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JPS5843460A - Electrophotographic receptor - Google Patents

Electrophotographic receptor

Info

Publication number
JPS5843460A
JPS5843460A JP56141774A JP14177481A JPS5843460A JP S5843460 A JPS5843460 A JP S5843460A JP 56141774 A JP56141774 A JP 56141774A JP 14177481 A JP14177481 A JP 14177481A JP S5843460 A JPS5843460 A JP S5843460A
Authority
JP
Japan
Prior art keywords
water
dye
layer
generating layer
charge generating
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.)
Granted
Application number
JP56141774A
Other languages
Japanese (ja)
Other versions
JPS645701B2 (en
Inventor
Fumio Kawamura
史生 河村
Masafumi Kamiyama
上山 雅文
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.)
Tomoegawa Co Ltd
Original Assignee
Tomoegawa Paper Co Ltd
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 Tomoegawa Paper Co Ltd filed Critical Tomoegawa Paper Co Ltd
Priority to JP56141774A priority Critical patent/JPS5843460A/en
Publication of JPS5843460A publication Critical patent/JPS5843460A/en
Publication of JPS645701B2 publication Critical patent/JPS645701B2/ja
Granted 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
    • G03G5/0664Dyes
    • G03G5/0666Dyes containing a methine or polymethine group
    • G03G5/0668Dyes containing a methine or polymethine group containing only one methine or polymethine group
    • G03G5/067Dyes containing a methine or polymethine group containing only one methine or polymethine group containing hetero rings
    • 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
    • G03G5/0609Acyclic or carbocyclic compounds containing oxygen
    • G03G5/0611Squaric acid

Landscapes

  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Photoreceptors In Electrophotography (AREA)

Abstract

PURPOSE:To obtain an easily manufacturable photoreceptor having good both polarity-chargeability and high sensitivity, by adding a squalenic acid methine dye dispersed into a water-soluble polymer to a charge generating layer in a function separation type electrophotographic receptor consisting of a charge generating layer and a charge transfer layer. CONSTITUTION:A squalenic acid dye has a general formula shown in which Z is a hetero ring containing N; X, X1, X2 are each an aromatic ring contg. N or O, optionally substd. by N(C2H5)2, OH, alkyl, or the like. A soln. of this dye dissolved in a water-insoluble solvent is dispersed into an aq. soln. of a water- soluble polymer such as casein, gelatin, or water-soluble polyvinyl butyral, and coated on a conductive substrate to form a charge generating layer after drying. A charge transfer layer contg. a charge transfer agent such as pyrazoline derivatives is formed on the charge generating layer, thus permitting a photoreceptor capable of being charged to both polarities and forming a high-quality image to be obtained.

Description

【発明の詳細な説明】 好な帯電能と光感度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 The present invention relates to an electrophotographic photoreceptor having good charging ability and photosensitivity.

従来、電子写真感光体に用いられる感光層には、セレン
、硫化カドミウム、酸化亜鉛等の無機系の光導電性物質
が広く用いられている。近年、ポリビニルカルバゾール
等の有機系の光導電性物質が盛んに研究されており、そ
のいくつかは実用化されている。この有機系の感光体は
無機系の感光体に比べて多くの優れた性質を有しており
、電子写真技術分野において広い応用 ゛技術を提供す
るものである。さらに有機系感光体では、いわゆる機能
分離型感光体への応用が盛んに行なわれている。この機
能分離型感光体黒3 においては、複写機に要求される条件である高信頼性、
省メインテナンス、機能の拡大多様化、高品質画像、操
作の容易性、無公害性、等に有利な条件を有していると
思われる。その為、ここ10年前後各方面においてこの
有機感光体の開発にかなりの努力が払われているのが現
状である。本発明者も、この有機物質を用いる感光体の
開発を進めていたところ、同一の帯電層で、正、負イス
れのコロナチャージにおいても、十分な帯電能と光感度
を有する感光体を得るに至った。しかも、その製作法は
極めて容易で従来技術で可能であり、何らの特殊な技術
を要しないものである。
Conventionally, inorganic photoconductive substances such as selenium, cadmium sulfide, and zinc oxide have been widely used in photosensitive layers used in electrophotographic photoreceptors. In recent years, organic photoconductive substances such as polyvinylcarbazole have been actively researched, and some of them have been put into practical use. This organic photoreceptor has many superior properties than inorganic photoreceptors, and provides a wide range of applications in the field of electrophotography. Furthermore, organic photoreceptors are being actively applied to so-called functionally separated photoreceptors. This function-separated photoconductor black 3 has the high reliability and
It seems to have advantageous conditions such as low maintenance, expansion and diversification of functions, high quality images, ease of operation, and non-pollution. Therefore, the current situation is that considerable efforts have been made in various fields in the past ten years or so to develop this organic photoreceptor. The present inventor was also progressing with the development of a photoreceptor using this organic material, and obtained a photoreceptor with sufficient charging ability and photosensitivity even in positive and negative corona charging with the same charging layer. reached. Furthermore, the manufacturing method is extremely easy and can be done using conventional technology, and does not require any special technology.

すなわち本発明は、晃の照射により光キャリアを発生し
うる化合物として、スクアリン酸メチン染料を用い、こ
の染料を水に可溶な高分子中に分散させた層を有:♀る
電子写真感光体に関するものである。
That is, the present invention uses methine squarate dye as a compound capable of generating photocarriers when irradiated with light, and provides an electrophotographic photoreceptor having a layer in which this dye is dispersed in a water-soluble polymer. It is related to.

本発明に用いるスクアリン酸メチン染料としては次の一
般式 〔式中、2としてはNを含む複素環、XXX11X2と
してはNおよび/又はOを含む、あるいは官能基により
置換された芳香族系の環より選択される〕で表わされる
化合物である。詳細には米国特許第361720号や同
第312170タタ号、等に開示されているものである
。これらの染料と、水溶性高分子との比は重量でカル勺
The methine squarate dye used in the present invention has the following general formula [where 2 is a heterocyclic ring containing N, and XXX11X2 is an aromatic ring containing N and/or O or substituted with a functional group. selected from ]. The details are disclosed in US Pat. No. 361,720, Tata No. 312,170, and the like. The ratio of these dyes to water-soluble polymers varies by weight.

の範囲で使用可能である。It can be used within the range of

この染料の溶媒としては有機第1アミンが使□ユ能アあ
る:)。1水にユ溶7高分侵、□は、・s4 通常の水溶性:゛高分子例えば、カゼイン、ゼラチb:
′、゛ ン、水溶性i″″″′1す、ビニルブチラール、ポリビ
ニルアルコール、等が使用可能である。この水溶性高分
子とスクアリン酸メチン染料とからなる層扁j を電荷発生層とする機能分離型感光体に応用する場合の
電荷輸送層としては、従来知られている化合物がほとん
ど使用できる。例えばポリビニルカルバゾール、高分子
中に溶解したピラゾリン誘導体などが挙げられる。
Organic primary amines can be used as solvents for this dye. 1 Soluble in water 7 Highly invasive, □ is, ・s4 Normal water solubility: ゛Polymer e.g. casein, gelatin B:
Water-soluble polymers such as vinyl butyral, polyvinyl alcohol, etc. can be used. A layer consisting of this water-soluble polymer and methine squarate dye is used as a charge generation layer. When applied to a functionally separated photoreceptor, most conventionally known compounds can be used as the charge transport layer. Examples include polyvinylcarbazole, pyrazoline derivatives dissolved in polymers, and the like.

以下実施例にて本発明を具体的に説明する。The present invention will be specifically explained below with reference to Examples.

実施例/’− 構造式(+)で示されるスクアリン酸メチン染料109
を1lO9のn−ブチルアミンに溶解せしめる。
Example/'- Methine squarate dye 109 represented by the structural formula (+)
is dissolved in 11O9 of n-butylamine.

構造式(+) この溶液をアンモニア水/fを加えた60℃の水100
ccに/lltのカゼインを溶解させた溶液に加える。
Structural formula (+) Add this solution to 60°C water 100% with ammonia water/f
Add cc/llt of casein to the solution.

得られた溶液にN、N−ジメチルアセトアミド30tを
加え、カッタープレー6 ドを持つ攪拌機により、カッグーブレードを/ 0.0
0 Or、pom、で回転させ2θ分間混合、分散する
。得られた溶液をアルミニウムを貼り合せたポリエチレ
ンテレフタレートフィルムのアルニウム側に厚さ2〜5
μmになるように塗布する。これを70℃の雰囲気下で
2時間乾燥し、得られた層を第一層とする。この第一層
の上に、構造式(1N)で示されるピラゾリン誘導体と
ポリカーボネート(帝人社製パンライトlx、zt)と
をそれぞれiotを1009の/、/−ジクロル工タ/
に溶解せしめた溶液を乾燥後10μmの厚さになるよう
に塗布して、第二層目を形成する。
30 t of N,N-dimethylacetamide was added to the obtained solution, and a stirrer with a cutter blade of 6/0.0
Mix and disperse for 2θ minutes by rotating at 0 Or, pom. The obtained solution was applied to the aluminum side of a polyethylene terephthalate film laminated with aluminum to a thickness of 2 to 5 mm.
Apply to a thickness of μm. This was dried in an atmosphere at 70° C. for 2 hours, and the obtained layer was used as the first layer. On this first layer, a pyrazoline derivative represented by the structural formula (1N) and a polycarbonate (Panlite LX, ZT manufactured by Teijin) were respectively added with an iot of 1009/, /-dichloromethane/
A second layer is formed by applying a solution prepared by dissolving the liquid to a thickness of 10 μm after drying.

構造式([) スクアリン酸メチン染料として構造式面で示/I67 される化合物を使用する以外は実施例/と同様である。Structural formula([) Structural formula shown as methine squarate dye/I67 The procedure is the same as in Example 1, except that the compound described above is used.

構造式(Ill) 実施例3 スクアリン酸メチン染料として構造式(財)で示される
化合物を使用する以外は実施例/と同様である。
Structural Formula (Ill) Example 3 The same as Example 3 except that a compound represented by the structural formula (Ill) was used as the methine squarate dye.

〇 ・′□:1[) 構造式■ 実施例弘 実施例1において、カゼイン水溶液のかわり71開昭5
8−4346(1(3) [/Qwt−fiのポリビニルブチラール樹脂(積木化
学社製エスレツクWJθ/)水溶液100tとする以外
は同様である。
〇・′□:1[) Structural formula ■ Example Hiroshi In Example 1, 71 Kaisho 5 was used instead of the casein aqueous solution.
8-4346 (1(3)

実施例j 実施例1において、カゼイノ水溶液のかわりにzOwt
−1のポリビニルアルコール(日本合成社NH−/ I
 )水溶液とする以外は同様である。
Example j In Example 1, zOwt instead of caseino aqueous solution
-1 polyvinyl alcohol (Nippon Gosei NH-/I
) The procedure is the same except that it is made into an aqueous solution.

比較例1 実施例1におけるスクアリン酸メチン染料のn−ブチル
アミン溶液のかわりに、ε型銅フタロシアニ/(東洋イ
ンキ製造社製Lionol BlueER)10fをN
、N−ジメデルアセトアミド≠02に混合した溶液を使
用する以外は実施例/と同様である。
Comparative Example 1 Instead of the n-butylamine solution of methine squarate dye in Example 1, ε-type copper phthalocyanine/(Lionol BlueER manufactured by Toyo Ink Manufacturing Co., Ltd.) 10f was used.
, N-dimederacetamide≠02 except that a mixed solution was used.

比較例2 実施例1におけるカゼイン水溶液のかわりに1、・、、
) 1すt′−5ネー1−脂(量大社製’75′f)Lr/
22k)10tを2Ofのへ/−ジクロルエタンに溶解
した溶液を使用する以外は同様であ扁り る。
Comparative Example 2 Instead of the casein aqueous solution in Example 1, 1...
) 1st'-5ne 1-fat (Yotaisha '75'f) Lr/
22k) The procedure is similar, except that a solution of 10t in 20/-dichloroethane is used.

以上の実施例及び比較例によし得られた感光体の特性を
川口電機製SP −4(21で測定した値を表−7に示
す。表中のV、はそれぞれ正、負、4KVのコロナ放電
をほどこした直後の表面電位〔V〕、E) Fij L
xの白色光を照射し、電位が半分となるまでの露光量〔
1uX−8eC〕  を示す。
The properties of the photoreceptors obtained in the above Examples and Comparative Examples were measured using Kawaguchi Electric SP-4 (21) and the values are shown in Table 7. In the table, V represents positive, negative, and 4KV corona, respectively. Surface potential [V] immediately after discharging, E) Fij L
Exposure amount until the potential is halved when irradiated with white light of x [
1uX-8eC].

、瓢10 本発明の応用例としては、同一の層において正、負いず
れの極性で帯電させても十分満足できる感光体特性を有
するので、例えば特開昭j3−/174t737号に示
されているような2色コピーを得る複写システム用の感
光体、又はネガ、ポジいずれの原稿からでも容易にポジ
画像の得られる複写システム、静電印刷用マスター、カ
ラーコピー用感光体等が考えられる。
, Gourd 10 As an application example of the present invention, the photoreceptor has sufficiently satisfactory characteristics even when charged with either positive or negative polarity in the same layer, so for example, it is shown in JP-A No. 174-737. A photoconductor for a copying system that can produce two-color copies, a copying system that can easily produce a positive image from either a negative or positive original, a master for electrostatic printing, a photoconductor for color copying, etc. can be considered.

しかし、この感光体の応用例はこれらに限られるもので
はなく、正、負いずれの極性の帯電でも良好な感光体特
性を有する感光体を容易に得る技術はほとんど知られて
いないので、その応用例は未知の分野であるといえる。
However, the applications of this photoreceptor are not limited to these, and there are few known techniques for easily obtaining a photoreceptor that has good photoreceptor characteristics even when charged with either positive or negative polarity. Examples can be said to be an unknown field.

今後広い応用分野が期待される有効な技術を提供するも
のである。
This provides an effective technology that is expected to find wide application in the future.

特許出願人 株式会社巴川製紙所patent applicant Tomoekawa Paper Mill Co., Ltd.

Claims (1)

【特許請求の範囲】 (1)  光の照射により光キャリアを発生しうる化合
物として、スクアリン酸メチン染料を用い、この染享士
を水に可溶な高分子中に分散させた層を有することを特
徴とする電子写真感光体。 (2)  上記染料の分散時に用いる溶媒中に水を含む
ことを特徴とする特許請求の範囲第1項記載の電子写真
感光体。 (3)  上記染料を溶解しうる溶媒に溶解した後、水
に可溶な高分子中に分散せしめることを特徴とする特許
請求の範囲第1項記載の電子写真感光体。 +41 1記の染料を溶解しうる溶媒が水に不溶である
ことを特徴とする特許請求の範囲第1項記載の電子写真
感光体。 屋2 (5)  上記の染料を含む層を電荷発生層とし、その
上または下に電荷輸送能をもつ層を形成したことを特徴
とする機能分離型の特許請求の範囲第1項記載の電子写
真感光体。
[Scope of Claims] (1) A methine squarate dye is used as a compound capable of generating photocarriers upon irradiation with light, and a layer is provided in which this dye is dispersed in a water-soluble polymer. An electrophotographic photoreceptor featuring: (2) The electrophotographic photoreceptor according to claim 1, wherein the solvent used for dispersing the dye contains water. (3) The electrophotographic photoreceptor according to claim 1, wherein the dye is dissolved in a solvent and then dispersed in a water-soluble polymer. +41 The electrophotographic photoreceptor according to claim 1, wherein the solvent capable of dissolving the dye described in item 1 is insoluble in water. (5) A function-separated type electronic device according to claim 1, characterized in that the layer containing the above dye is used as a charge generation layer, and a layer having a charge transporting ability is formed above or below the layer. Photographic photoreceptor.
JP56141774A 1981-09-10 1981-09-10 Electrophotographic receptor Granted JPS5843460A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP56141774A JPS5843460A (en) 1981-09-10 1981-09-10 Electrophotographic receptor

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP56141774A JPS5843460A (en) 1981-09-10 1981-09-10 Electrophotographic receptor

Publications (2)

Publication Number Publication Date
JPS5843460A true JPS5843460A (en) 1983-03-14
JPS645701B2 JPS645701B2 (en) 1989-01-31

Family

ID=15299860

Family Applications (1)

Application Number Title Priority Date Filing Date
JP56141774A Granted JPS5843460A (en) 1981-09-10 1981-09-10 Electrophotographic receptor

Country Status (1)

Country Link
JP (1) JPS5843460A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6041045A (en) * 1983-04-28 1985-03-04 リコ− システムズ インコ−ポレ−テツド Photosensitive body containing squalene acid methine dye
JPS6045253A (en) * 1983-04-11 1985-03-11 リコ− システムズ インコ−ポレ−テツド Photosensitive electrophotographic plate containing squaric acid methine dye dispersing in binder
JPS61103154A (en) * 1984-10-26 1986-05-21 Fuji Xerox Co Ltd Electrophotographic sensitive body
US5085909A (en) * 1988-04-28 1992-02-04 Ricoh Company, Ltd. Squarylium compounds and optical information recording medium using the same

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6045253A (en) * 1983-04-11 1985-03-11 リコ− システムズ インコ−ポレ−テツド Photosensitive electrophotographic plate containing squaric acid methine dye dispersing in binder
JPS6041045A (en) * 1983-04-28 1985-03-04 リコ− システムズ インコ−ポレ−テツド Photosensitive body containing squalene acid methine dye
JPS61103154A (en) * 1984-10-26 1986-05-21 Fuji Xerox Co Ltd Electrophotographic sensitive body
JPH0548911B2 (en) * 1984-10-26 1993-07-22 Fuji Xerox Co Ltd
US5085909A (en) * 1988-04-28 1992-02-04 Ricoh Company, Ltd. Squarylium compounds and optical information recording medium using the same

Also Published As

Publication number Publication date
JPS645701B2 (en) 1989-01-31

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