JPH0416853A - Electrophotographic sensitive body - Google Patents
Electrophotographic sensitive bodyInfo
- Publication number
- JPH0416853A JPH0416853A JP11987990A JP11987990A JPH0416853A JP H0416853 A JPH0416853 A JP H0416853A JP 11987990 A JP11987990 A JP 11987990A JP 11987990 A JP11987990 A JP 11987990A JP H0416853 A JPH0416853 A JP H0416853A
- Authority
- JP
- Japan
- Prior art keywords
- group
- electrophotographic photoreceptor
- pigment
- squareium
- methyl
- 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 21
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 6
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 5
- 125000003118 aryl group Chemical group 0.000 claims abstract description 5
- 108091008695 photoreceptors Proteins 0.000 claims description 27
- 239000000126 substance Substances 0.000 claims description 2
- -1 p-dimethyl-aminophenyl group Chemical group 0.000 abstract description 18
- 230000035945 sensitivity Effects 0.000 abstract description 6
- 230000003595 spectral effect Effects 0.000 abstract description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 3
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 abstract description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract description 2
- 239000010410 layer Substances 0.000 description 29
- 239000011347 resin Substances 0.000 description 11
- 229920005989 resin Polymers 0.000 description 11
- 239000011230 binding agent Substances 0.000 description 9
- 239000000463 material Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 239000004014 plasticizer Substances 0.000 description 4
- 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
- 239000003973 paint 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
- 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
- 238000000921 elemental analysis Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920005668 polycarbonate resin Polymers 0.000 description 2
- 239000004431 polycarbonate resin Substances 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920001225 polyester resin Polymers 0.000 description 2
- 239000004645 polyester resin Substances 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
- 239000000758 substrate Substances 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- SCGKCGMVFXMMSF-LYBHJNIJSA-N 2-[(E)-(diphenylhydrazinylidene)methyl]-N,N-diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1\C=N\N(C=1C=CC=CC=1)C1=CC=CC=C1 SCGKCGMVFXMMSF-LYBHJNIJSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000006024 2-pentenyl group Chemical group 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 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
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 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
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 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
- 150000007857 hydrazones Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 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 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 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
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 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
- 229920000642 polymer Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Landscapes
- Photoreceptors In Electrophotography (AREA)
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、電子写真用感光体の材料として、無定型セレン、
硫化カドミウム、酸化亜鉛等の無機系感光材料や、アゾ
化合物、スクェアリウム顔料等に代表される有機系感光
材料が広く知られている。Conventionally, amorphous selenium,
Inorganic photosensitive materials such as cadmium sulfide and zinc oxide, and organic photosensitive materials such as azo compounds and squareium pigments are widely known.
無定型セレン等は電子写真用感光体の材料として優れた
特性を有し、実用化されていることは周知の通りである
。しかし、この電子写真用感光体は毒性を有するため廃
棄が困難であった。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、繰り返し使用
に耐えない。It is well known that amorphous selenium and the like have excellent properties as materials for electrophotographic photoreceptors and are in practical use. However, this electrophotographic photoreceptor 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.
有機系感光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して十分な感度を有するものは得
られていない。Although organic photosensitive materials are excellent in processability such as film formation, no material with sufficient sensitivity has been obtained as a photoreceptor for electrophotography.
本発明の目的はこのような従来の課題を解決し、現在用
いられている電子写真プロセスすべてに使用可能な電子
写真用感光体であって、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
体を提供することである。The object of the present invention is to solve such conventional problems and to provide an electrophotographic photoreceptor that can be used in all currently used electrophotographic processes, and that has sufficient performance in a wide wavelength range from the visible region to the near-infrared region. An object of the present invention is to provide an electrophotographic photoreceptor having a high spectral sensitivity.
本発明に用いられるスクェアリウム顔料は一般弐＋Ｉ）
で示されるものである。The squareium pigment used in the present invention is general 2+I)
This is shown in .
（但し、式中Ｒ１は置換もしくは未置換の脂肪族炭化水
素基、アリール基、または複素環基を表し、Ｚｌ、Ｚ２
、Ｚ３、Ｚ４は置換もしくは未置換の環式炭化水素残基
、または複素環残基を表す。）Ｒ１で表される脂肪族炭
化水素基としてはメチル基、エチル基、プロピル基、ノ
ルマルブチル基、イソブチル基、ターシャリ−ブチル基
、５−メチルドデシル基、トリフルオロメチル基、３−
フェニルオクチル基、ビニル基、ニープロペニル基、イ
ンプロペニル基、１−ブテニル基、２−ブテニル基、２
−ペンテニル基、エチニル基等が挙げられる。アリール
基としてはフェニル基、ｐ−ジメチルアミノフェニル基
、ｐ−エチルメチルアミノフェニル基、３−メチルアゾ
−４−ジメチルアミノフェニル基、ｏ−エチルフェニル
基、３．５−ジクロロフェニル基、１−ナフチル基、１
−メチル−２−ナフチル基等が挙げられる。複素環基と
してはＮ−メチル−２−ピロリル基、２−チエニル基、
２−フリル基、２−ピリジル基、２−キノリル基、Ｎ−
メチル−４−ピペリジル基、ピペリジノ基等が挙げられ
る。Ｚｌ、Ｚ２、ｚ３、Ｚ４で表される環式炭化水素残
基としては表１に示したもの等が挙げられる。複素環残
基としては表２に示したもの等が挙げられる。(However, in the formula, R1 represents a substituted or unsubstituted aliphatic hydrocarbon group, aryl group, or heterocyclic group, and Zl, Z2
, Z3 and Z4 represent substituted or unsubstituted cyclic hydrocarbon residues or heterocyclic residues. ) The aliphatic hydrocarbon groups represented by R1 include methyl group, ethyl group, propyl group, n-butyl group, isobutyl group, tertiary-butyl group, 5-methyldodecyl group, trifluoromethyl group, 3-
Phenyloctyl group, vinyl group, nipropenyl group, impropenyl group, 1-butenyl group, 2-butenyl group, 2
-pentenyl group, ethynyl group, etc. Aryl groups include phenyl group, p-dimethylaminophenyl group, p-ethylmethylaminophenyl group, 3-methylazo-4-dimethylaminophenyl group, o-ethylphenyl group, 3.5-dichlorophenyl group, 1-naphthyl group. ,1
-Methyl-2-naphthyl group and the like. As the heterocyclic group, N-methyl-2-pyrrolyl group, 2-thienyl group,
2-furyl group, 2-pyridyl group, 2-quinolyl group, N-
Examples include methyl-4-piperidyl group and piperidino group. Examples of the cyclic hydrocarbon residues represented by Zl, Z2, z3, and Z4 include those shown in Table 1. Examples of the heterocyclic residue include those shown in Table 2.
表 １
（その１）
表 １
（その２）
表
（その３
表
（その５）
表
（その４
表
（その１
表
（その４）
表
（その３
表
（その５）
（その６
（その８
表
（その７）
このスクェアリウム顔料は下記構造式卸で示される３、
４−ジヒドロキシ−３−シクロブテン−１，２−ジオン
と、下記一般弐＠）で示されるアゾ化合物を溶媒中で反
応させることにより得られる。溶媒としては脂肪族アル
コール、例えばメタノール、エタノール、プロパツール
、ブタノール、アミルアルコール等が挙げられる。Table 1 (Part 1) Table 1 (Part 2) Table (Part 3 Table (Part 5) Table (Part 4) Table (Part 1 Table (Part 4) Table (Part 3) Table (Part 5) (Part 6 (Part 8 Table) (Part 7) This squareium pigment is shown by the following structural formula 3,
It is obtained by reacting 4-dihydroxy-3-cyclobutene-1,2-dione with an azo compound represented by the following general 2@) in a solvent. Examples of the solvent include aliphatic alcohols such as methanol, ethanol, propatool, butanol, amyl alcohol, and the like.
（但し、式中Ｒ１は置換もしくは未置換の脂肪族炭化水
素基、アリール基、または複素環基を表し、Ｚｌ、Ｚ２
、Ｚ３、Ｚ４は置換もしくは未置換の環式炭化水素残基
、または複素環残基を表す。）本発明の電子写真用感光
体の断面図を第１図から第３図に示す。(However, in the formula, R1 represents a substituted or unsubstituted aliphatic hydrocarbon group, aryl group, or heterocyclic group, and Zl, Z2
, Z3 and Z4 represent substituted or unsubstituted cyclic hydrocarbon residues or heterocyclic residues. ) Cross-sectional views of the electrophotographic photoreceptor of the present invention are shown in FIGS. 1 to 3.
第１図は、導電性支持体１０１上に電荷発生層１０２を
形成し、その電荷発生層１０２上に電荷輸送層１０３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１０１上に電荷輸送層１０３を形成
し、その電荷輸送層１０３上に電荷発生層１０２を形成
した積層型電子写真用感光体の断面図である。第１図お
よび第２図に示した積層型電子写真用感光体では、電荷
発生層１０２と電荷輸送層１０３とで感光層１０４をな
す。第３図は、導電性支持体１０１上に感光層１０４を
形成した単層型電子写真用感光体の断面図である。FIG. 1 is a sectional view of a laminated electrophotographic photoreceptor in which a charge generation layer 102 is formed on a conductive support 101 and a charge transport layer 103 is formed on the charge generation layer 102. Second
The figure is a cross-sectional view of a laminated electrophotographic photoreceptor in which a charge transport layer 103 is formed on a conductive support 101 and a charge generation layer 102 is formed on the charge transport layer 103. In the laminated electrophotographic photoreceptor shown in FIGS. 1 and 2, a charge generation layer 102 and a charge transport layer 103 form a photosensitive layer 104. FIG. 3 is a cross-sectional view of a single-layer electrophotographic photoreceptor in which a photosensitive layer 104 is formed on a conductive support 101.
電荷発生層は、導電性支持体上あるいは電荷輸送層上膜
けられ、その膜厚は０．１μｍから１．０μｍ、特に０
．３μｍから１．０μｍが好ましい。電荷発生層を形成
するのには、一般弐（Ｉ）で示されるスクェアリウム顔
料を単独で用℃、・るか、あるいはこのスクェアリウム
顔料をバインダ樹脂に分散させたものを用いる。スクェ
アリウム顔料を単独で用いる場合には、溶剤散布や真空
蒸着により電荷発生層を形成する。スクェアリウム顔料
をバインダ樹脂に分散させたものを用いる場合、スクェ
アリウム顔料のバインダ樹脂に対する比は１０重量％か
ら９０重量％、好ましくは２５重量％から３０重量％で
ある。この場合、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で十分に粉砕してバインダ樹脂に
分散する。バインダ樹脂としては、例えばポリビニルカ
ルバゾール、ポリ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使用できる。また、光導電
性を示さない絶縁性樹脂、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も使用で
きる。この際感光体の強度を向上させるため一般の高分
子材料と同様に可塑剤を用いることができる。可塑材と
しては、塩素化パラフィン、塩化ビフェニル、フォスフ
ェート系可塑剤等を用いることができる。可塑材はバイ
ンダ樹脂に対して２０重量％以下で感光体のもつ特性を
そこなわない範囲で用いられる。スクェアリウム顔料を
バインダ樹脂に分散させたものを用いる場合には、スプ
レ法、バーコーダ法等の方法で電荷発生層を形成する。The charge generation layer is formed on the conductive support or on the charge transport layer, and its thickness is from 0.1 μm to 1.0 μm, especially from 0.1 μm to 1.0 μm.
．． The thickness is preferably 3 μm to 1.0 μm. To form the charge generation layer, a squareium pigment generally represented by (I) is used alone, or a mixture of this squareium pigment dispersed in a binder resin is used. When a squareium pigment is used alone, a charge generation layer is formed by solvent spraying or vacuum deposition. When a squareium pigment dispersed in a binder resin is used, the ratio of the squareium pigment to the binder resin is 10% to 90% by weight, preferably 25% to 30% by weight. In this case, the squareium pigment is thoroughly ground in a ball mill or paint conditioner and dispersed in the binder resin. As the binder resin, for example, photoconductive polymers such as polyvinylcarbazole, polyvinylcarbazole derivatives, polyvinylnaphthalene, polyvinylanthracene, polyvinylpyrene, and other organic matrix materials having charge transport ability can be used. Insulating resins that do not exhibit photoconductivity, such as polystyrene, polyester, polycarbonate, and derivatives thereof, can also be used. At this time, in order to improve the strength of the photoreceptor, a plasticizer can be used in the same manner as in general polymer materials. As the plasticizer, chlorinated paraffin, chlorinated biphenyl, phosphate plasticizer, etc. can be used. The plasticizer is used in an amount of 20% by weight or less based on the binder resin, within a range that does not impair the properties of the photoreceptor. When a squareium pigment dispersed in a binder resin is used, the charge generation layer is formed by a spray method, a barcoder method, or the like.
導電性支持体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, for example, aluminum, nickel, zinc, platinum, gold, stainless steel, brass, iron, palladium, etc. can be used.
電荷輸送層は、電荷発生層または導電性支持体上に設け
られる。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
物質は単独ありいは２種類以上混合して用いることもで
きる。A charge transport layer is provided on the charge generation layer or conductive support. As charge transport substances, carbazole derivatives,
Examples include pyrazoline derivatives, triphenylamine, hydrazone derivatives, polyvinylpyrene, polyvinylanthracene, and polyvinylacridine. These charge transport materials can be used alone or in combination of two or more.
電荷輸送層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
、ポリサルフオン、ポリカーボネート等のポリマを用い
ることができる。この際電荷輸送物質のバインダ樹脂に
対する比は１５０重量％以下である。As the binder resin used in the charge transport layer, polymers such as acrylic resin, polystyrene, polyester, polyarylate, polysulfone, and polycarbonate can be used. At this time, the ratio of the charge transport material to the binder resin is 150% by weight or less.
以下、実施例を基に本発明の電子写真用感光体について
更に詳しく説明する。Hereinafter, the electrophotographic photoreceptor of the present invention will be described in more detail based on Examples.
実施例１
一般式（Ｉ［Ｉ） テＲ１がメチル基、Ｚｌ、Ｚ２、Ｚ
３、Ｚ４が環式炭化水素残基１０で表されるアゾ化合物
をｌ ｍｍｏｌ と、３，４−ジヒドロキシ３−ンクロ
ブテンー１．２−ジオ７０．５ ｍｍｏｄをベノゼンＩ
Ｑｍ／！、ｎ−ブタノール２０ ｍＪ中で１２０℃から
１２５℃で、反応中生成する水を共沸的に留去しながら
１５時間反応させた。生成した沈澱物をろ取し、下記構
造式で示されるスクェアリウム顔料１を収率３４９％で
得た。この生成物の元素分析の結果を表３に示す。Example 1 General formula (I [I) R1 is a methyl group, Zl, Z2, Z
3. 1 mmol of an azo compound in which Z4 is a cyclic hydrocarbon residue 10, 70.5 mmol of 3,4-dihydroxy-3-cyclobutene-1,2-dio, and benozene I
Qm/! , n-butanol in 20 mJ at 120°C to 125°C for 15 hours while water produced during the reaction was azeotropically distilled off. The generated precipitate was collected by filtration to obtain Squarium Pigment 1 represented by the following structural formula in a yield of 349%. The results of elemental analysis of this product are shown in Table 3.
表
実施例２〜２５
アゾ化合物を変えたほかは実施例１と同様に反応を行い
、表４で示されるスクェアリウム顔料２〜２５を合成し
た。このスクェアリウム顔料２〜２５の収率を表５に、
元素分析の結果を表６に示す。Table Examples 2 to 25 Squareium pigments 2 to 25 shown in Table 4 were synthesized by carrying out the reaction in the same manner as in Example 1 except that the azo compound was changed. The yields of Squarium pigments 2 to 25 are shown in Table 5.
Table 6 shows the results of elemental analysis.
表
（その１
表
表
（その２
表
（その３
実施例２６
ポリエステル樹脂のシクロヘキサノン溶液５重量％、２
０ｍ１に、実施例１で合成したスクェアリウム顔料１を
０．４８ ｍｍｏｌ加え、これをペイントコンディショ
ナを用いて１時間粉砕しながら分散させた。次にこれを
アルミ基板上にアプリケータで塗布し、膜厚０３μｍか
ら０．１μｍの電荷発生層を形成した。Table (Part 1 Table (Part 2) Table (Part 3) Example 26 Polyester resin cyclohexanone solution 5% by weight, 2
0.48 mmol of Squarium Pigment 1 synthesized in Example 1 was added to 0 ml, and this was dispersed while being pulverized for 1 hour using a paint conditioner. Next, this was applied onto an aluminum substrate using an applicator to form a charge generation layer having a thickness of 03 μm to 0.1 μm.
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樹脂に１００重量％加え、これ
を電荷発生層上に塗布し、膜厚２０μｍの電荷輸送層を
形成し、積層型電子写真用感光体を作製した。Paradiethylaminobenzaldehyde diphenylhydrazone was added in an amount of 100% by weight to a polycarbonate resin, and this was applied onto the charge generation layer to form a charge transport layer having a thickness of 20 μm, thereby producing a laminated electrophotographic photoreceptor.
この感光体にペーパーアナライザで−６ｋＶのコロナ放
電を２秒間行い、その後暗所に２秒間放置し、そのとき
の表面電位■。を測定した。次にタングステン−ハロゲ
ンランプで照度５ ｌｕｘの光を感光層に照射し、その
表面電位がｖｏの１７２になるまでに要する時間を測定
し、半減露光量Ｅ１／２を求めた。その結果表面電位■
。は−６５０Ｖであり、半減露光量Ｅｌ／２は３７１ｕ
ｘ・秒であった。A corona discharge of -6 kV was applied to this 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 as ■. was measured. Next, the photosensitive layer was irradiated with light at an illuminance of 5 lux using a tungsten-halogen lamp, and the time required for the surface potential to reach vo of 172 was measured to determine the half-reduced exposure amount E1/2. As a result, the surface potential■
. is -650V, and the half-decreased exposure amount El/2 is 371u
It was x seconds.
実施例２７〜５０
実施例２から２５で合成したスクェアリウム顔料２〜２
５を用い実施例２６と同様の方法で積層型電子写真用感
光体を作製し、その電気的特性を測定した。結果を表７
に示す。Examples 27-50 Squareium pigments 2-2 synthesized in Examples 2-25
A laminated electrophotographic photoreceptor was prepared using Example 5 in the same manner as in Example 26, and its electrical characteristics were measured. Table 7 shows the results.
Shown below.
表
（その１
表 ７
（その２）
表 ７
（その３）
実施例５１〜７５
バ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樹脂に１００重量％加え、これ
をアルミ基板上に塗布し、膜厚２０μｍの電荷輸送層を
形成した。Table (Part 1) Table 7 (Part 2) Table 7 (Part 3) Examples 51 to 75 Add 100% by weight of diethylaminobenzaldehyde diphenylhydrazone to polycarbonate resin, apply this on an aluminum substrate, and apply charge transport to a film thickness of 20 μm. formed a layer.
ポリエステル樹脂のシクロヘキサノン溶液５重量％、２
０ｍｌに、実施例１で合成したスクェアリウム顔料１を
０．４８ｍｍｏｌ加え、これをペイントコンディショナ
を用いて１時間粉砕しながら分散させた。次にこれを電
荷輸送層上にアプリケータで塗布し、膜厚０３μｍから
１．０μｍの電荷発生層を形成し、積層型電子写真用感
光体を作製した。Polyester resin cyclohexanone solution 5% by weight, 2
0.48 mmol of Squarium Pigment 1 synthesized in Example 1 was added to 0 ml, and this was dispersed while being pulverized for 1 hour using a paint conditioner. Next, this was applied onto the charge transport layer using an applicator to form a charge generation layer having a thickness of 03 μm to 1.0 μm, thereby producing a laminated electrophotographic photoreceptor.
次にこの感光体にペーパーアナライザで６ ｋＶのコロ
ナ放電を２秒間行い、その後暗所で２秒間放置し、その
ときの表面電位Ｖ０を測定した。つづいてタングステン
−ハロゲンランプで照度５Ｉｌｕｘの光を感光層に照射
し、その表面電位が■。の１／２になるまでに要する時
間を測定し、半減露光量Ｅ１／２を求めた。結果を表８
に示す。Next, this photoreceptor was subjected to corona discharge of 6 kV for 2 seconds using a paper analyzer, and then left in a dark place for 2 seconds, and the surface potential V0 at that time was measured. Next, the photosensitive layer was irradiated with light at an illuminance of 5 Ilux using a tungsten-halogen lamp, and its surface potential became ■. The time required for the amount to decrease to 1/2 was measured, and the half-reduction exposure amount E1/2 was determined. Table 8 shows the results.
Shown below.
スクェアリウム顔料２〜２５についても実施例５１と同
様に電子写真用感光体を作製し、その電気的特性を測定
した。結果を表８に示す。Electrophotographic photoreceptors were also produced using Squarium Pigments 2 to 25 in the same manner as in Example 51, and their electrical properties were measured. The results are shown in Table 8.
（その１
（その３
表
（その２）
実施例７６
実施例２６で作製した感光体に波長４５０ｎｍ、５５０
ｎｍ、６５０ｎｍ、７５０ ｎ ｍ、 ８５０ｎｍ。(Part 1 (Part 3 Table (Part 2)) Example 76 The photoreceptor produced in Example 26 was coated with a wavelength of 450 nm and a wavelength of 550 nm.
nm, 650 nm, 750 nm, 850 nm.
の単色光をそれぞれ１μＷ ／ ｅｒａで照射し、半減
露光量Ｅ１／２を求めたところ表９に示したような結果
が得られた。表９かられかるように本発明の電子写真用
感光体は、幅広い波長領域において十分な分光感度を有
するものである。When each monochromatic light was irradiated with 1 μW/era and the half-reduction exposure amount E1/2 was determined, the results shown in Table 9 were obtained. As can be seen from Table 9, the electrophotographic photoreceptor of the present invention has sufficient spectral sensitivity in a wide wavelength range.
表 ９
〔発明の効果〕
本発明の電子写真用感光体は、現在用いられて（・る電
子写真プロセスすべてに使用可能であって。Table 9 [Effects of the Invention] The electrophotographic photoreceptor of the present invention can be used in all electrophotographic processes currently used.
かつ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。It also has sufficient spectral sensitivity in a wide wavelength range from the visible region to the near-infrared region.
第１図ないし第３図は本発明の電子写真用感光体の断面
図である。
１０１・・・・・・導電性支持体、
１０２・・・・・・電荷発生層、
１０３・・・・・・電荷輸送層、
１０４・・・・・・感光層。1 to 3 are cross-sectional views of the electrophotographic photoreceptor of the present invention. 101... Conductive support, 102... Charge generation layer, 103... Charge transport layer, 104... Photosensitive layer.
Claims (1)
ることを特徴とする電子写真用感光体。 ▲数式、化学式、表等があります▼・・・（ I ） （但し、式中Ｒ１は置換もしくは未置換の脂肪族炭化水
素基、アリール基、または複素環基を表し、Ｚ１、Ｚ２
、Ｚ３、Ｚ４は置換もしくは未置換の環式炭化水素残基
、または複素環残基を表す。）[Claims] An electrophotographic photoreceptor characterized by containing a squarium pigment represented by the general formula (I). ▲There are mathematical formulas, chemical formulas, tables, etc.▼...(I) (However, in the formula, R1 represents a substituted or unsubstituted aliphatic hydrocarbon group, aryl group, or heterocyclic group, and Z1, Z2
, Z3 and Z4 represent substituted or unsubstituted cyclic hydrocarbon residues or heterocyclic residues. )
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11987990A JPH0416853A (en) | 1990-05-11 | 1990-05-11 | Electrophotographic sensitive body |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11987990A JPH0416853A (en) | 1990-05-11 | 1990-05-11 | Electrophotographic sensitive body |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0416853A true JPH0416853A (en) | 1992-01-21 |
Family
ID=14772504
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11987990A Pending JPH0416853A (en) | 1990-05-11 | 1990-05-11 | Electrophotographic sensitive body |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0416853A (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006097500A1 (en) * | 2005-03-18 | 2006-09-21 | Basell Polyolefine Gmbh | Metallocene compounds |
| US7728086B2 (en) | 2005-03-23 | 2010-06-01 | Basell Polyolefine Gmbh | Process for the polymerization of olefins |
| US7799880B2 (en) | 2005-03-23 | 2010-09-21 | Basell Polyolefine Gmbh | Process for the polymerization of olefins |
| US7842764B2 (en) | 2005-03-18 | 2010-11-30 | Basell Poliolefine Italia S.R.L. | Metallocene compounds |
| JP2011051985A (en) * | 2009-09-02 | 2011-03-17 | Samsung Mobile Display Co Ltd | Heterocyclic compound and organic luminescent element |
| US7964679B2 (en) | 2005-05-03 | 2011-06-21 | Basell Poliolefine Italia S.R.L. | Process for the polymerization of alpha olefins |
| US7985799B2 (en) | 2005-05-11 | 2011-07-26 | Basell Poliolefine Italia S.R.L. | Polymerization process for preparing polyolefin blends |
| WO2021112020A1 (en) * | 2019-12-04 | 2021-06-10 | Ａｇｃ株式会社 | Squarylium compound, optical filter, and image acquisition device |
-
1990
- 1990-05-11 JP JP11987990A patent/JPH0416853A/en active Pending
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006097500A1 (en) * | 2005-03-18 | 2006-09-21 | Basell Polyolefine Gmbh | Metallocene compounds |
| JP2008536813A (en) * | 2005-03-18 | 2008-09-11 | バーゼル・ポリオレフィン・ゲーエムベーハー | Metallocene compounds |
| US7803887B2 (en) | 2005-03-18 | 2010-09-28 | Basell Polyolefine Gmbh | Metallocene compounds |
| US7842764B2 (en) | 2005-03-18 | 2010-11-30 | Basell Poliolefine Italia S.R.L. | Metallocene compounds |
| US7728086B2 (en) | 2005-03-23 | 2010-06-01 | Basell Polyolefine Gmbh | Process for the polymerization of olefins |
| US7799880B2 (en) | 2005-03-23 | 2010-09-21 | Basell Polyolefine Gmbh | Process for the polymerization of olefins |
| US7964679B2 (en) | 2005-05-03 | 2011-06-21 | Basell Poliolefine Italia S.R.L. | Process for the polymerization of alpha olefins |
| US7985799B2 (en) | 2005-05-11 | 2011-07-26 | Basell Poliolefine Italia S.R.L. | Polymerization process for preparing polyolefin blends |
| JP2011051985A (en) * | 2009-09-02 | 2011-03-17 | Samsung Mobile Display Co Ltd | Heterocyclic compound and organic luminescent element |
| US8431241B2 (en) | 2009-09-02 | 2013-04-30 | Samsung Display Co., Ltd. | Organic light-emitting device |
| WO2021112020A1 (en) * | 2019-12-04 | 2021-06-10 | Ａｇｃ株式会社 | Squarylium compound, optical filter, and image acquisition device |
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