polyurethane, aluminum oxide, or the like.
下引き層の膜厚は5μm以下、好ましくは0.1〜3μ
mが適当である。The thickness of the undercoat layer is 5 μm or less, preferably 0.1 to 3 μm.
m is appropriate.
本発明の別の具体例として、前述のジスアゾ顔料と電
荷輸送物質を同一層に含有させた電子写真感光体を挙げ
ることができる。この際、電荷輸送物質としてポリ−N
−ビニルカルバゾールとトリニトロフルオレノンからな
る電荷移動錯体を用いることもできる。As another specific example of the present invention, an electrophotographic photosensitive member in which the above-mentioned disazo pigment and a charge transporting substance are contained in the same layer can be mentioned. At this time, poly-N is used as a charge transport material.
A charge transfer complex consisting of vinylcarbazole and trinitrofluorenone can also be used.
この例の電子写真感光体は、前述のジスアゾ顔料と電
荷移動錯体を適当な樹脂溶液中に分散させた液を塗布乾
燥して形成することができる。The electrophotographic photoreceptor of this example can be formed by applying and drying a liquid in which the above-mentioned disazo pigment and the charge transfer complex are dispersed in an appropriate resin solution.
いずれの電子写真感光体においても用いる顔料は一般
式(1)で示すジスアゾ顔料の結晶形は非晶質であって
も結晶質であってもよく、また必要に応じて一般式
(1)で示すジスアゾ顔料を2種類以上組み合せたり、
公知の電荷発生物質と組み合せて使用することも可能で
ある。The pigment used in any of the electrophotographic photoreceptors may be amorphous or crystalline in the form of the disazo pigment represented by the general formula (1). Combination of two or more disazo pigments shown
It is also possible to use in combination with a known charge generating substance.
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、レーザービームプリンター、CRTプリンタ
ー、LEDプリンター、液晶プリンター、レーザー製版、
ファクシミリなどの電子写真応用分野にも広く用いるこ
とができる。The electrophotographic photoreceptor of the present invention is used not only for electrophotographic copying machines, but also for laser beam printers, CRT printers, LED printers, liquid crystal printers, laser plate making,
It can be widely used in electrophotographic applications such as facsimile.
次に、本発明の電子写真感光体を備えた電子写真装置
並びにファクシミリについて説明する。Next, an electrophotographic apparatus and a facsimile provided with the electrophotographic photosensitive member of the present invention will be described.
第1図に本発明のドラム型感光体を用いた一般的な転
写式電子写真装置の概略構成を示した。FIG. 1 shows a schematic configuration of a general transfer type electrophotographic apparatus using the drum type photoreceptor of the present invention.
図において、1は像担持体としてのドラム型感光体で
あり軸1aを中心に矢印方向に所定の周速度で回転駆動さ
れる。該感光体1はその回転過程で帯電手段2によりそ
の周面に正または負の所定電位の均一帯電を受け、次い
で露光部3にて不図示の像露光手段により光像露光L
(スリット露光・レーザービーム走査露光など)を受け
る。In FIG. 1, reference numeral 1 denotes a drum-type photosensitive member as an image carrier, which is driven to rotate at a predetermined peripheral speed in the direction of an arrow around a shaft 1a. The photoreceptor 1 is uniformly charged at a predetermined positive or negative potential on its peripheral surface by a charging means 2 during the rotation process, and then exposed at a light exposure section 3 by an image exposure means (not shown) at an exposure section 3.
(Slit exposure, laser beam scanning exposure, etc.).
これにより感光体周面に露光像に対応した静電潜像が
順次形成されていく。As a result, an electrostatic latent image corresponding to the exposure image is sequentially formed on the peripheral surface of the photoconductor.
その静電潜像は、次いで現像手段4でトナー現像さ
れ、そのトナー現像像が転写手段5により不図示の給紙
部から感光体1と転写手段5との間に感光体1の回転と
同期取りされて給送された転写材Pの面に順次転写され
ていく。The electrostatic latent image is then developed with toner by a developing unit 4, and the developed toner image is transferred by a transfer unit 5 between a photosensitive unit 1 and a transfer unit 5 from a paper supply unit (not shown) in synchronization with the rotation of the photosensitive unit 1. It is sequentially transferred onto the surface of the transfer material P taken and fed.
像転写を受けた転写材Pは感光体面から分離されて像
定着手段8へ導入されて像定着を受けて複写物(コピ
ー)として機外へプリントアウトされる。The transfer material P having undergone the image transfer is separated from the photoreceptor surface, introduced into the image fixing means 8 and subjected to image fixing, and is printed out as a copy (copy) outside the machine.
像転写後の感光体1の表面はクリーニング手段6にて
転写残りトナーの除去を受けて清浄面化され、前露光手
段7により除電処理がされて繰り返して像形成に使用さ
れる。感光体1の均一帯電手段2としてはコロナ帯電装
置が一般に広く使用されている。また、転写装置5もコ
ロナ転写手段が一般に広く使用されている。The surface of the photoreceptor 1 after the image transfer is cleaned and cleaned by removing the untransferred toner by the cleaning unit 6, subjected to a charge removal process by the pre-exposure unit 7, and used repeatedly for image formation. As the uniform charging means 2 for the photoreceptor 1, a corona charging device is generally widely used. Also, the corona transfer means is generally widely used for the transfer device 5.
電子写真装置として、上述の感光体や現像手段、クリ
ーニング手段などの構成要素のうち、複数のものを装置
ユニットとして一体に結合して構成し、このユニットを
装置本体に対して着脱自在に構成しても良い。例えば、
感光体1とクリーニング手段6とを一体化してひとつの
装置ユニットとし、装置本体のレールなどの案内手段を
用いて着脱自在の構成にしても良い。このとき、上記の
装置ユニットのほうに帯電手段および/または現像手段
を伴って構成しても良い。As an electrophotographic apparatus, a plurality of components such as the above-described photoreceptor, developing means, and cleaning means are integrally connected as an apparatus unit, and this unit is configured to be detachable from the apparatus body. May be. For example,
The photoreceptor 1 and the cleaning means 6 may be integrated into one apparatus unit, and may be configured to be detachable using guide means such as rails of the apparatus body. At this time, the above-described device unit may be provided with a charging unit and / or a developing unit.
また、光像露光Lは、電子写真装置を複写機やプリン
ターとして使用する場合には、原稿からの反射光や透過
光、あるいは、原稿を読み取り信号化し、この信号によ
りレーザービームの走査、発光ダイオードアレイの駆
動、または液晶シャッターアレイの駆動などにより行わ
れる。In the case where the electrophotographic apparatus is used as a copier or a printer, the light image exposure L is performed by reflecting or transmitting light from the original, or by reading the original and converting it into a signal. This is performed by driving an array or driving a liquid crystal shutter array.
また、ファクシミリのプリンターとして使用する場合
には、光像露光Lは受信データをプリントするための露
光になる。When used as a facsimile printer, the light image exposure L is an exposure for printing received data.
第2図は、この場合の1例をブロック図で示したもの
である。FIG. 2 is a block diagram showing one example of this case.
コントローラ10は画像読取部9とプリンター18を制御
する。The controller 10 controls the image reading unit 9 and the printer 18.
コントローラ10の全体はCPU16により制御されてい
る。The whole of the controller 10 is controlled by the CPU 16.
画像読取部からの読取りデータは、送信回路12を通し
て相手局に送信される。相手局から受けたデータは受信
回路11を通してプリンター18に送られる。画像メモリに
は所定の画像データが記憶される。プリンタコントロー
ラ17はプリンター18を制御している。13は電話である。The read data from the image reading unit is transmitted to the partner station through the transmission circuit 12. Data received from the partner station is sent to the printer 18 through the receiving circuit 11. Predetermined image data is stored in the image memory. The printer controller 17 controls the printer 18. 13 is a telephone.
回線14から受信された画像(回線を介して接続された
リモート端末からの画像情報)は、受信回路11で復調さ
れた後、CPU16は画像情報の信号処理を行い順次画像メ
モリ15に格納される。そして、少なくとも1ページの画
像がメモリ15に格納されると、そのページの画像記憶を
行う。CPU16は、メモリ15より1ページの画像情報を読
み出しプリンタコントローラ17に信号かされた1ページ
の画像情報を送出する。An image received from the line 14 (image information from a remote terminal connected via the line) is demodulated by the receiving circuit 11, and then the CPU 16 performs signal processing of the image information and is sequentially stored in the image memory 15. . When the image of at least one page is stored in the memory 15, the image of the page is stored. The CPU 16 reads out one page of image information from the memory 15 and sends out one page of image information signaled to the printer controller 17.
プリンタコントローラ17は、CUP16からの1ページ画
像情報を受け取るとそのページの画像情報記録を行うべ
く、プリンタ18を制御する。Upon receiving one-page image information from the CUP 16, the printer controller 17 controls the printer 18 to record image information of the page.
なお、CPU16は、プリンタ18による記録中に、次のペ
ージの受信を行っている。Note that the CPU 16 is receiving the next page during recording by the printer 18.
以上のように、画像の受信と記録が行われる。 As described above, image reception and recording are performed.
[実施例] 実施例1〜15 アルミ基板上にメトキシメチル化ナイロン(重量平均
分子量10万)5gとアルコール可溶性共重合ナイロン(重
量平均分子量8万)10gをメタノール90gに溶解した液を
マイヤーバーで塗布し、乾燥後の膜厚が1μmの下引き
層を形成した。[Examples] Examples 1 to 15 A solution prepared by dissolving 5 g of methoxymethylated nylon (weight average molecular weight: 100,000) and 10 g of alcohol-soluble copolymerized nylon (weight average molecular weight: 80,000) in 90 g of methanol on an aluminum substrate using a Meyer bar. An undercoat layer having a thickness of 1 μm after coating and drying was formed.
次に例示顔料(2)を5gをシクロヘキサノン90gにブ
チラール樹脂(ブチラール化度70モル%)を2gを溶かし
た液に加え、サンドミルで24時間分散した。この分散液
を先に形成した下引き層の上に乾燥後の膜厚が0.15μm
となるようにマイヤーバーで塗布し、乾燥して電荷発生
層を形成した。Next, 5 g of Exemplified Pigment (2) was added to a solution of 2 g of butyral resin (degree of butyralization: 70 mol%) in 90 g of cyclohexanone, and dispersed in a sand mill for 24 hours. The thickness of the dispersion after drying is 0.15 μm on the undercoat layer formed earlier.
Was applied with a Meyer bar and dried to form a charge generation layer.
次に下記構造式で示すフルオレン化合物10g とビスフェノール型ポリカーボネート(重量平均分子量
5万)9gをクロロベンゼン70gに溶解し、これを電荷発
生層の上に乾燥後の膜厚が17μmとなるようにマイヤー
バーで塗布、乾燥して電荷輸送層を形成し、実施例1の
電子写真感光体を作成した。Next, 10 g of a fluorene compound represented by the following structural formula And 9 g of bisphenol-type polycarbonate (weight average molecular weight: 50,000) are dissolved in 70 g of chlorobenzene, and this is coated on a charge generation layer with a Meyer bar so that the film thickness after drying is 17 μm, and dried to form a charge transport layer. The electrophotographic photoreceptor of Example 1 was formed.
例示顔料(2)に代えて他の例示顔料を用い、実施例
2〜15に対応する電子写真感光体を全く同様にして作成
した。Electrophotographic photoreceptors corresponding to Examples 2 to 15 were prepared in exactly the same manner, using the other exemplary pigments instead of the exemplary pigment (2).
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Model SP−428を用いて−5KVのコロナ放電
で負に帯電し、暗所で1秒間保持した後、ハロゲンラン
プを用いて照度17ルックスで露光し、帯電特性を調べ
た。The prepared electrophotographic photosensitive member was negatively charged by a corona discharge of -5 KV using an electrostatic copying paper tester Model SP-428 manufactured by Kawaguchi Electric Co., Ltd., and held for 1 second in a dark place. It was exposed at an illuminance of 17 lux, and the charging characteristics were examined.
帯電特性としては、表面電位(VO)と暗所放置後の表
面電位が1/2に減衰するに必要な露光量(E1/2)を測定
した。結果を示す。As the charging characteristics, the surface potential (V O ) and the exposure amount (E1 / 2) required for the surface potential after being left in a dark place to attenuate to half were measured. The results are shown.
比較例1〜6 実施例1に用いたジスアゾ顔料を下記構造式で示す比
較顔料(A)〜(F)に代えた他は、実施例1と全く同
様にして電子写真感光体を作成し、同様に帯電特性を評
価した。結果を示す。 Comparative Examples 1 to 6 Except that the disazo pigment used in Example 1 was replaced with Comparative Pigments (A) to (F) represented by the following structural formulas, an electrophotographic photoreceptor was prepared in exactly the same manner as in Example 1. Similarly, the charging characteristics were evaluated. The results are shown.
この結果から、本発明の電子写真感光体は十分な帯電
能と優れた感度を有することが分かる。 From these results, it can be seen that the electrophotographic photoreceptor of the present invention has sufficient charging ability and excellent sensitivity.
実施例16〜30 実施例1で作成した電子写真感光体を−6.5KVのコロ
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ーを備えた電子写真複写機のシリ
ンダーに貼り付けた。Examples 16 to 30 The electrophotographic photosensitive member prepared in Example 1 was replaced with a cylinder of an electrophotographic copying machine equipped with a -6.5 KV corona charger, an exposure optical system, a developing device, a transfer charger, a charge-removing exposure optical system, and a cleaner. Pasted in.
初期の暗部電位VDと明部電位VLをそれぞれ−700V、20
0V付近に設定し、5千回繰り返し使用した際の暗部電位
の変動量(ΔVD)と明部電位の変動量(ΔVL)を測定し
た。Initial dark potential V D and the light portion potential V L respectively -700 V, 20
The voltage was set near 0 V, and the amount of change in the dark area potential (ΔV D ) and the amount of change in the light area potential (ΔV L ) were measured after repeated use of 5,000 times.
実施例2〜15で作成した電子写真感光体についても同
様に評価を行った。結果を示す。The electrophotographic photosensitive members prepared in Examples 2 to 15 were similarly evaluated. The results are shown.
なお、電位の変動量における負記号は電位の絶対値の
低下を表わし、正記号は電位の絶対値の増加を表わす。Note that a negative sign in the fluctuation amount of the potential indicates a decrease in the absolute value of the potential, and a positive sign indicates an increase in the absolute value of the potential.
比較例7〜12 比較例1〜6で作成した電子写真感光体を実施例16と
同じ方法で繰り返し使用時の電位変動量を測定した。結
果を示す。 Comparative Examples 7 to 12 The amount of potential change when the electrophotographic photosensitive members prepared in Comparative Examples 1 to 6 were repeatedly used in the same manner as in Example 16 was measured. The results are shown.
上記の結果から、本発明の電子写真感光体は繰り返し
使用時の電位変動が少ないことが分かる。 From the above results, it can be seen that the electrophotographic photoreceptor of the present invention has a small potential fluctuation upon repeated use.
実施例31 アルミ蒸着ポリエチレンテレフタレートフィルムのア
ルミ面上に膜厚0.5μmのポリビニルアルコールの下引
き層を形成した。この上に実施例4で用いたジスアゾ顔
料の分散液をマイヤーバーで塗布乾燥して、膜厚0.2μ
mの電荷発生層を形成した。Example 31 An undercoat layer of polyvinyl alcohol having a thickness of 0.5 μm was formed on an aluminum surface of an aluminum-deposited polyethylene terephthalate film. The dispersion liquid of the disazo pigment used in Example 4 was coated thereon with a Meyer bar and dried to form a film having a thickness of 0.2 μm.
m of the charge generation layer was formed.
次いで下記構造式のスチリル化合物10gと ポリカーボネート(重量平均分子量5万)9.5gをテトラ
ヒドロフラン80gに溶かした液を電荷発生層の上に塗布
乾燥して、膜厚16μmの電荷輸送層を形成した。Then with a styryl compound 10g of the following structural formula A solution prepared by dissolving 9.5 g of polycarbonate (weight average molecular weight: 50,000) in 80 g of tetrahydrofuran was applied on the charge generation layer and dried to form a charge transport layer having a thickness of 16 μm.
作成した電子写真感光体について帯電特性と耐久特性
を実施例1と実施例16と同じ方法によって測定した。結
果を示す。The charging characteristics and durability characteristics of the prepared electrophotographic photosensitive member were measured by the same methods as in Examples 1 and 16. The results are shown.
VO:−700V E1/2:0.90lux・sec ΔVD:+4V ΔVL:0V 実施例32 実施例23で作成した電子写真感光体の電荷発生層と電
荷輸送層を逆の順番で塗布した電子写真感光体を作成
し、実施例1と同じ方法で帯電特性を評価した。ただ
し、帯電は正帯電とした。V O : −700 V E1 / 2: 0.90 lux · sec ΔV D : +4 V ΔV L : 0 V Example 32 Electrons obtained by applying the charge generation layer and the charge transport layer of the electrophotographic photosensitive member prepared in Example 23 in reverse order. A photoreceptor was prepared, and the charging characteristics were evaluated in the same manner as in Example 1. However, the charging was positive.
VO:+695V E1/2:1.5lux・sec 実施例33 実施例15で作成した電荷発生層の上に3,5−ジメチル
−3′,5′−ジ−tert−ブチルジフェノキノン5gとポリ
カーボネート樹脂(重量平均分子量4万5千)5gをクロ
ロベンゼン(65重量部)−N,N−ジメチルホルムアミド
(35重量部)溶液40gに溶かした液をマイヤーバーで塗
布乾燥し、膜厚が15μmの電荷輸送層を形成した。V O : + 695V E1 / 2: 1.5lux · sec Example 33 5g of 3,5-dimethyl-3 ′, 5′-di-tert-butyldiphenoquinone and polycarbonate were placed on the charge generation layer prepared in Example 15. A solution prepared by dissolving 5 g of resin (weight average molecular weight: 45,000) in 40 g of a chlorobenzene (65 parts by weight) -N, N-dimethylformamide (35 parts by weight) solution is applied by a Meyer bar and dried, and a charge having a thickness of 15 μm is formed. A transport layer was formed.
作成した電子写真感光体について実施例1と同じ方法
で帯電特性を評価した。ただし、帯電は正帯電とした。The charging characteristics of the produced electrophotographic photosensitive member were evaluated in the same manner as in Example 1. However, the charging was positive.
VO:+694V E1/2:3.7lux・sec 実施例34 例示顔料(22)を0.5gをシクロヘキサノン9.5gと共に
ペイントシェイカーで5時間分散した。ここへ実施例1
で用いた電荷輸送材料5gとポリカーボネート樹脂5gをテ
トラヒドロフラン40gに溶かした液を加え、更に、1時
間振とうした。こうして調製した塗布液をアルミ基板上
にマイヤーバーで塗布乾燥して膜厚18μmの感光層を形
成した。V O : + 694V E1 / 2: 3.7lux · sec Example 34 0.5 g of Exemplified Pigment (22) was dispersed together with 9.5 g of cyclohexanone in a paint shaker for 5 hours. Example 1 here
A solution prepared by dissolving 5 g of the charge transporting material used in the above and 5 g of the polycarbonate resin in 40 g of tetrahydrofuran was added thereto, and further shaken for 1 hour. The coating solution thus prepared was applied to an aluminum substrate with a Meyer bar and dried to form a photosensitive layer having a thickness of 18 μm.
作成した電子写真感光体を実施例1と同じ方法で帯電
特性を評価した。帯電は正帯電とした。The charging characteristics of the produced electrophotographic photosensitive member were evaluated in the same manner as in Example 1. The charging was positive.
VO:+694V E1/2:4.9lux・sec [発明の効果] 本発明の電子写真感光体は、感光層に特定構造のジス
アゾ顔料を用いたことにより、感光層内部における電荷
キャリアの発生効率ないしは注入効率のいずれか一方あ
るいは双方が改善され、感度や繰り返し使用時の電位安
定性に優れた特性が得られるという顕著な効果を奏す
る。V O : + 694V E1 / 2: 4.9lux · sec [Effect of the Invention] The electrophotographic photoreceptor of the present invention uses a disazo pigment having a specific structure in the photosensitive layer, so that charge carrier generation efficiency or charge carrier generation in the photosensitive layer is achieved. Either one or both of the injection efficiencies are improved, and a remarkable effect is obtained that characteristics excellent in sensitivity and potential stability during repeated use are obtained.
また、上記電子写真感光体を電子写真装置並びにファ
クシミリにおいて用いた場合にも同様の効果を奏する。Similar effects can be obtained when the electrophotographic photosensitive member is used in an electrophotographic apparatus and a facsimile.
第1図は一般的な転写式電子写真装置の概略構成図であ
る。 符号1は電子写真感光体、2はコロナ帯電装置、3は露
光部、4は現像手段、5は転写手段、6はクリーニング
手段、7は前露光手段、8は像定着手段、Lは光像露
光、Pは像転写を受けた転写材である。 第2図は電子写真装置をプリンターとして使用したファ
クシミリのブロック図である。 符号9は画像読取部、10はコントローラー、11は受信回
路、12は送信回路、13は電話、14は回線、15は画像メモ
リ、16はCPU、17はプリンタコントローラ、18はプリン
ターである。FIG. 1 is a schematic configuration diagram of a general transfer type electrophotographic apparatus. Reference numeral 1 denotes an electrophotographic photosensitive member, 2 denotes a corona charging device, 3 denotes an exposure unit, 4 denotes a developing unit, 5 denotes a transfer unit, 6 denotes a cleaning unit, 7 denotes a pre-exposure unit, 8 denotes an image fixing unit, and L denotes an optical image. Exposure, P, is a transfer material that has undergone image transfer. FIG. 2 is a block diagram of a facsimile using the electrophotographic apparatus as a printer. Reference numeral 9 denotes an image reading unit, 10 denotes a controller, 11 denotes a receiving circuit, 12 denotes a transmitting circuit, 13 denotes a telephone, 14 denotes a line, 15 denotes an image memory, 16 denotes a CPU, 17 denotes a printer controller, and 18 denotes a printer.
Claims (4)
ジスアゾ顔料を含有する感光層を有することを特徴とす
る電子写真感光体。 一般式 式中、Ar1およびAr2は同一または異なって置換基を有し
てもよい炭素環式芳香族基または複素環式芳香族基を表
わし、R1およびR2は水素原子、アルキル基またはシアノ
基を表わし、A1およびA2は同一または異なってフェノー
ル性水酸基を有するカプラー残基を表わす。1. An electrophotographic photoreceptor comprising a photosensitive layer containing a disazo pigment represented by the following general formula (1) on a conductive support. General formula In the formula, Ar 1 and Ar 2 are the same or different, and each represents a carbocyclic aromatic group or a heterocyclic aromatic group which may have a substituent, and R 1 and R 2 represent a hydrogen atom, an alkyl group or a cyano aromatic group. A 1 and A 2 are the same or different and represent a coupler residue having a phenolic hydroxyl group.
を含有する電荷発生層と電荷輸送層の少なくとも二層か
らなる請求項1記載の電子写真感光体。2. The electrophotographic photosensitive member according to claim 1, wherein the photosensitive layer comprises at least two layers of a charge generation layer containing a disazo pigment represented by the general formula (1) and a charge transport layer.
子写真装置。3. An electrophotographic apparatus comprising the electrophotographic photosensitive member according to claim 1.
子写真装置およびリモート端末からの画像情報を受信す
る受信手段を有することを特徴とするファクシミリ。4. A facsimile comprising: an electrophotographic apparatus provided with the electrophotographic photosensitive member according to claim 1; and a receiving means for receiving image information from a remote terminal.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2152873A JP2739375B2 (en) | 1990-06-13 | 1990-06-13 | Electrophotographic photoreceptor, electrophotographic apparatus provided with the electrophotographic photoreceptor, and facsimile |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2152873A JP2739375B2 (en) | 1990-06-13 | 1990-06-13 | Electrophotographic photoreceptor, electrophotographic apparatus provided with the electrophotographic photoreceptor, and facsimile |
Publications (2)
Publication Number | Publication Date |
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JPH0445450A JPH0445450A (en) | 1992-02-14 |
JP2739375B2 true JP2739375B2 (en) | 1998-04-15 |
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