JPH02259768A - Electrophotographic sensitive body - Google Patents
Electrophotographic sensitive bodyInfo
- Publication number
- JPH02259768A JPH02259768A JP1080848A JP8084889A JPH02259768A JP H02259768 A JPH02259768 A JP H02259768A JP 1080848 A JP1080848 A JP 1080848A JP 8084889 A JP8084889 A JP 8084889A JP H02259768 A JPH02259768 A JP H02259768A
- Authority
- JP
- Japan
- Prior art keywords
- pigment
- layer
- electrophotographic photoreceptor
- formula
- squareium
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000000049 pigment Substances 0.000 claims abstract description 35
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 108091008695 photoreceptors Proteins 0.000 claims description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000010410 layer Substances 0.000 abstract description 30
- 239000011230 binding agent Substances 0.000 abstract description 11
- 239000000463 material Substances 0.000 abstract description 11
- 239000011347 resin Substances 0.000 abstract description 7
- 229920005989 resin Polymers 0.000 abstract description 7
- 230000035945 sensitivity Effects 0.000 abstract description 5
- -1 hydrazone compound Chemical class 0.000 abstract description 4
- 230000003595 spectral effect Effects 0.000 abstract description 3
- 239000000758 substrate Substances 0.000 abstract description 3
- 238000010030 laminating Methods 0.000 abstract description 2
- 239000002356 single layer Substances 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000000034 method Methods 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 6
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- 239000004014 plasticizer Substances 0.000 description 3
- 229920000515 polycarbonate Polymers 0.000 description 3
- 239000004417 polycarbonate Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- JGOAZQAXRONCCI-SDNWHVSQSA-N n-[(e)-benzylideneamino]aniline Chemical compound C=1C=CC=CC=1N\N=C\C1=CC=CC=C1 JGOAZQAXRONCCI-SDNWHVSQSA-N 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 229910052711 selenium Inorganic materials 0.000 description 2
- 239000011669 selenium Substances 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- WUPHOULIZUERAE-UHFFFAOYSA-N 3-(oxolan-2-yl)propanoic acid Chemical compound OC(=O)CCC1CCCO1 WUPHOULIZUERAE-UHFFFAOYSA-N 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229910001369 Brass Inorganic materials 0.000 description 1
- 101100532579 Mus musculus Utp3 gene Proteins 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 239000010951 brass Substances 0.000 description 1
- 229910052980 cadmium sulfide Inorganic materials 0.000 description 1
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- PONXTPCRRASWKW-KBPBESRZSA-N diphenylethylenediamine Chemical compound C1([C@H](N)[C@@H](N)C=2C=CC=CC=2)=CC=CC=C1 PONXTPCRRASWKW-KBPBESRZSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- JQMRSZJEVQNIPB-UHFFFAOYSA-N n,n'-diphenylpropane-1,3-diamine Chemical compound C=1C=CC=CC=1NCCCNC1=CC=CC=C1 JQMRSZJEVQNIPB-UHFFFAOYSA-N 0.000 description 1
- KPNVMOKSYWQETM-UHFFFAOYSA-N n-[[3-(anilinomethyl)phenyl]methyl]aniline Chemical compound C=1C=CC(CNC=2C=CC=CC=2)=CC=1CNC1=CC=CC=C1 KPNVMOKSYWQETM-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229920002382 photo conductive polymer Polymers 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- PWEBUXCTKOWPCW-UHFFFAOYSA-N squaric acid Chemical compound OC1=C(O)C(=O)C1=O PWEBUXCTKOWPCW-UHFFFAOYSA-N 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、電子写真プロセスにおいて使用される電子写
真用感光体に関する。更に詳しく言えば、本発明は一般
式（Ｉ）で示されるスクェアリウム顔料を含有する電子
写真用感光体に関するものである。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to an electrophotographic photoreceptor used in an electrophotographic process. More specifically, the present invention relates to an electrophotographic photoreceptor containing a squareium pigment represented by the general formula (I).
従来、電子写真用感光体材料として、無定型セレン、硫
化カドミウム、酸化亜鉛等の無機系電子写真用感光体材
料やアゾ化合物、スクェアリウム顔料等に代表される有
機系電子写真用感光体材料が広（知られている。Conventionally, electrophotographic photoreceptor materials include inorganic electrophotographic photoreceptor materials such as amorphous selenium, cadmium sulfide, and zinc oxide, and organic electrophotographic photoreceptor materials typified by azo compounds and squareium pigments. wide (known)
無定型セレン等は電子写真用感光体材料として優れた特
性を有し、実用化されていることは周知の通りである。It is well known that amorphous selenium and the like have excellent properties as photoreceptor materials for electrophotography and are in practical use.
しかしその製造には蒸着といった工程を経ねばならず、
製造された電子写真用感光体は毒性を有するため廃棄が
困難という欠点を持っている。酸化亜鉛を樹脂中に分散
させた電子写真用感光体は機械的強度に難点があり繰り
返ｌ−使用に耐えない。However, its production requires a process such as vapor deposition.
The produced electrophotographic photoreceptor has a drawback that it is difficult to dispose of because it is toxic. Electrophotographic photoreceptors in which zinc oxide is dispersed in a resin have poor mechanical strength and cannot withstand repeated use.
有機系電子写真用感光体材料は被膜形成等の加工性に優
れているものの電子写真用感光体と１．て十分な感度は
得られない欠点があった。Although organic electrophotographic photoreceptor materials have excellent processability such as film formation, they differ from electrophotographic photoreceptors in 1. However, there was a drawback that sufficient sensitivity could not be obtained.
本発明の目的は従来の電子写真用°感光体の課題を解決
し、現在用いられている電子写真プロセス全てに使用可
能な可視領域から近赤外領域の広波長領域において十分
な分光感度を有する電子写真用感光体を提供することに
ある。The purpose of the present invention is to solve the problems of conventional photoreceptors for electrophotography, and to have sufficient spectral sensitivity in a wide wavelength range from the visible region to the near-infrared region, which can be used in all currently used electrophotographic processes. An object of the present invention is to provide a photoreceptor for electrophotography.
本発明に用いられるスクェアリウム顔料は下記一般式（
Ｉ）で示される。The squareium pigment used in the present invention has the following general formula (
I).
（Ｒ１は炭素数１から１０の直鎖または分校アルキル基
を示し、Ｒ２は単結合または炭素数１から１０の二価の
脂肪族炭化水素基またはフェニレン基を示す。ｎは２か
ら１５の自然数を示す。、）このスクェアリウム顔料は
下記構造式Ｉで示される３、４−ジヒドロキシ−３−シ
クロブテン−１，２−ジオンと下記一般式＠）（Ｒｓは
炭素数１から１０の直鎖または分枝アルキル基を示し、
Ｒ２は単結合または炭素数１から１０の二価の脂肪族炭
化水幕またはフェニレン基を示す。）で示されるアニリ
ン誘導体を溶媒中で反応させることにより一般式（Ｉ）
で示されるスクェアリウム顔料を得ることが出来る。溶
媒としてハ脂肪族アルコール、例えばメタノール、エタ
ノール、フロハノール、フタノール、アミルアルコール
等が挙げられる。(R1 represents a straight chain or branched alkyl group having 1 to 10 carbon atoms; R2 represents a single bond or a divalent aliphatic hydrocarbon group having 1 to 10 carbon atoms or a phenylene group; n is a natural number of 2 to 15; ,) This squareium pigment is composed of 3,4-dihydroxy-3-cyclobutene-1,2-dione represented by the following structural formula I and the following general formula @) (Rs is a straight chain having 1 to 10 carbon atoms or represents a branched alkyl group,
R2 represents a single bond, a divalent aliphatic hydrocarbon group having 1 to 10 carbon atoms, or a phenylene group. ) by reacting the aniline derivative represented by formula (I) in a solvent.
A squareium pigment represented by can be obtained. Examples of the solvent include aliphatic alcohols such as methanol, ethanol, furohanol, phthanol, and amyl alcohol.
一般式（Ｉ）で示されるスクェアリウム顔料は電子写真
用感光体に用いることが出来る。その電子写真用感光体
の構造を第１図から第３図に示す。The squareium pigment represented by the general formula (I) can be used in electrophotographic photoreceptors. The structure of the electrophotographic photoreceptor is shown in FIGS. 1 to 3.
第１図は、導電性支持体１上に電荷発生層２を積層し、
更にその上に電荷輸送層６を積層して感光層４を形成し
た積層型電子写真用感光体の断面図である。第２図は、
導電性支持体１上に電荷輸送層３を積層し、更にその上
に電荷発生層２を積層し感光層４を形成し、た積層型電
子写真用感光体の断面図である。第３図は、導電性支持
体１上に感光層４を形成させた単層型電子写真用感光体
の断面図である。導電性支持体１または電荷輸送層６上
に、スクェアリウム単独あるいはノ（インダ樹脂を混合
して電荷発生層２を積層することができ５゜スクェアリ
ウム顔料のバインダ樹脂に対する比は１０から９０重量
％、好ましくは２５から３０重量％である。バインダ樹
脂を用いない場合にはスクェアリウム顔料を溶剤塗布す
るか真空蒸着法により導電性支持体１上に電荷発生層２
を積層することができる。電荷発生層２の膜厚は０．１
から１．Ｑμｍ、好まし、（は０．３から１．Ｏｊｊｍ
である。バインダ中に分散させる場合にはスクェアリウ
ム顔料ヲボールミルやペイントコンディショナを用いて
公知の方法で十分に粉砕した後に用いる。In FIG. 1, a charge generation layer 2 is laminated on a conductive support 1,
FIG. 2 is a cross-sectional view of a laminated electrophotographic photoreceptor in which a photoreceptor layer 4 is formed by further laminating a charge transport layer 6 thereon. Figure 2 shows
1 is a sectional view of a laminated electrophotographic photoreceptor in which a charge transport layer 3 is laminated on a conductive support 1, and a charge generation layer 2 is further laminated thereon to form a photosensitive layer 4. FIG. FIG. 3 is a cross-sectional view of a single-layer electrophotographic photoreceptor in which a photosensitive layer 4 is formed on a conductive support 1. As shown in FIG. The charge generating layer 2 can be laminated on the conductive support 1 or the charge transport layer 6 by mixing squareium alone or with an indica resin.The ratio of squareium pigment to binder resin is 10 to 90% by weight. %, preferably 25 to 30% by weight.If a binder resin is not used, the charge generating layer 2 is applied to the conductive support 1 by coating the squareium pigment with a solvent or by vacuum deposition.
can be stacked. The thickness of the charge generation layer 2 is 0.1
From 1. Qμm, preferably (is 0.3 to 1.Ojjm
It is. When dispersing the pigment in a binder, the squareium pigment is thoroughly pulverized by a known method using a ball mill or a paint conditioner before use.
電荷発生層２のバインダとしては光導電性を有している
ものも、また有していないものも使用できる。例えば、
ポリビニルピレン（ゾール、ボッビニルカルバゾール誘
導体、ポリビニルナフタレン、ポリビニルアントラセン
、ポリビニルピレン等の光導電性ポリマやその他の電荷
輸送能を有する有機マトリックス材料などがある。光導
電性を有していない公知の絶縁性樹脂も用いることが出
来る。As the binder for the charge generation layer 2, it is possible to use either a binder having photoconductivity or a binder not having photoconductivity. for example,
These include photoconductive polymers such as polyvinylpyrene (sol, bobbinylcarbazole derivatives, polyvinylnaphthalene, polyvinylanthracene, polyvinylpyrene, etc.) and other organic matrix materials with charge transport ability.Known insulating materials that do not have photoconductivity Polymer resins can also be used.
例えばポリスチレン、ポリエステル、ポリカー・ボネー
トやこれらの誘導体等が使用できる。この際電子写真用
感光体の強度を上げるため可塑剤を用いることも出来る
。可塑剤としては、塩素化パラフィン、塩化ピフェニル
、フォスフェート系可ｆｆｉ剤等を用いることが出来る
。可塑剤はバインダに対して０から２０重量％で電子写
真用感光体の持つ特性をそこなわない範囲で用いられる
。スクェアリウム顔料を分散させたバインダはスプレ法
、バーコーダ法等の既知の方法を用いて塗布することに
より電荷発生層２を形成することが出来る。For example, polystyrene, polyester, polycarbonate, and derivatives thereof can be used. At this time, a plasticizer can also be used to increase the strength of the electrophotographic photoreceptor. As the plasticizer, chlorinated paraffin, chlorinated piphenyl, phosphate type ffi agent, etc. can be used. The plasticizer is used in an amount of 0 to 20% by weight based on the binder, within a range that does not impair the properties of the electrophotographic photoreceptor. The charge generation layer 2 can be formed by applying the binder in which the squareium pigment is dispersed using a known method such as a spray method or a barcoder method.
導電性支持体１の材料としては例えばアルミニウム、ニ
ッケル、亜鉛、白金、金、ステンレス鋼、真鍮、鉄、パ
ラジウム等を用いることができる。As the material of the conductive support 1, for example, aluminum, nickel, zinc, platinum, gold, stainless steel, brass, iron, palladium, etc. can be used.
電荷輸送物質に使用する電荷輸送物質としては、カルバ
ゾール誘導体、ピラゾリン誘導体、トリフェニルアミン
、ヒドラゾン誘導体、ポリビニルピレン、ポリビニルア
ントラセン、ポリビニルアクリジン等が挙げられる。こ
れらの電荷輸送物質は単独あるいは２種類以上混合して
用いることもできる。電荷輸送物質に使用されるバイン
ダ樹脂としてはアクリル系樹脂、ポリスチレン、ポリエ
ステル、ボリアリレー・ト、ポリサルフォン、ポリカー
ボネート等のポリマを用いることができる。電荷輸送層
６は、電荷発生層２あるいは導電性支持体１上に積層す
ることができる。電荷輸送物質のバインダ樹脂に対する
比はＯから１５０重量％である。Examples of the charge transport substance used as the charge transport substance include carbazole derivatives, pyrazoline derivatives, triphenylamine, hydrazone derivatives, polyvinylpyrene, polyvinylanthracene, and polyvinylacridine. These charge transport materials can be used alone or in combination of two or more. As the binder resin used for the charge transport material, polymers such as acrylic resin, polystyrene, polyester, polyarylate, polysulfone, and polycarbonate can be used. The charge transport layer 6 can be laminated on the charge generation layer 2 or the conductive support 1 . The ratio of charge transport material to binder resin is from O to 150% by weight.
以下、実施例を基に本発明を説明する。 The present invention will be explained below based on Examples.
（実施例１）
ろ水を共沸的に留去しながら１５時間反応させ、生成し
たスクェアリウム顔料を沈澱物としてろ取しスクェアリ
ウム顔料隆１を０．１６９ ｇ得た。(Example 1) The reaction was carried out for 15 hours while the filtrate was azeotropically distilled off, and the produced squalium pigment was collected by filtration as a precipitate to obtain 0.169 g of squalium pigment Lung 1.
（実施例２）
ジフェニルエチレンジアミン０．２６８．９を用いた他
は実施例１と同様に合成し、スクェアリウム顔料隘２を
０．２１８．９得た。スクェアリウム顔料型２の赤外吸
収スペクトルの図を第４図に示す。(Example 2) Synthesis was carried out in the same manner as in Example 1, except that 0.268.9% of diphenylethylenediamine was used, and 0.218.9% of Squarium Pigment 2 was obtained. FIG. 4 shows an infrared absorption spectrum of Squarium pigment type 2.
ンジアミｙ ０．２４０ ｆｉ （１ｍｍｏｌ）と３．
４−ジヒドロキシ−３−シクロブテン−１，２−ジオン
０、１１４ ｊｉ （Ｊ、ｍｍｏＪ）をベンゼｙｌＱｍ
Ａ！、ｎ−ブタノール’１０ｍ１中で１２０から１２５
℃で生成す（実施例３）
へ、ヘーンメテルーへ、
ヘーンフェニルエチレ
ジフェニルトリメチレンジアミン０．２５４９を用いた
他は実施例１と同様に合成し、スクェアリウム顔料Ｎ［
Ｌ３を０．０９９７得た。0.240 fi (1 mmol) and 3.
4-dihydroxy-3-cyclobutene-1,2-dione 0,114 ji (J, mmoJ) was converted into benzene ylQm
A! , n-butanol'120 to 125 in 10ml
(Example 3) Squarium pigment N[
0.0997 of L3 was obtained.
ンジアミンにかえてＮ、Ｎ′−ジメチル−Ｎ、＊−ジフ
ェニルテトラメチレンジアミン０．２６８ｇを用いた他
は実施例１と同様に合成し、スクェアリウム顔料隘５を
０．０６８ｇ得た。Synthesis was carried out in the same manner as in Example 1, except that 0.268 g of N,N'-dimethyl-N,*-diphenyltetramethylene diamine was used instead of diamine, to obtain 0.068 g of Squarium Pigment 5.
（実施例４）
（実施例６）
ジフェニルトリメチレンジアミン０．２８２ｇを用いた
他は実施例１と同様に合成し、スクェアリウム顔料ＮＱ
４を０．０６５ｇ得た。(Example 4) (Example 6) Squarium pigment NQ was synthesized in the same manner as in Example 1 except that 0.282 g of diphenyltrimethylenediamine was used.
0.065g of 4 was obtained.
ジフェニルテトラメチレンジアミン０．２９６．９を用
いた他は実施例１と同様に合成し、スクェアリウム顔料
隘６を０．０４９ｇ得た。Synthesis was carried out in the same manner as in Example 1 except that 0.296.9 g of diphenyltetramethylene diamine was used to obtain 0.049 g of Squarium Pigment 6.
（実施例５）
へ、ヘーシメテルーへ、
ヘーシフェニルエテレ
（実施例７）
ンジアミンにかえてＮ、Ｎ−ジメチル−Ｎ、Ｎ−ジフェ
ニル−ｐ−キシリレンジアミン０．３１６ｇを用いた他
は実施例１と同様に合成し、スクェアリウム頷料隘７を
０．３５８．９得た。(Example 5) Hesimeter, Hesiphenylethere (Example 7) Example except that 0.316 g of N,N-dimethyl-N,N-diphenyl-p-xylylene diamine was used instead of diamine. It was synthesized in the same manner as in 1 to obtain 0.358.9 of Squarium nodule 7.
を用いた他は実施例１と同様に合成し、スクェアリウム
顔料述９を０．３６３ｇ得た。The synthesis was carried out in the same manner as in Example 1 except that 0.363 g of Squarium Pigment No. 9 was obtained.
（実施例８）
（実施例１０）
Ｎ％Ｎ−ジメチル−Ｎ１
Ｎ−ジフェニルエチレ
ジフェニル−ｐ−キシリレンジアミン０．３４４９を用
いた他は実施例１と同様に合成し、スクェアリウム顔料
ＮｌＸ８を０．３３４．９得た。(Example 8) (Example 10) N%N-dimethyl-N1 N-diphenylethylediphenyl-p-xylylenediamine 0.3449 was used, but the same procedure as in Example 1 was used to synthesize the squareium pigment NlX8. 0.334.9 was obtained.
ジフェニル−〇−キシリレンジアミン０．３４４９を用
いた他は実施例１と同様に合成し、スクェアリウム顔料
隘１０を０．０２６９得た。Synthesis was carried out in the same manner as in Example 1 except that 0.3449 g of diphenyl-0-xylylene diamine was used to obtain 0.0269 g of Squarium Pigment 10.
（実施例９）
（実施例１１）
Ｎ、Ｎ−ジメチル−Ｎ１
Ｎ−ジフェニルエチレ
ジフェニル−ローキシリレンジアミン０．３１６ｇジフ
ェニル−ｍ−キシリレンジアミン０．３１６ｐを用いた
他は実施例１．と同様に合成し、スクェアリウム顔料嵐
１１を０．０８４ｇ得た。(Example 9) (Example 11) Example 1 except that N,N-dimethyl-N1 N-diphenylethyldiphenyl-low-xylylenediamine 0.316g diphenyl-m-xylylenediamine 0.316p was used. It was synthesized in the same manner as above to obtain 0.084 g of Squarium Pigment Arashi 11.
（実施例１２）
一ジフェニルーｍ−キシリレンジアミン０．３４４１を
用いた他は実施例１と同様に合成し、スクェアリウム顔
料Ｎｕ１２を０．３９７９得た。(Example 12) Synthesis was carried out in the same manner as in Example 1 except that 0.3441 of monodiphenyl-m-xylylene diamine was used to obtain 0.3979 of squareium pigment Nu12.
（実施例１３）
スクェアリウム顔料隘ｌをペイントコンディジ嘗すを用
いてメノー球と共に１時間粉砕する。粉砕されたスクェ
アリウム顔料隔１をポリエステル樹脂（バイロン２００
）に３０重量％加えてからシクロヘキサノンを加えて分
散させ、アルミニウム基板上に膜厚０．３から１．０μ
ｍでアプリケータを用いて電荷発生層を積層する。この
上にバラジエチルアミノベンズアルデヒドジフェニルヒ
トラゾンをポリカーボネート樹脂に１００重量％加えた
電荷輸送層を膜厚２０μｍで積層し、感光層を形成した
。(Example 13) Squarium pigment volume is ground with agate spheres using a paint conditioner for 1 hour. The crushed Squarium Pigment Part 1 was mixed with polyester resin (Vylon 200
), then add cyclohexanone and disperse, and form a film with a thickness of 0.3 to 1.0μ on an aluminum substrate.
A charge generation layer is laminated using an applicator in step m. A charge transport layer containing 100% by weight of valadiethylaminobenzaldehyde diphenylhydrazone added to a polycarbonate resin was laminated thereon to a thickness of 20 μm to form a photosensitive layer.
次にこの電子写真用感光体にペーパーアナライザを用い
て−６ｋＶのコロナ放電を２秒間行い、その後２秒間暗
所で放置し、そのときの表面電位■。を測定し、ついで
照度５ ｌｕｘのタングステン−ハロゲンランプを照射
し、その表面電位が■。Next, a corona discharge of -6 kV was applied to this electrophotographic photoreceptor for 2 seconds using a paper analyzer, and then it was left in a dark place for 2 seconds, and the surface potential at that time was measured. was measured, and then irradiated with a tungsten-halogen lamp with an illuminance of 5 lux, and the surface potential was ■.
の１／２になるまでの時間（秒）を測定して半減感光量
Ｅ １ ／ ２を求めた。その結果Ｖ。＝−６５０Ｖ、
Ｅ １／ ２ ” ３．５ ｌｕｘ −秒であった。The time (seconds) until it becomes 1/2 of that was measured to determine the half-decrease photosensitivity E 1/2. The result is V. =-650V,
E 1/2" 3.5 lux-seconds.
（実施例１４〜２４）
実施例１３のスクェアリウム顔料Ｎａ１の代わりにスク
ェアリウム顔料遅２〜隘１２を用いたほかは同様の方法
で電子写真用感光体を作成し表面電位■。および半減感
光量Ｅ１／２を測定した。結果を表１に示す。(Examples 14 to 24) Electrophotographic photoreceptors were prepared in the same manner as in Example 13, except that the squareium pigments Na1 were used instead of the squareium pigments Na1, and the surface potential was ■. And the half-sensitivity amount E1/2 was measured. The results are shown in Table 1.
表
流側１３と同様の処理を施したスクェアリウム顔料遅１
を含有する電荷発生層（膜厚０．３〜１．０μｍ）をア
プリケータで積層し、感光層を形成した。このようにし
て作成した電子写真用感光体の特性を実施例１３と同様
な方法で測定し、結果を表２に示す。Squarium pigment slow 1 treated in the same way as surface side 13
A charge generation layer (thickness: 0.3 to 1.0 μm) containing the following was laminated using an applicator to form a photosensitive layer. The characteristics of the electrophotographic photoreceptor thus prepared were measured in the same manner as in Example 13, and the results are shown in Table 2.
スクェアリウム顔料］東２から述１２を用い同様にして
作成した電子写真用感光体の特性を表２に示す。[Squarium Pigment] Table 2 shows the properties of electrophotographic photoreceptors prepared in the same manner using Examples 2 to 12.
表 ２
（実施例２５〜３６）
アルミニウム基板上に、パラジエチルアミノベンズアル
デヒドジフェニルヒドラゾンをポリカーボネートｍ指に
１００重量％加えた電荷輸送層を膜厚２０μｍで積層し
た。この電荷輸送層上に実（実施例３７）
実施例１３で作成した電子写真用感光体を用いて４５０
，５５０．６５０，７５０、ｇ５Ｑｎｍの各波長の単色
光１μＷ／Ｃｒｌ１を照射し、Ｅ１／２を求めたところ
表３に示したように幅広い波長領域において感度を示す
ことが判った。結果を表３に示す。 表 ３
（比較例１）
スクェアリウム顔料猶１と類促の構造（一般式（Ｉ）で
Ｒ，＝メチル、Ｒ２−単結合）を有し、ｎが１８から３
０の電荷発生物質を用いたほかは実施例１３と同様な方
法で電子写真用感光体を作成し、その特性を測定した。Table 2 (Examples 25 to 36) A charge transport layer in which 100% by weight of paradiethylaminobenzaldehyde diphenylhydrazone was added to a polycarbonate finger was laminated on an aluminum substrate to a thickness of 20 μm. The electrophotographic photoreceptor prepared in Example 13 was coated with 450 yen on this charge transport layer (Example 37).
, 550, 650, 750, and g5Qnm, and E1/2 was determined by irradiating the sample with 1 μW/Crl1 of monochromatic light of each wavelength. As shown in Table 3, it was found that sensitivity was exhibited in a wide wavelength range. The results are shown in Table 3. Table 3 (Comparative Example 1) It has a structure similar to that of Squarium pigment No. 1 (R,=methyl, R2-single bond in general formula (I)), and n is 18 to 3.
An electrophotographic photoreceptor was prepared in the same manner as in Example 13, except that a charge generating material of 0 was used, and its characteristics were measured.
その特性値は、
ＶＯ＝−６５０Ｖ、 Ｅ １／２ニア、５６ｕｘ ｓ秒
であった。Its characteristic values were VO=-650V, E 1/2 near, 56ux s seconds.
現在用いられている電子写真プロセス全てに使用可能な
可視領域から近赤外領域の広波長領域において十分な分
光感度を有する電子写真用感光体を得ることが出来た。It was possible to obtain an electrophotographic photoreceptor having sufficient spectral sensitivity in a wide wavelength range from the visible region to the near-infrared region, which can be used in all currently used electrophotographic processes.
第１図、第２図および第３図は電子写真用感光体の構造
を表わす断面図であり、第４図はスクェアリウム顔料陥
２の赤外吸収スペクトル図である。
１・・・・・・導電性支持体。
２・・・・・・電荷発生層、
６・・・・・・電荷輸送層、
４・・・・・・感光層。
田嘴Ｊｉ＠−ｔFIGS. 1, 2, and 3 are cross-sectional views showing the structure of an electrophotographic photoreceptor, and FIG. 4 is an infrared absorption spectrum diagram of the squareium pigment cavity 2. FIG. 1... Conductive support. 2...Charge generation layer, 6...Charge transport layer, 4...Photosensitive layer. Tagaku Ji@-t
Claims (1)
することを特徴とする電子写真用感光体。 一般式（ I ） ▲数式、化学式、表等があります▼・・・（ I ） （Ｒ＿１は炭素数１から１０の直鎖または分枝アルキル
基を示し、Ｒ＿２は単結合または炭素数１から１０の二
価の脂肪族炭化水素基またはフェニレン基を示す。ｎは
２から１５の自然数を示す。）[Claims] An electrophotographic photoreceptor characterized by containing a squarium pigment represented by the general formula (I). General formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼... (I) (R_1 represents a straight chain or branched alkyl group having 1 to 10 carbon atoms, R_2 is a single bond or a carbon number 1 to 10 represents a divalent aliphatic hydrocarbon group or phenylene group. n represents a natural number from 2 to 15.)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1080848A JPH02259768A (en) | 1989-03-31 | 1989-03-31 | Electrophotographic sensitive body |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1080848A JPH02259768A (en) | 1989-03-31 | 1989-03-31 | Electrophotographic sensitive body |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH02259768A true JPH02259768A (en) | 1990-10-22 |
Family
ID=13729770
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1080848A Pending JPH02259768A (en) | 1989-03-31 | 1989-03-31 | Electrophotographic sensitive body |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH02259768A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101413075B1 (en) * | 2011-12-26 | 2014-06-30 | 제일모직 주식회사 | Photosensitive resin composition for color filter and color filter using the same |
-
1989
- 1989-03-31 JP JP1080848A patent/JPH02259768A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101413075B1 (en) * | 2011-12-26 | 2014-06-30 | 제일모직 주식회사 | Photosensitive resin composition for color filter and color filter using the same |
| US8900780B2 (en) | 2011-12-26 | 2014-12-02 | Cheil Industries Inc. | Photosensitive resin composition for color filter and color filter using the same |
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