JPH0431868A - Electrophotographic sensitive body - Google Patents
Electrophotographic sensitive bodyInfo
- Publication number
- JPH0431868A JPH0431868A JP13699190A JP13699190A JPH0431868A JP H0431868 A JPH0431868 A JP H0431868A JP 13699190 A JP13699190 A JP 13699190A JP 13699190 A JP13699190 A JP 13699190A JP H0431868 A JPH0431868 A JP H0431868A
- Authority
- JP
- Japan
- Prior art keywords
- group
- heterocyclic
- region
- electrophotographic
- sensitive body
- 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 14
- 125000003118 aryl group Chemical group 0.000 claims abstract description 9
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 125000003277 amino group Chemical group 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
- 125000005843 halogen group Chemical group 0.000 claims abstract description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 4
- 108091008695 photoreceptors Proteins 0.000 claims description 25
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 7
- 230000035945 sensitivity Effects 0.000 abstract description 5
- 230000003595 spectral effect Effects 0.000 abstract description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 3
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 29
- -1 isopropylamino group Chemical group 0.000 description 20
- 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 9
- 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
- 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
- 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
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 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
- IJGGFSGEISKIHB-UHFFFAOYSA-N 2-[(diphenylhydrazinylidene)methyl]-n,n-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1C=NN(C=1C=CC=CC=1)C1=CC=CC=C1 IJGGFSGEISKIHB-UHFFFAOYSA-N 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
- 125000000175 2-thienyl group Chemical group S1C([*])=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
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-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
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 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
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 239000010951 brass Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000006309 butyl amino group Chemical group 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 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
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 125000002425 furfuryl group Chemical group C(C1=CC=CO1)* 0.000 description 1
- 125000002541 furyl group Chemical group 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
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000006316 iso-butyl amino group Chemical group [H]N(*)C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H] 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
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000006308 propyl amino group Chemical group 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 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
- 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
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.
無定型セレン等は重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
に耐えないっ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。It is well known that amorphous selenium and the like have excellent properties as materials for photoreceptors for photosensitive materials 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 resin have poor mechanical strength and cannot withstand repeated use.Although organic photosensitive materials have excellent processability such as film formation, No material with sufficient sensitivity has yet been obtained.
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司能な電子
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 can be used 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 sufficient spectral sensitivity.
本発明に用いられるスクェアリウム顔料は一般式（Ｉ）
で示されるものであろう
（但し２、式中Ｒ１、Ｒ２は水素原子、ハロゲン原子、
置換もしくは未置換の脂肪族炭化水素基、アルコキシ基
、アミノ基、アリール基、複素環基または水酸基を表し
、Ｒ３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，Ｒ２で表されるハロゲン原子として
はフッ素、塩素、臭素、よう素が挙げられる。アルコキ
シ基としてはメトキシ基、エトキシ基、プロポキシ基、
イソプロポキン基、ブトキシ基、ペンチルオキシ基、ベ
ンジルオキ７基等が挙げられる。The squareium pigment used in the present invention has the general formula (I)
(However, in the formula, R1 and R2 are hydrogen atoms, halogen atoms,
Represents a substituted or unsubstituted aliphatic hydrocarbon group, alkoxy group, amino group, aryl group, heterocyclic group, or hydroxyl group, R3 represents a substituted or unsubstituted aliphatic hydrocarbon group, aryl group, or heterocyclic group , Zl, Z2, and Z3 represent substituted or unsubstituted cyclic hydrocarbon residues or heterocyclic residues. ) Examples of the halogen atoms represented by R1 and R2 include fluorine, chlorine, bromine, and iodine. Alkoxy groups include methoxy group, ethoxy group, propoxy group,
Examples include isopropoquine group, butoxy group, pentyloxy group, and benzyloxy group.
アミノ基としてはメチルアミノ基、エチルアミノ基、プ
ロピルアミノ基、イソプロピルアミノ基、ブチルアミノ
基、イソブチルアミノ基、ターシャリ−ブチルアミノ基
、３−フェニルオクチルアミノ基、エチルフェニルアミ
ノ基、ジメチルアミノ基、ジエチルアミノ基、ジエチル
アミノ基、ジイソプロピルアミノ基、ジー３−フェニル
オクチルアミノ基等が挙げられる。Examples of amino groups include methylamino group, ethylamino group, propylamino group, isopropylamino group, butylamino group, isobutylamino group, tertiary-butylamino group, 3-phenyloctylamino group, ethylphenylamino group, dimethylamino group, Examples include diethylamino group, diethylamino group, diisopropylamino group, and di-3-phenyloctylamino group.
Ｒ１，Ｒ２、Ｒ３で表される脂肪族炭化水素としてはメ
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、１−７０ベニル基、インプロペニル基、１
−ブテニル基、２−フチニル基、２−ペンテニル基、１
−シクロへキセニル基、エチニル基等が挙げられる。Aliphatic hydrocarbons represented by R1, R2, and R3 include methyl group, ethyl group, propyl group, normal butyl group, isobutyl group, tert-butyl group, 5-methyldodecyl group, trifluoromethyl group, and 3-phenyl group. Octyl group, vinyl group, 1-70 benyl group, impropenyl group, 1
-butenyl group, 2-phthynyl group, 2-pentenyl group, 1
-cyclohexenyl group, ethynyl group, etc.
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％０−ｘ
ｆルフェニル基、３．５−ジクロロフェニル基、３−メ
チルアゾ−４−ジメチルアミノフェニル基、ｌ−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−ヒロリル基、１，５−
ジメチル−２ｅ ｏ Ｉ）ル＆、２−チエニル基、２−
フリル基、フルフリル基、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。Aryl groups include phenyl group, p-dimethylaminophenyl group, p-ethylmethylaminophenyl group%0-x
Examples include f-ruphenyl group, 3.5-dichlorophenyl group, 3-methylazo-4-dimethylaminophenyl group, l-naphthyl group, and 1-methyl-2-naphthyl group. Examples of the heterocyclic group include N-methyl-2-hyloryl group, 1,5-
dimethyl-2e o I) 2-thienyl group, 2-
Examples include furyl group, furfuryl group, 2-pyridyl group, 2-quinolyl group, N-methyl-4-piperidyl group, piperidino group, and the like.
Ｚｌ、Ｚ２、Ｚ３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。Examples of the cyclic hydrocarbon residues represented by Zl, Z2, and Z3 include those shown in Table 1. Examples of the heterocyclic residue include those shown in Table 2.
表 １ （その１）
表
■
（その２）
表
（その４）
表
（その３
表
（その５）
表
（その１
表
（その３）
表
（その２
表
（その４
表
（その５
表
（その７
表
（その６
表
（その８）
このスクェアリウム顔料は下記構造式１１１．Ｄで示さ
ｔＬ６３．４−ジヒドロキシ−３−ンクロブテンー１２
−ジオンと、下記一般弐Ｃｍ）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。溶媒どしては
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 (Part 2) Table (Part 4) Table (Part 3 Table (Part 5) Table (Part 1 Table (Part 3) Table (Part 2) Table (Part 4 Table (Part 5) Table (Part 5) 7 Table (Part 6 Table (Part 8)) This squareium pigment is represented by the following structural formula 111.D.
It can be obtained by reacting -dione with an azo compound represented by the following general 2Cm) in a solvent. Examples of the solvent include aliphatic alcohols such as methanol, ethanol, propatool, butanol, and amyl alcohol.
（但し、式中Ｒ１，Ｒ２は水素原子、）・ロゲン原子、
置換もしくは未置換の脂肪族炭化水素基、アルコキシ基
、アミノ基、アリール基、複素環基または水酸基を表し
、Ｒ３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 and R2 are hydrogen atoms.) - Rogen atom,
Represents a substituted or unsubstituted aliphatic hydrocarbon group, alkoxy group, amino group, aryl group, heterocyclic group, or hydroxyl group, R3 represents a substituted or unsubstituted aliphatic hydrocarbon group, aryl group, or heterocyclic group , Zl, Z2, and Z3 represent substituted or unsubstituted cyclic hydrocarbon residues or heterocyclic residues. ) A cross-sectional view of the electrophotographic photoreceptor of the present invention is shown in FIG.
It is shown in FIG.
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１０６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 106 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に
設けられ、その膜厚は０１μｍから１０ｉｔ ｍ、特Ｖ
Ｃ０３μｍから１０μｍが好ましし・っ電荷発生層を形
成するのには、−形成＋Ｉ）で示されるスクェアリウム
顔料を単独で用いるか、あるいはこのスクェアリウム顔
料な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をボールミルやペイ
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（・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。可塑剤と
しては、塩素化ハラフィン、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。可塑剤はバイ
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 provided on the conductive support or the charge transport layer, and has a thickness of 01 μm to 10 m, and a special V
C0 is preferably 3 μm to 10 μm. To form the charge generation layer, the squareium pigment represented by -formation+I) is used alone, or 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 pulverized using 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. In addition, insulating resins that do not exhibit photoconductivity, such as polystyrene, polyester, polycarbonate, and derivatives thereof, can also be used.In this case, in order to improve the strength of the photoreceptor, a plasticizer may be added as with general polymer materials. As the plasticizer, chlorinated halaffin, chlorinated biphenyl, phosphate plasticizer, etc. can be used.The plasticizer may be used in an amount of 20% by weight or less based on the binder resin, so as not to damage the properties of the photoreceptor. When a squareium pigment dispersed in a binder resin is used, the charge generation layer is formed by a method such as a spray method or a barcoder method.
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
物質は単独あるいは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。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
一形成＠）でＲ１、Ｒ２が水素原子、Ｒ３がメチル基、
Ｚｌ、Ｚ２、Ｚ３が環式炭化水素残基１０で表されるア
ゾ化合物を１ｍｍｏｄと３，４−ジヒドロキシ−３−シ
クロブテン−１，２−ジオンＱ、 ５ ｍｍｏ ｌをベ
ンゼンＩＱｍｌ、ｎ−ブタノール２０ｍ１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３５６
％で得た。Example 1 In the formation @), R1 and R2 are hydrogen atoms, R3 is a methyl group,
1 mmod of an azo compound in which Zl, Z2, and Z3 are represented by 10 cyclic hydrocarbon residues, 5 mmol of 3,4-dihydroxy-3-cyclobutene-1,2-dione Q, IQml of benzene, and 20 ml of n-butanol. 120℃ inside
to 125°C for 15 hours while water produced during the reaction was azeotropically distilled off. The generated precipitate was collected by filtration, and Squarium pigment 1 represented by the following structural formula was obtained in a yield of 356.
Obtained in %.
この生成物の元素分析の結果を表３に示す。The results of elemental analysis of this product are shown in Table 3.
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に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。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
表
（その１）
表 ６
（その２）
表 ６
（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０．３μｍ
から１．０μｍの電荷発生層を形成した。Table (Part 1) Table 6 (Part 2) Table 6 (Part 3) Example 26 Cyclohexanone solution of polyester resin 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, apply this onto an aluminum substrate with an applicator to a film thickness of 0.3 μm.
A charge generation layer having a thickness of 1.0 μm was formed from the above.
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。100% by weight of dimethylaminobenzaldehyde diphenylhydrazone was added to a polycarbonate resin, and this was applied onto the charge generation layer to form a charge transport layer with 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Ｖ。を測定した。次にタングステン−ハロゲ
ンランプで照度５ ｆｌｕｘ 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。その結果表面
電位■。は−６５０Ｖであり、半減露光量Ｅ Ｉ ／
２ ハ３．６（４ｕｘ・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 V at that time was measured. was measured. Next, the photosensitive layer was irradiated with light with an illuminance of 5 flux 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. As a result, the surface potential■. is -650V, and the half-decreased exposure amount E I /
2 Ha was 3.6 (4ux・sec).
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）
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) Examples 51 to 75 100% by weight of diethylaminobenzaldehyde diphenylhydrazone was added to a polycarbonate resin, and this was coated on an aluminum substrate to form a charge transport layer with a thickness of 20 μm.
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 ｒｒｍｏｌｌ 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０
３μｍ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 rrmol of Squarium Pigment 1 synthesized in Example 1 was added to 0.0 ml, and this was dispersed while being pulverized for 1 hour using a paint conditioner. Next, apply this onto the charge transport layer using an applicator, and the film thickness is 0.
A charge generation layer having a thickness of 3 μm to 1.0 μm was formed to produce 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■。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５ ｌｕｘの光を感光層に照射
し、その表面電位がＶ。の】／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, 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. was measured. Next, the photosensitive layer was irradiated with light with an illuminance of 5 lux using a tungsten-halogen lamp, and the surface potential was V. ] /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.
表 ８ （その１） 表 ８ （そ−）２） 実施例７６ 実施例２６で作製した感光体に波長４５ Ｑ ｎ ｍ。Table 8 (Part 1) Table 8 (So-)2) Example 76 A wavelength of 45 Qnm was applied to the photoreceptor produced in Example 26.
５５０ｎｍ、６５０ｎｍ、７５０ｎｍ、８５０ｎｍの単
色光をそれぞれ１μＷ／ｉ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。Monochromatic light of 550 nm, 650 nm, 750 nm, and 850 nm was irradiated at 1 μW/i, respectively, and the half-reduction exposure amount E1/
2, the results shown in Table 9 were obtained.
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
るっ表 ９
て十分な分光感度を有する。As can be seen from Table 9, the electrophotographic photoreceptor of the present invention has sufficient spectral sensitivity in a wide wavelength range.
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。
〔発明の効果〕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. 〔Effect of the invention〕
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、Ｒ２は水素原子、ハロゲン原子、置
換もしくは未置換の脂肪族炭化水素基、アルコキシ基、
アミノ基、アリール基、複素環基または水酸基を表し、
Ｒ３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 and R2 are hydrogen atoms, halogen atoms, substituted or unsubstituted aliphatic hydrocarbon groups, alkoxy groups,
Represents an amino group, aryl group, heterocyclic group or hydroxyl group,
R3 represents a substituted or unsubstituted aliphatic hydrocarbon group, aryl group, or heterocyclic group, and Z1, Z2, and Z3 represent substituted or unsubstituted cyclic hydrocarbon residues or heterocyclic residues. )
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13699190A JPH0431868A (en) | 1990-05-29 | 1990-05-29 | Electrophotographic sensitive body |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13699190A JPH0431868A (en) | 1990-05-29 | 1990-05-29 | Electrophotographic sensitive body |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0431868A true JPH0431868A (en) | 1992-02-04 |
Family
ID=15188231
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13699190A Pending JPH0431868A (en) | 1990-05-29 | 1990-05-29 | Electrophotographic sensitive body |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0431868A (en) |
Cited By (7)
| 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 |
-
1990
- 1990-05-29 JP JP13699190A patent/JPH0431868A/en active Pending
Cited By (10)
| 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 |
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